#742: Tony Robbins and Jerry Colonna

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0:04:20 [Music]
0:04:45 Hello, boys and girls, ladies and germs.
0:04:46 This is Tim Ferriss.
0:04:48 Welcome to another episode of the Tim Ferriss Show.
0:04:50 Where it is my job to sit down with world-class performers
0:04:52 from every field imaginable to tease out the habits, routines,
0:04:56 favorite books and so on that you can apply and test in your
0:04:59 own lives.
0:05:01 This episode is a two for one and that’s because the podcast
0:05:04 recently hit its 10th year anniversary, which is insane to
0:05:07 think about and past one billion downloads.
0:05:11 To celebrate, I’ve curated some of the best of the best some
0:05:15 of my favorites from more than 700 episodes over the last
0:05:18 decade.
0:05:19 I could not be more excited to give you these super combo
0:05:22 episodes and internally we’ve been calling these the super
0:05:25 combo episodes because my goal is to encourage you to yes,
0:05:28 enjoy the household names, the super famous folks, but to also
0:05:32 introduce you to lesser known people I consider stars.
0:05:36 These are people who have transformed my life and I feel
0:05:39 like they can do the same for many of you.
0:05:42 Perhaps they got lost in a busy news cycle.
0:05:44 Perhaps you missed an episode.
0:05:46 Just trust me on this one.
0:05:47 We went to great pains to put these pairings together and for
0:05:52 the bios of all guests, you can find that and more at tim.log/combo
0:05:58 and now without further ado, please enjoy and thank you for
0:06:02 listening.
0:06:02 First up, Tony Robbins, entrepreneur, philanthropist
0:06:08 and the nation’s number one life and business strategist and
0:06:12 the number one New York Times bestselling author of Money,
0:06:16 Master the Game, Life Force and Awaken the Giant Within.
0:06:21 You can find Tony on Twitter and Instagram @TonyRobbins.
0:06:25 Looking at the longevity of your career, the scope and scale
0:06:31 of the Tony Robbins empire, so to speak, your endurance has
0:06:35 really impressed me and so I’m wondering after these decades,
0:06:40 what are your some of your daily routines?
0:06:42 My regimen is I start with something to strengthen and jolt
0:06:46 my nervous system every second day.
0:06:48 I will sometimes ease into it.
0:06:50 I’ll go in the hot pools and I’m fortunate to have multiple
0:06:52 homes, my home and Sun Valley have natural hot pools that
0:06:54 come out of the ground to steaming hot and I go in the hot
0:06:56 pools and then I go there in the river.
0:06:57 Here I go in a 57 degree plunge pool that I have and I have
0:07:01 on every home I have.
0:07:01 This will be immediately upon waking up.
0:07:03 Waking up, just like boom, every cell in the body wakes up
0:07:07 and it’s also just like training my nervous system to rock
0:07:11 that there is no, I don’t give a shit how you feel.
0:07:12 This is how you perform.
0:07:14 That’s what you do.
0:07:14 Even when I’m taking vacation, I do it.
0:07:16 It’s just, I don’t know.
0:07:17 Now I like it.
0:07:17 I like that simple discipline that reminds me the level of
0:07:22 strength and intensity that’s available at any moment.
0:07:25 Even if I’m relaxing, I can bring that up at will.
0:07:27 It’s smiling.
0:07:28 I also have a cryotherapy unit in all my homes.
0:07:31 Sorry, do you try cryotherapy?
0:07:32 I haven’t.
0:07:33 You know what it is?
0:07:34 Maybe you could.
0:07:35 I can, I can put the two words together and probably.
0:07:39 Oh my gosh, with all that you do, you’re going to love this.
0:07:41 I’m surprised.
0:07:42 I’m glad I’m teaching Tim Ferriss something for sure.
0:07:44 I’ve done ice math.
0:07:45 Oh, not the first time.
0:07:46 I suck.
0:07:47 Ice math suck.
0:07:48 Trust me.
0:07:48 I’m on stage in a weekend.
0:07:50 I do my unleashed power within program three days to 50 hours.
0:07:53 Yeah.
0:07:54 You know, I’ve been to a vet.
0:07:54 I, you know, you got to come as my guest to an event.
0:07:56 I would love to, but I’m going to give you an idea.
0:07:58 People won’t sit for a three hour movie that somebody spent
0:08:00 $300 million on and I got like usher or Oprah going on.
0:08:04 You know, I love you, but two hours, most I get doing 12
0:08:06 hours later, Oprah standing on a chair going, this is the
0:08:08 most incredible experience of my life on camera.
0:08:10 And I was just like, dude, I’m in for all three days.
0:08:12 But for me, one of those days alone, I wear a odometer and
0:08:17 I’m fit that and it’s 26 and a half miles on average.
0:08:19 Wow.
0:08:20 We started at 830 in the morning.
0:08:21 I finished at 130 or two.
0:08:23 There’s one one hour break.
0:08:24 People can vote with their feet and no one leaves.
0:08:26 You know, there’s on average 20 minutes of just crazy ass
0:08:31 standing ovations, music stuff that happens at the end because
0:08:33 people are just, it’s like a rock concert.
0:08:35 It’s so much fun.
0:08:36 But the wear and tear of doing, you know, basically marathon
0:08:40 after marathon after marathon on the weekend back to back.
0:08:42 It’s pretty intense.
0:08:43 And so over the years, like the inflammation of my body, the
0:08:46 demands I’ve had to do everything I can to reduce it.
0:08:48 Nothing has come close to cryotherapy.
0:08:50 Cryotherapy was developed in Poland and Eastern Germany and
0:08:53 the Eastern Bloc countries.
0:08:54 And what it does is it uses nitrogen.
0:08:57 So there’s no water and unlike an ice bath, what you do and
0:08:59 you get spasms and you got to do them still, right?
0:09:01 If you’re a boxer, you’re a runner, you’re an athlete, which
0:09:04 is what I would do before.
0:09:05 I hated them.
0:09:06 None of that process, but it reduces your body temperature
0:09:09 to minus 220 Fahrenheit and you do it three minutes and it’s
0:09:13 mind boggling.
0:09:14 In fact, I have one here and I’ll throw you in at the end if
0:09:17 you want.
0:09:17 I would love to.
0:09:18 I have a unit here.
0:09:19 I’ll do it for you.
0:09:20 But what it does is and I do about three times a week usually
0:09:23 when I come back from an event, I do it, you know, a couple days
0:09:25 in a row.
0:09:25 And what it does is it takes all the inflammation out of your
0:09:27 body and you know what inflammation does to every aspect
0:09:29 of the body and the breakdown.
0:09:30 But it also it sends and merges signals to your brain.
0:09:34 Like resetting your neurological system because your brain
0:09:37 going, you’re going to freeze the death.
0:09:38 Sounds horrific.
0:09:39 It really isn’t.
0:09:40 You’ll find out it’s not that painful.
0:09:41 Going in my cold plunge of 57 degrees feels more jolting than
0:09:45 this does even though it’s colder because, you know, the fluid
0:09:48 of water versus the nitrogen around is different.
0:09:49 Right, the connectivity.
0:09:50 The connectivity, exactly right.
0:09:52 But what happens is your nervousness gets a signal.
0:09:54 So it’s like everything in your body connects because it’s
0:09:56 like emergency.
0:09:57 Every part is a reset of your nervous system.
0:09:59 You get an explosion of endorphins in your body, which
0:10:02 is really cool.
0:10:02 So you get this natural high, you feel this physiological
0:10:06 transformation and you get the reduction of inflammation.
0:10:08 What it was used for originally is for people with arthritis
0:10:11 and I found my first one because my mother-in-law was
0:10:13 calling up and she was just crying and pain and no medication
0:10:16 was enough for her.
0:10:17 And I hate somebody medicated anyway.
0:10:19 And so I started doing this research and it just started
0:10:22 to come to the U.S.
0:10:22 And now the LA Lakers, most football teams that it’s spreading
0:10:26 like wildfire amongst the sports teams.
0:10:28 And so that’s where it took off.
0:10:29 So I went and got her one and I mean, took her I think three
0:10:33 sessions and she’s out of pain and now there’s another day
0:10:35 she’s in pain.
0:10:36 Now most people can’t afford to go buy a unit, but there are
0:10:39 local places now they’re popping up all over the United
0:10:41 States where athletes go where people go where people go for
0:10:43 juvenations, amazing for the skin.
0:10:45 But it’s one of the great things I got it first, I got it
0:10:47 for me and now I’m addicted.
0:10:48 But other than that, I don’t do much unique or different
0:10:50 with my life.
0:10:51 I don’t believe that entirely.
0:10:54 I’ll keep digging.
0:10:55 How far after so what is if you were to kind of speck out
0:10:58 the first hour of your day?
0:11:00 The first every day I do the water, I take in the environment
0:11:04 and then the first thing I do for do anything else my day is
0:11:06 I do what I call priming and priming to me is different than
0:11:09 meditating.
0:11:10 I’m never really a meditator per se.
0:11:12 I know the value of it.
0:11:12 But the idea for me of sitting still and having no thoughts
0:11:15 just didn’t really work out for me.
0:11:17 I was just a pain in the ass and I just thought it’s not natural
0:11:20 right?
0:11:21 It’s like that’s where it works.
0:11:22 But when I’m in nature, I feel that form of meditation when
0:11:25 I stand on stage and someone stands up and my brain, it’s done.
0:11:28 I don’t even know what it is, but person suicidal.
0:11:30 I’ve never lost a suicide, for example, in 37 years.
0:11:32 Not going to what does mean I won’t someday, but I never have
0:11:34 it a thousand so we followed up with them.
0:11:36 So it’s like there’s something that comes through me and it’s
0:11:39 quite meditative.
0:11:40 It’s like I experience it as a witness, you know, afterwards
0:11:43 is it’s one of the most beautiful gifts in my life.
0:11:45 So I know that meditation.
0:11:46 But for me, what priming is if you want to be have a prime
0:11:49 life, you got to be in a prime state and weeds go automatically.
0:11:53 I don’t give a damn what it is.
0:11:54 It might teach Jim around just to say that.
0:11:56 And so what I do is I get up and I do a very simple process.
0:11:58 I do an explosive change in my physiology.
0:12:00 I’ve done the water already, right?
0:12:02 Cold, hot.
0:12:02 Then I do it with breath.
0:12:04 I know, you know, all forms of Eastern meditation all understand
0:12:07 that the mind is the kite and breath is the string.
0:12:10 So if I want to move that kite, I move the breath.
0:12:12 So I have a specific pattern of breathing that I do.
0:12:14 I do 30 of these breaths and I do them at three sets of 30.
0:12:18 That creates a profound physiological difference in my
0:12:21 body and from that altered state, I usually listen to some
0:12:24 music and I go for, I promise myself 10 minutes and I usually
0:12:28 go 30.
0:12:29 And you do that in this room that we’re sitting in?
0:12:31 No, I do it all up.
0:12:32 This one room is where I do it.
0:12:33 This has got a great vibe.
0:12:34 I’ll do this one.
0:12:34 I do it at night.
0:12:35 I usually will go outside because I love the wind on my face
0:12:37 and I love taking the elements and so forth, but I do it in
0:12:40 multiple places.
0:12:41 I’m on the road.
0:12:41 I do it.
0:12:42 Doesn’t matter what day.
0:12:42 I always, I do not miss priming.
0:12:44 The reason is you don’t get fit by getting a lucky.
0:12:47 You don’t get fit by working out for a weekend.
0:12:49 You know, you live your life that way.
0:12:51 Fitness is because it’s becomes just part of who you are.
0:12:54 So what I do during that time is I do three simple things and
0:12:56 I do it minimum 10 minutes.
0:12:57 Three minutes of it is just me getting back inside my body and
0:13:01 outside of my head, feeling the earth and my body experience
0:13:04 and then feeling totally grateful for three things and I make
0:13:07 sure one of them is something very, very simple.
0:13:10 The wind on my face, you know, the reflection of the clouds
0:13:12 that I just saw there, but I don’t just think gratitude.
0:13:15 It’s like I let gratitude fill my soul because when you’re
0:13:18 grateful as we all know, there’s no anger.
0:13:20 It’s possibly angry and grateful simultaneously.
0:13:23 So when you’re, when you’re grateful, there is no fear.
0:13:25 You can’t be fearful and grateful simultaneously.
0:13:27 So I think it is one of the most important power emotions of
0:13:30 life and also to me, there’s nothing worse than an angry,
0:13:33 rich man or woman.
0:13:34 You know, somebody’s got everything and they’re pissed off.
0:13:36 I want to surprisingly high numbers.
0:13:37 Yeah, it is because they develop a life that’s based on
0:13:40 expectation instead of appreciation.
0:13:42 Agreed.
0:13:42 I tell people you want to change your life fast.
0:13:44 Then trade your expectation for appreciation.
0:13:46 You have a whole new life.
0:13:47 So every day I anchor that in and I do it very deeply emotionally
0:13:51 and then the second three minutes I do is a total focus on
0:13:55 feeling presence of God, if you will, however you want to
0:13:59 language that for yourself, but this inner presence coming in
0:14:02 and feeling that heals everything in my body, my mind,
0:14:04 my emotions, my relationships and my finances.
0:14:07 I see it as solving anything that needs to be solved.
0:14:10 I experience the strengthening of my gratitude of my joy of
0:14:14 my strength of my conviction of my passion and I just let
0:14:16 those things happen spontaneously.
0:14:18 And then I focus on celebration and then service because my
0:14:21 life is about service as it makes me feel alive.
0:14:23 So I flood myself with that with a breathing pattern that I
0:14:26 take that does the opposite.
0:14:27 It takes the breath down through my body and back up again.
0:14:30 And then the last three minutes are me focusing on three
0:14:34 things I’m going to make happen, my three to thrive.
0:14:36 I have some big things that I’ll do and sometimes I’ll do
0:14:38 things that are smaller, but I see them feel them experience
0:14:40 them.
0:14:40 So it’s a really simplistic process.
0:14:42 10 minutes, but I come out of it in my power.
0:14:46 It doesn’t matter if I had two hours sleep.
0:14:47 I’m now ready and I do this even when I have no sleep.
0:14:50 I, that’s how committed I am.
0:14:51 And as I said, I’ve always said there’s no excuse not to do
0:14:54 10 minutes.
0:14:55 If you don’t have 10 minutes, you don’t have a wife, right?
0:14:57 And that’s how I got myself to do it.
0:14:59 And now that I’ve done it, you know, 20 to 30 minutes is almost
0:15:02 always what it is because it actually feels extraordinary.
0:15:03 I have to ask what type of music do you usually listen to?
0:15:07 I have a variety, but for that meditation, I have one in
0:15:10 particular, which is a oneness meditation that a friend of
0:15:12 mine made it, who’s from India that I find really profound as
0:15:15 no singing in or anything like that is just the sound of a
0:15:19 vibration that’s going on and I just love it.
0:15:21 But that’s what I’m doing currently in the past over the
0:15:23 years.
0:15:23 I’ve used all kinds of different pieces of music, but I don’t
0:15:25 use modern music or pop music or rock me.
0:15:27 I do that to work out, you know, rap.
0:15:29 I don’t know.
0:15:30 It just feels weird to be doing rap while you’re meditating.
0:15:32 But again, what’s different is I don’t look at his meditation
0:15:34 because I look at it as it’s priming courage, love, joy.
0:15:37 It’s priming gratitude.
0:15:39 It’s priming strength.
0:15:40 It’s priming accomplishment.
0:15:41 It’s priming, you know, when I’m doing my gratitude piece, I’m
0:15:44 doing the circle of who’s closest to me and, you know,
0:15:46 circling that out to everybody I love and sending that energy
0:15:48 and healing out to them as well.
0:15:49 So to me, if you want primetime life, you got to prime daily.
0:15:53 I like the term priming also because I think that most people
0:15:56 who struggle with meditation or even attempt to use meditation
0:15:59 are utilizing it for that purpose.
0:16:01 They’re doing it first in the morning.
0:16:02 And, you know, when you said, if you don’t have 10 minutes,
0:16:04 you don’t have a life, it reminded me of something that
0:16:05 Russell Simmons said to me, which was if you don’t have 30
0:16:07 minutes to meditate, you need three hours.
0:16:09 And I don’t always do 30 minutes, but I do meditate in
0:16:13 the morning and it’s been a very consistent pattern among all
0:16:16 of the people that I’ve interviewed so far on the podcast.
0:16:19 I tell you, four things I saw that stood out and one is overly
0:16:23 simplistic and that’s why people don’t pay attention to it.
0:16:25 But these guys pay attention to it.
0:16:26 They don’t lose.
0:16:27 Half the key to weakening is not losing and they are obsessed.
0:16:31 Every single one is obsessed and not losing money.
0:16:34 I mean, a level of obsession that’s mind boggling.
0:16:37 It isn’t just these investors, you know, Sir Richard Branson,
0:16:39 for example, you know, people see Richard and he’s such an
0:16:42 outgoing, playful, crazy guy.
0:16:44 He’s kind of introverted in some areas, but when it comes to
0:16:46 athletics and taking on challenges, he’s out in the world.
0:16:49 But you know, his first question to every business is what’s
0:16:52 the downside and how to protect it?
0:16:53 Right.
0:16:54 Like when he did his piece with Virgin, I mean, that’s a big
0:16:57 risk and start an airline.
0:16:58 He went to Boeing and negotiated a deal that he could send
0:17:00 the planes back if it didn’t work out and he wasn’t liable.
0:17:03 But that’s the level these guys think at.
0:17:05 So they look to see how do I not lose money first?
0:17:08 Because the average person has no clue.
0:17:10 If I lose 50% in 2008, well, guess what?
0:17:13 You’re going to make 100% to get even, not 50% because your
0:17:17 principal’s gone down so much.
0:17:18 So it’s like people don’t understand you lose 60%.
0:17:20 It’s 200% to get even.
0:17:22 And so the average person, you know, lives in a world where
0:17:26 they try not to lose money, but they’re not obsessed.
0:17:28 These are obsessed.
0:17:29 Second thing they all have in common.
0:17:30 Every single one of them is obsessed with asymmetrical
0:17:33 risk reward, which is a big word.
0:17:35 It simply means they’re looking to use the least amount of
0:17:38 risk to get the maximum amount of upside.
0:17:41 And that’s what they live for.
0:17:43 Here’s what I found with Paul Tudor at the very beginning
0:17:44 and back on track.
0:17:45 When he said his best, he made sure every single trade had
0:17:50 what he called a five to one.
0:17:51 That means if he was going to risk a dollar, he wasn’t about
0:17:54 to risk it unless he was certain he was going to make five.
0:17:57 You’re not always right.
0:17:58 So guess what?
0:17:59 If I risk a dollar make five and I’m wrong, I can risk another
0:18:02 dollar, I still make four.
0:18:04 I can be wrong four times out of five and still break even.
0:18:08 Their secret is not that they’re not wrong.
0:18:10 It’s they set themselves up where they risk small amounts for
0:18:13 big rewards proportionally.
0:18:15 Paul, you know, if he’s right at one out of three times,
0:18:17 he still makes 20%.
0:18:18 So the average person risks a dollar trying to make how much?
0:18:21 Dollar 10.
0:18:23 That’s right.
0:18:23 About about 10.
0:18:24 If I could get 10%, wow, my dollar right of 20% would be
0:18:27 unbelievable.
0:18:28 How often can you be wrong?
0:18:29 Not very often.
0:18:30 Not at all.
0:18:31 Right.
0:18:32 You’re in the hole.
0:18:32 You’re starting from the hole and you got to build back up.
0:18:34 So they’re asymmetrical words like I was with Kyle Bass and
0:18:37 Kyle Bass risked.
0:18:38 Check this out in the middle of the subprime crisis.
0:18:41 He made $2 billion out of 30 million because he risked for
0:18:45 every six cents he risked.
0:18:46 He had an upside of a dollar.
0:18:48 Six cents for a hundred.
0:18:49 Well, you could be wrong 15 times and you’re still okay in
0:18:53 that area.
0:18:53 I mean, he was brilliant to figure it out.
0:18:56 He’s a genius figured out, but that risk reward is why it is.
0:18:59 He showed his kids.
0:18:59 He taught.
0:19:00 I said, how do I teach us the average investors?
0:19:02 And he said, well, you can teach them when I taught my kids.
0:19:05 And I said, you know, he goes, we bought nickels.
0:19:07 So what do you mean you bought nickels?
0:19:09 He said, well, I did research.
0:19:11 I had this question.
0:19:12 That’s another thing that all these guys do.
0:19:13 They ask a better question that we talked about.
0:19:15 They get better answers, right?
0:19:16 Better quality question, better quality answer.
0:19:18 What’s wrong with me?
0:19:18 You’ll come up with stuff.
0:19:19 How do I make this happen?
0:19:20 No matter what, you’ll come up with different answers.
0:19:22 So his question was, where in the world is there a riskless
0:19:25 trade with total upside?
0:19:27 And he started looking around and he said, I’m worried about
0:19:31 inflation.
0:19:31 So he decided, well, gosh, of all the currencies in the world,
0:19:34 a nickel, what it’s made of today.
0:19:36 It’s not made mostly of nickel, by the way.
0:19:37 He said, it’s costing the US government nine and a half cents
0:19:42 to make a nickel.
0:19:43 That’s how our government functions.
0:19:44 It’s been almost 10 cents to make something worth half as much,
0:19:48 right?
0:19:49 The Pentagon plan.
0:19:49 Yeah, perfect plan.
0:19:51 So he said, but you know what?
0:19:52 Just the actual material value, right, is 6.8, whatever it was,
0:19:57 six, something, six and a half.
0:19:58 I’ll call it for round numbers.
0:19:59 So he said, if I buy a nickel, it’s never going less than a
0:20:02 nickel, unless you believe the US government’s gone.
0:20:04 So I’ve got something that never goes down in value.
0:20:06 So I got a guaranteed return.
0:20:08 You know, I’m not going to lose my principle.
0:20:09 But day one, it’s worth 36% more than the day I bought it.
0:20:13 How many investments can you have a hundred percent guarantee of
0:20:15 no loss and have 36%?
0:20:17 I said, yeah, but that’s not value.
0:20:18 And I saw they passed the law a few years ago.
0:20:20 I think Charlie Rangel over was going to push it through and
0:20:22 he goes, yeah, but Tony said, that doesn’t matter.
0:20:24 He’s, let me tell you why.
0:20:26 He said, look at pennies.
0:20:27 When they changed it from pure copper to 10 and all things they
0:20:30 changed, what happened to the old pennies?
0:20:33 There’s a scarcity of them.
0:20:35 And now a penny from those days, the worth two cents.
0:20:37 It’s a hundred percent more valuable.
0:20:38 So he said that at some point, the government cannot continue
0:20:41 to do something cost twice as much.
0:20:43 Some point they’ll make a change in the materials and then
0:20:45 all these nickels are worth an unbelievable amount.
0:20:47 So he said, I just show on my kids, here’s a risk.
0:20:50 You need to think different than everybody else.
0:20:51 Don’t think I have to take huge risk for huge rewards.
0:20:53 Say, how do I take no risk and get huge rewards?
0:20:56 And because you ask that question continuously and you
0:20:58 believe in answer, you get it.
0:20:59 So he said, listen, if I could convert my entire wealth in
0:21:02 nickels right now, I’d do it.
0:21:04 I said, you’re insane.
0:21:05 He goes, I am insane.
0:21:05 But it’s the best possible fundamental investment.
0:21:08 He started telling me how to do it.
0:21:09 He bought 40 million nickels.
0:21:11 Wow.
0:21:12 He has 40 million nickels.
0:21:14 He fills up a room.
0:21:15 They were the nests, right?
0:21:16 He’s gonna be on the ground floor.
0:21:17 And he had his kids ragging at the end and he was laughing,
0:21:19 having fun at me in this like their little treasure room.
0:21:21 So he can legitimately do like the Scrooge McDuck backstroke.
0:21:24 You’re a pool full of nickels.
0:21:26 For real, the nickels.
0:21:27 So that’s asymmetrical.
0:21:29 I’ll give you one more and I’ll shut the hell up.
0:21:31 No, no, I’m not here for that.
0:21:32 You’re asking me what the, you’re telling me the differences.
0:21:34 I want to, you know, there are differences.
0:21:35 We can spend hours and hours on the differences.
0:21:36 But what I think is useful is what’s aligned because then it
0:21:39 gives something universal that can be applied.
0:21:40 Absolutely.
0:21:41 The other one for them is they absolutely beyond a shot of
0:21:45 a doubt know they’re going to be wrong.
0:21:46 You look at these talking hands on television and people screaming
0:21:49 you and hitting bells and telling you what to buy and they’re
0:21:51 right, right, right.
0:21:52 The best on earth, the red values, right?
0:21:55 The Pabbles, the, you know, I don’t give it who you talk about.
0:21:58 You want to look at Carl Icon.
0:21:59 They all know they’re going to be wrong.
0:22:00 So they set up an asset allocation system that will make
0:22:03 them successful.
0:22:04 They all agree asset allocation is the single most important
0:22:06 investment.
0:22:07 There wasn’t one person in terms of your vehicle, but it wasn’t
0:22:09 the most important thing.
0:22:10 No matter how they attacked it, asset allocation was the
0:22:12 element there.
0:22:13 And the last one is they are lifelong learners.
0:22:16 I mean, these people are machines like you, like me, like
0:22:18 Peter, like most of the people you and I share as friends.
0:22:21 They just are obsessed with knowing more because the more
0:22:24 they know, the more they realize what they didn’t know.
0:22:26 And then they apply that and they go to another level.
0:22:28 And every time you think you’re the best, you can be
0:22:30 in anything in life, your body or motion, spirit, your
0:22:32 finances, there’s always another level.
0:22:34 And these guys live by it.
0:22:36 And the last one that I found almost all of them were real
0:22:38 givers, not just givers on the surface, like money givers.
0:22:41 That’s wonderful, but really passionate about giving.
0:22:44 And it showed up once they saw what I was doing was legitimate
0:22:47 and was really real.
0:22:47 That I mean, then they’re opening up three hours of their
0:22:49 time with something.
0:22:50 Let me disguise will never give.
0:22:51 Just a quick thanks to one of our sponsors and we’ll be right
0:22:58 back to the show.
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0:23:56 And now Jerry Kelowna co founder and CEO of executive
0:24:06 coaching and leadership development firm reboot dot
0:24:09 IO and author of reboot leadership and the art of growing
0:24:15 up.
0:24:15 You can find Jerry on Twitter at Jerry Kelowna Jerry.
0:24:22 Welcome to the show.
0:24:23 Hey Tim, it’s great to be here.
0:24:25 I’m really excited to talk to you.
0:24:26 We have so much we could possibly talk about you and I
0:24:29 have spoken before had quite a few conversations over the
0:24:34 last God knows how many years with particular density a
0:24:37 handful of years ago and I thought we could start with
0:24:41 the spider tattoo which you just showed me over video.
0:24:44 It is not a small tattoo.
0:24:45 So perhaps much like a novel I greatly enjoy the girl with
0:24:50 the dragon tattoo.
0:24:51 This would be the coach with the spider tattoo, but I
0:24:53 don’t know the story.
0:24:55 Why do you have a gigantic spider tattoo on your chest?
0:24:58 Yeah, so spider is a good friend of mine.
0:25:00 Spider is my spirit guide.
0:25:03 So in 2007 I went on a retreat led by a Jungian echo
0:25:13 psychologist named Bill Plotkin PLOT KIN and on that
0:25:20 retreat is a long story.
0:25:21 Tim, you ready for it?
0:25:22 Oh, I’m ready.
0:25:23 We have nothing but time on that retreat.
0:25:26 I started to go really deep into some of the important
0:25:31 structures of my life and I had a dream and it was after
0:25:36 a night of ecstatic dancing in which I danced nearly naked
0:25:41 in a drum circle and I’d fallen asleep and I had this
0:25:46 dream in which I was going to a house that I owned on
0:25:50 Long Island and I got to the house and house was completely
0:25:54 white and I was really terrified and I went into the
0:25:58 house and it was supposed to be my house, but it didn’t
0:26:00 feel right and I ended up in the basement and in the basement
0:26:03 basement floor was covered with this sort of like the floor
0:26:06 of a forest and these mushrooms were sprouting up and I got
0:26:10 very scared and I tore the mushrooms from the ground and
0:26:13 I ran out of the house.
0:26:14 So the next morning I went into circle again and I shared
0:26:18 that dream and Bill turns to me and he says, “Go leave, leave
0:26:24 the circle right now.
0:26:25 I want you to go into the forest and I want you to find
0:26:27 those mushrooms and I want you to apologize to those
0:26:30 mushrooms and ask it what it was that you were supposed
0:26:34 to hear from them that you were too afraid to hear.”
0:26:36 So I left the circle and I started wandering around and
0:26:39 I’m like, “What the fuck am I doing?
0:26:40 I’m walking around this forest trying to find these
0:26:43 mushrooms and I actually have to have a conversation with
0:26:46 these mushrooms.”
0:26:46 And to be clear, I was not ingesting the mushrooms,
0:26:49 okay, because I know who I’m talking to.
0:26:51 So I’m walking around and all of a sudden I see on the
0:26:56 ground the exact same white long stringy mushrooms and I’m
0:27:01 like freaked out and I dropped to my knees and I start
0:27:04 crying and I said, “I’m so sorry.
0:27:06 I’m so sorry.
0:27:07 What were you here to teach me?”
0:27:09 And they said, “The mushrooms said to me, ‘You’re too
0:27:13 afraid, go into the forest and find your place.'”
0:27:16 And now I’m like freaking out even more.
0:27:19 So I just standing up and I’m like stumbling around and
0:27:22 this is a time period in my life where I’m just a
0:27:24 freaking wreck and I’m crying and I’m wandering through
0:27:27 the forest and I find this little sort of indentation,
0:27:31 this little spot and I sit down and I’m like sitting on
0:27:33 my rump and I’ve got my hands on my knees and my head
0:27:38 and I’m just crying and I look up and off into my right
0:27:42 is this gorgeous spiderweb and it actually has little
0:27:46 dew drops glistening on it and I’m like, “Okay,
0:27:48 this, they look like crystals.”
0:27:50 And this little spider comes walking out.
0:27:53 It’s this Virginia garden spider and I look at it and
0:27:57 I said, “Okay, I give up.
0:27:59 What the fuck are you here to teach me?”
0:28:01 Because I have no idea and the spider says to me, “You
0:28:05 worry too much.
0:28:06 Your children are going to be fine.”
0:28:11 And I just start shaking because there’s no message
0:28:13 that I needed to hear more than that.
0:28:15 And so I came out of that forest.
0:28:18 I came out of there at retreat and a few weeks later
0:28:21 was my 45th birthday there about the actual year.
0:28:26 Doesn’t matter so much as the fact that it was my
0:28:29 birthday and on my birthday, I got this spider tattoo
0:28:32 above my heart so that I can never forget the fact
0:28:38 that I worry too much and that my kids are going
0:28:40 to be all right.
0:28:41 So that’s the spider.
0:28:43 Has it remained relevant to you?
0:28:47 Is it something that you consciously notice or because
0:28:51 it’s so continuously present, do you find yourself
0:28:54 sometimes losing sight of it?
0:28:56 Both, meaning I’m often reminded as I was when
0:29:00 you asked and you said, “Oh, I’m going to ask you
0:29:02 about the spider.”
0:29:03 I’m often reminded.
0:29:06 So thank you for reminding me that the point of
0:29:10 that spider’s visitation to me was to remember who
0:29:14 I am and I can use that reminder every day because
0:29:19 I forget every day.
0:29:20 Not only do I forget who I am, but I forget that
0:29:23 my kids are all right and that I worry too much.
0:29:26 Thank you for the story and it makes me think of
0:29:33 given the spider, Lakota mythology and Ictomy.
0:29:39 There are various names for Ictomy, but Ictomy is
0:29:41 a spider trickster spirit, bit of a hero and perhaps
0:29:47 one of the ways that you are productive trickster is
0:29:50 by asking questions that are very uncomfortable or
0:29:54 that can be very uncomfortable.
0:29:57 And I think that’s one of your arts and we’re going
0:30:00 to come back to that for sure.
0:30:03 But I thought we could revisit another perhaps chapter
0:30:07 or event in your life that seems to have been
0:30:10 very impactful.
0:30:12 Could you talk to, I believe it was February 2002
0:30:16 after something involving the Olympics or the
0:30:19 Olympic bid meeting?
0:30:21 If you know what I’m referring to.
0:30:24 So February 2002, I was working at J.P.
0:30:28 Morgan at the time.
0:30:29 I was co-leading the technology investment practice
0:30:33 for a fund that was about $23 billion on a management.
0:30:36 So a large fund and this was after having left flat iron
0:30:42 partners in I think around the middle of 2001.
0:30:47 And just for clarity, that was billions with a B.
0:30:49 That was billions with a B.
0:30:51 Yeah, that’s a large fund.
0:30:53 It’s a large fund.
0:30:54 I mean, but we were very diversified.
0:30:57 We did everything from Brazilian railroads to, you
0:31:00 know, funding the launch of JetBlue Airlines to the
0:31:05 latest web-based startup in some capacity.
0:31:08 Anyway, a few months prior, it had been cleared that my
0:31:12 previous fund flat iron partners needed to be wound
0:31:15 down and Fred and I needed to make some decisions
0:31:19 about what to do.
0:31:20 And I was in the midst of trying to sort through
0:31:23 what I was going to do with the rest of my life.
0:31:25 I did not have the internal capacity to raise a new
0:31:29 fund.
0:31:30 I know now that I was in the midst of a very
0:31:34 profound depression that was exacerbated by the
0:31:38 attacks on 9/11.
0:31:40 And one of the ways I responded to the attacks on 9/11
0:31:44 was to throw myself into the Olympic bid effort.
0:31:47 We were bidding to bring the 2012 games to New York.
0:31:52 And for me, this was a profoundly important effort
0:31:56 because now you’re going to make me cry.
0:31:59 My city was attacked.
0:32:01 The city that I love, the city where I grew up, the
0:32:07 city of Brooklyn, the place that had so much meaning
0:32:11 for me was attacked.
0:32:12 And I remember the feeling helpless during the
0:32:17 fall, following the attack.
0:32:19 Anyway, around the same time, I had to decide whether
0:32:22 or not I was going to accept an offer to join J.P.
0:32:24 Morgan, which had been one of the funders and the
0:32:27 funding partners for Flatired Partners.
0:32:30 And eventually I did that and Fred linked up with Brad
0:32:33 Burnham and they launched Union Square Ventures.
0:32:36 By the way, worst decision of my life.
0:32:38 But anyway, to join J.P.
0:32:41 Morgan and not go to Union Square Ventures.
0:32:43 Anyway, so he went off and did that.
0:32:45 I joined J.P.
0:32:46 Morgan and by February 2002, I was a wreck.
0:32:51 And what you’re referring to is February 2, 2002.
0:32:57 I left an Olympic bid committee meeting which was
0:33:01 being held downtown, not far from ground zero.
0:33:05 And I found myself outside of the stinking smoking
0:33:10 hole that was the pile as they referred to it of
0:33:16 ground zero.
0:33:17 And I remember feeling completely overwhelmed and
0:33:21 feeling like there were ghosts flying around that
0:33:24 area and I wanted to die.
0:33:28 And I was obsessed with the idea of running down to
0:33:32 the Wall Street subway station and leaping in
0:33:34 front of our subway.
0:33:35 And I ended up deciding not to do that, but wisely
0:33:41 and thankfully instead called my therapist, Dr.
0:33:44 Sayers, who said to me promptly get in a cab and
0:33:49 come out and see me.
0:33:51 And I did just that and saved my life at that point.
0:33:56 What did your therapist do when you arrived?
0:34:01 What was that session like?
0:34:02 Can you describe that session?
0:34:04 So Dr. Sayers is a psychoanalyst and so I very
0:34:08 traditionally almost like a New Yorker cartoon would
0:34:10 lay on the couch and I can’t help but think of that
0:34:15 and think of like somehow it’s a dog sitting in the
0:34:17 therapist chair.
0:34:18 So it’s like that’s some sort of New Yorker thing.
0:34:21 Anyway, so I’m laying on the couch, staring up the
0:34:24 ceiling as I did all the time.
0:34:26 And I remember saying to her, just stick a fork in
0:34:31 me, I’m fucking done.
0:34:32 Put me in the hospital, throw away the key.
0:34:35 And you know, to be clear, the threat was real
0:34:38 because when I was 18, I did try to kill myself.
0:34:40 And so no fooling around here, right?
0:34:45 I mean, this isn’t just some idle ideation going on
0:34:48 here.
0:34:49 This was like, I was in it.
0:34:51 I was 38.
0:34:52 I was being cooked and I was declaring that I was
0:34:56 done.
0:34:56 And Dr. Sayers, who was also from Brooklyn, said the
0:35:00 most magical thing possible.
0:35:02 She said, what the hell do you want to go to a
0:35:04 hospital for?
0:35:04 The food sucks.
0:35:06 Go to Canyon Ranch.
0:35:09 You’ll get a massage every day.
0:35:10 You’ll be so much better.
0:35:11 What is Canyon Ranch?
0:35:15 Canyon Ranch is a health spa and it’s a very nice
0:35:19 place.
0:35:20 I loved it.
0:35:21 It was really sweet, but it’s about as far removed
0:35:25 from a psychiatric hospital as you can imagine.
0:35:27 Because by the way, I did spend three months in
0:35:30 a psychiatric hospital.
0:35:31 So I sort of knew what I was getting, what I was
0:35:33 asking for, if you will.
0:35:34 So that’s what I did.
0:35:37 I made plans to go down to Arizona.
0:35:39 I think it was the Arizona branch of Canyon Ranch.
0:35:42 And that moved was the beginning of me being
0:35:46 rebuilt.
0:35:47 When and why did you spend time in a psychiatric
0:35:50 hospital?
0:35:50 I mentioned the suicide attempt.
0:35:53 Right.
0:35:53 I was 18 and I had on January 2nd, something about
0:35:58 the number two, right?
0:36:00 January 2nd, I guess, was 1981.
0:36:05 I’m losing track of the time.
0:36:06 I had just turned 18 and I tried to kill myself.
0:36:12 I cut my wrists and first went to, it was taken
0:36:17 to the emergency room to make a hospital.
0:36:20 The Trump Pavilion, that’s all I’m going to say.
0:36:23 And then I was transferred from there to Creedmore
0:36:28 State Hospital, which is just this side of hell.
0:36:32 And then from there, after three days at Creedmore,
0:36:36 I was transferred to a hospital that actually is
0:36:39 no longer a hospital, Cabrini Medical Center in
0:36:43 Manhattan, where I was there for three months.
0:36:46 I’d love to, I think this is a good point to come
0:36:51 back to questions and good questions.
0:36:55 And you’re very skilled in this department.
0:36:58 So I’m going to pose one of your questions to you
0:37:01 and you can feel free to tweak it, paraphrase it,
0:37:04 correct it any way you like.
0:37:06 But if you look back to 2002.
0:37:09 How are you complicit in creating the conditions in
0:37:14 your life that you would have said you didn’t want?
0:37:17 Nice turn, which is a great question.
0:37:22 So maybe you could repeat it for folks because it
0:37:25 is so important.
0:37:27 And this is something that has greatly aided me when
0:37:30 you introduced it to me many moons ago.
0:37:33 Yeah.
0:37:33 And then if you could speak to that as it applies to
0:37:36 that particular period in your life.
0:37:38 I’ll unpack the question.
0:37:39 So the way I usually ask the question goes like this.
0:37:42 How have I been complicit in creating the conditions?
0:37:46 I say I don’t want.
0:37:47 And the reason for the language is very, very
0:37:51 purposeful.
0:37:51 I like to use the word complicit and not responsible.
0:37:55 90% of the time when I first asked that question,
0:37:58 people hear the word.
0:37:59 How have I been responsible for the conditions?
0:38:03 Complicitness is important because it’s not.
0:38:06 It’s relieving the person from the burden of feeling
0:38:10 responsible for all the shit in their lives because
0:38:12 that’s not fair to carry that responsibility.
0:38:15 But it’s helpful to think of ourselves as somehow being
0:38:22 served by the challenges that we’re going through.
0:38:25 The second piece of that is that I say I don’t want
0:38:29 and that sort of unpacks that notion even further,
0:38:32 which is there’s something oftentimes about the way in
0:38:36 which we operate and the way we set up the conditions
0:38:39 of our lives to be in unconscious service to us.
0:38:44 The psychological term is secondary gain.
0:38:47 But there are ways in which we find ourselves repeating
0:38:51 patterns in our life.
0:38:52 We always date the same type of person.
0:38:54 We are always finding ourselves in the same kind of job.
0:38:57 We’re always frustrated by the same sorts of situation.
0:39:01 And so it’s really useful to sort of start to unpack that.
0:39:04 So that’s that question.
0:39:06 And before I even answer your question,
0:39:09 I want to say one other thing.
0:39:10 The discomfort of difficult and powerful questions
0:39:14 reminds me of something my daughter Emma likes to say
0:39:18 about me, which is that I imagine growing up with a man
0:39:20 who asks you questions that you really rather not answer.
0:39:24 So shout out to Emma.
0:39:29 So I think that the way I was complicit.
0:39:34 I guess we should thank Emma for being the crash test dummy
0:39:38 for the questions that you use now in your career.
0:39:42 You got it.
0:39:43 Well, Emma, Michael, Emma and her brothers, Michael and Sam,
0:39:46 for sure, for sure.
0:39:48 God love them.
0:39:49 They put up with so much with me.
0:39:51 Oh, my God, Dad, stop coaching me.
0:39:53 So before I can answer that question,
0:39:59 honestly, what I would say is Dr.
0:40:02 Sayers taught me three additional questions.
0:40:04 And those questions are what am I not saying that needs to be said?
0:40:10 What am I saying that’s not being heard?
0:40:13 And what’s being said that I’m not hearing?
0:40:15 So again, what am I not saying that needs to be said?
0:40:20 What am I saying that’s not being heard?
0:40:23 And what’s being said that I’m not hearing?
0:40:27 And so for me, the way I was complicit was I wasn’t speaking.
0:40:33 I wasn’t saying what I needed to say.
0:40:36 And more often than not, Tim, the suffering that I encounter
0:40:40 can almost always be rooted back to somebody not saying something
0:40:45 that needs to be said.
0:40:46 And if there’s a little correlated to that and not saying it
0:40:51 or not saying it in a way that it can be heard, because oftentimes
0:40:55 we speak without words, but by our actions and we go unheard.
0:41:01 Could you give an example of something that you needed to say
0:41:06 during that period of time that you didn’t say or it wasn’t heard?
0:41:11 Yeah, yeah, something very, very simple.
0:41:13 I wasn’t happy that despite all the outward trappings of success,
0:41:18 I was empty and hollow inside that I wasn’t speaking truthfully.
0:41:25 That I wasn’t living in integrity and that I was too afraid of losing
0:41:32 the good graces and esteem of everybody around me to actually
0:41:37 talk about the fact that I did not want to do what I was doing
0:41:41 with my life at that point.
0:41:42 Oh, by the way, I didn’t know what else I was going to do,
0:41:45 but that’s a separate issue, right?
0:41:48 I mean, I knew when I decided not to continue working with
0:41:52 Fred Wilson, stupid man that I was, I knew that it was actually
0:41:57 the right thing for me to do.
0:41:58 But when I agreed to take a job at JPMorgan, it wasn’t because
0:42:03 I wanted to continue doing that work.
0:42:05 It’s because I was too terrified to do anything other than that.
0:42:09 And I certainly didn’t want to lose the esteem and the good wishes.
0:42:14 I mean, think about your reaction just a few minutes ago,
0:42:17 when you pointed out that it was a $23 billion fund and even
0:42:22 in that moment, I felt a little bit of that pride mixed with
0:42:26 a little bit of the shame because I walked away from that.
0:42:29 And I didn’t want to lean into that space of like,
0:42:33 what if I don’t matter anymore?
0:42:35 What if nobody calls me?
0:42:38 How did you get over that?
0:42:40 What are the things that contributed to you making it through
0:42:45 those questions because a lot of people seemingly don’t make it
0:42:48 through those questions, right?
0:42:49 They stay in a given track in a given relationship.
0:42:54 They stay stuck exactly for five, 10, 15, 20 or more years.
0:43:00 So what are lifetime?
0:43:01 What did Emerson say?
0:43:04 The vast majority of men, what’s updated?
0:43:06 The vast majority of people lead lives of quiet desperation.
0:43:11 So how did I get out of it?
0:43:16 I guess your question implies an agency.
0:43:19 That I didn’t feel at the time, meaning, huh, I wake up one day
0:43:24 and I decide I’m going to be different.
0:43:27 No, it wasn’t that.
0:43:29 It was that I ran out of the ability to continue to operate
0:43:35 anymore.
0:43:35 It was that moment above the lip of ground zero and that moment
0:43:42 where I chose not to leap in front of the subway, but to get
0:43:46 into the cab and go to see Dr. Sears.
0:43:48 And it was that moment where I decided to follow her advice
0:43:52 and go to Canyon Ranch.
0:43:53 It was the series of moments where it was like, okay, I know
0:43:58 it’s not working.
0:43:59 I admit it’s not working.
0:44:01 I don’t know what I’m going to do, but what I have been doing
0:44:05 hurts too much.
0:44:07 And if I have to suffer the consequence of the loss of status,
0:44:12 approbation, affirmation, all the external trappings, so be it.
0:44:18 It was like my soul basically said, listen, motherfucker,
0:44:22 you better sit down and pay attention to your life because
0:44:27 the stakes are too high.
0:44:28 I think I read that in the Bhagavad Gita, if I’m correct.
0:44:31 Brooklyn edition.
0:44:36 It’s the Buddha from Brooklyn.
0:44:40 Yeah.
0:44:40 Now, how did you find your way to, I’ll use this term.
0:44:52 It may not be the best term, but how did you find your way to coaching?
0:44:55 So on that plane ride from New York to Arizona to Canyon Ranch,
0:45:01 I read three books.
0:45:03 When things fall apart by Anni Pema Chodron, Faith by Sharon
0:45:08 Salzburg and Let Your Life Speak by Parker Palmer.
0:45:13 And before fully answering your question, I’ll give you this.
0:45:16 I must have done something really, really good in a past life
0:45:19 because I have the benefit of considering all three of those
0:45:23 people, Anni Pema, Sharon Salzburg and Parker Palmer as my friends.
0:45:29 I didn’t know them at the time, but I have the good grace and
0:45:33 the incredible good fortune to say I’m friends with them.
0:45:38 They are my teachers.
0:45:39 So what was your question?
0:45:41 The question was, how did you find your way to coaching?
0:45:45 And just to reiterate something that you just said at the time,
0:45:49 they were not your friends.
0:45:50 That’s right.
0:45:51 But you had the books and so asked how you found your way to coaching.
0:45:56 You went back to the plane ride.
0:45:57 Right.
0:45:58 And so in reading those books and those, those three books were
0:46:01 really important because they did lead indirectly to me becoming a
0:46:06 coach.
0:46:06 Each one of those books presented something different to me.
0:46:09 Faith presented this notion of really being honest with myself
0:46:13 with what was going on when things fall apart was the first laying
0:46:19 out of Buddhist Dharma as a path, but it was let your life speak,
0:46:24 which is a brilliant, beautiful, short little collection of essays
0:46:28 that really shifted the dialogue for me.
0:46:30 Partially because Parker is so open and honest and authentic
0:46:34 about his own struggles and depression.
0:46:36 Okay.
0:46:37 So to your question, let me fast forward it.
0:46:39 Probably four or five years later, I’m still working my way
0:46:43 through all of the issues that I’m carrying at that point and
0:46:47 trying to sort myself out.
0:46:49 I’m in an office.
0:46:51 I’m sharing office space with Fred Wilson and Brad Burnham from
0:46:55 Union Square Ventures, but I have a little sub office within their
0:46:58 space and I’m doing a bunch of different things.
0:47:01 I’m serving in a bunch of boards of directors.
0:47:03 I’m making little angel investments here and there,
0:47:06 but I’m just sort of hanging around the hoop if you will.
0:47:08 And this young guy comes to see me.
0:47:10 He’s there to quote network.
0:47:12 You know, this is the thing everybody is supposed to do.
0:47:14 Network is way too new job.
0:47:16 And you know, you ask about questions.
0:47:19 So here’s the story.
0:47:21 So he comes in and he’s a lawyer and he wants to get a job in
0:47:24 the startup industry.
0:47:25 So he wants to find a way to get some sort of position.
0:47:28 And I turned to him and he’s probably in his late 20s and I
0:47:31 said, I’m happy to help you, but just answer a question for me.
0:47:36 It’s kind of my first coaching question, right?
0:47:38 And I said, what made you become a lawyer in the first place?
0:47:41 And he starts crying to me and he starts telling me about pleasing
0:47:45 his father and about how it was, you know, his father had taught
0:47:50 him that if all else fails, at least he could make a living as
0:47:54 a lawyer and the kid was just miserable, just miserable.
0:47:59 And so I reached up to the shelf and I pulled down a copy of
0:48:03 Let Your Life Speak.
0:48:04 And I said, here, read this and then get back to me.
0:48:07 He left the office and I turned around and I said, fuck, I think
0:48:12 I need to be a coach.
0:48:13 I need to do that more frequently.
0:48:16 And so within a few days, I’d signed up for a coach training program.
0:48:21 Okay, let me pause for one second.
0:48:23 So what did you feel?
0:48:25 What did you experience?
0:48:27 What was it about that encounter that made you so decisively
0:48:32 say that to yourself?
0:48:33 A couple of things.
0:48:35 I could see relief in his eyes.
0:48:37 The first thing I felt was empathy.
0:48:41 I knew his feelings because even though the content of the story
0:48:46 was different, my experience was so similar.
0:48:50 I had been so ruled by fears that I was living in a box.
0:48:55 I had lived in a box that was not of my making.
0:48:58 It was somebody else’s box.
0:49:01 It was the wrong box.
0:49:03 It was the wrong suit of clothes.
0:49:05 It was not me and I could feel all that.
0:49:08 And when I reached for Let Your Life Speak, I was reaching
0:49:11 for the very same thing that had gotten me out of the box.
0:49:14 And I said, here, here’s a path.
0:49:17 And there was just relief, relief.
0:49:19 Not that he had read the book yet, but just relief that somebody
0:49:22 actually understood his feelings and had given words to his
0:49:26 feelings that he hadn’t been able to give to.
0:49:28 Remember that question?
0:49:29 What have I not been saying that I need to say?
0:49:32 There was that going on for him.
0:49:34 So then I said, wait a minute, dude, you can do something
0:49:40 about relieving suffering.
0:49:41 You’re not the mess.
0:49:43 And it’s not always just your prefrontal cortex that’s going
0:49:46 to figure everything out because I didn’t have an answer for him.
0:49:50 I didn’t say, here, here’s the job you should do.
0:49:52 That’s perfect for you so that you no longer go to bed at night
0:49:56 feeling like crap, wondering whether or not you should wake
0:49:59 up in the morning.
0:50:00 I just had to listen to my heart and I did something completely
0:50:05 non-intuitive.
0:50:06 I reached onto my bookshelf and I gave him a book and the feeling
0:50:11 that I had was poignant pain coupled with the sense of being
0:50:18 able to do something.
0:50:19 I could be helpful.
0:50:20 This may be overreaching, but how much of your call to coaching
0:50:26 do you think, if any, was finding relief and taking the focus
0:50:31 outside of yourself?
0:50:33 It wasn’t just the call to begin coaching.
0:50:37 This helps me every day.
0:50:40 I mean, this is the craziness about the work that I do about
0:50:44 living my vocation like this.
0:50:46 Even today in my worst moments, when I can be with another person’s
0:50:53 pain, by the way, which is the root etymological meaning of the
0:50:58 word compassion, to be with someone else’s feelings, I magically
0:51:04 feel relief from my own unbearable feelings.
0:51:07 Because I think that’s the essence of being human together.
0:51:11 We get to actually, oh, jeez, we look at each other across
0:51:15 the campfire, I keep imagining us in sort of pre-civilization
0:51:20 going, like looking across campfire and again, must be in Brooklyn
0:51:24 and going, dang, it’s hard, right?
0:51:26 Isn’t it hard being human?
0:51:28 Yeah, it’s really hard.
0:51:29 Okay, let’s do this together.
0:51:31 So I think the call was that.
0:51:35 But if I, if I may, I think the call was also to retroactively
0:51:41 go back in time and save myself.
0:51:43 Interesting.
0:51:44 See, this makes a lot of sense to me.
0:51:46 In saying that, do you mean, and I don’t know if you’ve ever heard
0:51:49 of IFS, internal family systems, in so much as by helping people
0:51:55 who are in similar positions with similar states or pains as
0:52:01 you experienced earlier, you are healing that younger version
0:52:04 of yourself in some capacity?
0:52:06 Well, first of all, to answer your quick question, I have
0:52:09 heard of IFS.
0:52:10 I have not been trained in IFS and I know a few of my clients
0:52:14 have benefited from it, but broadly speaking, you want to
0:52:18 understand Buddhism.
0:52:19 It’s what we’re talking about right now.
0:52:21 Yeah.
0:52:22 You want to understand wisdom traditions across the world.
0:52:25 It’s what we’re talking about right now.
0:52:27 It’s like even the best of Christianity, even the best of
0:52:31 what Jesus taught.
0:52:33 It’s like, God, I mean, I just imagine him exasperated, sitting
0:52:36 his thing, for God’s sake, love one another.
0:52:39 Just, you know, come on, can you just stop the nonsense and
0:52:42 just reach across and just be with each other?
0:52:45 Think of it this way, Tim.
0:52:46 There’s almost like a universal wellspring of pain that you
0:52:52 and I share and in the similar fashion, there’s a universal
0:52:56 wellspring of happiness and joy that you and I share.
0:52:59 And so if you’re in this painful spot, I can tap that universal
0:53:04 wellspring of happiness and joy and point it a little bit more
0:53:09 at your suffering and you can do the same for me.
0:53:11 So let me ask you a question and you and I have spent a good
0:53:16 amount of time on the phone together and to those people
0:53:20 listening who are self-described high achievers who don’t want
0:53:25 to lose their edge, who are looking for the tactical
0:53:27 practical, if they hear that and they’re kind of rolling their
0:53:31 eyes and they’re like, all right, you had me at 9/11, you had
0:53:35 me at the books, but I don’t see how this applies.
0:53:39 I’m too busy for that shit.
0:53:40 I don’t have time to go to Burning Man and do fire dancing.
0:53:43 Like this, this is serious business.
0:53:45 I have serious work to do.
0:53:46 Sorry.
0:53:47 How do you relate that to someone who in their first meeting
0:53:50 fits that profile?
0:53:52 Perhaps.
0:53:53 What do you do with them in a first meeting?
0:53:55 My job isn’t to necessarily convince people that they need
0:53:59 help.
0:53:59 And so the first thing I say is and the first thing I would
0:54:02 say to anybody who’s listening is if everything’s working for
0:54:06 you, go at it.
0:54:07 Have a great time.
0:54:08 Go enjoy yourself.
0:54:09 Go ahead.
0:54:10 But you know, there’s a simple little trick.
0:54:12 You know, I had this little reputation that I make people cry
0:54:15 and all this stuff.
0:54:16 You know what I do?
0:54:17 I ask them a simple question.
0:54:19 How are you?
0:54:20 And I often follow it up with like, no, really, don’t bullshit
0:54:23 me.
0:54:23 How are you?
0:54:24 How are you really feeling?
0:54:26 Because here’s the thing.
0:54:28 You described this would be resistant person as a high
0:54:31 achiever.
0:54:31 Here’s the thing about high achievers.
0:54:33 In my experience, high achievers early on in their
0:54:37 life figure out how to get an A.
0:54:39 They figure it out because the whole system is geared towards
0:54:42 that great.
0:54:43 And then we take that entire system from our childhood and
0:54:47 we move it into work and it’s just getting A’s getting A’s
0:54:50 getting A’s getting A’s and the highest achieving people
0:54:53 oftentimes come into me scared because there’s a little whispery
0:54:58 voice in their ear that says you are a fucking fraud.
0:55:01 You have no idea.
0:55:03 And when they figure out that all you’re doing is reading the
0:55:07 tea leaves and what it takes to get an A, they’re going to
0:55:10 toss you out of the tribe.
0:55:11 They’re going to toss you out on your ass.
0:55:13 They’re going to push you away or they say to themselves
0:55:19 because they haven’t experienced loss or they haven’t
0:55:23 experienced failure.
0:55:25 They think they haven’t experienced failure.
0:55:27 They’re just waiting.
0:55:28 They’re just playing a waiting game.
0:55:30 They’re just waiting for something for fate to catch
0:55:33 up to them and bang, the harm is going to come down.
0:55:37 Now, if this resonates with you, you might also then recognize
0:55:43 the anxiety that comes in where you put your head down at
0:55:46 the pillow at night and you go, my God, I don’t know if I
0:55:49 can do it again tomorrow.
0:55:51 Maybe they’ll catch me tomorrow.
0:55:53 And if that’s what you’re working with, then there’s
0:55:57 an opportunity in all that we’re talking about.
0:55:59 Forget universal suffering.
0:56:01 Forget about wellsprings.
0:56:02 Forget about spiders.
0:56:04 Forget about burning man, which I’ve never been to, by
0:56:06 way, and I don’t believe in substances.
0:56:08 But that’s all a different issue.
0:56:09 Forget about all that stuff.
0:56:11 I’ve been three times.
0:56:13 I’m a fan at least once in your lifetime.
0:56:16 What we had a separate separate conversation.
0:56:19 So the truth is are probably too scared to ingest any material
0:56:24 inside of my body, but leave that aside for a moment.
0:56:26 Forget all that.
0:56:28 Okay.
0:56:29 All the esoteric stuff like that.
0:56:31 Here’s the simple question.
0:56:33 How’s it working for you?
0:56:36 Cause if it’s not working for you, why are you in pain?
0:56:40 Why are you doing it?
0:56:41 And would you like a little relief and here you want to
0:56:44 know the secret like nasty little trick that I play?
0:56:48 Yes.
0:56:49 I get them if they either have children or hope to have
0:56:52 children someday.
0:56:53 I will ask them.
0:56:55 What would they like their children to feel when they’re
0:56:59 at the same age?
0:57:00 Because if they would like them to feel something other than
0:57:03 what they’re feeling, now’s the time to start changing the
0:57:07 way they organize their lives.
0:57:08 That’s a really good question.
0:57:10 What if and this could combine with what we’re talking
0:57:15 about right now, someone comes in, they don’t feel imposter
0:57:19 syndrome necessarily, but they are simply overwhelmed.
0:57:23 You ask them how they are.
0:57:24 No, really.
0:57:24 And they’re like, I’m good.
0:57:26 I’m just busy.
0:57:27 I’m stressed.
0:57:28 I just have too much.
0:57:29 I’m overwhelmed.
0:57:31 If that’s the breed of client that shows up, how do you
0:57:37 begin to work with that?
0:57:39 Well, once you’ve established a certain level of trust and
0:57:44 relating through empathy and, you know, don’t necessarily
0:57:49 try to step in and fix it.
0:57:51 The first question I would start to ask or elicit is how
0:57:56 is that being busy serving you?
0:57:58 Remember that?
0:57:59 How have I been complicit in creating the conditions?
0:58:02 I say I don’t want, right?
0:58:03 Here’s the thing about busyness.
0:58:05 Busyness can feel fucking awesome.
0:58:08 It can feel so amazing internally.
0:58:13 Like look at all the great stuff I got done externally.
0:58:17 Look at how busy I am.
0:58:18 I must be important.
0:58:20 That’s an interesting statement.
0:58:22 Busyness can also serve to distract you from those voices
0:58:29 inside that say, Hey, I’m not happy.
0:58:32 Hey, I’m not happy.
0:58:35 Hey, I’m serious.
0:58:37 I’m going to throw you down on the ground with some sort
0:58:39 of somatic illness, lower back problem, irritable bowel
0:58:44 syndrome, migraine headaches.
0:58:45 That was my specialty.
0:58:47 I’m going to throw you down until you pay attention to me.
0:58:52 Okay, you’re too busy.
0:58:53 Okay, I got you.
0:58:53 Okay.
0:58:54 Because, you know, here’s the thing to somewhere around 35
0:58:58 to 50 years old.
0:58:59 The systems start to break down the systems that got you
0:59:03 at childhood that got you into adulthood that got you established
0:59:07 that got you to the point where you think you got it all
0:59:09 figured out and then all of a sudden, holy shit, the whole
0:59:12 thing starts to collapse.
0:59:13 Now what do I do?
0:59:15 And when I see someone who’s busy, who’s kind of in the early
0:59:20 twenties, I see a striver trying to establish themselves.
0:59:24 But when I see somebody who’s busy, who actually doesn’t
0:59:28 need to be that way, I get really, really curious.
0:59:34 What internal need is trying to be met by all that busyness?
0:59:38 And that’s the place to inquire.
0:59:40 What are some of the more common patterns that you see with
0:59:45 that busyness?
0:59:46 I’m very curious about this.
0:59:48 I promise not to coach you.
0:59:50 But why is it so curious?
0:59:51 No, just kidding.
0:59:52 I can tell you.
0:59:54 No, I can tell you why it’s curious or interesting to me.
0:59:57 We can jump into some.
0:59:58 I’m game.
0:59:58 I’m game to hit some volleys if you want.
1:00:02 Well, for instance, I’m looking at an apologies to everyone.
1:00:04 I have not replied to, but that is sort of my ethos and the
1:00:10 gist of everything I’ve written.
1:00:12 So I feel like I’ve bought some permission, but I currently
1:00:15 have 618,952 on red email and combination on two different
1:00:22 tracks of 165 plus 255 on red text messages.
1:00:27 And that’s the tip of the iceberg.
1:00:28 So I actually feel surprisingly low anxiety about that.
1:00:34 Nonetheless, a small amount of anxiety and in the process of
1:00:38 literally rebooting those various phone numbers and addresses
1:00:42 because it’s not physically possible to address that.
1:00:46 Right.
1:00:47 And it’s perhaps similar to many of your experiences.
1:00:50 It’s given me an opening line or common sentiment of
1:00:59 commiseration that opens up the floodgates to similar types
1:01:02 of problems and other people.
1:01:04 So they confess.
1:01:05 I’m like the productivity guy in the confessional box for
1:01:10 people who want to tell me about similar things.
1:01:12 And those are a few things that come to mind when you ask me
1:01:15 why is that curious?
1:01:16 I think it’s very common.
1:01:18 I just think it’s very common.
1:01:19 I think it’s hugely common.
1:01:20 And I think that you asked the question by using a particular
1:01:24 descriptive word.
1:01:25 You described it as feeling overwhelmed.
1:01:27 And, you know, if we were to do a dream analysis, we might
1:01:31 talk about being flooded.
1:01:32 That’s typically the psychological signal that the
1:01:37 system is overwhelmed.
1:01:39 So, again, we use our construction and we talk about
1:01:42 complicitness, not necessarily responsibility.
1:01:45 I’m going to use you as an example as a high achiever
1:01:48 who is incredibly busy and so busy that he has over 600,000
1:01:56 unanswered emails.
1:01:58 And we’ll just stick on that one for a moment.
1:02:00 By the way, you’re allowed to declare bankruptcy at that
1:02:02 point.
1:02:03 Okay, you’re done.
1:02:04 And what I hear you say is I no longer, you said I don’t
1:02:07 feel anxiety, just a small piece of it.
1:02:10 I would argue that you probably have been so overwhelmed
1:02:13 by it that you’ve actually given up feeling anxious about
1:02:15 it and it’s just like, forget it.
1:02:17 I’m not going to get to it.
1:02:18 So, here’s the question for you and you don’t have to answer
1:02:21 it, but hang out with it.
1:02:23 Couple of questions.
1:02:24 The first might be something like, when did you start
1:02:27 feeling overwhelmed and how long have you felt overwhelmed?
1:02:33 And while feeling overwhelmed, did you take on more tasks?
1:02:37 Right?
1:02:38 In your case, Tim, did you sign up for another book and another
1:02:42 show or another thing which only produced more stuff?
1:02:46 Because that’s what I do.
1:02:47 If there’s a tiny bit of open space in my life, I tend
1:02:51 to fill it.
1:02:52 And then the magical question is how familiar is that feeling
1:02:56 and how does that feeling serve you?
1:02:58 I’m willing to play on this one and I will say before I get
1:03:03 started that I do think I have much better systems and rules
1:03:09 and perspectives in place now, but to answer your questions,
1:03:13 I’d say it started probably middle of undergraduate college,
1:03:18 right, this feeling of overwhelm, or at least that’s when it
1:03:21 was most noticeable.
1:03:23 And the feeling of overwhelm was then kind of ebbed and flowed,
1:03:29 but certainly up until at least 2004, my solution to feeling
1:03:34 anything I didn’t want to feel was to add more activities.
1:03:38 Okay, can you just pause and say that again?
1:03:40 Your solution to feeling anything I didn’t want to feel in
1:03:44 retrospect, I recognize that’s what it was.
1:03:46 So if I felt anything I didn’t want to feel, I would add
1:03:50 more activities to drown it out.
1:03:52 Some people use heroin, some people use Coke, some people
1:03:55 use work and I used activities.
1:03:58 At the time, I also use stimulants.
1:03:59 So I was in fact using both, but that changed quite a bit
1:04:06 in 2004 by building in empty space.
1:04:08 And I think that still now there are vestiges of behaviors
1:04:16 that in some sense helped me to find a toehold in financial
1:04:22 security that are no longer serving me that are nonetheless
1:04:25 default gears, if that makes sense.
1:04:27 And to that extent, the vast amount of my focus for the
1:04:33 last year has been on saying no to practically everything
1:04:37 more than a year.
1:04:38 I mean, the last several years.
1:04:39 Nonetheless, there is a part of me.
1:04:42 I think you had a, was it a crow or raven on the shoulder?
1:04:45 We’ll come back to the crow.
1:04:48 And no, it’s not another dream sequence for people wondering.
1:04:51 No drug induced dream sequence.
1:04:53 Yeah, we’ll come back to the crow.
1:04:56 Something on my shoulder saying you might need this person.
1:04:59 You might need this person in reference to any given email
1:05:06 that might come in.
1:05:07 And so for what I find in my life is that the vast majority
1:05:11 of stuff is clearly noise and I can ignore.
1:05:15 There are categories of activities.
1:05:17 I’m not particularly good at moderation, whether that’s
1:05:20 with chips or chocolates or speaking engagements or fill
1:05:25 in the blank.
1:05:26 There’s certain things where I need to either be considering
1:05:31 each item that presents itself or not consider them at all
1:05:35 as a category.
1:05:36 So I’ve decided certain things just from a binary perspective
1:05:39 like speaking, I will not do any of unless they happen to be
1:05:42 10 minute drive from my house and fit 20 other parameters.
1:05:46 Otherwise it’s an automatic no and I don’t even see it where
1:05:49 I think I find more difficulty is where there are people who
1:05:54 have been very helpful in the past who perhaps were very
1:05:59 supportive in the early days who now have lots of favors to
1:06:04 ask.
1:06:04 But if I’m listening to my body, it’s absolutely not a full
1:06:10 body.
1:06:10 Yes, there’s a large part of me that knows I do not want to
1:06:13 acquiesce.
1:06:14 I do not want to agree.
1:06:15 I do not want to accept.
1:06:16 I do not want to do whatever it is they’re asking me to do
1:06:18 because it doesn’t feel right and or it’s unreasonable.
1:06:23 Nonetheless, those are the types of emails that tend to pile
1:06:27 up and those are the types of emails also that even if I
1:06:30 have someone like an assistant or multiple assistants
1:06:33 filtering the names are probably noticeable enough or old
1:06:38 enough that they’ll get brought to my attention.
1:06:40 So let’s see here.
1:06:42 Is it familiar?
1:06:43 Yes, it’s familiar.
1:06:44 How does it serve me?
1:06:47 This I have more trouble with.
1:06:49 So maybe you could walk me through, I would imagine many
1:06:52 people.
1:06:53 I’m not going to say it doesn’t serve me because I’m willing
1:06:55 to at least as a thought exercise to accept that if it
1:06:59 didn’t serve me, I would have already found some clean
1:07:02 solution or I wouldn’t have any emotional difficulty fixing
1:07:05 it.
1:07:05 How would you walk me through figuring out how it serves
1:07:09 me?
1:07:09 Well, I want to reflect back a couple of things that I’m
1:07:11 hearing so that we can just sort of establish it.
1:07:14 The first thing I would say is I really admire all the
1:07:16 filtering that you’ve put into your life and the structures
1:07:20 that you’ve put into your life to create boundaries and
1:07:23 saying no.
1:07:24 And I think that the rules as you define them and they
1:07:30 might be rules for like, Hey, every morning I’m going to
1:07:33 do X and every afternoon I’m going to do Y or I’m only
1:07:36 going to work from ours.
1:07:37 Those are all important, but ultimately insufficient for
1:07:44 complete relief from some of these feelings.
1:07:48 They’re really, really helpful.
1:07:50 They’ve reduced your anxiety from overwhelming to small,
1:07:55 but 620,000 emails, right?
1:07:59 And so I want to bring your attention to two other
1:08:01 feelings.
1:08:02 One was you said something about missing something that
1:08:08 might be important to you seeing someone that that has
1:08:11 been helpful to you in the past or something that’s
1:08:15 important to you that you might miss something.
1:08:18 So that’s one fear is that right?
1:08:20 I would say so.
1:08:21 I think the greater fear is that people who would at
1:08:26 least believe that they have supported me without asking
1:08:30 for a quid pro quo in the past would get upset and this
1:08:34 does happen.
1:08:34 It has happened where people take things very personally
1:08:38 and I recognize I can’t take responsibility for everyone
1:08:42 else’s feelings and responses to things.
1:08:45 I do think that’s a fear more than missing an opportunity
1:08:48 because I’m not concerned about missing financial
1:08:51 opportunities.
1:08:52 Not anymore.
1:08:54 Not anymore.
1:08:55 I once was, but I also, you know, I stopped startup investing
1:08:59 completely in 2015 because the noise simply wasn’t worth it.
1:09:06 The cortisol fueled unnecessary hurrying associated with
1:09:13 that culture was causing more harm than good.
1:09:15 So I stopped in 2015.
1:09:17 So I missed a pretty, pretty decent bull run, which I’m
1:09:19 okay with.
1:09:20 So it’s not a financial concern so much as social costs and
1:09:27 fallout if that makes sense.
1:09:28 Yeah.
1:09:28 Yeah.
1:09:29 What I’m hearing is a fear of disappointing someone who
1:09:31 matters to you.
1:09:32 Yeah.
1:09:33 Yeah.
1:09:34 That would be a piece of it.
1:09:34 That would be a piece of it and this is helpful to me to
1:09:37 talk through because it’s not just disappointment.
1:09:42 In some cases I can’t.
1:09:44 I actually really dislike interacting with some of these
1:09:47 more recent acquaintances, but for whatever reason they view
1:09:53 their position is very entitled in so much as they expect a
1:09:56 fast and very compliant response for me on many things and
1:10:01 they know a lot of people in the same circles.
1:10:04 And so that causes concern.
1:10:06 So there’s an implicit internal existential threat.
1:10:11 I think that’s fair.
1:10:12 I think that’s fair to say.
1:10:13 Yeah, if I could say one more thing.
1:10:15 Yeah, yeah, yeah.
1:10:15 Just so I don’t sound totally like I’m living in a land of
1:10:20 make-believe.
1:10:21 I have run into many, many instances.
1:10:24 This is more than a dozen at least where say someone will
1:10:29 send me an email.
1:10:29 They want a blurb for a new book.
1:10:31 They want this, this, this, this, this and this and by the
1:10:33 way, it’s coming out in four weeks or whatever it is.
1:10:36 There’s some set of requests slash demands.
1:10:41 I don’t reply, this has happened with journalists as well,
1:10:44 where for whatever reason I won’t help them and then a hit
1:10:47 piece comes out or then there’s some type of blowback slash
1:10:51 vengeful behavior, whether that’s shit talking me on stage
1:10:54 or whatever it might be.
1:10:55 So there’s evidence to support the fear, but here I am.
1:11:01 I’ve survived.
1:11:01 I’m fine.
1:11:02 That is also true.
1:11:04 So I just wanted to add that color.
1:11:06 Right.
1:11:07 And so I want to reflect back to you empathetically and
1:11:09 rationally, you’re not nuts.
1:11:12 The threats are real.
1:11:14 At least not, at least not in that department.
1:11:15 That’s right.
1:11:16 That’s right.
1:11:17 So what I often say is that there are three basic risks
1:11:21 that we’re all trying to manage all the time.
1:11:23 Love, safety and belonging.
1:11:25 We want to love and be loved.
1:11:27 We want to feel safe physically, emotionally, spiritually
1:11:32 and we want to feel that we belong and what I’m hearing.
1:11:36 So if you resonate with those at all, the existential threat
1:11:40 and I want to bring your attention to existential because
1:11:43 I think that the threat is to the essence of who you are or
1:11:47 at least the perceived threat.
1:11:49 And when someone trash talks you on stage, what the trash
1:11:54 talking is you, the you, not the meat bag, but the essence
1:12:00 of you.
1:12:02 And so I think that the fear, I know for myself that the fear
1:12:07 of disappointing others is a threat to my belonging.
1:12:10 I’m not going to be in my family anymore.
1:12:13 My children won’t love me.
1:12:15 My partners won’t love me.
1:12:18 And so therefore I will be unsafe.
1:12:22 I will be bereft.
1:12:24 I’ll be by myself.
1:12:26 I’ll be alone in the woods fending for myself.
1:12:31 And there are a few things that threaten me more than the threat
1:12:34 to belonging.
1:12:35 I don’t know.
1:12:37 Does that resonate with you?
1:12:38 It does resonate.
1:12:40 I think that a lot of what I’ve done and been able to do has
1:12:45 been dependent on maintaining very long term relationships
1:12:52 with people who I enjoy being friends with who happen to also
1:12:55 be very, very good at what they do, whatever that is.
1:12:57 And so I think there’s a bit of, you know, what got you here
1:13:00 won’t get you where you want to go or won’t get you there.
1:13:02 And that does resonate and we don’t have to jump to this.
1:13:06 But what I’d love to talk about or listen to you describe
1:13:11 because I think a lot of people would benefit from it is when
1:13:13 you run into someone who like me is fielding a lot of inbound
1:13:20 and it could be from one person, but they for whatever reason
1:13:24 are having difficulty saying no or establishing boundaries.
1:13:27 What are tools or books or approaches that you found helpful
1:13:32 for people in that position, whether it’s non-violent
1:13:37 communication or fill in the blank?
1:13:38 Anything at all or questions?
1:13:41 Anything at all?
1:13:42 How do you begin to advise someone like that?
1:13:46 Well, there’s a couple of things come to mind and I’m going
1:13:49 to reference two friends of ours, Seth Godin and Sharon
1:13:52 Salzburg.
1:13:52 The first thing was when I was really struggling with this
1:13:56 early on in my career, my adult career, Seth Godin gave me
1:14:00 some wonderful advice, which boiled down to this phrase,
1:14:03 “I wish I could, but I can’t.”
1:14:05 And that became a kind of interesting little fence around
1:14:09 my life, a boundary marker.
1:14:11 And so the idea was that you would be able to say to someone,
1:14:15 someone who reaches out, “Can you do this favor for me,
1:14:18 this thing for me?”
1:14:19 And you get to say, “I wish I could, but I can’t.”
1:14:21 So you just pause around that.
1:14:22 The problem is, of course, there’s an inauthenticity that
1:14:26 can set in, which is, “I actually don’t wish I could.”
1:14:29 And I can, but I really don’t want that.
1:14:33 Yeah, that’s a whole note of like, “I can, but I won’t.”
1:14:35 And so then it becomes a little bit of like, “Listen,
1:14:38 I’m trying to take my own advice to heart and the advice I
1:14:42 give clients is to take care of themselves first.”
1:14:46 And so that becomes a kind of useful tool.
1:14:50 But then you reference something before about not being
1:14:53 responsible for someone else’s feelings.
1:14:55 And that brought to mind a teaching that Sharon Salzberg
1:14:59 gave me, which goes like this.
1:15:01 All beings own their own karma.
1:15:03 Their happiness or unhappiness depend upon their actions,
1:15:07 not my wishes for them.
1:15:08 Say that one more time, please.
1:15:10 Yeah.
1:15:11 So all beings own their own karma, karma being the cause
1:15:16 and effect, the consequences of their actions.
1:15:20 Their happiness or unhappiness depend upon their actions,
1:15:24 not my wishes for them or the corollary to that is not the
1:15:28 actions that I take or don’t take.
1:15:30 Now, they may say to you when they’re reaching out to you,
1:15:33 Tim, “Tim, if you don’t do this thing that I’m asking you
1:15:37 to do, then I will be unhappy.
1:15:39 And if I’m unhappy, I will be mean to you.”
1:15:43 I mean, that’s essentially the existential threat.
1:15:45 I wish they would actually just send that email because then
1:15:49 I would say, “Gotcha, bitch.
1:15:50 I have a blog.
1:15:51 Shouldn’t have sent that email.”
1:15:52 Which has actually happened with writers from the New York
1:15:57 Times, believe it or not, which is horrible to say.
1:16:02 They’re explicit in their threat.
1:16:03 Oh, yeah.
1:16:03 And then as soon as they realize what they’ve done,
1:16:06 they’re like, “Oh, shit.”
1:16:07 And then they cool their jets.
1:16:09 But yeah.
1:16:10 So here’s a little tool that I have come up with that helps
1:16:14 me is I often think of creating these little fences and I
1:16:18 often visualize a chain link fence so that I can see through
1:16:21 it and it has a gate in it and the gate only opens one way
1:16:26 inward and I get to control whether or not the gate opens.
1:16:29 And so then I can see someone on the other side and then the
1:16:33 phrase that comes up is, “Love them from afar.
1:16:36 Be kind to them in my heart.
1:16:39 Set clear boundaries.
1:16:41 I have, as your friend, as your guide, as somebody who hopefully
1:16:45 is standing shoulder to shoulder with you is sort of in this
1:16:47 crazy journey.
1:16:48 I really feel for all the people who have reached out to
1:16:52 you 620,000 times in your inbox and all of that stuff.
1:16:58 And I feel for you and I would advise you to delete every
1:17:03 one of those things and to basically love all of those
1:17:07 people who are going to get unanswered from afar and be
1:17:11 kind to them in your heart and recognize that on the whole,
1:17:16 you’re doing the best that you can because you are.
1:17:19 I wish I could give you like, here’s the tool, you know,
1:17:22 like NVC Nonviolent Communications has some brilliant
1:17:26 tools or here’s the book that magically unlocks that.
1:17:29 To me, the challenge isn’t not having the tool, the challenges
1:17:33 in the meaning that we put into the situation that is the
1:17:37 hardest thing to come over and to recognize that you’re okay,
1:17:41 even if you’re not necessarily being at your kindest or at
1:17:45 your best, because like you, like everybody else, like me,
1:17:49 we all get resources that are thin at times.
1:17:51 My God.
1:17:52 And so, you know, if you’ve not answered a text message for
1:17:56 me, Tim, or if you’ve not answered an email for me, I am
1:17:58 never, ever, ever going to think ill of you.
1:18:01 Well, I appreciate that.
1:18:02 Wish I could transmit that composure to all of my 620,000
1:18:11 senders. Let me ask you a situational question and this
1:18:16 is true in my life and I’m sure it’s true for many people
1:18:19 listening that I have a handful of people who are kind of close
1:18:27 to me very much in the same circles playing at a high level
1:18:32 who tend to reach out to me only when there is an ask of
1:18:37 some type and there tends to be some great degree of
1:18:40 discomfort associated with the ask in so much as perhaps they
1:18:45 have two or three people who are close friends of mine attending
1:18:48 an event of theirs or investing in blah, blah, blah, whatever
1:18:52 might be so that it is there’s a great degree of discomfort
1:18:57 that I feel in ignoring the email.
1:19:01 Maybe I actually get texted by one friend and then the email
1:19:04 from this person.
1:19:05 There are a few people who are repeat characters kind of like
1:19:10 Numan and Seinfeld and Seinfeld shakes his fist.
1:19:12 Numan.
1:19:14 Yeah.
1:19:14 So I have I have at least a half a dozen Numan’s who are
1:19:19 pretty tough to get rid of and they’re not very good at
1:19:22 reading hints or they deliberately ignore hints that
1:19:27 I don’t want to do things that I don’t want to respond.
1:19:29 Have you coached people through breaking up with friends
1:19:34 or having direct conversations with their own Numan’s and
1:19:39 that maybe the Numan is a co-founder.
1:19:40 Maybe the Numan is a somewhat on the board of directors.
1:19:42 Maybe fill in the blank for having a really direct
1:19:48 conversation about this type of dynamic.
1:19:51 Sure.
1:19:52 Can we put aside just for a moment co-founder and board
1:19:56 member because there are power dynamics there that are
1:19:59 different than the Numan’s that you’ve been talking about.
1:20:02 Yeah.
1:20:02 Let’s leave out co-founder and board member.
1:20:04 I agree that adds complexity or we can circle back to it
1:20:07 separately but here’s the thing.
1:20:09 If we start with a basic basic basic basic premise that
1:20:14 goes like this am I a good person am I doing the best that
1:20:17 I can and if I can answer that question relatively
1:20:21 straightforwardly and honestly then I don’t have to feel
1:20:26 guilty because that’s what we’re talking about right.
1:20:28 That’s the emotion that gets manipulated.
1:20:31 I don’t have to feel guilty saying to somebody I don’t
1:20:34 have the space to do the thing that you would like me to
1:20:37 do which might include maintaining this contact and
1:20:41 there’s an image that I often use whether it’s with a client
1:20:45 or with my own self and it’s come to me as I’ve gotten older
1:20:49 and I’m obsessed right now with myself being old and the
1:20:53 images of a bonsai tree which over its lifetime you know
1:20:58 you can see this one foot tall bonsai tree and it could be
1:21:02 anywhere from 10 years old to 300 years old.
1:21:05 You have really no idea and what I see is something that
1:21:10 has been carefully pruned into a thing of beauty and I think
1:21:15 that that’s our opportunity in life now if we start with
1:21:18 the supposition that we are never enough that we are not
1:21:22 good enough and that we therefore not only you said
1:21:25 before become addicted to busyness in order to make
1:21:28 ourselves not feel the things that we don’t want to feel
1:21:32 remember that one of the things that we do is we maintain
1:21:36 unhealthy relationships in order to not feel the things that
1:21:40 we don’t want to feel even when those unhealthy relationships
1:21:44 make us feel other things we don’t want to feel whereas
1:21:47 if we start with the basic premise that we are enough
1:21:50 just as we are and that there is no great loss to you him
1:21:56 if over time you lose some connection and you use this
1:22:01 term several times to some high powered person.
1:22:04 Oh my goodness this high achieving person this high
1:22:08 performer person there’s no real great loss like think of
1:22:13 the people that you have interviewed over the years
1:22:15 the people that maybe began in some powerful position and
1:22:20 that have gone on to some powerful position.
1:22:22 Oh my God if I lose that connection that I once had to
1:22:25 them then somehow I met a loss take a breath we breathe
1:22:30 into that the Buddha taught us one thing you are basically
1:22:35 good just as you are not because of the connections that
1:22:40 you have maintained and those people who love you and care
1:22:44 about you and understand the essence are going to be fine
1:22:48 even if you say hey I’m sorry I actually can’t maintain
1:22:53 this connection may ask a question.
1:22:55 Sure all right so I agree with everything you said and what
1:23:01 I’d love to hear you elaborate on is any practices or tools
1:23:08 that you use or recommend people use to get from intellectually
1:23:15 agreeing with what you just said to embodying that in some
1:23:21 way that translates to different behavior does that make
1:23:25 sense because I mean one of my favorite quotes is I guess
1:23:27 it’s Ted Geisel but Dr. Seuss which is the people who matter
1:23:31 don’t mind and the people in mind don’t matter I mean I love
1:23:33 that quote I remind myself of it all the time nonetheless I do
1:23:40 have this guilt that crops up on occasion that I recognizes
1:23:43 counterproductive nonetheless it crops up and causes me to
1:23:47 behave in ways that I know are not necessary nor productive
1:23:53 and I’m wondering how you help people to make that leap from
1:23:58 kind of the intellectual uh-huh yep I get it to the other
1:24:03 lily pad of behavioral change.
1:24:05 Well the first thing I would say is that the practice that
1:24:09 you just described embodying the Ted Geisel Dr. Seuss quote
1:24:14 that is a practice and the first thing to do is to remember
1:24:19 that the thing about the word practice is that we actually
1:24:22 never achieve we’re always moving towards we’re always
1:24:27 going there but oftentimes achieving it permanently
1:24:32 sustained persistently yeah that’s a tough one so in those
1:24:38 moments when we fail to understand and remember that
1:24:42 those of us who those who love us won’t mind when we fail
1:24:47 to remember that it can be helpful to remember what I was
1:24:51 saying before about I am enough and I’m doing the best that
1:24:55 I can or as Dr. Sayers once taught me not bad considering
1:25:00 not bad considering how rough you may have had it not bad
1:25:05 considering how hard your life is right now you’re okay you’re
1:25:09 okay and if I can say that to myself every day in one form
1:25:14 or another bringing a kind of mindful attention to the points
1:25:18 when I fail with a kind of forgiveness to myself well
1:25:23 then wow okay that can be helpful. Do you use journaling
1:25:29 for this I know journaling is very important to you and I
1:25:33 want to discuss that as a topic and there are a million in
1:25:36 one ways to journal so like to learn more about how you use
1:25:39 journaling but is journaling one of the ways that you remind
1:25:45 yourselves of these things. Yes and if so what does it look
1:25:49 like down to the mundane details do you write down I am
1:25:52 enough as a prompt and then write for two paragraphs on why
1:25:55 that is the case or how does one implement this. So just
1:25:59 to for context I have been journaling consistently so it’s
1:26:03 about 13 years old daily and I’m 55 so a hell of a lot of
1:26:09 journals and again to be consistent and I think you do
1:26:13 the same thing I handwrite I do you and what may be unusual
1:26:19 is I never go back and reread because it’s not about
1:26:23 figuring shit out it’s about the experience and so my
1:26:28 general prompt the thing I almost always start with is
1:26:32 right now I’m feeling and I simply bring my attention to
1:26:36 it and so I might be feeling to talk about this very specific
1:26:41 situation guilt. So for example and I’ll use this sort of
1:26:46 mindful attention if I were to journal about our conversation
1:26:49 one of the things I might journal is about the guilt that
1:26:52 I have felt over the years as to whether or not I was reaching
1:26:56 out to you when you might be in trouble or if I was one of
1:27:01 those folks who put you in an uncomfortable situation and I
1:27:05 bring that up not to elicit a response from you but as an
1:27:09 example of an exploration of the guilty feelings that I might
1:27:13 have where are they coming from what are they doing was I
1:27:16 kind that sort of thing and then I blow a kiss to myself
1:27:21 easy there buddy boy easy this is all a journaling exercise
1:27:26 I’m just talking it out and I remember something that’s really
1:27:30 important about that word guilt guilt is self-focused remorse
1:27:37 is about the other remorse is oh I hurt someone’s feelings
1:27:42 and I would like to not be hurtful so I’m going to try not
1:27:46 to be hurtful guilt is oh my god I can’t believe this I’m
1:27:50 ruminating ruminating ruminating ruminating I find myself
1:27:53 journaling in a ruminating kind of way I try to bring
1:27:57 attention to that and that’s the moment where I say easy boy
1:28:02 easy you’re a good man who sometimes fails to live up to
1:28:07 your aspirations that’s it that simple I also promised I would
1:28:13 return to the crow this might be a good place yeah now I’m
1:28:19 going to get the pronunciation wrong Mary help me with the
1:28:23 last name P O N Ponset Poet yeah and it’s Marie Marie Marie
1:28:30 always a tricky one alright so Marie Ponset Ponset and she’s
1:28:36 still with us thank God and the crow what does she describe
1:28:40 in terms of the crow this that might fit might not but I
1:28:42 want to make sure I fulfill my promise to oh I think it does
1:28:45 fit I think it does fit so Marie was one of my professors
1:28:50 in college she taught poetry but I also took a particular
1:28:54 track in teaching writing and so she was also my mentor and
1:28:59 she used to talk all the time about the crow who sits on
1:29:02 your shoulder telling you what a piece of shit you are that’s
1:29:06 a piece of shit I can’t believe you wrote that you know it’s
1:29:08 like I hear that voice and it sits on your shoulder and it
1:29:12 tells you all the things that you have done wrong and all the
1:29:15 things that are happening and oftentimes in my journal
1:29:20 sometimes I’ll take a second pen so that there are two different
1:29:24 colors I will allow the crow to speak this is really important
1:29:30 this isn’t a jujitsu move because the mistake I think a lot
1:29:35 of people make is they try this for rocks at the crow and shut
1:29:39 the crow up and that crow is a really interesting voice that
1:29:45 crow tells us all the things that we are doing wrong and the
1:29:49 ways in which we are not enough and that’s the linkage back
1:29:53 to what we’re just talking about this notion that we are not
1:29:57 enough just by ourself that’s the fuel by which the crow is
1:30:00 there now this is the move to make the crow’s mission is to
1:30:07 preserve your ability to be loved to feel safe and that you
1:30:11 belong what it makes you feel like shit though yes it makes
1:30:16 you feel like shit but its motivation is for you not to feel
1:30:19 ashamed and so the crow is doing your favor the crow is trying
1:30:26 to keep you safe the problem is the crow is so attentive and
1:30:31 so vigilant that it’s a little too active and so what we want
1:30:35 to say at that moment is thanks a lot buddy I really appreciate
1:30:39 it but all those people who might be angry with me because I
1:30:45 didn’t respond to them or do the thing they wanted me to do
1:30:48 they actually don’t really see me and if they don’t see me
1:30:52 they don’t know that I’m doing the best that I can so I’ll
1:30:55 blow my kiss I’ll put them on the other side of that chain
1:30:57 link fence and I’ll love them from afar.
1:30:59 This is really important and by this I mean everything that
1:31:04 we’ve been talking about pretty much since the get go but
1:31:06 especially I’m referring to the journaling and creating an
1:31:10 outlet for the crow or the monkey mind or what Tim Urban of
1:31:17 weight but why would call the mammoth and I highly recommend
1:31:19 that everybody check out an article he wrote called taming
1:31:22 the mammoth which is on this subject that if you hate that
1:31:27 part of yourself and try to contain it at least in my
1:31:31 experience that does nothing but exacerbate it does nothing
1:31:36 but worsen the problem but along the lines of say morning
1:31:41 pages you know Julia Cameron and so on writing freehand in
1:31:44 morning and providing that monkey mind and opportunity to
1:31:49 fix itself on paper at least for me gives me tremendous amount
1:31:55 of increased levity during the day it removes a huge burden
1:31:59 do you tend to journal first thing upon waking up could you
1:32:04 walk us through when you’re at your best when do you wake up
1:32:08 what is your first kind of 60 to 90 minutes look like or two
1:32:11 hours whatever you choose it’s two hours and when I’m at my
1:32:14 best I wake I clean up so a shower and stuff like that and
1:32:19 I have caffeine because you do not want to be around me without
1:32:23 caffeine what time you wake up generally between five and six
1:32:27 almost without fail usually without without an alarm clock
1:32:31 so I’m really awful around nine o’clock at night I’m a very
1:32:34 boring person I do not look at my phone let me say that again
1:32:39 I do not look at my phone I do not look at my phone because
1:32:44 it’s just too painful and with a cup of coffee coffee not coffee
1:32:50 as I say from Brooklyn and then I journal usually for an hour
1:32:55 and then I sit in meditation usually for an hour a half
1:32:59 hour sometimes 45 minutes it sort of depends on how the day
1:33:03 is going and what’s going on but the entire period feels like
1:33:08 one quiet meditative period so that’s me at my best the
1:33:13 journaling for an hour I want to dig into that a bit because
1:33:16 I think it’s such a powerful tool and I’d like to hear more
1:33:22 about how that hour is spent so I’m looking at a page in the
1:33:29 new book appropriately named reboot and you have in this
1:33:34 book different journaling invitations so you might have
1:33:38 let’s give a few examples in what ways do I deplete myself
1:33:41 and run myself into the ground where am I running from and
1:33:44 where to why have I allowed myself to be so exhausted you
1:33:47 mentioned earlier that you often start the journaling with
1:33:52 right now I’m feeling dot dot dot are there other prompts
1:33:56 that you personally tend to use more than others well I would
1:33:59 never say that I would use the prompts like I’m going to use
1:34:03 the same prompt every time the one thing that I do consistently
1:34:08 is right now I’m feeling and then generally speaking I might
1:34:12 review the past 24 hours almost in a diary kind of fashion
1:34:16 you know so yesterday I woke up and then I also don’t worry
1:34:21 about explaining people so I might say and then I met with
1:34:24 Mary Jane and I don’t have to explain who Mary Jane is because
1:34:28 who cares I’m never going to read it again and nobody is
1:34:30 ever going to read it I get rid of all that monkey mind bullshit
1:34:33 chatter right and I just go right into it and I presume that
1:34:38 the journal knows all sees all has been there with me all
1:34:42 along that’s an important point secondarily I will ask myself
1:34:48 many questions like how long have I felt this way which will
1:34:53 then bring me back to some early memories and I will start to
1:34:59 be able to elucidate the patterns of my life and that’s
1:35:03 really important because it’s the patterns that actually
1:35:07 point out where we have some struggles can I circle back to
1:35:11 a point that you were making before about accepting the
1:35:14 totality of what’s going on because the journaling can help
1:35:16 me in that yes and help one that so I mentioned before about
1:35:22 maybe utilizing different pens to speak for the different
1:35:26 parts of ourselves before I even go further let me make this
1:35:30 observation I think it’s super helpful for you Tim to speak
1:35:36 openly about the ways in which there are different parts of
1:35:39 you you know for those of us who are mildly curious about
1:35:42 this space that’s an obvious fact but there’s still very much
1:35:47 a point of view in the world that there’s just one mind that
1:35:52 there’s just one point of view and all those other voices we
1:35:55 pretend aren’t there they’re not part of ourselves and you
1:35:59 were absolutely right when those voices are not given air
1:36:03 time they get really pissed off really really angry and the
1:36:09 energy that they hold is really important and so if we go back
1:36:13 to journaling for a moment by giving voice to those other
1:36:17 voices by giving air time to those other voices we get to
1:36:21 lay out in fact all the conflicts that exists within us and
1:36:26 Buddhism that we’re taught that there are seven layers of
1:36:29 consciousness seven is an observer observing observing
1:36:33 observing observing there are all these layers of what’s
1:36:35 going on right and by taking the time in a good journaling
1:36:40 session you can allow you don’t even have to swap all these
1:36:43 pens you can allow dialogue you can allow conflict you can
1:36:49 allow argument and it’s in that expression that’s a manifestation
1:36:56 of that full acceptance that you were talking about before
1:36:59 oh wait I can contain multitudes isn’t that what Whitman
1:37:03 said do I contradict myself I do I am large I contain
1:37:08 multitudes amen whether we are aware of it or not we all
1:37:13 do a book that helped me a lot with this and I found so much
1:37:18 value in the first let’s say 50 to 100 pages that I wanted to
1:37:22 get to work immediately I was like okay that’s plenty of
1:37:27 grist for the mill let me get started was radical acceptance
1:37:30 by Tara Brock oh God what a great book yeah and I think the
1:37:33 title is fairly sterile or milk toast but the book is so good
1:37:40 and in my particular case my default emotional home in a
1:37:46 way was anger and the way I dealt with that was by fighting
1:37:50 anger if that makes sense yeah and trying to cage and contain
1:37:55 it and radical acceptance offered me an entirely different
1:37:59 way of relating to that which I found extremely valuable are
1:38:04 there any other tools meditations books anything at all
1:38:10 that might be helpful in assisting people to accept or
1:38:17 reconcile with different parts of themselves or at the very
1:38:21 least recognize different you know you know how before you
1:38:24 were saying like you you know you take a breath because you
1:38:27 wanted to jump in I’m having all those same feelings yeah
1:38:30 so much here first of all shout out to Tara Brock for radical
1:38:33 acceptance would have what a brilliant book what a gift she
1:38:37 is as a teacher yes yes yes on the acceptance you know you
1:38:41 talked about anger being your default mechanism for me growing
1:38:45 up with the violence that I experience as a kid rage was a
1:38:50 major part of my childhood but the challenge that I experienced
1:38:55 was that anger rage was so dangerous that I actually turned
1:38:58 it into anxiety all the time and so actually you can’t see it
1:39:03 because the video is off but on my desk or two little action
1:39:07 figures one is Hulk and the others Thor and one part of me
1:39:13 that I learned to accept was the Hulk because the Hulk when I
1:39:18 was a kid I remember this one time I have a younger brother
1:39:23 named John and in my mind’s eye he’s still 10 years old even
1:39:26 though he’s in his fifties so hey John anyway when I was a
1:39:30 kid we lived in a part of Brooklyn where we’re called
1:39:33 Bensonhurst and I we lived in the second floor of a two family
1:39:37 house and I remember looking out the window and one day this
1:39:40 kid was throwing rocks over the fence at my brother John and I
1:39:45 went ballistic and I ran downstairs and I grabbed this
1:39:48 kid and I pulled him over the fence and I threw him on the
1:39:51 floor and I pounded the crap out of his face because here’s
1:39:55 the thing you do not fuck with my people you do not fuck with
1:39:59 Hulk’s people the problem was that Hulk was often dangerous
1:40:05 and would often lead to something negative happening to
1:40:07 me so I would shut him up and I’d pretend that he’s not
1:40:11 there and he would show up in all sorts of ways like really
1:40:16 cleverly dissecting somebody’s argument and being really
1:40:20 wordy and verbose and shutting people down and all these awful
1:40:24 behaviors and what I had to do was radically accept that that
1:40:31 guy that big green guy exists in me for one reason only to
1:40:37 keep myself and those who love me safe and by the loving Hulk
1:40:43 I transformed him into Thor who’s just as strong just as
1:40:48 powerful less likely to be out of control and motivated by
1:40:52 justice. Better hair too. And much better hair much better
1:40:56 skin. So that radical acceptance that accepting the fullness
1:41:02 of of ourselves oh my god it’s so liberating isn’t it? It is
1:41:07 and what’s liberating also is simply the realization that
1:41:15 you can in some fashion reconcile these different parts
1:41:18 of you and that they serve a purpose not only do they serve
1:41:21 a purpose but that they were probably in some way fundamental
1:41:26 to your survival whether that’s physical emotional or
1:41:30 otherwise and that they were incredibly incredibly important
1:41:35 and may still be very important for certain things certain
1:41:38 situations. That’s right and you know that recalls Carl Young’s
1:41:43 notion of the shadow which is the place he describes as the
1:41:47 place we put the dismembered parts of ourselves and this is
1:41:52 really important not only do we put the parts of ourselves
1:41:56 that society may say are obviously not good. Let’s say
1:41:59 a rage like anger but also the parts of ourselves that are
1:42:05 actually quite powerful quite positive and quite lovely but
1:42:10 because they threaten say our belonging. They have to actually
1:42:15 be put in the shadow as well well they too get really pissed
1:42:18 off right and they too cause trouble and so you might put
1:42:24 into the shadow your intellect or your capabilities or your
1:42:28 ability to write a book and you might sit for two or three
1:42:32 decades knowing that you want to write a book and not doing
1:42:35 it because it might threaten you in some way or another.
1:42:39 This is a good segue for difficult decisions and by difficult
1:42:44 I mean emotionally difficult and so the for instance sitting
1:42:49 on the desire to write a book for 1020 years and then finally
1:42:53 taking whatever the steps are the first steps to finally write
1:42:57 that book potentially maybe that’s leaving a job maybe
1:43:00 that’s starting a job could be any number of things could you
1:43:03 speak to you can choose which of these questions you would
1:43:07 like to answer when did you say no to something that was at
1:43:10 the time very difficult to say no to which in retrospect was
1:43:13 very important to your life and then the other is when was
1:43:18 the time when you decided to kind of block out all the noise
1:43:22 block out everything else and focus on something very
1:43:24 narrowly and that ended up being extremely important in
1:43:29 retrospect what occurs to me is that the answer to both
1:43:32 questions is the same meaning probably the most consequential
1:43:38 career choice that I made the consequential saying no that
1:43:44 I ever did was to walk away from the venture business and to
1:43:48 stop being a professional investor and the rest of my life
1:43:53 unfolded and I’m sitting here talking to you today I mean we
1:43:57 might have been friends Tim had I taken that path who knows
1:44:02 but I’m sitting here talking to you about something that feels
1:44:06 like the most profound fruition of who I am my vocation my
1:44:11 belief systems all of this because I said no to the thing
1:44:16 that I was actually really successful at which is a
1:44:22 mindfuck if you think about it because because like if I was
1:44:25 failing as an investor you could sort of say well of course
1:44:28 he walked he walked away haha he failed but I actually walked
1:44:32 away when I was successful because it was too painful could
1:44:37 you walk us through how that happened because you had to
1:44:40 have this feeling for I would imagine more than 20 minutes
1:44:45 maybe it was days maybe was weeks maybe it was months what
1:44:47 was the 24 hour period the dinner the conversation the 48
1:44:52 hours whatever it might have been when you’re like enough is
1:44:54 enough I’m actually sending the email having the conversation
1:44:59 and walking it was actually years in the making I would have
1:45:03 to go back to 99 2000 right around that time period where
1:45:08 if you recall the market crashed the NASDAQ crashed I forget
1:45:13 the absolute numbers because they would be miniscule compared
1:45:16 to the numbers we’re dealing with now but the market crashed
1:45:19 around March 1999 and I remember it because I was on a family
1:45:23 holiday to Washington DC when Fred I think texted me said
1:45:29 did you see the NASDAQ you know oh my god you know and I
1:45:32 think it had dropped like 700 points or something which at
1:45:35 the time was like a phenomenal number anyway right around
1:45:38 that time I started having this I just couldn’t sleep I was
1:45:43 just not happy I was 37 38 years old so in hindsight it was
1:45:47 clearly entering midlife and like the systems were collapsing
1:45:51 all around me and then I thought I couldn’t go out and
1:45:56 fundraise with Fred and raise a new venture capital fund for
1:45:59 flat iron and so I decided to leave the fund but I decided
1:46:04 to leave the fund and go to JPMorgan because I thought that
1:46:07 the problem was changing the externalities and so then I
1:46:11 took a position starting January 1st 2002 and as we’re talking
1:46:15 about before by February it was just not working and I remember
1:46:20 going in to see my boss at the time a guy named Jeff Walker
1:46:24 who’s vice chairman of the bank is still a very very close
1:46:26 friend and I remember saying I can’t do it I just can’t do
1:46:30 it and I think it was probably a few months after the Canyon
1:46:33 Ranch visit and I said I’m not going to renew my contract
1:46:37 the end of this year and he said well what are you going to
1:46:40 do and I said I don’t know but for the first time in my life
1:46:44 I’m going to be without a job since first time since I was
1:46:46 about 13 and I’m going to be liberated from this definition
1:46:51 from remember I would you know this notion of like wearing
1:46:54 somebody else’s suit of clothes. It was incredibly scary.
1:46:59 It was incredibly hard.
1:47:01 Was the trigger I hate to interrupt but was the trigger that
1:47:04 you had a preset scheduled meeting for the renewal of the
1:47:08 contract. It was kind of like shit or get off the pot in the
1:47:11 sense. No, no, it was a dinner. It was a dinner. Okay.
1:47:15 It was the dinner. It’s like Jeff I need to have a dinner.
1:47:19 I need to talk about this because the presumption everybody
1:47:21 renew their contract.
1:47:22 Did something prompt was there like a particular day or
1:47:26 moment that prompted you asking him out to dinner.
1:47:29 You know so I went down to Canyon Ranch and I read these
1:47:32 books let your life speak. Holy shit. I’ve actually not been
1:47:36 listening to my life and I started to spend the next few
1:47:40 months. That was the beginning of my meditation practice.
1:47:45 I first meditated at Canyon Ranch and I would argue I first
1:47:49 began listening to my life to my heart and over the next few
1:47:55 months up until November that year. I think we had dinner
1:47:59 right around November 2nd or so. There’s that number two again.
1:48:02 I never noticed that pattern before. We had dinner and I
1:48:06 said to him you know it was like one of those moments. Do I
1:48:08 say that at the beginning of the dinner or do I say that you
1:48:11 know just one last small thing before we go. I’m not going to
1:48:16 be your partner anymore and I said it at the beginning and I
1:48:19 knew in my heart that he would still be my friend. In fact
1:48:23 we remain super close but the fear was like what was it going
1:48:28 to do and I didn’t know and no idea. Thank you for bringing
1:48:33 me back to that time because it’s important for me to remember
1:48:37 that I’m feeling that right now.
1:48:39 What was the day after you walked like do you remember
1:48:43 what that what you did on the first one or two days after
1:48:47 you walked out.
1:48:48 I remember starting to tell people I told the woman who is
1:48:53 my assistant at the time. She remains a very close friend.
1:48:56 See there’s a pattern Kerry Racklin and I said you know Kerry
1:49:00 I’m not going to do it. I don’t remember all of the details.
1:49:03 It was so long ago. This is 17 years ago now but I remember
1:49:09 the feeling and the feeling was a combination of utter relief
1:49:14 and absolute terror both feeling simultaneous.
1:49:18 What’s your advice to someone who’s in that position and I
1:49:23 could phrase it as what advice would you have given yourself
1:49:27 when feeling those two things at that point in time which you
1:49:30 can answer or since you have experience with so many
1:49:35 executives founders and so on when people are experiencing
1:49:40 this sense of relief combined with abject terror of facing
1:49:46 the unknown. What’s your advice.
1:49:49 The first thing I would say and I would have said to myself
1:49:53 is that welcome to midlife for sure and I say this often now
1:49:59 because I often can see the connection to where I was talking
1:50:03 to the CEO of a very successful company who was just talking
1:50:09 to him this morning and he’s 39 years old and it’s like
1:50:12 everything’s working. Why do I feel groundless is like well
1:50:16 let’s talk about that.
1:50:17 So what I often say is remember you’re not alone and the second
1:50:22 is that there are adults men and women who are on the other
1:50:28 side of that golf and we’re fine and you’ll be fine and they
1:50:34 have trod the path before you and you’re going to be OK.
1:50:38 How many references to books have you made Tim. Those were
1:50:43 all written by people you know Tara’s book was written just
1:50:47 as much for herself as it was written for anyone else you
1:50:51 know and all of those people they’re there. They’re like
1:50:56 ancestors guiding us through that period and saying come on
1:51:02 over the water is fine. He’s going to be OK. Don’t be so scared.
1:51:07 What has helped most with or what helped most if it’s past
1:51:13 tense with your anxiety with your worrying when you
1:51:17 transmuted rage into anxiety or if anxiety bubbled up is from
1:51:24 other sources. What are some of the things that have helped
1:51:28 you most with that. I’ll speak about the rage for a moment
1:51:32 the rage and then turned into anxiety. It would often turn
1:51:36 into anxiety but it would equally as often turn into
1:51:39 migraines and that’s when doctors say is first taught me the
1:51:42 first of those three questions which is what am I not saying
1:51:45 that needs to be said and by linking speaking to the rage
1:51:53 and to the migraines and to the anxiety I gave voice to the
1:51:58 feelings and that didn’t magically make them go away but
1:52:03 it lessened the power of that anxiety lessen the power of
1:52:07 all of those feelings. So learning to speak whether it’s
1:52:10 in my journal or actually learning to speak like an adult
1:52:15 with another human being. Hey that hurt me or hey I’m scared
1:52:19 that thing that you said last night scared me and as a result
1:52:24 I want to do the thing that I would normally do which is
1:52:26 withdraw and cut off connection to you but I’m going to stay
1:52:30 here and be an adult and engage with you. That move it doesn’t
1:52:36 make the anxiety go away but it puts me back in control puts
1:52:41 the adult me back in control. The other thing that I do
1:52:45 is I start to ask the anxiety questions like you really want
1:52:50 to work with what’s going on in that amygdala which is where
1:52:53 that source of anxiety tends to be right the amygdala. Ask
1:52:57 your questions what’s the threat what am I afraid of have I
1:53:00 heard this before those questions fire off the prefrontal
1:53:03 cortex which can relieve the anxiety. Do you personally
1:53:07 tend to ask this questions before meditation in journaling
1:53:11 what form does the asking take. Yeah I do well remember I
1:53:15 journal before I meditate so a lot of times I will be sitting
1:53:19 down at the cushion. This is what I’m working with and you
1:53:25 know I’ll tell you what happened this morning in my
1:53:27 meditation session I was working with some really difficult
1:53:30 feelings that came up over the weekend and I was sitting in
1:53:34 meditation I had had a conversation with Sharon
1:53:36 Salzburg yesterday and it was really helpful and all of a
1:53:39 sudden she came back in it just as I sat down. I’m a very
1:53:43 ritualized meditator right so I have candles I have incense.
1:53:46 You know I’m a former Catholic so I like all that ritual stuff
1:53:51 you know if somebody can ring a bell it makes me happy right
1:53:53 so I’m doing all that stuff I’m sitting on the cushion and
1:53:56 all that’s emerging and all of a sudden I start visualizing
1:54:00 the area of my chest where my heart is and the object of my
1:54:05 meditation this morning was open your heart open your heart
1:54:09 your heart’s closing stay open stay open and in that moment
1:54:15 I realized that what I was continuing to work with was the
1:54:19 impulse to close down this weekend that I was feeling in
1:54:24 response to the fears. And so the naturally arising thought
1:54:30 that came from that session in that moment was open open open
1:54:38 which very very quickly turned into loving kindness meditation
1:54:42 for myself for people who don’t know correct me if I’m wrong
1:54:46 here but loving kindness meditation if you want to learn
1:54:49 more about it but highly recommend diving into that also
1:54:52 known as meta me tta meditation to folks worth checking out
1:55:01 Jack cornfield who’s been on this podcast before specifically
1:55:04 speaking about meta and loving kindness Sharon’s also spoken
1:55:07 about it on the podcast and those are good those are great
1:55:11 places to start very very effective short least can be
1:55:17 short meditation that really punches above its weight class
1:55:20 sense and I think in part for me I’m really glad we’re talking
1:55:24 about this because it’s a type of meditation that I haven’t
1:55:27 used in a while and I really should is at least for me it’s
1:55:31 a vacation from obsessing on myself if it is directed at
1:55:39 other people now as was pointed out to me during my first ever
1:55:43 extended meditation retreat I was talking about loving kindness
1:55:47 and how much I enjoyed it and they asked on the way out just
1:55:50 a quick suggestion have you applied this to yourself at
1:55:54 all and it was so nonsensical to me like it didn’t like they
1:56:00 might have been speaking to me and cling on I was like loving
1:56:03 kindness to myself what like that doesn’t make any sense and
1:56:07 lo and behold I did find it very valuable I really enjoy
1:56:10 combining that with also loving kindness meditation for other
1:56:14 people and if you’re just kind of rolling your eyes at the
1:56:19 sort of a new age hippie sounding wording of loving kindness
1:56:22 then we could switch to a different language and look
1:56:24 up meta METT meditation same same but different Jared let me
1:56:28 ask you just a couple more questions we could go for many
1:56:31 many hours more and we certainly have spoken for many hours
1:56:36 before but for the purposes of right now I think we’re getting
1:56:39 close to a really good getting reacquainted chat and round one
1:56:44 of the podcast I’ll ask you just a few more questions one is
1:56:49 what is the new behavior in the last handful of years it
1:56:55 could be anytime really or belief that is most or I should
1:57:01 say greatly improved your life quality of your life new
1:57:04 behavior or belief in the last film the blank number of years
1:57:09 that has significantly improved the quality of your life the
1:57:12 main one that comes to mind is that I am a good man the
1:57:20 belief that’s a belief I believe that I am a fundamentally
1:57:25 good person and that I accept the fact that I often fail to
1:57:31 act in accordance with that but that feels to this guilt
1:57:38 ridden anxious ridden angry child from Brooklyn way back when
1:57:43 that feels radically transformative what I’m good just
1:57:49 as I am no yeah I’m good that’s huge hard to imagine something
1:57:57 bigger by the way I have to practice it every day but you
1:58:04 know I’m a good enough partner I’m a good enough business
1:58:07 person I’m a good enough coach I’m good enough parent that’s
1:58:11 the hardest one for me have I wounded my children yes does
1:58:17 that undermine whether or not I’m a good man and a good
1:58:20 father no and that allowance has done something really magical
1:58:26 it’s allowed them to accept themselves so yeah it’s a big
1:58:30 move that is a big move the next question might segue might
1:58:34 be completely different but if you could put a message on a
1:58:38 billboard metaphorically speaking to get a quote a word a
1:58:43 question anything noncommercial out to billions of people
1:58:48 what might you put on such a billboard I’m going to add two
1:58:51 sentences it’s a big billboard so there’s a big vote board so
1:58:55 it doesn’t say impeach Trump just kidding it says you’re not
1:58:59 alone and just because you feel like shit doesn’t mean you are
1:59:02 shit the you are not alone is really really important because
1:59:08 we feel so broken because we question our worthiness all the
1:59:11 time we exacerbate the feelings of I must be the only one who’s
1:59:20 going through this and this is crazy because despite all the
1:59:23 evidence whether it’s myths whether it’s stories whether
1:59:27 it’s religions whether it’s philosophical traditions everybody
1:59:31 saying the same thing you’re fundamentally good yeah there
1:59:36 are things you can do to improve your life but you’re
1:59:37 fundamentally good relax it’s okay that’s that equanimity that
1:59:43 I often talk about like okay so I guess you’re not alone and
1:59:48 just because you feel like shit doesn’t mean you are shit and
1:59:52 if I’m not shit then this feeling of it being crappy right
1:59:56 now well this will pass so let’s add another one this to show
2:00:01 pass can I add onto that you can add you can keep adding Tim
2:00:05 think of the times in which you have struggled you’ve been
2:00:08 very open about your struggles and by the way thank you for
2:00:10 doing that because you model something that’s really
2:00:13 important think about when you’ve been at your worst and how
2:00:17 alone it feels and how it becomes this self-reinforcing
2:00:22 negative view that you must be crap because you feel like
2:00:26 crap it’s like no stop you must be human because you feel
2:00:31 struggle and there are billions of humans and have been
2:00:35 billions and there will be billions more and struggle is
2:00:39 universal that is part of the amusement ride that’s right
2:00:46 yeah and you bought a ticket they might as well go for a ride
2:00:49 can’t be on magic castle indefinitely you’re going to go
2:00:51 to the haunted house occasionally Jerry thank you so much
2:00:58 for taking the time today to share and to catch up and to
2:01:04 teach I always enjoy our conversations so point number
2:01:09 one thank you very much well thank you and thank you for
2:01:12 giving me the opportunity and thank you for asking gorgeous
2:01:17 questions that really helped me think and feel and thank you
2:01:21 for doing what you do every day it really means a lot to the
2:01:24 world my pleasure I really appreciate you saying that and
2:01:27 it helps me as much as I hope it helps other people and there’s
2:01:33 that weird crazy esoteric thing that all those people high
2:01:37 achieving people so there he goes oh helping me helps other
2:01:40 people helping other people up to me yeah right Tim’s living
2:01:43 proof of that so there it’s true it’s true I mean I think
2:01:48 that I’ve been very fortunate to somehow stumble my way like
2:01:54 a drunk in the dark into a career that involves having
2:01:58 conversations like this so thank you lady fortune for that
2:02:02 and it’s also just a tremendous opportunity to explore some
2:02:07 of these things that perhaps aren’t explored as often as
2:02:12 they should be and you are great companion on the path with
2:02:17 that so thank you again and we’re the best places to say
2:02:23 hello to you online or to learn about what you’re up to of
2:02:28 course the book reboot subtitle leadership and the art of
2:02:32 growing up is available and certainly something I would
2:02:36 recommend people check out has the many of the prompts and
2:02:39 more that we’ve talked about a lot of case studies personal
2:02:42 history and a distillation of a lot of what you’ve learned
2:02:46 working with hundreds thousands of clients at this point yeah
2:02:51 and what else should people know anything else yeah I mean
2:02:56 probably the best way to sort of follow what’s going on is
2:02:59 reboot dot IO slash book but also if you just go to the
2:03:04 reboot dot IO website we’ve got a bunch of resources podcast
2:03:09 self-guided courses journaling exercises all sorts of things
2:03:14 designed to help folks all for free because you know hey what
2:03:19 the heck you know let’s help each other out and that’s
2:03:22 probably the best way you can also follow me on Twitter at
2:03:26 Jerry Kelowna you mentioned that earlier but pick up the
2:03:29 book pretty proud of it and I hope it makes a difference makes
2:03:34 a dent in the world that’s the best that we can hope for and
2:03:39 for people listening I’ll link to everything that we’ve
2:03:41 discussed the website book website Twitter and everything
2:03:46 else that came up in this conversation in the show notes
2:03:49 as always at tim dot blog forward slash podcast you can just
2:03:53 search Jerry J R R Y or Kelowna if you want to take the black
2:03:58 diamond route instead of using the easy option and you’ll be
2:04:03 able to find it very very quickly Jerry any other comments
2:04:07 requests anything at all you’d like to say before we wrap up
2:04:11 now it just that it was a real heartfelt pleasure was really
2:04:15 a blast likewise thanks so much Jerry and everyone out there
2:04:19 thank you so much for listening and until next time pick up a
2:04:24 damn journal and real pens give it a shot it’s amazing what
2:04:32 you can discover when you take what you think are clear
2:04:35 thoughts and put them on paper and that’s it for now so until
2:04:39 next time thanks again for listening.
2:04:41 Hey guys this is Tim again just one more thing before you take
2:04:45 off and that is five bullet Friday would you enjoy getting
2:04:49 a short email from me every Friday that provides a little
2:04:52 fun before the weekend between one and a half and two million
2:04:55 people subscribe to my free newsletter my super short
2:04:58 newsletter called five bullet Friday easy to sign up easy to
2:05:02 cancel it is basically a half page that I send out every Friday
2:05:07 to share the coolest things I found or discovered or have
2:05:09 started exploring over that week kind of like my diary of cool
2:05:13 things it often includes articles I’m reading books I’m
2:05:15 reading albums perhaps gadgets gizmos all sorts of tech tricks
2:05:21 and so on they get sent to me by my friends including a lot of
2:05:24 podcast guests and these strange esoteric things end up in my
2:05:28 field and then I test them and then I share them with you so
2:05:33 if that sounds fun again it’s very short a little tiny bite of
2:05:37 goodness before you head off for the weekend something to think
2:05:39 about if you’d like to try it out just go to tim.blog/Friday
2:05:43 type that into your browser tim.blog/Friday drop in your
2:05:48 email and you’ll get the very next one thanks for listening.
2:05:50 This episode is brought to you by 8 Sleep I have been using 8
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2:10:10 (audience cheering)
2:10:13 [BLANK_AUDIO]