Three Things #48: December 18, 2022

Things I Regret

It’s that time of year again: time to reflect on our successes and failures and on how we can do better in the new year. Time to set some new year’s resolutions (still working on those). I tried thinking of lessons learnt this year, or things I wish I had known a year ago, but I ended up thinking about things I wish I had known, or had done differently, years ago.

If only I had met Ms. Lee Ester Alita Lee a little earlier, I might’ve avoided these mistakes. We all need a friend who’s the Most Truthful & the Best! Photo by Different Resonance on Unsplash

Thing #1: Waiting Too Long to Have Kids

We had our first child in the middle of this year. The experience has been joyful in a thousand ways—all the ways they tell you it will be, and many many ways I didn’t previously expect or understand. Having a child has filled my life with a powerful sense of energy and purpose. My son by default fills every nook and cranny of my life. When I have a few minutes in between meetings, I check on him, “chat” with him, or play with him. When I’m not sure what to do, or why I’m doing what I’m doing, I remember him and it gives me renewed sense of meaning and purpose. When I’m bored, loney, or frustrated, he’s always there to cheer me up. There are no words adequate to describe what you feel when your baby smiles at you.

I expected being a parent to be hard. That’s what they tell you. That’s what everyone says, what Hollywood wants you to believe. When you think of parents with babies, especially urban parents working stressful, full time jobs, you think of sleepless nights and microwave dinners, moribund social lives and trying to juggle six things at once and a general, overall harried, flustered life experience.

That is not at all what my experience has been. Sure, there have been harried, stressful moments, but they’re few and far between and just totally dominated by all the fun, funny, joyful moments. They don’t tell you how fun and joyful the experience of being a parent is (probably because, again, words fail). Every day is quite literally more unique, more interesting, more fun, and full of more unexpected discovery and joy than the last because the baby matures so quickly. If you’re able to really be present with the child, to at least attempt to see the world through his eyes, it’s even more fun and more eye-opening.

Having a child has made me a better person in a thousand ways. It’s made me more careful, more diligent, and more thoughtful. It’s made me more productive, not less, because I focus more in the limited hours I have to get things done and because my work is imbued with a far deeper sense of meaning than ever before. I used to have some vague notion of making the world a better place in an abstract sense for people over there, somewhere. I still feel that, but I also feel that I’m working directly, every day, in a very concrete way, to make my son’s future better. The difference is enormous.

Let me be blunt: everything you’ve heard, been told, or read about waiting to have kids was a lie. It’s something you unfortunately just cannot understand until you’ve done it, but the great travesty is the way in which modern society has convinced us all that we’re better off childless well into our thirties. It’s abominable. If I had known, if only, I would’ve gotten a much earlier start. It’s one of those epiphanies that, once experienced, changes everything and that you simply cannot unsee.

We might get lucky and have a second or even a third child. Maybe. But we should’ve started a long time ago. I want to be a young dad to my children, and conception, pregnancy, childbirth, and recovery are far easier on younger women. I don’t know what the sweet spot is, and obviously it depends on the couple and their life situation, but I think 29-30 would’ve been ideal for us: financially stable and with most of the BS of our twenties behind us, but not too late. If you’re younger than this and you’re considering having kids later than this, please reconsider. I’d be happy to talk about it and try to convince you to change your mind! 🙂

Over the past few months I’ve had plenty of conversations with friends in their twenties, and their responses are so predictable they feel scripted: I’m not ready yet. I’m nowhere near ready to have kids! It’s way too early. Etc. They’re wrong, but they don’t know that they’re wrong and I don’t know how to make it clear to them.

Sure, reconciling pregnancy and parenthood with a busy career is challenging, doubly so for women. But the best things in life are always the most challenging. Where there’s a will, there’s a way. Work is important, but family is far more important over the long run. Be creative and you will find a way to make it work. Fortunately we live in a time and place where it’s possible to be far, far more flexible in our work routine than ever before! No excuses.

My advice: have kids early and often. You’ll thank me later.

For more: Read If— by Rudyard Kipling, one of the greatest poems ever written. If you have a child, read it to him or her! If not, imagine reading it to your first child.

Thing #2: Not Getting Off the Career Ladder Earlier

During university and for the first few years of my career I sort of followed the rules. I went to relatively bad public schools in rural and suburban communities, so I must’ve felt that I had something to prove when I got to college. I felt fortunate to get into a good college and I worked really hard, checking all of the boxes, doing all the things I thought you were supposed to do to get ahead. At the end I recruited for the sorts of jobs I thought you were supposed to apply for coming out of a top engineering program: big tech, finance, and consulting. I started a career at a hedge fund in New York. I left after a few years for business school. Up to that point, I had spent 11-12 years working really hard and playing by the rules, working my way up some perceived career and social ladder, trying to “get ahead.” Of course, I was totally focused on the things I thought society expected of me, things like wealth and status, and not at all on holistic health: social, spiritual, etc.. I was in a rat race and I didn’t even realize because everyone around me was, too.

The first year of business school, something changed. I can think of two triggers. The first is a personality profile called a Career Leader survey that I took at the beginning of the MBA program. You spend an hour answering questions, comparing scenarios and expressing preferences—e.g., “Would you rather be influential in your field, working long hours, running a successful business, or would you rather be a stone mason who earns very little but has a lot of time with a large family?” At the end, the system spits out recommended roles and industries on the basis of your profile. At the top of my list were things like Entrepreneurship and Management in Science and Engineering. Finance and Consulting were nowhere near the top of the list.

The second was my first time participating in a Startup Weekend. I can’t speak highly enough of the experience. It was exhilarating and it was the first time I truly felt that I had found my calling. I showed up intending to just observe or to join a team, but ended up pitching a wacky idea on a whim, recruiting a team, working on a prototype all weekend and then giving my first startup pitch. After having been pigeonholed for years into a very narrow role with very few creative degrees of freedom, the ability to lead a team, be creative, think outside the box, and get things done quickly was a lot of fun, challenging in new ways, and deeply rewarding.

On the basis of these two experiences, I decided to try my hand at entrepreneurship for real. I cofounded a tech startup with a classmate during the first year of business school, and it went pretty well. Even at this point, I thought I’d hedge my bets and reevaluate how things were going at the end of the summer. Plan A was still to have some fun, try my hand at something new, and then go back to what I knew best: the world of finance. I thought it’s where I’d find the most success and have the biggest impact—a sort of over-rational analysis based on a deeply flawed understanding of how the world actually works (which, incidentally and dangerously, is precisely the kind of analysis that Effective Altruism is based on).

There was no single, magical moment when I realized I was happily, permanently off the career ladder. It was a gradual process. Things went well with the startup, we decided to keep working on it after school, and I skipped recruiting season completely, which was pretty scary (since a high paying post-MBA job is the reason most people go to business school in the first place). After the startup I stumbled into crypto and the rest is history.

So far it’s worked out. I’m far happier today than I was while in finance. I feel a much greater sense of freedom and purpose. I try not to live a life of regret or spend too much time pondering what ifs, but I can’t help but feel that I could and probably should’ve walked away from the hedge fund job earlier. I was there for six years and the learning curve had already flattened out considerably. There were limited opportunities for growth and career advancement. I ended up being one of the oldest students in my MBA course (most work for about three years prior to business school). And it’s never too soon to try your hand at entrepreneurship. In fact, I probably would’ve been just fine if I had skipped business school, too, and invested that time and money into a startup instead, but the counterfactual here is much harder because I didn’t have the network, the breadth of skills, the confidence, or the pure chutzpah to do it before business school.

In retrospect, when I finished college I was optimizing for the wrong things. I was blindly chasing prestige, recognition, and financial gain—because I didn’t know better and I never really stopped to think about my true motivators—in spite of the fact that I’m not really motivated at all by those things, relative to things like the ability to work with great people, intellectual challenge, freedom and creativity, etc.. I regret not spending more time earlier in my career reflecting honestly on the things that really matter to me—but I’m happy to report that I did eventually figure this out! It pains me to think how many people, especially young people, are toiling away at jobs and in careers they don’t love because it’s where they think they’re supposed to be or where they think society expects them to be.

It’s critical for young people to realize that there is no one correct, received, proper career path. Yes, college and internships probably still make sense for most people, but clearly not for everyone. And it’s hard to say more than that even in general. The only way to be truly successful in your career and in life is to be creative, think outside the box, chart your own course, and play by your own rules. In other words, define success for yourself before you try to be successful! This was always true, but it’s doubly true today because the world and economy are changing so rapidly and we can’t rely on things we could rely on even a few years ago.

It’s a big, big world, and getting bigger. There are many possible realities to explore, and many more to create. This is the attitude I’d encourage of anyone starting a career today.

For more: Try taking a self-assessment career survey! Career Leader is not cheap, but there are also numerous free tools available. Here are lists from Cleverism, Kellogg, and Harvard (I can’t personally vouch for any of these specific tools, but let me know your experience with them!).

Thing #3: Not Having the Confidence to be Totally Honest

For most of my life, I wasn’t totally honest with the people around me. We all tell little white lies all the time without thinking about it, as a form of social lubrication. But I told worse lies. I wasn’t entirely honest with my colleagues about what I thought of them, and in order to avoid conflict I didn’t always raise the issue or challenge them when I disagreed with them. Worst of all, I wasn’t honest with the people I loved most. I cheated on multiple partners and couldn’t bring myself to tell them. I misled some partners about my feelings or intentions.

I justified this behavior to myself on two grounds. First, I told myself the behavior was temporary. I would get certain behaviors “out of my system,” and there would come a time when I’d be ready to “man up,” take on more responsibility, and behave the way I “should.” Why bother sharing things that would hurt someone else or damage a relationship when those behaviors would soon be a thing of the past anyway? Second, I simply disagreed with certain social norms. Rather than trying to change society, which feels impossible, and rather than conforming, which I had no interest in doing, I figured the path of least resistance was to pretend to conform on the surface while actually rebelling against the system in secret. I felt that such rebellious behavior was justified if it was directed against stupid, senseless rules that I understood but disagreed with and that therefore shouldn’t apply to me.

I carried on this way for years without giving it much additional thought. It just didn’t feel important enough. I was able to get away with this behavior most of the time because I was pretty good at it. It’s uncomfortable to admit this, but I was pretty good at deception. And I felt that it was serving a greater good, since my life was dedicated to serving a greater good.

If all of this sounds petty, immature, arrogant, and ultimately quite dangerous, you’re absolutely right. I was all of those things.

Eventually, a series of things happened. Unsurprisingly, I did end up hurting a few people. I badly hurt people I truly loved, and people that trusted me. I began to get tired of lying, since it’s quite exhausting. It increases anxiety and has a negative overall impact on health and quality of life. I became more confident in myself and my life choices.

It was a yearlong transition that began and ended at Burning Man. Burning Man gave me two things that I was missing. The first is the opportunity to really reflect on the pain that I had caused others. When I took the time to really, deeply understand and internalize this, the guilt and remorse hit me like a tidal wave. I understood that, in particular, I had hurt a number of amazing women, women who deserved far better.

The second thing Burning Man gave me is the confidence to be myself. It sort of sounds like a small, obvious thing, but it’s not. One of the Burning Man principles is radical self-expression. Burning Man is a place where people bring their full, authentic selves, where people aren’t shy or afraid of revealing their true selves in all of their beauty and ugliness. Somehow, this experience—being around people who revealed amazing things to me, things that would never have arisen or been shared in day to day life, and having the opportunity to do the same thing with others—was a real epiphany, a wake up call for me. It made me realize that I don’t need to play by anyone else’s rules.

I set off on a campaign to introduce radical honesty to all of my relationships, especially those that I had already damaged. It was really, really scary in the beginning. I assumed that, if I told people the truth, they would be upset or maybe even walk away completely. In the event, by and large the experience was quite positive. I didn’t understand this at the time, but it turns out that being vulnerable and admitting one’s failures—and coming clean about past transgressions and apologizing for lying—are actually powerful ways to build trust. (In the interest of space, I’m leaving out a lot of detail and making the process sound fast, easy, and clean. It’s not, and it wasn’t. It took years. But the outcome was good.)

Since this experience I’ve adopted this radical honesty policy in all areas of my life. It’s not always easy. It’s often uncomfortable. Some people don’t like it very much—some people quite literally can’t handle the truth—and that’s fine. Not everyone has to be my friend, and I certainly don’t work well with people who hide from the truth. It’s gotten me in trouble on several occasions, but I don’t regret doing it. That’s the right kind of trouble.

Radical honesty coupled with radical self expression brings fresh air into my life and relationships and reduces stress and anxiety considerably. Today I couldn’t live without it. And in retrospect I wish I had started much sooner.

For more: Reflect on one important relationship that you may have damaged by lying or by being less than totally truthful. Tell that person the truth, and apologize. It’s a simple act but it’s powerful. If the thought is daunting, start small: less important relationships, and apologize for small transgressions. Honesty is addictive!