10 lessons from my 20s

One lesson from each year I’ve been twenty-something.

I turn 30 this year, so it felt appropriate to distill the learnings from my favorite failures and successes before time takes the teeth out of them. While most readers will have left their twenties in the rearview, I hope this Letter can be helpful to your children, and provide some context on the phase of life you’re in now.

Read Back-Issues Here

10 Lessons, Loosely organized by age:

20) Accrue Skills. If you’re working at 20, you don’t need advice from me – you’ve got it all figured out. Likewise if you’re on a defined professional track such as medicine or law, you know what you need to do. For the rest of the college juniors, it can be too easy to lose sight of the target. This results in spending immense effort on low-return activities. Club activities, sports, and GPA maintenance are amongst those. What’s high-return? Study abroad if you have the means, so you can get some stories to talk about in interviews. It’s hard to live abroad intentionally once you join the workforce. Take classes that imbue you with marketable skills: writing, coding, economics. Think about the day to day work of your chosen profession and use your spare time to achieve mastery of the platforms, techniques, and technologies that will enable you to shine. (Consulting? Powerpoint, not case studies. Banking? Excel, not problem solving tests. Real Estate? Contract law, not networking.)

21) Work. Every job interviewer is 10x more interested in your summer jobs than your college coursework. So, spend 10x more time and effort optimizing those work experiences and internships. Relevance to your field of intended career is less important than you might think. Just focus on ownership of a project, no matter how small, so you can speak to your involvement in the full life cycle of a business activity. “Seeing it through” something constrained is more valuable than “getting started” on something ambitious.

22) Career path is a dangerous myth. If you’re not in grad school, you’re in the workforce now. Your first job should and will be entry-level. Worrying about your “path” or “momentum” is counterproductive. Likewise, any consideration of your colleagues as obstacles or opponents is poisonous. Just as you did in your summer jobs, aim to take ownership of small discrete projects and finish them to a high degree of competence. Competence is not perfection, rather it is the combination of “good” and “on-time.” Define both of those parameters upfront, always, and with sufficient buffer to ensure your success. A career path comes organically from the mastery of increasingly important tasks. It does not come from master planning.

23) Get obsessed with a cheap and active hobby. The most important thing you can do for your financial and physical health is to become durably excited by an inexpensive pastime which involves activity. “Going to the gym” is certainly fine for some people, but for most young professionals fitness is easier maintained when it contains a social and skilled aspect. Avoid growing an interest in hobbies which are either expensive or sedentary. I’ve noticed that an interest in automobiles ticks both of those boxes. Remember, if your life has room for expensive hobbies they will expand to fit the space you give them. Here are a few ideas to get you started: Join a local park rugby league. Decide that running is “your thing.” Take no-gi Brazilian jiu-jitsu classes. Pick a mountain to climb every quarter, so you can spend your spare time training and planning. Seek type-2 fun over type-1 fun.

24) Seek ownership of projects, not people. By your third year at work, you’ll inevitably start thinking about a promotion or new role. Recognize the inherent egoism of those thoughts, and fight back against them. The urge to “move up” is often accompanied by the desire to be “on top” of other people. You want a team, you want an assistant, you want to be a boss. This is equally true whether your startup raised a hard-won $500k seed round or if you’re instead working within a larger company. Resist. The only thing that matters is your ownership of meaningful projects. To the extent you complete them, you gain skills, increase your ability to build consensus, and build a reputation for competence. This individual contributorship, when coupled with the right soft skills, is what drives careers and young companies alike. Just as a career path does not come from master planning, promotions do not come from power grabs.

25) Avoid dinners. You’re a young professional, you’re in a large and vibrant community. If you wanted to, you could have dinner with friends or colleagues every night of the week. Resist even a weekly indulgence. Are you sharing a nice apartment with 2 friends at $1500 a month? Four $200 nights a month, easy to accomplish or exceed in any major city, is over half your rent. They’re not improving your health, they’re not a mandatory medium for seeing your friends or advancing your career, and they’re robbing you of >$10,000 a year you could be putting towards your future. How about going out once mid week, and then Friday and Saturday nights? Doesn’t sound extreme, but can easily and insidiously exceed the rest of your expenses combined. Be known differently. Be known as the person who organizes hikes, or invites friends to home-cooked Sunday brunch. You’ll all remember more in the light of day. Have to go to dinner or drinks? Carry cash. Tabs always get combined, and Venmo is socially complicated. Pay your own, plus a generous tip.

26) Question your motives. You are an unreliable narrator of your own biography. Like all humans, you make assumptions about your motivations that are unfounded, and you harbor beliefs about what will make you happy which are untrue. Why do you want to found a startup? Why do you want to leave your job? Why do you want to buy a Range Rover? Why do you want to live where you do right now? Why do you want to join that group vacation? Why do you want to go to that dinner? Why do you care so much more about increasing your salary than decreasing your spending? Why is so much of your social worth tied up in your title on LinkedIn? Happiness is elusive. Give it the benefit of reflection. Enlightenment doesn’t come in one fell swoop. It comes from a life of consistent and empathetic reflection. Check in with yourself. Cut yourself slack. Give yourself a chance to be happy where you are right now.

27) Save over half your after-tax salary. I’ll spare you the math lecture. If you save more than half your living expenses each year and invest them in low-cost broad spectrum index funds, you will reach financial independence in a decade. Resist traditional retirement advice for pitiful 10-20% saving rates. They’ll have you working through the healthiest years of your life. Resist lifestyle inflation, the inexorable force that increases your spending in line with income. Resist hedonic adaptation, and the sallow feeling that comes from ever-increasing overindulgence. There’s no law that says you have to retire when you reach financial independence. However, the empowerment that comes from being able to choose your own opportunities unfettered by material need cannot be matched.

28) Invest in your thought leadership. John Mulaney once jokingly referred to himself as meaning “a lot to very few people, like Minister Farrakhan.” There’s wisdom in that approach. Find the minimum viable subject area where you can become a thought leader, and invest into that community. Pick one medium, and attack that area with consistency. If you’ve sufficiently constrained yourself, you will become the “go-to” in that sector in short order. Consistency is, after all, in short supply. Give without asking in return. Don’t be afraid of specificity. The greatest generalists in the world are “T-Shaped,” with deep expertise in one area that colors the rest of their knowledge with invaluable pattern recognition. This is how careers and reputations are built.

29) Good relationships are easy. If you think fights are a mandatory part of being in a romantic or business relationship, you owe it to yourself to experience a good one. Good relationships are not free of conflict. Rather, that conflict is resolved compassionately with conversation, not emotionally with spurts of anger. Learn about non-violent communication,and commit to solving your inevitable disputes in that framework. If you are unable to effortlessly confront and work through key issues, the problem isn’t you – it’s your partner. Save both of your precious time and find someone more compatible.

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