Download The Podcast MP3

I wanted someone to interview me.

And Amy Morin was the perfect choice. She’s been on the podcast a few times. And she knows me well.

“I’ll try to wear my mentally strong author hat rather than my therapist hat,” Amy said.

I interrupted.

“No. Wear your therapist hat.”


“Yeah. I need that.”

“Game on.”

I could tell she prepared. She chose questions that led deep into my successes and failures. We talked about everything from anxiety to my writing process. But also:

– Anxiety

– Writing

– Reinventing yourself

– How to say “no” (and when to say “yes”)

– WHY you should invest in yourself & how to diversify that investment

That’s all in Part 1 of the interview…

And in Part 2 (out Thursday), we talk about:

– Going from idea to implementation (and why so many people get stuck at the execution phases)

– Learning new skills

– Some of my personal investment philosophies

– Why I think I’m stupid (and how this helps me)

– Burnout

– Relationships

– Building your inner circle

And more.

(Subscribe to make sure you get to hear Part 2)

I put together a list of 10 questions Amy asked me. And let me just say these barely scrape the surface of everything we talked about.

QUESTION 1. How do you say “No”?

I’m historically bad at saying “no.” I used to lose friends over this. That’s how bad I was. I’d get invited to do something and instead of saying “no,” I’d just ignore them.

I thought it was easier for me to do this because I don’t like confrontation.

But it backfired.

I was losing my network and my friends. And, eventually, these people stopped talking to me.

So I decided to learn how to say “no.”

And it took me a long time. I had to figure out what to say “no” to and also HOW to say “no.” I even wrote a book about it called “The Power of No.”

Someone might say, “Why are you writing a book about how to say ‘no’ if you don’t know how to say ‘no?’” And the answer is simple.

I wanted to learn.

I can’t learn anything from exploring what I’m naturally good at it. Because I don’t know HOW I got good at those things. There’s no experience there. No hard work.

The things I struggled to learn are deeply ingrained in my experience. So when I write, I start with the low point, whether it’s being broke or being in a bad relationship or being suicidal. There’s an arch. Similar to any other arch where finally at the end I’m able to come back and say what I’ve learned.

So this is what I learned about saying, “no.”

In your 20’s you should say “yes” more than in your 30’s and 40’s and so on.

I say “no” to almost everything now.

My kids and relationship come first.

Then my creative work (writing, podcasting, comedy). These are the things that excite me the most. Then, I focus on business.

Saying “no” to one thing is equal to saying “yes” to something else. I won’t go to a party over writing.

It takes years to master the art of saying “no”. I wish I learned my priorities early on. It’s not easy. And I’m still learning. It’s such a critically important aspect of every part of life.

Now instead of ghosting, I tell the truth. I don’t give a reason. Maybe that’s personal or whatever. But I try to be really honest and upfront with whoever’s asking.

QUESTION 2. How do you deal with anxiety?

When my anxiety was at its peak, I took Klonopin. I got horribly addicted.

It was the worst experience in the world.

Amy works with a lot of people who deal with anxiety. She’s a therapist.

“You’ve been really upfront saying, ‘I’m an anxious guy and here’s all the things I do anyway’, how do you do that?” Amy asked me.

“Anxiety, as you know, can be totally debilitating. And it comes from a lot of different sources. But I would say for me, anxiety is linked to prior trauma or feelings of low self-esteem. For instance, I’ll get anxious with money.”

I used to feel so much less confident about making money. And if I ever felt like I was in a bad money situation, I would get so panicky.

I would feel like I was having a heart attack. I couldn’t sleep. And I’d write on pads all night long trying to figure out how I was going to live.

But all this worry did nothing. Worry never accomplishes anything. It just wastes time.

I still get anxious, but I try to tell myself the anxiety is a tool. I’m aware of it, instead of living it.

What’s the worst that could happen?

QUESTION 3. Do you ever get a vulnerability hangover?

I have a rule. I don’t publish an article unless I’m afraid I’m sharing too much.

I use this rule 90% of the time.

It can get me in trouble. But there’s a tactic behind it. I’ll say anything about myself, so people know I’m telling the truth. It’s like a test. But I won’t say anything bad about anybody else.

“You share a lot of really personal stuff in your podcast and in the articles you write. Do you ever feel like you share too much? Is it ever awkward or uncomfortable for you when you share about your personal life?”

Amy called it a “vulnerability hangover.” I liked that. But my answer was “no” because I know that if I’m not close to the edge, then I’m not saying anything worth reading.

QUESTION 4. Do you think you can learn any skill you want?

I started doing comedy as an absolute zero beginner. And I’ve gotten good because I learned the microskills.

Every skill has microskills.

Look at basketball. There’s no one skill called “basketball.” There’s dribbling, shooting, running, balance, etc.

This is my method for getting good at any skill: Write down the microskills, study each one, and practice.

QUESTION 5. Do you struggle with imposter syndrome?

I used to think self-sabotage was fake. I didn’t think anyone would consciously make a decision to ruin their life.

But I used to self-sabotage all the time. And I didn’t realize it.

I did it with money. I did it with relationships. It was a blindspot that developed from having low-self esteem in those areas.

So when Amy asked if I struggle with imposter syndrome, I said yes. I feel like imposter syndrome and self-sabotage go hand in hand.

But I can combat it. What I do now is just try to be aware of when I’m feeling low self-esteem. Then I can find the source of my imposter syndrome. And maybe stop myself from sabotaging.

QUESTION 6. Do you actually think you’re stupid?

The first time I sold a business, I thought, “Oh I made a lot of money. That must mean I’m a genius. I’m smart in everything now.”

I thought everything I touched would turn to gold.

And then I lost all of my money. ALL of it.

So I had to teach myself not to be arrogant in that way. I have to tell myself I’m only smart in one or two areas. And stupid in almost every other area.

I have to be willing to learn all the time.

QUESTION 7. How much do you care what people think of you?

Sometimes, I’ll read articles about myself and some of them are unbelievably hateful. They make up lies about me. I don’t understand why. Hate hurts. But I get a lot of non-hate, too.

It’s common for people to focus on the hate. Because they’re more vocal.

Amy asked me, “How much do you care what people think of you?”

“Usually zero.”


She asked more questions.

“Do you read reviews about yourself?”

“Not really, no.”

“Do you read comments on your blog?”

“This is how I treat comments on my blog,” I said. “I don’t invite someone into my living room if I think they’re going to shit on the floor. If someone is just insulting me for no reason, then I’ll delete it. But I’ll engage in a debate.”

QUESTION 8. Where do you put your mental energy to set yourself up for success?

When I lived in Airbnbs I never cooked. I always ordered food out. And then I realized I was losing weight. Because you can’t order a bag of Doritos from a restaurant. And I know myself. If I go to a grocery store, I’ll buy junk food. And I’ll eat the whole bag in one sitting.

I called it the Airbnb diet.

I can only be successful if I’m healthy. Physically, emotionally and creatively.

“You only have so much time, so much energy, so many resources…” Amy said. “So how do you decide where to put it? And what about burnout?”

I do a little bit less of everything now.

I try to be 1% better at whatever I’m working on. And that compounds.

Because for me, the sign of burnout is that I’m not able to do 1% better everyday.

QUESTION 9. How do you implement your ideas?

The second time Amy came on the podcast, we talked about her side hustle. She was an open book about it.

And after the podcast aired, she got emails from tons of people saying “I’m going to do this, thank you so much. This was inspiring.” Some people had questions.

“I told every single one of those people, when you set up your website, come back if you have questions or problems. Or share your success stories.”

No one emailed her back. Because they stopped. And maybe gave up.

Amy asked me why…

“Do you think that’s a stumbling block for most people? They come up with an idea or borrow somebody else’s idea, but then they don’t do it. How do you go from thinking about it to actually doing it?”

“First, something has to excite you,” I said.

Sometimes people don’t know what excites them. I usually make a list of ideas. Books or articles to write. Businesses to start. Or ideas for other businesses and friends.

And then I’ll pick the idea I like the most and make another list where I bullet out 10 really easy execution steps. This lets me see if this idea is going to fail or not.

I’ll give you an example.

One of my friends said he was going “steady” with a woman. I didn’t know what that meant. Especially in society today.

He told me they each deleted their dating apps. And I thought, “What if there’s an app that can automatically delete dating apps off your significant other’s phone when you both sign up.” It’s the “going steady” app.

That was on a Saturday. On Sunday I specced out what the app would look like. I made a list of features it would need to have. Then I put the project on to see if there was anyone out there who could develop it for me.

I got back 30+ responses.

But all the developers said it wasn’t possible. Because an iPhone can’t see someone else’s apps.

The idea was bad. I was able to fail fast. And I learned something from it.

Anytime I don’t DO an idea, it’s because I’m looking at the goal rather than the process. Always start with the easy and actionable. The “now” steps.

QUESTION 10. How do you decide what’s next?

I’m thinking of starting a reality show next. Here’s the idea: I’ll teach you to be a millionaire.

I take 10 random people from the street. I’ll give them each a different strategy. I follow their lives over the course of a year. I’ll bring in celebrity coaches. And then I’ll either make them millionaires or… fail.

I’m convinced I can take anyone off the street and make them a millionaire.

But I’ve had this idea for a while. Maybe a year now. It wasn’t “what’s next” a year ago. But it might be now.

Sometimes, “what’s next” is a decision. And sometimes it’s just what happens…

That’s why I don’t set goals. I just try to be focused on what I love and what’s next comes.


Amy asked me at least 50 other questions. We had two hours together. Some of the questions were really hard. And some were as simple as her just going, “Really?”


I want to keep using this podcast as a way to experiment. A year ago I started experimenting with having more conversational podcasts and less straight interview.

Now I’m doing a YouTube channel, too, where I sit with the guest and analyze what we could’ve done better or differently.

And in five months, for my five year podcast anniversary, I’ll be doing some more (surprise) experiments.

Who knows. Maybe you’ll interview me next…

Links and Resources

13 Things Mentally Strong People Don’t Do: Take Back Your Power, Embrace Change, Face Your Fears, and Train Your Brain for Happiness and Success by Amy Morin

13 Things Mentally Strong Parents Don’t Do: Raising Self-Assured Children and Training Their Brains for a Life of Happiness, Meaning, and Success by Amy Morin

There Are Only 4 Times You Should Agree to Work for Free” by Amy Morin on Inc.

Ep. 259 – Amy Morin: 13 Things Mentally Strong People Don’t Do

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

Also Mentioned

My interview with Nell Scovell

My Google talk

The Power of No” by me (James Altucher)

“The Tonight Show” with Jay Leno

My latest book, “Reinvent Yourself

My interview with Richard Branson

My interview with Judy Blume

Parker Posey

Judd Apatow