Born On Third


This is the 200th Sunday Moontower since this experiment began in March 2019. I’ll stray from the typical format for this one. No options talk. This is about spirit. Sprinkled with some middle-agedness and being a parent. And flourishing. Let’s wind through some ideas —you can rummage through them and keep what you need. Maybe not what you want, but what you need.

As an audience you are strivers. Addicted to growth. Always dissatisfied. Looking for an edge. But you’re also self-aware. The most viral Moontower post in 200 issues was Ambition As An Anxiety Disorder. You get it.

Alex Lieberman, co-founder of Morning Brew, sold his company for $75mm before he turned 30. While only a handful of you will relate to this level of wealth, your aspirational selves will see his reflection as honest:

I have very real financial anxiety.

The fascinating part is I never used to.

I’ve talked to 100+ founders and they’ve shared the same feeling.

Only after selling Morning Brew for life-changing money has rumination & fear around finances lived rent-free in my head.

So why is that?

If I rationally have enough, why doesn’t it feel like enough?

I’ve spent a TON of time thinking about it & I believe it boils down to 4 things:

  1. Learned scarcity mindset

What caused this?

A combo of zero visibility into finances as a kid, family members talking about $ anxiously, and my dad passing, leaving no family breadwinner.

Plus, a dose of imposter syndrome that I was more lucky than good with Morning Brew, which leads me to believe what I have in the bank is all I’ll ever have.

“Protect the nest egg at all costs” has become my motto.

  1. Greater visibility into cost of life

I never realized how expensive life was growing up.

But now that I’m married, living in a HCOL city and I’m eyes wide open to the costs of a family, this knowledge makes me ruminate more about $.

Shit’s expensive.

  1. Comparison to others

When talking about money, wealth is all about your reference point.

I’m in a text group of founders who sold their businesses.

To some I’m wealthy, but when folks are worth 9-figures and talk about flying private and building their 4th billion dollar business, I don’t feel wealthy financially.

Comparison really is the enemy of contentment.

  1. Feeling of importance

In our society, especially in the US, professional success & financial success are treated as high status.

They command respect, they get you access, they create attention.

We all want more of what makes us feel important & valued and I’m not immune to this feeling.

I responded to his thread with my own take, but we’ll get to that later. I feel like we need to tear down to build back up to a healthier perspective. Alex is ambitious. His early triumph has summoned demons successful people usually don’t meet until middle age.

Tom Morgan’s diagnosis in What Nobody Tells You gives me shivers (emphasis mine):

I frequently encounter people in various degrees of distress caused by being stuck or lost, mostly professionally. I offer them all a profoundly optimistic insight. I believe your present suffering is directly proportional to your future potential. I can’t see how it could be any other way. If you had no latent potential, and were content to be stuck in a mediocre life, there would be no psychological pain.

The vast majority of us start our professional lives as parts of a larger organization. This can provide us with marketable skills and necessary discipline. But it sometimes means adopting a professional persona that increasingly conflicts with your internal sense of integrity. The mask that eats your face. Too often we’re paid to stagnate, not to grow.

Contrary to a lot of self-help and spiritual literature, I’m not sure that we can travel from “corporate value” to “personal value” either quickly or easily. This is because in order to get paid to be yourself, you first need to know what your unique gifts are and then match them to what the world needs. This process often requires an intense suffering you wouldn’t voluntarily buy, even if you could find a guru crazy enough to sell it to you.

A substantial benefit of private wealth, for you or your family, is that it can provide some shelter from the storm during a transformation. As long as it doesn’t get so comfortable in there we forget to change.

“Your armor is preventing you from growing into your gifts.” Only once we’ve started to do that, I find economic value often follows. The degree to which your outer life sometimes reflects your inner life is nothing short of mystical. You always seem to have to take the first step yourself, to cross the threshold voluntarily. It’s easier to act yourself into a new way of thinking, than it is to think yourself into a new way of acting.

Once you hear the call to adventure, you have the choice of the pain of stagnation or the uncertainty of exploration. Both are impossibly daunting, but only one of them definitely ends in a literal or metaphorical death.

This line knocks:

If you had no latent potential, and were content to be stuck in a mediocre life, there would be no psychological pain.

The pain comes from not wanting to answer. Scratch that. We want to answer. More than anything actually. The pain comes from our subconscious knowledge of what it takes to answer.

Look at what Trent Reznor tells Rick Rubin in a recent interview:

Purple Rain had come out and at that time [Prince] was playing most of everything himself. What marveled me about him was how realized he seemed as an artist. I could identify a song with his guitar playing or the vocal or the drum program, and I kind of felt like it may not be virtuosity in all those things, but it was a point of view.

Around that same time, I realized I’m wasting my time in other people’s bands because what I’m really doing is trying to appear busy — a recurring theme in my life. Avoiding something that’s scary because I’m afraid. I was afraid of finding out that I don’t have anything to say.

I know if I like something or don’t like something but something my piano teacher told me haunted me “You know, a great performer doesn’t mean a great artist and a great executor doesn’t mean a great composer.”

It’s obvious, but I hadn’t really thought of it that way. And part of me was thinking “What if I find out I’m a shitty writer?” I don’t know. But I didn’t want to find that out. So a way of not finding that out was just avoiding it by feeling busy.

Trent’s eventual success required his fear of failure to concede to his fear of living like a shadow.

From writer Steven Pressfield:

“Sometimes, when we’re terrified of embracing our true calling, we’ll pursue a shadow calling instead. The shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.”

I had to overcome fear to leave my job when I felt I was being paid to stagnate.1

I was filling a tank without a thought as to where I wanted to go.

I remember brainstorming ideas with Paul Millerd shortly after leaving corporate life. We were going back and forth but then he paused. He recognized a pattern in my language that he’d seen in the hundreds of conversations he’d had with friends in transition:

You’re doing the thing everyone does at the beginning of a solo path — you’re looking to be saved. No company, no other person’s playbook, or metric of success will save you. The only thing that matters is coming back to the thing you are meant to do.

You must do it on your terms. Men waste years trying to avoid this.

Dammit Paul.

He could hear the fear buried in the theater of business talk. I knew it was true when he said it.


I have a reader friend, Matthew Michalewicz, whom I chat options with occasionally. One afternoon, he asked for my address. He wanted to send a self-help book he had written several years ago. I might indulge in the occasional self-help podcast or article but it’s not something I want to make an 8-course meal out of. Still, I built a lot of respect for him through our conversations. I pushed it to the front of the queue when it arrived.

The book shines in its methodical approach to achieving goals (the topic of goals is a whole other can of worms — I’m not especially goal-oriented in the first place. I am, without fail, my worst enemy and maybe Matthew could see this). But the book’s most shining moment is how it talks about fear.

Here are excerpts from Life In Half A Second:

  • The more I’ve thought about fear over the years, turning it over in my mind, analysing it, the more I realized that fear = progress. Whenever I felt fear, it meant I was making progress, I was moving towards my goals. And because my goals were always something new, something that I had never done or achieved before, I was always leaving my comfort zone behind and finding myself in a perpetual state of discomfort. Had I stayed stationary in life, in the same business, same country, same everything, then my fear would have departed. But it’s impossible to achieve success without moving out of our comfort zone, and for that reason, it’s impossible to achieve success without fear.
  • Cavemen who possessed a heightened sense of fear were more likely to survive and reproduce, it means we are the offspring of the most paranoid and fearful cavemen that ever lived. The brave and fearless humans who explored deep caves, ate unknown plants, slept in the open, and approached wild animals, are no longer part of the gene pool. What’s left are the fear-soaked that make up genes of the Homo sapiens species as it exists today. In our climb from flint and fire to the modern age, fear has protected us – it has been a prerequisite for survival. But as our environment changed – as we migrated from caves to cities, no longer fleeing from predators or fighting frost and famine – our heightened sense of fear remained the same. We tend to forget that everything we are today, we inherited. We’re still wired for survival, but living in a world where that wiring is working against us. And since there are no wild animals to fear, we direct our survival mechanism in other directions – the wrong directions to fear embarrassment, rejection, failure, criticism, and more.
  • I sometimes think that the difference between animals and humans is not self-awareness, intelligence, or the presence or absence of a soul, but in what we fear. When an animal falls, its fear is centered on its well-being and survival. If they’re injured, they may be unable to hunt, escape a predator, or protect their offspring – it might be the end for them. But if a human slips on a banana peel and goes flying into the air, feet up, arms flailing, onto their back in the middle of a busy street, their immediate fear has nothing to do with their well-being or survival, but with their self-image. ‘Did anybody see me fall?’ they think. How embarrassing!
    [Kris: Remember what author David McCraney said —

    The great sociologist Brooke Harrington told me that, if there was an E=mc2 of Social Science, it would be: the fear of social death is greater than the fear of physical death. If your reputation is on the line, if the ship is going down, you’ll put your reputation in the lifeboat and you’ll let your body go to the bottom of the ocean.]

I’m going to paraphrase the remedy from the book:

Almost all fear is learned by association (there’s a citation about the only inborn fears being falling and loud noises!). Similarly, fear can unlearned by association. Fear can be fought with:

  • Visualization (by pre-familiarizing)
  • Desire
  • Be around those with similar goals
  • Knowledge
  • Backup plans…and remembering that regret from trying is short-lived. Regret from not trying is deathbed stuff.

Back to Alex’s financial insecurity fears.

An amazing bit of advice comes from Graham Duncan’s Letter To A Friend Who Just Made A Lot Of Money. It’s a must-read but the directly relevant quote is actually via Taleb:

When you become rich, the pain of losing your fortune exceeds the emotional gain of getting additional wealth, so you start living under continuous emotional threat. A rich person becomes trapped by belongings that take control of him, degrading his sleep at night, raising the serum concentration of his stress hormones, diminishing his sense of humor, perhaps even causing hair to grow on the tip of his nose and similar ailments. Seneca fathomed that possessions make us worry about downside, thus acting as a punishment as we depend on them. Even more: dependence on circumstances — rather, the emotions that arise from circumstances — induces a form of slavery.

Graham adds:

I meet a lot of rich people and many of them are what Taleb and Seneca might describe as surprisingly fragile — the events of fate pose more downside than upside for them. Don’t let your new fortune make you fragile!

responded to Alex’s tweet thusly:

This is an honest tweet so respect to that.

Many people will be shocked to discover that financial freedom has little to do with your finances.

Rich and poor people alike are trapped in the prisons of their mind. Comparison can be the enemy. But if you compare to people whose minds are financially free and think about why that might be true it can inspire.

I live in the Bay Area. I’m a chump. I have no exits. Just a run-of-the-mill high earner, one of thousands of neighbors. I have money concerns. But they don’t tip into anxiety because as long as you have your character and some skills you’ll find a way.

Doesn’t mean it will be easy but you will find a way to make it rewarding still. Being poor is off the table. What a fucking amazing place to be to be able to feel that way. Look around. You know how many people I meet that have less than me despite more talent?!

Guess what? That’s true of you too. You’re financial bounty has nothing to do with your skill. That you are successful at all does, but the degree is a lot of luck.

Every a.m. be thrilled to wake up. Know you live in unrivaled historical security…then go make something of your dissatisfaction. It’s the gift of fuel.

Wrapping it up in financial insecurity? That’s unnecessary and blind-to-the-reality-of-the-world brainworms. Your dissatisfaction should come from the gap between what you can do and what you are doing.

Pass it forward

I lied earlier. There’s an even brighter moment in Life In Half A Second. The bit about self-belief.

Michalewicz calls self-limiting beliefs belief barriers. Just as fleas will acclimate to a lid on a jar and not jump out when you remove the lid, or how the 4-minute mile was broken many times after Bannister first set the mark, our beliefs have a tyrannical impact on what we will attempt.

Notable excerpts:

  • More important than accents, vocabulary, and behavioral quirks is the influence our environment has on self-belief. The greatest influence from our childhood is what our parents make us believe about ourselves. Some kids are lucky, like me. My parents always said I could do anything, be anyone, and I grew up believing that. The only thing that separated me from what I wanted in life was hard work. I believed that as a child and I believe it now – it’s the truth.
  • Other kids aren’t so fortunate. Their parents might neglect them, ignore them, never be around, or tell them they’ll never amount to much, that they’re nothing special, that there are limits to what they can do in life, to who they can be. Such kids have difficulty in school not because they’re incapable of performing well, but because they’re incapable of believing they can perform well. Studies show that a child’s self-belief has more bearing on academic success or failure than actual competence. And when these kids become adults, they spend decades trying to unlearn false beliefs, discovering that the world isn’t flat after all, that what others have done, they can also do. Some succeed, others don’t. That’s why the greatest gift parents can give their children is self-belief. The beliefs kids develop and hold true about themselves become vital forces in their success or failure in everything they do in life.
  • Choose people around you carefully as they will either help or hinder. Change your environment to change your self-belief.

The emphasis on environment is hopeful, compassionate, and ultimately, I believe, correct.

I was always grateful for how I was raised. My mother saw that education was the ticket. And she pushed me without a lick of restraint or shame. When I said I’d go to Rutgers on a scholarship because that’s what we could afford, she assured me that we could make Cornell work.

I grew up thinking, hell not thinking, expecting to do better than my parents. I expected to move away from a place that didn’t feel right for me. I expected to be rich. And when I read those excerpts I realized I had taken the self-belief for granted.

My mother dragged me right through my belief barriers.

I had never quite seen it that way. The failson who we traditionally say is “born on third” is lucky only in the narrowest sense of survival. Not thriving. (At the risk of sounding preachier than I already do —you insult yourself when you envy rich idiots.)

tweeted this over frustration about policies that try to level math tracking in the name of equality. But the main point is to show what enviable luck actually looks like:

I grew up middle class in a blue collar town. Immigrant single mother. No college education.

She spent every dime on education for my sister and I who both went to Cornell.

I had a math tutor in 1994 for $50/hr.

I went to a LaSalle all-boys HS that was exceptional.

My mother noticed I had an interest in words at age 12. Bot me and my friend the whole series of vocab books that we liked in school.

Crushed them all and had a private contest of how many ridiculous words we could stuff into our school essays.

My mother couldn’t afford one of those years in HS. Begged the school on my behalf. They comped the tuition that year.

She was a bulldog on helping me get non-loan aid at Cornell.

A middle class person that values education will find a way. The only people who won’t are truly the most vulnerable. And in the process you have made that middle class person’s life that much harder with this artificial ceiling shit.

If this is enviable luck, then this is really what you want to give people. Be someone who teaches others to fish. And then let them do it.

I’ve hinted at this before — the proudest moments I have of my kids are when they are courageous. In the moment it hurts to watch. But my spirit knows what they need. My mind is a sniffly hall monitor writing meaningless permission slips. Without risk, your spirit will die.

Give your children the gift of self-belief. That means opportunities to practice persistence and courage. They won’t believe it unless they earn it. You can’t just do this with affirmations. They need a chance to earn self-confidence. They need room to fail and struggle. When you take that away, you are comforting yourself in the near term. But you’re robbing them.

When Alex Lieberman says, even after he’s hit it big, that he still feels anxious, he’s doing you a favor. Read between the lines. It’s a silent scream “THE FAT FINANCIAL SAFETY NET FOR YOUR KIDS IS NOT THE ANSWER YOU THINK IT IS!”

If that’s what you’re busting your ass for, you’re trying to disappear your own fears when what you really need is to help your kids to charge into theirs.


For what it’s worth, I’m not saying I do this well.

In fact, I just realized — I’m writing to myself.

To the next 200 Moontowers 🌛

I have to say — the gift of your attention is so cool. Thank you.

Stay groovy,


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