The Profile: The Steve Jobs of Wall Street & the immortal startup founder

Good morning! And welcome to all the new Profile subscribers. I’m glad you’re part of the club :)

Today, I’m excited to share a guest column written by Trevor McKendrick, the author of a weekly newsletter called How It Actually Works and the chief of staff at Lambda School. I met Trevor in Austin, Texas earlier this year, and it didn’t take long to figure out that he has a fascinating story we can all learn from. I’ll let him take it away:


The Courage to Design Your Life by Trevor McKendrick

We all say we want to be contrarians in our professional lives: invest in the right startup, buy the underrated cryptocurrency, find the underutilized talent. It’s taken as gospel that going against the grain is where the greatest returns hide.

And yet for all the talk about being contrarian at work, we never talk about being contrarian in our personal lives. This is an area where I have some experience. Imagine rejecting the beliefs, rejecting the traditions, rejecting the entire foundation your family and predecessors laid before you. Imagine rejecting all that you stand for. Imagine questioning everything in a world that shuns independent thought.

I didn’t have to imagine. I lived it. Here’s my story.


The worst part about leaving Mormonism is you don’t know how to be an adult.

Having never sipped a cup of coffee, Starbucks menus were foreign words to me. The first time I ordered a drink at a bar I was asked if I wanted to “open a tab.” I had no idea what that meant, so I just said yes. In those moments, I realized just what I had done — I had given up a comfortable life for a blank canvas.

In the Mormon faith, your entire life is planned for you: Go to church every Sunday, go on a 2-year mission, get married in a Mormon temple, get a 9-5 job, have kids … you get the picture.

And yet, if you stop to think about your own life you’ll quickly realize how little of it was independently conceived. Getting married, having kids, being ambitious, buying a house… all these things that we assume are markers of The Good Life, when some of them might be terrible choices for certain individuals.

Human beings are programmed to want to be like each other. René Girard called this ‘mimetic desire,’ the idea that we naturally imitate the desires of people around us. This is useful when it helps us learn from each other and from previous generations. But taken too far, we become trapped by the thinking of other people, and we become too afraid to examine our unique individual wants.

As someone who dutifully went to church for three hours every Sunday for 26 years, went on a mission to Mexico, earned two degrees from Brigham Young University, and got married in a Mormon temple, it felt psychologically impossible to leave the Mormon church.

I’d had doubts — serious questions about Mormonism — since I was a freshman in college. But because the church was so integral to my life, I was always terrified to leave.

You don’t really realize it until you try to get out, but the church solves a lot of life holes for you. Simple and not-so-simple things like: How do I make adult friends? Who should I sleep with? When? Who do I meet when I move to a new city? How do I live a meaningful life?

And so the church wasn’t just the center of my life. It was the only way I knew how to live.

And then six months after I got married, I did something radical — I listened to my gut and finally left the church for good.


I’d been so bored and frustrated at church, listening to yet another speaker go on about some random nonsense that I knew wasn’t real. I was leaning my head against the wooden pew in front of me, scrolling through my phone week after week.

Over a few months I started attending church less and less. And casually, suddenly, I wasn’t going at all. It was the most freeing feeling in the world. Imagine getting a whole extra day of your weekend back! I got to stop wearing Mormon underwear. I was free to experience the full, beautiful, complex world.

It did have some downsides: my wife was very sad and her family was pretty shocked and disappointed. Thankfully I had an above average experience with them and we’re all on very good terms today. (My wife ended up leaving about a year after me.)

I was more afraid to tell my friends. At the time, I lived in Utah and my entire social circle was Mormon. Even though this was only some 7 years ago, it wasn’t nearly as socially acceptable to leave then as it is today.

One by one I told a few friends. I posted a few things on Facebook… no coming out announcements but enough to hint that I was no longer in the church. Most people reacted… fine.

My fears ended up being almost totally baseless. In fact, being an ex-Mormon is sometimes now even an asset. When I was in the church I didn’t even know what a dinner party was, and now being an “ex-Mormon” is my go-to dinner party story. People often love hearing about what it was like to leave.

But the point here isn’t that if you make a hard decision it will go well and you’ll be happy. The point is that “being a contrarian” means recognizing you will be OK if you make a bad decision, and then marching forward into the unknown. It means doing the things that you believe in your bones to be true, even though you’ll never know if you’re right until you’re on the other side. It means doing what you think will lead to the most fulfilling life, regardless of the views and thoughts of others.


We hate uncertainty.

We’re all afraid of making the big decisions — even if we think they’re the right thing to do — because we’d rather be certain about something that’s bad than uncertain about a potential good. Why? Because we want to protect our identity.

We’re afraid of big decisions because of how we believe the downside will affect who we think we are. We can’t even acknowledge it though, because to acknowledge it is to admit the possibility that we might not be who we want to be in the first place.

I know an entrepreneur who, after seven years of hustling to start his company, decided to instead move on and get his first corporate job at Microsoft. He wrote a fantastic post about it, which included this great line: “I prioritized the perception of me, over me.”

As is often the case, good things come out of uncertainty. For me, leaving Mormonism has given me a guide to making difficult life decisions. Below are some questions you can ask yourself to gain clarity:

1) How much do you care about truth?

We all say we care about truth, but most of us don’t. It feels better to stay right than it does to consider the full implications of where a new line of thought might lead. This is why I couldn’t leave for so long. I couldn’t grok what it would mean for my life if I left Mormonism. So I refocused on staying in and justifying why I’d still be happy. You have to be willing to mentally go all the way before you can truly consider a big decision. So often we’re merely looking for evidence to back up the easier decision.

2) What lies are you telling about yourself?

I tried to convince myself for years that I was OK with Mormonism. “I’ll have a good life. My kids will have good values. I’ll be happy.” These are insidious lies because they’re mostly true. They’re justifications to help me avoid making the harder but better decisions.

3) What are you willing to give up for what you want?

Once you figure out what you want, you have to identify the cost. As much as you possibly can, ignore thinking about the cost until you figure out what you want. It’s the conflation of the two that so often prevents us from deciding what we truly want in the first place.

The bottom line is that we often view big life decisions in terms of risk and reward. But for the biggest decisions, we often know what’s right in our deepest gut. What stops us is nothing other than fear.

It’s the same reason I couldn’t leave Mormonism: What was on the other side? What if I was wrong? What if I lost everything? At some point you know what to do, you just need to be brave and jump.

Living through the fear of seeing what’s on the other side is what makes life interesting, meaningful, and worth living.

What’s stopping you?

👉 If you liked reading this column by Trevor, click here to tweet so others can enjoy it too.

And now, on to this week’s profiles:

The Steve Jobs of Wall Street [**HIGHLY RECOMMEND**]
— The Socialist who renounced Socialism
— The world’s most regular actor
— The invisible boys
— The preppy retailer that lost its soul
The immortal startup founder


The Steve Jobs of Wall Street: Larry Fink, the 66-year-old chairman and CEO of BlackRock, has steered his firm through several crises since its creation in 1988. Considered a legend in the asset management world, Fink is seen as “the glue keeping this business together.” Who will be the candidate to replace the irreplaceable Larry Fink?

“You can’t replace a Larry Fink with a Larry Fink.”

The Socialist who renounced Socialism: Lenin Moreno, who spent years as a member of the Marxist Movement of the Revolutionary Left, ran for president of Ecuador on a platform of unabashed populism. And then, months into his presidency, he made a sudden political leap toward … democracy. Moreno launched a national dialogue on economic and political reform, railed against corruption, and worked to restore an independent press and judiciary.

“I won’t allow Ecuador to become a failed society, a failed state.”

The world’s most regular actor: When Billions star David Costabile is out in public, he typically gets, “‘You're that guy...What's your name again?’” And he really doesn’t mind the anonymity. Why? Because looking like your average Joe has served his career well — he’s played a quirky chemist on Breaking Bad, an icy Baltimore Sun publisher on The Wire, and an anonymous banker on The Office. Whatever he’s doing, he’s recognized as that.

“It allows me the freedom inside of my job to do lots of different things. I do comedy and drama. And I play fat guys, and ineffectual losers.”

The invisible boys: This profile follows a young boy whose mom was deported to Honduras when he was 15 years old, and he ended up at a nonprofit that supports and houses children who have been separated from their parents. This story explains what it’s like to grow up in a facility for underage undocumented immigrants, where more kids are fighting longer than ever to stay in the U.S. because, “We’re all better off here than somewhere else.”

“I don’t have patience, but I don’t have another option.”


The preppy retailer that lost its soul: J. Crew — the retailer built on privilege and prep — is trying really hard to get back on its feet. Since 2014, J. Crew has been shedding money, influence, and executives. The last CEO who was supposed to stabilize the business lasted a mere 16 months. To make matters worse, its insurmountable debt made any turnaround plans the equivalent of “rearranging deck chairs on the Titanic.” The question remains: Can J. Crew find itself—and its customers—again?

“There was room to improve. Our image was a little elitist, a little posh, very homogenous.”


The immortal startup founder: When Eugenia’s best friend died, she re-built him using artificial intelligence. Gone were the days of static memories relived through old text messages and photos. This futuristic project gave her comfort during her time of need, while giving us insight into how our digital footprints will be used once we’re gone. This half-morbid, half-inspiring story is one of my all-time favorites because it will leave you with more questions than answers.

“Is it letting go, by forcing you to actually feel everything? Or is it just having a dead person in your attic? Where is the line? Where are we? It screws with your brain.”