Kids 3.0

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Originally published on Substack — February 22nd, 2022


My wife and I welcomed baby number 3 into the family this week. Dax, Jed, and our newest addition: Eve. We're big into 3-letter names. So with plenty to keep me busy enjoying our new addition I wrote a shorter post than usual, mostly to keep up with my goal of writing every week. In between feeding, crying (me, not Eve), and sleeping (Eve, not me) I've had plenty of time for casual reflection.


Below are the frameworks that have helped me effectively reflect on my life and career. I think all the time about feedback loops and how rarely life is straightforward enough to let us experience something, learn from it, and apply what we've learned in the future.

But the more you establish frameworks, whether for investing, building, or living your life, the more capable you'll be of running feedback loops in your own life.

The Lily Pads of Life

In January 2020 I caught up with Jake Saper at Emergence and the advice he gave me has been wildly helpful and contributed to the first three of these frameworks.

The first thing he shared was about recognizing the lily pads in our lives. What are the experiences that you've jumped to and from? And what have they contributed to who you are?


Recognizing the stepping stones in your life and reflecting on your story is more than just good practice to crush it in investment banking interviews. When I think about the experiences I've had I realize how poorly I've predicted how my life would go or what would make me the happiest or the most successful. Things may not always go the way I expected or hoped, but the experiences are worth learning from nonetheless.

“Regardless of how you begin your career, it is important to realize that your life will not necessarily move in a straight line. You have to recognize that the world is an unpredictable place. Sometimes even gifted people will get knocked back on their heels. It is inevitable that you will confront many difficulties and hardships during your lives. When you face setbacks, you have to dig down and move yourself forward. The resilience you exhibit in the face of adversity — rather than the adversity itself — will be what defines you as a person.” (Stephen A. Schwarzman)

Every year or so I make a conscious effort to write down the experiences I've had and what I learned from them. My goal is to establish a clearer view of who I'm becoming. And if you don't like the picture it's painting then changing course sooner rather than later will let compounding work for you instead of against you.

Live The Library

This concept of "living the library" has been in my head for a long time. Originally the idea actually struck me in a quote from the TV show Lost. One character carries around a sealed copy of Our Mutual Friend by Charles Dickens.

"I've read everything Mr. Dickens has ever written. Every wonderful word. Every book except this one. I'm saving it so it will be the last thing I ever read." (Desmond Hume)

I thought to myself, "what book would I carry around as the last thing I ever want to read? And to even know who might make the list I had to be more deliberate in considering who was in the library to choose from. Who are the people whose ideas and career can act as a guide for your own? Who can you learn from to become who you want to be?

That list can change all the time. The important thing is not who is on your list of influences, but that you have a list. That you are living life deliberately enough to have mentors. People to point to that you're actively learning from.

Since then I've kept track of some of the best examples of "Live the Library" to both refine my list and help evolve my way of thinking about my own library.

"Naval is a world-class operator instead of an armchair philosopher. But I don’t [just] take his perspectives, maxims, and thoughts seriously because of the business stuff. There are lots of miserable “successful” people out there. Be careful about modeling those, as you will get all the bathwater with the baby." (Tim Ferris, The Almanack of Naval Ravikant)
"The fastest way to improve is to learn from others. Read good books. Talk to people who have done it. Soak up the lessons of the past. Learn from the experiments history has already run and you can start the race halfway finished." (James Clear)

What Gives You Energy?

In Walter Isaacson's biography of Leonardo Da Vinci he points to a question asked by a lot of experts who have studied Da Vinci's life. "Why didn't Da Vinci finish many of the masterful projects he began? Or talked about? Why did he spend so much time pursuing random projects and hobby interests?"

"If posterity is poorer because of the time Leonardo spent immersed in passions from pageantry to architecture, it is also true that his life was richer." (Walter Isaacson)

In the grand scheme of existence (billions of years) our individual lives are ridiculously finite. If you think making professional sacrifices in order to make money will give you more flexibility to pursue richness, then choose wisely. But focus on those experiences that will matter the most to you, not to everyone else. You can fail at the thing you don't want to do. So you might as well try doing what gives you energy.

What takes away energy? What do you love doing? What do you dread doing? Over your career you develop more agency and can pick and choose more of what your career consists of, so start paying attention now to better choose when you can choose.

This idea reminds me of a question that can be pretty insightful depending on how you answer it, though I have no idea where I heard it.

“Would you rather have a Harvard degree or a Harvard education?”

So many people want the clout that comes with a Harvard degree. There are plenty of questions about whether the education itself is worthwhile. If you could only get the education without any of the social clout, would you still do it?

And if the answer is no you can reflect on the reason why. Pursuing the things that give you energy are often, by nature, deprioritizing the things that will make people think more highly of you.

"Be 'selectively ignorant.' Ignore topics that drain your attention. Unfollow people that drain your energy. Abandon projects that drain your time. Do not keep up with it all. The more selectively ignorant you become, the more broadly knowledgable you can be." (James Clear)
“Sometimes we feel like our work is draining our energy and we can only move forward if we put more and more energy into it. But sometimes it is the opposite. Once we get into the workflow, it is as if the work itself gains momentum, pulling us along and sometimes even energizing us. This is the kind of dynamic we are looking for.” (Sönke Ahrens, How To Take Smart Notes)

Munger's Three Career Rules

This framework has helped me guide where I want to work and what I want to be doing. There are always things wrong with any job but the more effectively I've been able to live by these three rules the happier I've been in my career.

"I have three basic rules. Meeting all three is nearly impossible, but you should try anyway: (1) Don't sell anything you wouldn't buy yourself. (2) Don't work for anyone you don't respect and admire. (3) Work only with people you enjoy." (Charlie Munger)

Even if you're not exactly "selling" something, ask yourself if the position your job puts you into would be the same positions you would be in even if you didn't have the job. Whether it's pitching your firm, a strategic decision, a stock, or a hire. The more you find yourself thinking "this is what I need to do because I'm at Firm XYZ but it's not what I would do if it were my own [money/time/attention/energy]," then you're going to be less and less happy.

“In the history of Wall Street I think there are two types of firms — I think there are firms where you’re putting out products that you believe in, you work your ass off to make them the best possible products, you put your own money in them, and you build a culture that these are things you believe in. Then you have a lot of firms that will put out whatever they can to capitalize and make as much money as they can on the themes of the day.” (Meb Faber)

Beyond that the people you work for and with are going to be a ridiculous portion of your time each day. The more you reflect on those people and the impact they have on you the better you'll understand yourself.

My Personal Punch Card

The final framework here is a much longer-term project. This is what I call my "punch card" for personal life choices. Buffett has this framework for investments:

"I could improve your ultimate financial welfare by giving you a ticket with only 20 slots in it—so that you had 20 punches representing all the investments that you got to make in a lifetime. And once you'd punched through the card, you couldn't make any more investments at all. Under those rules, you'd think really carefully about what you did, and you'd be forced to load up on what you'd really thought about. So you'd do so much better." (Warren Buffett)

But instead of only being to make 20 investments, I ask myself "what if I could only make 20 choices? That's 5 every 20 years or so. What were the only 5 decisions that really mattered from ages 0 to 20? Or ages 20 to 40?

When you simplify and intensify the weight of your most important decisions you recognize the wide-ranging impact they have on your life. I made the decision to get married when I was 22. I had my first kid when I was 24. Those have dramatically impacted how I've lived my life during my 20s and into my 30s. There will certainly be 2 or 3 other really big decisions but I shouldn't lose sight of how transformational those core decisions are. That's why they're on my punch card.

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