39 Lessons Learned in 39 Years

Yesterday I turned 39. Each birthday, I reflect on what life has taught me. (Read my prior lists here: ages 35, 36, 37, and 38.)

This year’s lessons loosely cluster around a few core themes:

1. Growth Mindset: Anyone can learn anything. You are malleable—but only if you choose to be.
2. High Agency: You can choose whether to take action or be acted upon.
3. Stoicism: Control what you can control. Don’t waste time worrying about the rest.
4. Learn, Curate, Simplify, & Share: Spotlight the best stuff you’re learning so others can learn too.
5. Candid & Kind: Speak up. And when conflict arises, assume positive intent.

Without further ado, here are the 39 biggest lessons I learned this past year:

Growth Mindset → You Can Learn Anything

Don’t get jealous—learn. I sometimes look at others and think, “Dang, look what he has accomplished…and he’s younger than me!” That type of comparison is destructive when it pushes me toward jealousy, bitterness, or excuses. But I’ve learned it can also be constructive if it leads me to deeper introspection and learning, like “Strategy X worked for them. Maybe I should try that.” The key is to focus on learning, not jealousy.

Believe in your ability to solve problems. Don’t hide behind excuses like “I’m not a math guy” or “I’m not a creative person.” Each of us is given a different default setting for how easy it is to acquire particular skills, but everything is ultimately learnable.

“Optimism is not the belief that there are no problems. Optimism is a belief that we can fix the problems.” -Shawn Achor

Spend time with living trees (nature) and dead trees (books). You’ll immediately become happier and more relaxed. (Shout-out to Alex & Books for this framing.)

Exhibit mental liquidity. Be willing to defend your passions but equally willing to listen to others. Aim for strong opinions, loosely held. (HT: Morgan Housel)

Choose truth over being right. Egocentric people care about being right, but lifelong learners care about getting it right. Be the latter.

“There are two types of people: Those who want to know more and those who want to defend what they already know.” -Morgan Housel

High Agency → Take Action

When you’re feeling stuck, ask yourself, “What would a high agency person do in this situation?” Doing so can change your mental frame and help you begin generating potential solutions.

One of the best ways to accomplish something is to lower the bar for getting started. When I tell myself I should start writing the next chapter of my book, I hesitate to do anything because it seems daunting. But when I tell myself I want to open my writing platform and “just play around a bit,” I end up writing a chapter. To accomplish more, lower the barrier to entry.

Don’t get constipated with learning. Consuming information (books, articles, YouTube videos, etc.) is great. But there comes a point when you need to ACT. Decide today to take imperfect action with what you know so far. Never use learning as a delaying technique for doing the real work.

“Your entire life will change when you stop gathering information and start acting on the information you already have.” -Sahil Bloom

Just make a decision—any decision. It’s tempting to wait until you have full information before making a decision, but that’s often the worst thing you can do. Instead, choose a path and start walking down it. Often, you can iterate later anyway.

“Actions produce information. If you’re stuck on a problem or a decision, just do anything. If it turns out to be wrong, you can adjust, and you’ll reach the right path much faster than if you wait for certainty.” -Giacomo Falcone

Action eases anxiety. Most of the time when I’m feeling nervous about something, I realize I’m only anxious because there’s some action I could take that I haven’t yet (e.g., practice a speech, study for a quiz, do more research). As soon as I act, I feel better.

You can just do things. Rather than waiting for a gatekeeper or authority figure to tell you what’s possible, pursue what you want. Or, as Jay Yang puts it, take permissionless action.

“Life can be much broader, once you discover one simple fact, and that is, everything around you that you call life was made up by people that were no smarter than you. And you can change it, you can influence it, you can build your own things that other people can use.” -Steve Jobs

Live with a maniacal sense of urgency. Tomorrow is better than next week, and today is better than tomorrow. If a task will take five minutes or less, just tackle it now.

“Urgency is the best predictor of personal success.” -Shane Parrish

Be a nonfungible human. Own your weirdness. It’s not only the best way to be remembered, it’s also the only way to live a truly authentic life.

“I used to think anyone doing anything weird was weird. Now I know that it is the people that call others weird that are weird.” -Paul McCartney

Commit to the bit. Life is more fun when you lean into the crazy moments. Two examples: If you’re singing karaoke, stand on a chair and belt it out. Or if you’re playing games with your nieces or nephews, go all-in on the imaginary world they’re creating, just like a kid would. Think like an improv comedian: commit to the bit. Don’t hide the fullest parts of yourself.

Clarity = Speed. In work and life, the greater clarity you have, the faster you’ll be able to move. This is especially true in leadership. If your team knows what’s expected of them (e.g., clear job descriptions, defined expectations), they’ll move much faster.

Stoicism → Control What You Can Control

Choose optimism. When I was 17, I met two bankers at a community event. One told me he had a boring, stuffy job pushing papers. The other told me she had the best job in the world: she got to help people buy their first homes. I looked them up on LinkedIn afterward, and they both had the exact same job. Perspective is everything.

“I have learned from experience that the greater part of our happiness or misery depends on our dispositions, and not upon our circumstances.” -Martha Washington

Realize that you’ve always held the key. Most of the time when I struggle to complete something, the issue is internal—not external. I am my own biggest problem. The issue is my own lack of courage, initiative, or creativity. I hold the key.

“We are the prison guards of the jail that we’re complaining about.” -Chris Williamson

Don’t complain. Find a way. It’s easy to wallow when life doesn’t go the way you want. When that happens, give yourself five minutes to wallow, then get back to work. It’s possible that the challenge you’re facing just opened up a new opportunity for growth or a new vector of attack you can use.

"There are those who see what should be, and complain that they do not get their due. And then there are those who see what is, and figure out how to use it to their advantage. Or at the least, overcome it." -James Islington (The Will of the Many)

Everything comes back to Intention and Obstacle. Screenwriter Aaron Sorkin says Intention and Obstacle drive every memorable movie: someone wants something, and something is standing in their way. But that’s how life works too. In life, gain clarity on what you want and what challenges you’ll have to overcome to get there. Be honest.

Seek out intimidating foes. Winners become winners by training against difficult opponents. That’s not just true in athletics; it’s also true in life. Volunteer for the tough project at work. Challenge yourself with a home improvement project beyond your current skills. Sign up for a Spartan Race, even if you aren’t sure you can finish.

“The purpose of life is to be defeated by greater and greater things.” -Rainer Maria Rilke

Live with centered ambition. It’s okay to have massive career goals, but you shouldn’t let those goals drown out more important aspects of life: family, friends, etc. Set massive goals but draw constraints for yourself of what you are (and aren’t) willing to sacrifice to achieve them. (HT: Barrett Brooks)

Learn, Curate, Simplify, & Share

Writing and speaking are just forms of public thinking. They’re downstream from many, many hours of thoughtful preparation. That means making a great speech is more about private preparation than public eloquence. If you’ve put in the time to brainstorm, outline, and prepare, the end product will be solid.

“All good public speaking is based on good private thinking.” -Scott Berkun

…And your private thinking is a result of what you choose to consume. That means one of the most important things that will govern your life as an entrepreneur, artist, writer, pastor, teacher, leader, or musician is the books, podcasts, movies, and social media accounts you allow into your brain.

“Almost every idea you have is downstream from what you consume...The person who creates better information flows gets better thoughts.” -James Clear

Breathe in, breathe out. Consuming and creating are both necessary for anyone who wants to put a mark on the world. Consuming is like breathing in: you inhale good ideas from others through the books you read, the podcasts you listen to, and the conversations you have with thought-provoking people. But then, you must breathe out: exhale the lessons you’ve learned by sharing them with others.

Speak more about failures than successes. Stories about wins tend to be boring. (It’s hard to cheer for someone who’s tooting their own horn.) Your most powerful and engaging stories will be the ones you earn through your mistakes. They’re humanizing and will make others want to root for you.

Quantity → Quality. Many creators debate whether quantity or quality is paramount, but that argument is a false dichotomy. Often, the best way to create something of quality is to create a lot of stuff.

The specific is the universal. The surest way to connect with a crowd is to tell a personal story, and the best way to inspire someone to donate is to talk about a single person in need. To appeal to the masses, find the most specific example you can.

Think small to go big. In a world of social media and mass marketing, it’s tempting to think the best way to sell something is to blast it out to the masses. But the best way to drive an initiative is often to start with one-on-one conversations. Focus on individuals, not the masses.

Candid & Kind

When sharing feedback: heart first, mouth second. People can always tell whether your heart is in the right place. If it is, you’ve won half the battle already. And the more you care, the harder you can go with your message.

In an argument, the more you can empathetically feel why someone else is frustrated, the more you can tamp down your own frustration toward them. If two people are upset with each other, they’re usually coming at a problem from different angles. Once you understand their angle and can feel what they’re feeling, it’s easier to empathize and begin finding common ground instead of getting mad at them.

Disagree without being disagreeable. Doing so is the highest bar for communication. If you can do that, everyone will want to work with you: colleagues, clients, etc.

Say what others refuse to say. Ask the question that others are scared to ask. Speak truth and avoid political games.

“The easiest way to be interesting is to be honest.” -Scott Berkun

Tough conversations are worth the stress. Most relationship issues derive from a hesitancy to say something that needs to be said. Feedback is often one minute of scary for months of benefit.

“Conflict avoidance slowly rots your whole life, and many people are about eight awkward discussions from a much-improved existence.” -Sasha Chapin

Ladder up to vulnerability. Small talk sucks, but too often, we get stuck in it because no one is willing to make the first move by saying something honest and vulnerable—something that breaks the script. Something that leads to a real conversation. Wouldn’t it be cool if you could be that person?

“Connection starts the moment someone decides to stop protecting themselves and make it safe for others to do the same.” -Francesca Tighinean

Misc.

Don’t pinch pennies while flushing nickels. Too many people try to save money on small things while not realizing the bigger picture.

Give others skin in the game. People care most about a task when they have ownership over it. This is one of the most important lessons in leadership.

“Good leaders give their teams a reason why they might want to do things that they want done. Make sure your vision and your goals are not just yours, but theirs too.” -Prakash Iyer

Use time to buy money until you can use money to buy time. Early in a career, it’s natural to work more hours to make more money. But as soon as you’re able, flip that dichotomy: spend money to buy back time (e.g., paying for food delivery, hiring a neighborhood kid to mow your yard). Use your time leverage to invest minutes in the things you care about most, like spending time with family and friends, pursuing a hobby, or developing a new skill.

Flip the arrow of money. For almost my entire life, I’ve viewed a job as a necessary means to make money. But I’m trying to reverse that mindset: to make enough money to pursue the type of work I most enjoy—the work I feel called to do.

“Is the purpose of work to make money? Or is the purpose of money to be able to do one’s work?” -Jim Collins (What to Make of a Life)

Remember that emotion guides decisions, and rationality justifies them later. Don’t forget that people buy out of emotion—and this applies to not only products but also things like ideas and worldviews. The best way to convince someone is often to speak to their heart, not their head.

I hope you enjoyed the 39 lessons I’ve learned this year.

I'm already looking forward to what I'll learn next year!