Ep. 297 – Rich Roll: Surrendering Does Not Mean Failure

“If you were on the outside looking in you’d probably think, ‘This guy’s got a really good life.’ And on paper I did, but on the inside I felt like I was dying. I was depressed. I was unenthusiastic about my life because I knew I was in a career that was ill suited to me. But I just couldn’t see my way out of it,” Rich Roll said.

He told be about the time he felt a tightness in his chest. He couldn’t walk up the stairs. He had to take a break halfway up the flight.

Rich was 39 and dying.

Rich and I talked about his story before… how he transformed himself from a depressed and overweight alcoholic to a plant based, vegan eating, mega athlete / bestselling author / podcaster / writer and total peak performer.

But THIS time we dove even deeper.

“I was trying to force this round peg into a square hole for most of my life,” he said.

I wanted to understand the switch that led him to himself… He told me his secret. And I believe him.

“Surrender.”

He went to rehab. And got help for a problem he couldn’t handle on his own.

That’s Rich’s meaning of “surrender.” Getting help when you need.

But it’s hard to know when it’s the right time to get help. I probably need help right now. It’s the first time I’ve felt physically sick in five years. My body is tired. And I’m trying to rest. But sometimes, I can’t pull myself away from what I love.

So I talked to Rich and then my friend Ryan Holiday. And then prepped for two more interviews.

I like this interview with Rich for a lot of reasons. I’ll tell you one though… It’s because when he says something, it feels just confessing. He’s sharing what’s true for him. And helping you heal in the process. (You’ll know what I mean if you start listening)

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Things I Refuse To Worry About In 2018

“You sound like a moron,” one of my closest friends recently told me. It was because I was feeling sick but I haven’t been to a doctor since I was 18.

In one month I turn 50.

The last doctor i went to was my pediatrictian before I went to college. I don’t even know what doctors do now.

“You could be a hypochondriac,” another friend of mine told me. “Maybe you’re so afraid you might be sick that you refuse to get a check-up.”

So I don’t know if I should go to a doctor or get even more scared. Sometimes I’m always scared.

---

“You have to move into your own apartment,” my friend above told me. “Moving around from Airbnb to Airbnb is creepy,” she said.

A few months ago I finally did it. I was scared to do it. I don’t know why. I don’t like buying things for myself.

I don’t like roots. I don’t like to lock myself into a place. Bad things happened to me when I do that.

But I did it. I didn’t want to be “creepy”.

It was really hard. I have never had a credit card. So I have no credit score. So nobody wanted to rent to me.

And then I had no furniture. I only had one bag with two outfits and a toothbrush and a computer.

I’m 49. I’ve never moved into my own apartment by myself.

“You will feel stable,” my friend told me. “You don’t even realize how good you will feel.”

She’s right. It’s amazing.

---

I’m still a 14 year old with acne and braces and afraid to talk to people and begging for people to like me.

I beg my children to like me. Sometimes I try to show off just for them.

I want to please people all the time. And I don’t want to disappoint people so I make promises and say “Yes” to things I can’t live up to. And then I disappoint people.

Aren’t you the guy who wrote “The Power of No”.

Yes.

---

I can’t predict next year. Last year came out 100% different than I thought it would.

But I feel like (I hope) I’m moving in the right direction.

And here are the things I hope I don’t worry about in 2018.

Please, Force, let me surrender these worries to you:

MONEY

We need money to pay the bills. I get it. We need money to support our families. We need stability.

I get it. I get it. All my life. All my fucking life. I’ve been worried about money. I’m so sick and tired of it.

My parents went broke. I paid for every dime of my college and graduate school.

I moved to NYC with a single garbage bag with an outfit or two in it and lived in a one room apartment with a roommate.

But worrying about money never made me money.

The ONLY times I’ve ever made any money was when I solved someone else’s problem, communicated my ability to solve it for them, and got paid for it.

Look around you. Your friends, your colleagues, your bosses, other companies. Everyone needs help.

And if you are at the right place and the right time, then some of those people will pay you to help them solve a problem. Not always (so you can’t be. disappointed) but sometimes.

Right place, right time, right solution, right communication, right execution, right pay. Then repeat.

That’s a business. That’s an income stream. Then make more.

It’s so hard. And it’s EVERY. DAY. the stress of making money. But I won’t worry about it. When I worry, I’m going to look around, solve a problem, communicate, execute, get paid.

---

POLITICS

I’m completely ignoring politics. Trump was elected over a year ago. An entire total of ONE bill that he has proposed has passed Congress and ZERO vetos. He does nothing. His one bill (tax bill) does nothing as far as I can tell.

The ONLY thing he has been good at is making one side of the country hate the other side. Good JOB!

I won’t fall for it.

Change happens when YOU and I DO things. Not when we argue.

Everyone has critical issues. No one set of issues you care about will ever align with a perfect candidate who agrees with you on anything.

I’m the father of an 18 year old and a 15 year old. The only purpose of war, as far as I can naively tell, is to send teenagers to other countries to kill other teenagers.

I’ve never seen a Senator go off to war. Or a “supreme leader”. Or a king.

This is my main issue.

Kids killing kids. People killing people over hate.

If it all blows up, I don’t really care. I just don’t want my kids to be sent to any war. I wish we had never gotten into the wars we were in, and I don’t know why we are still in them (and why 1/3 of my taxes goes towards paying for them).

Earlier this year, someone wrote a blog post suggesting I run for governor of NY on the Libertarian Party. For the fun of it, I even met with the actual guy who is running for governor on that party (a party I am not a member of).

I would be the worst governor or congressman or whatever of anything because I have so little cares about what is happening in the world.

Naive or not, that is the way I feel.

OTHER PEOPLE’S OPINIONS

Please God, please please please let me not pander to other people’s opinions.

It’s ok to listen. It’s ok to entertain and make people happy. It’s ok to judge your progress with the applause (or lack of) of others.

But never get stuck in the hole of where everyone else wants you to be.

Everyone wants to have status over you. I need to remember this. To remember that only I have the power to give myself status.

To never out-source my self-esteem to others. Oh god, please please please.

Anybody who is creative, will start off striving and yearning to be better at what they do.

They see the nuances and the beauty in the art created by masters before them.

I want to have those nuances in the things I do: in writing, in podcasting, in comedy, in career, in whatever I attempt to be creative at.

But people will always hate. And it’s the ones closest to you to be the most careful around. They will hate. Or disappoint. Or accidentally crush you. Or mistakenly make you feel so sad you don’t know how to ever create again.

It’s never the neighbor down the street. It’s the friend you let into your house.

Pandering to what they like, or what the crowd likes, is the one creative sin.

They dig the hole, they put you in a casket, they bury the casket.

But only if you pander to them. Breaking free from the grave might make them angry or disappointed or scared. They don’t want you to escape the nice grave they buried you in.

But it’s the only way to live.

THE FUTURE

It’s so easy to mortgage the present in exchange for a better future.

To think: if only she/he were like THIS, then I would be HAPPY.

To think: if only I had this amount, then I will be a SUCCESS

If only, this effort works, then I will be WHERE I WANT.

The fiber of life is drunk by our souls only when we squeeze all of the juice out of the current moment. Ugh. That sounds like a cliche.

Also a cliche to say, “be mindful of the current moment”.

So how else can I say it?

Hmmm….

What can I be grateful for right now?

Hmmm. Cliche also.

We are insignificant on this tiny dot? Cliche.

I don’t know. I don’t know. I’m just not going to worry about it.

PLEASING OTHERS

Every day I feel like I’m disappointing someone. I don’t try to. But it happens.

I’m sorry.

I’m sorry I can’t do everything I promised. I’m sorry I let you down. But it happens. We can work it out. Or not. But I can’t worry about it anymore.

I’m doing my best. Please believe me.

I love to do what I love doing, regardless of personal benefit.

Podcasting makes me zero. Writing makes me zero. Almost everything I do makes me zero and costs me aggravation if I let it.

This past year I started doing standup comedy up to six nights a week. I’ve always loved it. And I’ve always analyzed it. But now I’m trying to get good at it. TRYING. It’s so HARD. AGGHHGHAH!!!

And it’s so “in your face”.

I go on the stage, and I say things, and they might not respond how I want. Right then, they might not like me, or they might not understand me, or they might not care. Or they might be tired or drunk.

Or I might be just bad.

I videotape each set. I watch it. I write more. I study. I talk to comedians. I try to learn. Every time I go on stage I want it to be better than the last time.

We’ll see.

But in a microcosm it represents every attempt I have at pleasing others.

My one NEW mantra for comedy, and my one mantra for going on TV, or having a meeting, or being with friends, or being with family, or being with a life partner. or being with colleagues is:

THE PARTY IS WHERE I AM AT

And everyone who wants to join in is invited.

Those are the things I will try (please please please) not to worry about in 2018.

YOU ARE CORDIALLY INVITED.

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Ep. 296 – Linda Papadopoulos: Validation: Why It’s Dangerous…

We all have vulnerabilities. And I exposed mine to Linda because it’s a free therapy session. She’s a well-known psychologist and bestselling author born in Canada, living in the UK.

I had to ask her about all her theories. And all her books. But mostly these 2:

1. “What Men Say, What Women Hear”
2. “Unfollow: Living Life on Your Own Terms”

Because I am still outsourcing my self-worth to new measures. First, it was money. So I gave up Wall Street (for many reasons). And then it became book sales and now podcast downloads or laughs when I’m on stage doing stand up.

And so I asked Linda “why?”

Why am I sacrificing my art for identity?

“We create because it’s in,” she said. “We’re social beings and our identity is bound up in what we create. That identity needs to be confirmed by others, right? It’s an interesting thing: identity. It’s simultaneously what makes us different but it’s also what binds us with a group”

Then she told me about the evolution of acceptance.

“Years ago you’d have a much smaller group validating that. Now, you have people out there, James, that don’t have a vested interest in you feeling good about yourself. Actually, there are people out there that would find it interesting if you didn’t. And you’ve got to ask yourself, ‘Is the source not important?’”

“What do you mean?”

“It’s like a big bathroom door,” she said. All the comments on message boards or Facebook or Twitter…

Think about this. You go to a public bathroom. And the door is covered in ink. Is any of it positive? Or even worth reading?

That’s social media. (According to Linda.)

She said, “Look at who’s giving you that validation and explore if it’s quality or quantity. And, maybe that’s that’s what we’ve sold our souls for… quantity.”

Then she gave me tips. Really useful tips that I started practicing as soon as the podcast ended (like taking note of when I’m on social media, and how my mood is, and how much power someone else has). And then I asked her about women.

She broke down all the reasons people get divorced. And the most common misunderstandings. And how to get rid of them for good.

Because fighting hurts. It comes back to what Linda said about vulnerabilities. We all have them. And they’re impossible to forget. It’s like they put a mark on you. And follow you from place to place. Never letting you forget…

(Linda gave me advice for that too.) “The vulnerabilities are there,” she said, “but the assets are the people that tell you it’s okay to have them…”

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Ep. 295 – Jon Alpert: Behind the Camera: How to Be the Catalyst for Social Change

“This guy tried to kill me. He had a gun to my head,” Jon said.  “We were leaving the country.  We got intercepted.”

Wait.

What?

I was interviewing Jon Alpert.  He was trying to smuggle controversial footage out of Iraq.

“I was basically a complete failure up until the moment that I started making films,” Jon said.

He was constantly trying to make his community a better place, but his attempts were always unsuccessful.

“I want to make this country better. And I’m not a good soldier. And I’m not a politician. So I can’t go represent in Congress, but I can be a good reporter,” he said.

He took two passions (camera and country) and combined the two to become creative in the intersection.

His documentaries show aspects of social change that I’ve never seen anywhere else. There’s this undercurrent of a larger problem… an issue or a cause that people are fighting for. I feel like, in talking to Jon, that I want to be fighting for something too. Jon had a core. A direction. And a destination. All in one.

“The camera is a license for me to go up to you and to invade every single part of your life,” he said. “The camera is a license to invade people’s personal space.”

“And I’m doing it because I love my country and that’s how I believe I can be the best patriot.”

He told me about his newest documentary, “Cuba and the Cameraman.” 45 years! It took him 45 years to make this.

It’s his life work.

He went through a thousand hours of footage. Editing took a year. And what resulted (what we finally get to see) is one of the greatest films about the Cuban Revolution. Ever.

And this podcast is the story behind those stories. We hear about the leaders. The criminals. And what was inside their refrigerator.

These are the war stories you don’t hear. This is the filmmaker’s journey.

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Ep. 294 – Jackie Martling: The Joke Man… I Talk with Howard Stern’s Lead Writer

I started to get really itchy. Inside my head.

I didn’t know how to scratch it. So I avoided it. Until I broke out into hives and finally forced myself on stage.

I think it started when I interviewed Gary Gulman, one of the greatest comedians ever. It was over two years ago. And even though he was deeply depressed, I was jealous.

Because he was living my dreams. He was scratching my itch.

So I started to interview more comedians. And writers of comedy. I had so many questions. I interviewed Jim Norton, Nancy Cartwright (the voice of Bart Simpson!) Fred Stoller, Chris Smith (who worked with Jon Stewart), Paul Shaffer (the famous band leader on Jay Leno), Bonnie McFarlane. The list keeps growing.

And there are so many branches of comedy:

Stand up, voice overs, writers, monologue performers, sidekicks. And each branch has its own microskills.

That’s true for every skill. They all require you to learn hundreds of micro-skills.

So getting started can be scary. Very scary. Some people die with itches unscratched.

When I want to get better at something, I go underneath the skill. I imagine a small version of myself looking up at my dreams. If I can see how far away I am from greatness, I feel the desire to get there. That’s what this podcast is about. Picking apart greatness.

Jackie Martling came to the studio. He was the lead writer at “The Howard Stern Show” for 18 years and now he’s the author of “The Joke Man Bow to Stern.”

I don’t know anyone who’s looked at their crappy job and said “I’m going to do this for 18 years.”

So I wanted to hear him talk about what it’s like to love what you’re doing with your life. To feel good and dedicated.

That’s where I hope to find us help. (I say “us” because I’m still itchy). I still want to be a standup comedian. Not just “do” standup. Doing and loving leads to being.

I’m still at “doing.” Because love comes from having a deep relationship with the skill.

Jackie loves what he does.

So I’ll keep scratching.

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Ep. 293 – AJ Jacobs: Why We Experiment (And Why You Should Also)

I like the idea of experimenting for two reasons. A) widen comfort zone B) become a better person.

I’ll tell you about A first then B.

But first, let me reintroduce my good friend AJ. If you listen to this podcast then you already know who AJ is. But just in case, AJ Jacob’s is a professional at experimenting. All his books are experiments. Four are bestsellers.

He told me about one he did with the comedian Jim Gaffigan. They looked up the oldest jokes in the world. From hundreds of years ago. And told them to live audiences today. Sometimes Jim bombed, some jokes he skipped (because a lot of jokes were about lettuce… lettuce used to be thought as an aphrodisiac), but others worked.

And he didn’t know what to expect.

That’s A) widening your comfort zone.

So for this podcast, AJ and I came up with ideas to experiment with. And we want you to join us. You’ll hear what we’re testing right now. And what’s next.

I found that if I do a new experiment a day or week, it becomes a micro step to creating a healthy life. For example, I told AJ that I try very heard not to say anything bad about anybody. And it’s hard because things come up throughout the day. But ultimately it makes me feel happier to not gossip. And I’ve been doing this now for about seven years. AJ tried it too. “It was fascinating,” he said, “because I realized 70% of my speech was trash talking and it made such a difference in my life when I cut that out because it made me more positive and happier.”

And it’s true. Because we all know that eating trash makes you feel like trash. And it’s true for your brain too.

These are the nuances hidden in experimenting. You have a secret with yourself. A promise to uphold. And you live up to some unknown potential sometimes.

That’s B.

 

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How To Win a Trip to New York City (And Sit In On a Podcast Taping)

I didn’t even want to do a podcast. Too much work!

I’m too shy to ask people to come on.

And I get so nervous I hope each podcast will get cancelled. Or a natural disaster will happen.

But I wanted an excuse to ask people how they made their lives better. Maybe I could do it also.

I’ve gone from successful to broke more than once. I’ve gone all the way down, then come back up. I’ve gained then lost multiple times, so I needed to talk to my super heroes…

I would read a book and think to myself: I wish I could ask Judy Blume, Peter Thiel, Coolio, Tim Ferriss, Jewel, Mark Cuban, etc. MORE about what they just said.

But if I just called them, would they return the call?

Definitely not. I needed a front. A lame excuse. I’d pick up the phone… “I have a podcast.”

People ask me “what’s this podcast about?”

To me it’s about interviewing people who are peak performers. Maybe even the best in the world at what they do.

It’s not about business or entrepreneurship. But about going deeper and exploring what it means to be human and achieve well-being in a world that is increasingly complicated.

This is what people struggle with in their lives, it’s the layer underneath the bills, the relationships, the sicknesses. All of that are just byproducts of finding well-being in life.

It’s been four years and now 300 interviews later. I’ve had close to 50 million downloads overall. More when I include other podcasts I’ve been involved in.

The podcast has saved my life. I’ve spoken to so many of my heroes. (People who I would never have expected to have a conversation with.)

Having Judy Blume, my favorite author as a child, give me relationship advice – might be the highlight of my life.

Or Brian Grazer, producer of many of my favorite movies and TV shows, give me advice about creativity.

Talking to Wayne Dyer, Coolio, Steven Pressfield, Seth Godin, Tim Ferriss, Judy Blume, Cheryl Strayed, Amanda Palmer, and on and on, has taught me so much about the world.

I hope I remember them. I hope I live what I learned. I try to.

Often people ask me what my favorite episode is… I can’t possibly tell you.

I’ve learned so much. Every one of the 300 people have changed my life in some way.

I could sit here and write 300 things… one from each podcast. But I wanted to try something different.

Now I want to hear what you’ve learned. Or how this podcast has helped you.So I’m doing  a contest…

Here’s how you can enter. (And if you win, I’ll fly you out to New York City for a live podcast taping with me and one of my guests)

It’s simple. (And takes less than a minute.) Tell me your favorite podcast and how it’s changed your life.

I’ll go through each video and pick out the best one, fly you to new york for a live podcast episode (or two).

We’ll hang out…

You can ask me about the time I blew off Trump’s inauguration to interview Sara Blakely. Or how I was able to get Mark Cuban, Arianna Huffington, and Gary Vaynerchuck on the phone for an interview.

You can’t change 300 things in your life. But you can file a few things away and pull them out as necessary.

I learned about creativity, nutrition, persistence, peak performance, happiness.

Every day I think, “I’m going to quit this podcast. It’s too much work.”

But then I read a book. Or I see a person I’m curious about. And I think, “I need to know more about this.”

So I call them. I arrange to meet them. I pull out a recorder.

I start asking questions.

I also learned they’ll pick up. They’ll share their stories. I said I wanted to be like my heroes… Enter the contest. I’ll pick up.

 

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Ep. 292 – Tiffany Haddish: Stop Telling Yourself You’re Not Good Enough

Got to interview one of my favorite comedians for the podcast, Tiffany Haddish, star of “Girls Trip,” her recent comedy special. “She Ready”, and 20 years a stand up.

I asked her what was the biggest change in her first few years of doing standup. (She’s been doing it over 20 years).

She said, “I learned to change the fear into fun”.

I think all of the above is great advice to achieve success in everything worth doing.

I had a gift for Tiffany.

It was a suitcase. I gave her a suitcase for the kids.

Let me explain. Because a suitcase is an odd kind of gift.

Tiffany was placed in foster care when she was 12 years old and stayed in the system until she was a legal adult. When she moved from home to home she didn’t have a suitcase or any kind of bag to put her clothes. They make the kids put all their belongings in trash bags. And it made her feel like garbage.

“You’re garbage,” she said. “Garbage moved around from house to house.”

“When I was 13, I said to myself if I ever get any sort of power, any sort of influence at all, I’m gonna figure out a way to make sure no kid feels like a piece of trash.”

And she’s succeeding (and you can help).

So she’s been collecting suitcases for kids through the Felix Organization. If you’re reading this and want to donate a suitcase, look up the Felix Organization.

I wanted to know how she rose up from foster kid to superstar comedian. And the first black female to host Saturday Night Live.

“I try to manifest what it is I want to be,” she said. And she told me her self talk…

“You got divine order all over you,” she said. “Everything is happening in the order and the way it’s supposed to happen.You got this girl. Pull that energy from your uterus. You got it that’s where your soul at. Pull it up from your soul. You got this girl.”

I couldn’t stop laughing.

She said she tried to find the joy and the fun in everything she’s ever gone through.

Here’s a quote from her new book, “The Last Black Unicorn”:

“In stand-up, you do need to be having fun up there like Richard Pryor said, but you have to know yourself well, too…You start learning and it’s like playing a piano. You know exactly what keys to stroke, ’cause really with comedy, you’re like fiddling with people’s souls. You resonate on the same frequency as them, trying to greet them to relate…”

“To do that, you gotta put yourself out there. And in order to put yourself out there, you’ve gotta have an idea who you are.”

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Ep. 291 – Stephen Tobolowsky: Write Your Own Story Because We’re All Living On Borrowed Time

If you’re reading this, you probably don’t know the name Stephen Tobolowsky.

But I’ll give you some hints.

Ned Ryerson. (From “Groundhog Day”)

Jack Barker. (From “Silicon Valley”)

Sound familiar? Stephen Tobolowsky is one of the main characters and actors in one of my favorite TV Shows, Silicon Valley. He also plays the MOST annoying character in Groundhog Day. He’s been in 200 movies and a thousand other things including Seinfeld, Thelma & Louise, Heroes and the list goes on.

But he did something weird.

He wrote a book.

And when I read it I thought, “who the hell is this guy?”

There are only two ways someone could write this book…” My Adventures with God”.

ONE: If they were incredibly broken as a human being somewhere in their lives and then they climbed back out of that hole by thinking all these intense and philosophical thoughts.

TWO: They were just born this way…

I still haven’t figured out which one.

I have to admit I didn’t understand parts of Stephen’s book. And not because it was bad, (I loved it), but because I had to stop and think. His thoughts are so valuable and I really wanted to know what they meant. I was pretty happy he was able to come on my podcast.

He taught me that we’re all writing and choosing our narratives to some extent…

“Well I think on a personal level, we all end up developing narratives,” Stephen said, “Either it’s instinct or sometimes it’s choice. I think we live in the dark so much of the time that we need metaphors to find our way. And I believe having a philosophy is only useful if it helps you see in the dark.”

So I asked him how do we begin to take control of our own narratives?

Because we to some extent, I can’t just surrender to the narratives that has  been  given to me.

That takes away my freedom and ability to reinvent.

Stephen told me this, “We’re all living on borrowed time.”

This podcast shows you a window into a man’s desire to connect with the deeper meaning on time and what it means to be alive.

 

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Ep. 289 – Amy Morin: The Easiest Side Hustle You Can Start Right Now

You may remember Amy, she came on my podcast a few weeks ago. We discussed her book, “13 Things Mentally Strong People Don’t Do.”

I asked her why is it a book about what people DON’T do instead of SHOULD do. It seemed counterintuitive to me.

But her reasoning made sense. The book wasn’t written for other people. It was actually just a letter to herself at first. And then she put it online. And it became viral… that led to a book deal.

The podcast was really popular. But I feel like you didn’t get the full story…

Amy’s not just an author, therapist, social worker/mentally strong person. She’s also an entrepreneur.

She was making money in her sleep…

“I’ve always had some sort of a side hustle usually something fun or strange,” she said.

I knew immediately I needed to have her back on the show. I wanted her to  share this with my listeners. Because these are “choose yourself” ideas. Simple, easy to execute, and anyone can do it.

“I had a friend who had a jewelry store,” Amy said, “so I knew the markup on jewelry was incredible, like 200 hundred or 300 hundred percent.”

And she knew jewelry was fairly inexpensive to ship because it didn’t weigh anything. Over the years she and her husband thought about how they could turn this into something they could monetize. And finally they did it.

I asked so many questions about how she pulled the trigger. And got the courage. I wanted to know how she made this business work. I also gave her ideas about how she could scale.

I really believe this: anyone who listens to this podcast can start doing their own side hustle right now.

“Over time it went from a few dollars to a few hundred and then before I knew it we were up to a few $1,000  dollars a month.”

You could quit your job I told her.

“That was the dream,” she said.

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Ep. 288 – Mike Van Cleave: A Conversation About Cancer & Learning How to Discard the Meaningless

I got a call from my friend Mike Van Cleave a year ago. He told me had cancer. We hadn’t spoken for years.

“It’s like mold in your refrigerator,” he said. “All of a sudden you’re like, ‘What the hell happened? It’s only been a week.”  

You never know who’s going to call you out of the blue someday with cancer. It’s scary, but luckily we don’t live with these thoughts in our minds. We only think of ourselves. “Will I get cancer?” And that’s important. These selfish thoughts keep us alive.

I’ve always admired my friend Mike. I felt honored to have him on this podcast. He told me the science of his cancer (thyroid cancer) and the ways he’s surviving every day.

I’ll take emotional pain over physical any day. So my bones can keep typing.

“Do you have pain in your bones?” I asked him.

He did. And it went away. “I have no bone pain right now. So there’s a very good chance that all the bone metastasis is working,” he said.

That takes away 80% of the “badness”. He spoke casually. And sometimes I laughed inappropriately.

I guess I was scared.

In 18 months, his medicine will stop working. The cancer will keep growing again. And he’ll be on a new drug.

He told me about the success rate of his next drug (only 50% of people are helped and it only helps for 6 months).

“What’s the best case scenario?” I asked.

I cried afterwards. Not in front on him.

Not there…

But later, when I was alone with my fear, I cried for hope. He’s down to his second to last drug. The second to last hope.

Unless they create a new medicine…

“We’re look at a maximum of three years,” I said… “What happens next?”

“Honestly, really bad things happen,” he said.

Then he told me, “All of a sudden there was meaning… The desire to connect with meaning overwhelmed the time I had for the meaningless. In some ways, you can’t understand it. And the one thing I’ve come to understand completely is there’s only one thing in your life that matters and that’s the quality of your relationships. It’s such a cliche. You can look back at thousands of quotes from people who are old and dying and they always talk about the people in their lives. Nobody cares how much money you have when you die.”

I stayed silent. I wanted to catch all his words. And learn from them.

“Most of the things we sit around worrying about, you realize, at this stage, has no meaning. Now, it’s important. Maybe. Ya know, it’s important that I have a job, but the job itself only has the importance that you place in it.”

I hope this podcast is a special moment for you like it was for me. I took it as a chance to step back from my life. And the problems I think about over and over again.

This interview allowed me to care for a friend. And I hope it lets you care for a stranger. That’s something I want to do a little bit more each day. Until the day is full with selfless thoughts between selfish thoughts.

Maybe that’s part of the medicine.

 

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The Greatest Pleasures In Life

At age six, Jaqueline Du Pre, was running, cello over her head, down the performance hall where she was one of the performers that day.

She was smiling and laughing and running.

A janitor, figuring she must have just performed and was relieved and happy at how she did said, “You must have just performed. Congratulations!”

And she said, “I didn’t perform. I’m about to!”

—-

She died at age 42 in 1986. She’s one of the greatest cellists in history.

But that day, at age six, she was so excited to perform that she was running TO something.

She was running towards an exciting and uncertain and even scary future (“I have to perform and do well!”). She wasn’t running with relief and the fading of fear. She was running towards the fear.

She grew up to be one of the greatest cellists of all time.

I have to give a talk later today and tomorrow. I’m always nervous as hell. And then standup on Saturday.

I have to teach myself to run TOWARDS something, with cello overhead.

I want to do this every day.

Laughing, happy, excited. I am about to perform!

---

Happiness is a scam.

I wrote the above post about DuPre a year ago today.

I am always trying to make my articles “evergreen”. And here it is: I can post the exact same article today.

It’s to remind me how important it is to run TOWARDS something.

To DO rather than plan and think and analyze and hope.

To ask a question and leave it in the air, unanswered, floating, but simply asking it. Even that is “DOING”.

To “choose myself” rather than waiting for others to choose me. Ultimately, if I choose myself it means I am choosing freedom.

How can I take a little more control today, that I didn’t do yesterday, over the things I value most? How? HOW?

—-

A good friend of mine has a family member in the hospital right now. He is depressed and having problems.

Too often, we chase happiness: the next party, the latest drug, the next “love”, the clapping of others, the salary increase, the promotion, and all the other metrics society has approved as “worthy” for us.

But I told my friend what I always remind myself.

Happiness is useless.

What is useful:

COMMUNITY:

Good friends and relationships. 100% of the people in my life need to add to my life, just as I hope and strive to add to theirs.

IMPROVEMENT:

The goal is the direction. I want to be better at the things I love to do: a kinder person (father, friend, relationship, etc), a better writer, a better performer (podcast, speaking, standup, etc etc), healthier.

FREEDOM:

What is freedom? It’s not money. I’ve had it all and it didn’t give me freedom.

Money is good to pay for experiences and conveniences and pay for the bills. It’s certainly important.

Money is often the prison door. But it’s not locked.

Money will solve our money problems. But it is not the key to freedom.

Freedom is that feeling: to run TO something.

We know when we are free when it’s in our heart. In our bodies.

It’s that feeling of curiosity about the world around us. And permission to ask the questions.

It’s that feeling of “I learned today. Even if it was painful and horrifying”. Because almost every moment of new freedom, involves figuring out what prison is enslaving us.

The prison might be a job, a relationship, the incorrect goal, the wrong direction, or just a feeling that something is amiss.

“I chose myself” is that feeling of, “I can be myself. Even if I don’t really know who that is and I never will. Even if I feel like such a failure most of the time.”

“I choose myself” is that feeling of, “I can run towards something, not FROM something”.

My idea list for today: what are the ten things I am excited to be running TOWARDS.

Hopefully one of those is you.

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Ep. 287 – Scott Galloway: How the Four Most Influential Companies on the Planet Took Over the Market and Changed Humankind

I don’t know where to begin. I’m a fan of Scott. I think he reminds me of someone I went to highschool with. He was bright and always cursing at the right time. I remember laughing. Because I felt close to being free. But he was the one with the ability to put himself in the middle of controversy.

That’s something I (still) can’t do.

He’d say eff this or eff that. Part of me felt compelled to egg him on. But he didn’t need it. He was comfortable being cynical and right.

Scott Galloway does this with business. I watch his weekly  “Winners & Losers” videos where he tells you things like “Brands are dying” and “Amazon will be broken up” Then he’ll dress up like Spock and I’ll lose my mind.

I get these videos emailed to my phone. And I’m also subscribed to his YouTube channel.

He came on my podcast to talk about his new book, “The Four: The Hidden DNA of Amazon, Apple, Facebook, and Google.”

But we also talked about his past: creating and selling companies. Being on the board of The New York Times, wanting to salvage the newspaper industry (his idea back then was brilliant).

“I got laughed out of the room,” he said.

“What was your idea?”

“That the stupidest thing we did is buy into this bullshit lie that ‘information wants to be free.’”
He’s right. I remember the beginning on the internet. We gave information  away… And now they’re profiting off us. Scott called it “the hot girl effect”

“Everybody wants to hang out with the hot girl,” he said. “So, to say you’re doing a deal with Google made you feel younger and more interesting.”

They said “information wants to free.” So deals were made.

He told me exactly how he would’ve turned it around. And I felt like I was listening to the possibility of new reality.

That’s what Scott Galloway brings to the table. Beyond strategy or analysis. Beyond brilliance, he brings possibility. And teaches you that it’s not over.

“The Four” are winning.

But I told Scott nobody really cares. Nobody cares which one of these companies “wins.”

I’m interested in is learning how to win too. I want to know HOW Amazon, Apple, Facebook & Google became influential. And disruptive. So I can be influential and disruptive, too.

Scott said all Fortune 500 CEO’s have one thing in common… or at least “450 of them have one thing in common.”

They’re likable.

“Even the ones that are psychopaths?” I said.

“Yeah…”

He explained: ”During the day these people are Darwin and Darth Vader, make no mistake about it. They play full body contact business and they make very brutal decisions. They dominate markets. They put companies out of business. And they don’t put warning labels on your iPad even though your kid has a crack-like addiction to the thing.”

He called them “wolves in sheeps clothing.”

Zuckerberg, Jobs, Bezos, Page, Brin.

But then he told me the principles they standby…

There’s five in total.

And we go through them all on this podcast. Listen learn HOW you can copy the 4 most on influentialal companies

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Ep. 286 – Dennis Woodside: How Do You Know When Something is The Next Big Thing (Advice from Dropbox’s COO)

Dennis Woodside left Google, for DropBox. Everyone thought he was crazy.

DropBox was this little tiny company.

What was he thinking?

“So you ask why I would go from Google to Dropbox. Just play the movie forward. Where’s it going to be in ten years? It’s logical to me that the company that pioneered this notion of putting your files in the cloud is going to have all kind of opportunities and going to solve problems for everybody in the world. A lot of people don’t think that way. They think very linearly. That’s how we’re taught as kids. That’s how you’re taught in college.”

(And that’s how Dennis was taught to think in law school. But he got out of that rut. More on that later…)

“You have to rewire your brain a bit,” he said.

You have to ask yourself, “What trends do I understand to be true?”

And “If I extrapolate that trend to its logical conclusion, what does the world look like?”

That’s what Dennis did. And that’s how he found Google. And later, Dropbox.

He said Google was tiny when he first joined.

“What year?”

“2003”

There were only a thousand employees.

“When I joined Google everybody thought I was crazy because it was a little tiny company,” he said, “but I felt one of the most exciting things you can do with a career in Silicon Valley is to help grow a company. And be there early… There’s a lot of uncertainty. And competition is really hard. You have to figure everything out. That’s the hardest part, but the most rewarding.”

Dennis is now the COO of DropBox. How did he go from lost lawyer to a leader in Silicon Valley?

I wanted to know.

“Ultimately, I realized I wasn’t going to be a great lawyer,” Dennis said.

This is where his career path changed from one end of the spectrum to the other. He reinvented. He learned a whole new set of skills. And he adapted to an ever changing digital world.

Most people are thinking about the next ten days, Dennis is thinking about the next ten years.

He saw DropBox as a pioneer. And is vision paid off. DropBox is one of the fastest growing companies maybe ever. And there are billions of people who are signing up every month.

I wanted to learn how to cultivate that same skill. The one that lets you have a vision. And believe in it.

Also Mentioned:

• Sapiens: A Brief History of Humankind by Yuval Noah Harari
• International Refugee Assistance Project – one of DropBox’s clients

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