27 learnings from 27 years

I turn 27 in a couple of months, so I figured I’d share a handful of learnings that have shaped my 20s so far. Over the last ~5 years, I’ve discovered an awful lot about how I want to live my life.

So here's what I got: Read as unsolicited advice to myself.

1. Travel, but not too much

When you first start to travel, it’s wonderful. The excitement of seeing new places and connecting with new and unique people from all over the globe is unmatched—you get outside of your bubble and empathize with different perspectives.

But at a certain point—for some people—travel for the sake of novelty can become an addiction. This is often a sign of discomfort at home; escapism. I have many friends who return from trips to their “normal lives” and immediately start planning their next trip—they’re never satisfied.

Travel, consciously and in moderation. A couple of trips per year feels about right. These days I like to travel slow—foregoing the common attractions and the “best” restaurants to meet locals and experience a place truly as if I was living in there myself.

As Emerson once said, “Travelling is a fool's paradise...They who made England, Italy, or Greece venerable in the imagination did so by sticking fast where they were, like an axis of the earth."

And Thomas Jefferson advised: “[b]e good, be learned, & be industrious, & you will not want the aid of travelling, to render you precious to your country, dear to your friends, happy within yourself.”

2. Most things that happen in our lives are out of our control

Surrender to this simple fact, and life becomes much easier. It’s better to manage how you respond to those things. Learn to love dancing in the rain. Because if you can’t, life could be painful. Thank you, Stoicism.

3. People won't sacrifice convenience for the sake of the planet

That’s why we need climate tech—to build better things so that people (selfishly) want those better things. Most won’t change for the planet. We can simply look at the global response to Covid for proof. But people will change for themselves—typically if it means acquiring nicer things. It’s a sad, but good, learning.

But even climate tech won’t turn things around quickly enough. We’ll need policy to get there. Policy stamped into law by the most powerful governments in the world—so that we force change until climate tech creates better things.

4. When stressed, turn to Cosmic Insignificance Therapy

Coined by Oliver Burkeman, Cosmic Insignificance Therapy is the idea that, in the grand scheme of things, my life isn’t really all that important. The universe has been around for 14 billion years—it'll move on pretty quickly after my time here on earth comes to an end.

The learning? Don’t. Take. Life. So. Seriously. Don’t sweat decisions. Don’t put the weight of the world on your shoulders.

This idea is actually liberating—if my life doesn’t matter all that much in the context of history, I don’t need to feel as though I must satisfy some great life purpose. Or save the world from nuclear war, climate change, or AI. I can just live a modest life, be a good human, and give back locally. That’s enough.

5. if you want to get smarter, study the world through a historical and evolutionary context

Once you step outside the bubble that is the post-industrial revolution world (the last 200 years as opposed to the 200,000+ years our species has existed), you can open your mind to the reality that the way we’re living now isn’t the way that humans evolved to live. This modern life is not “normal.”

So when making decisions, consider how humans from 200,000 BC until ~1800 lived. What did they eat? How did they spend their time? What made them feel happy and fulfilled? The answers to these questions will likely make you much happier and healthier than you would be if you’re continually fixated on the modern world.

At the same time, you must have patience for people who don’t yet realize historical, evolutionary, and climate context. 

Some people think that humans are the only thing on this planet that’s important. And so they talk about things a certain way—not taking into account the fact that our climate decisions impact every living thing on this planet. Trees. Fungi. Animals. And of course, all people.

6. Exercise and fitness are best optimized for longevity

What type of fitness will help me live my best life until the day I die? It’s not lifting heavy weights. It’s not high-intensity workouts. It’s certainly not soccer.

I want to be able to mountain bike until I’m 75. I want to jog around town in old age. I want to walk to the food store to pick up groceries for my whole life.

So I optimize my exercise to help me stay healthy for years and years: Fun, outdoor cardio, like cycling (low impact), hiking, and some light running. Build and maintain endurance. Keep the heart healthy. Soak in the outdoors and spend time in nature. Then add mobility and calculated strength training. This is a key to longevity in my exercises. Flexibility, mobility, and balance.

And another point on fitness: Stop measuring workouts.

Move from a tracking mindset to one of enjoyment and pleasure. Exercise for its mind-body benefits instead of training for a specific goal. Prolific author Brad Stulburg was once told by a friend, “Stop trying to win at your hobby.”

This is why I ride bikes and get my physical exercise outside—I enjoy the process and it’s not about results or times.

7. walk yourself into a healthy, thoughtful life

Take a long walk every day, rain or shine. I try to walk between 3-6 miles each day with my dog. Spend part of it thinking. And another part meditating. Just pay attention to your surroundings. Notice trees, houses, the way your body feels as you move.

A daily walk might well be the key to a healthy mind.

“Every day I walk myself into a state of well-being and walk away from every illness; I have walked myself into my best thoughts, and I know of no thought so burdensome that one cannot walk away from it.” —Soren Kierkegaard.

8. Figure out how you actually want to connect with friends

It’s no longer a real debate. We’re simply way worse off with social media. It’s rarely ever a good thing. You don’t need to know what your friends are doing all the time. It’s created mental health issues beyond our comprehension.

Instead, if you used the time you previously spent on social media to call the 10 people in your life you actually love each month, your life would improve dramatically. Your relationships would improve, as would your mental health.

If you can’t imagine your life without socials, delete every app except your favorite. Then unfollow every single person who you wouldn’t want to sit in a room one on one with. Just like that, your life will noticeably improve.

9. Find the balance between drive and contentment

Socrates famously said, “An unexamined life is not worth living.”

Examining your life requires ambition, drive, and desire. Just as most things that are known to lead to happiness in life require these traits. A healthy body. A healthy mind. Quality relationships. Self-actualization and transcendence.

But it’s a paradox.

Ryan Holiday writes, “No one achieves excellence or enlightenment without a desire to get better, without a tendency to explore potential areas of improvement. Yet the desire—or the need—for more is often at odds with happiness.” And, “The need for progress can be the enemy of enjoying the process.”

The learning? It comes down to balance. You can work towards your goals and be happy in the present moment...the process. They're not mutually exclusive.

10. Journaling is the key to clear thinking

Pick up a journal. Write down your thoughts. Never let your thoughts stir too long in your brain without writing them down. It’s better for your mind and you’ll have a catalog of improved thinking.

11. Meditation is to the mind what exercise is to the body

Funny how we train our bodies but completely neglect our minds. Change that. You must think of meditation as training. You rarely miss workouts. Don't miss meditations.

The goal is to train the mind to become aware of the present moment...to be aware of your consciousness. Feeling your breath. Noticing the warmth when the sun hits your face. The way a tree sways slightly in the wind. The smell of the grass. The hum of a plane high above. 

I literally get this strong, visceral response when I tap into the present moment. Sort of like chills, but more powerful. Everything else fades away. It’s the sign of a healthy and clear mind.

12. The best way to connect with people? Ask. More. Questions.

I now have a simple test in social interactions to see whether people are actually interested in getting to know me, or whether they’re socializing to scratch their own itch: Do they ask me personal questions?

The superpower of all superpowers is to learn how to actually listen to people. Ask questions, then listen. Don’t unconsciously think about what you’re going to say in response. Listen, then think, then respond (if it’s necessary).

Also, always be the person who, when someone is interrupted, goes back and asks, “You were saying?”

13. I’ve won many lotteries in my life

That’s called privilege.

I won the lottery of parents; I have two parents who instilled incredible values in me. They've always been there for me. And given the fact that I was born into an upper-middle-class family, I started out in a stronger financial situation than most people in the world.

I won the lottery of passport; I was born in the United States where human rights are (generally) respected.

I won the lottery of genetics; I’m a white man. I never feel uncomfortable in my own skin, and I don’t face the same obstacles that my non-white and female friends do.

But you don’t have to carry around the burden of privilege. That won’t help anyone. Instead, you can live a virtuous life. Go out of your way to create change for people less fortunate. For the planet. Virtue is the greatest good. When you live a virtuous life, you use your lottery winnings to make the world a better place.

14. You can belong to many different communities

Communities (or tribes) that form around hobbies are often all or nothing. For example, most mountain biking communities are filled with riders who are only into mountain biking. They ride, read mountain biking blogs, and watch biking YouTube videos. All of their friends ride.

But life doesn’t have to be all or nothing. I have many hobbies. I can be a part of multiple communities without sacrificing the rest of my hobbies for one of them.

In hobbies as in career, being a dilettante is more fulfilling than it’s chalked up to be. Be a creative generalist—a renaissance person.

15. Your work doesn’t have to consume you—even if you’re ambitious

There’s often a dichotomy in careers:

Ambitious, disciplined people end up working 12-15 hour days slaving away at high-earning companies. It’s what they have been trained to do their entire lives through our education system and often sports. 

On the other end of the spectrum, unambitious people sleepwalk through jobs they hate—bored, looking at the clock so they can leave at 5 pm.

You don’t need to fall into this trap. You can have ambitious, fulfilling work that doesn’t overtake you. And you can keep your hours in check so you can prioritize the things that matter more in life: health, relationships, interests, serving others, curiosity.

Just because you’re creative and ambitious doesn’t mean you have to work for a company that doesn’t value life outside of work.

Anyway, humans can only really do 4-6 hours of creative work per day. It comes down to understanding your values and carving out a work situation that is right for you—whether as an employee or an entrepreneur.

And ambition isn’t only about a career. You can be ambitious about your career AND your life outside of your career. Some of the most ambitious people I know work minimum wage jobs so they can earn just enough to get after their real passions in their free time.

16. You must always be open to meeting new friends

You are constantly growing as a person. And it’s likely your current friends are growing at a different rate than you are. It’s okay to nurture those relationships—some of my deepest friendships were forged in middle school.

But if I met these same people today for the first time, we likely wouldn’t become friends. Our roots keep us together, but if we lacked the roots, we wouldn’t connect on present interests alone.

If you’re open to making new friends, you’ll meet people who will better connect with you now. I met best friends in the last year because their interests are currently similar to mine—and our level of understanding about the world is similar.

If I wasn’t open to making new friends and instead relied on old ones, I would have missed out on these amazing friendships.

17. Don’t start a business unless you’re willing to sacrifice the rest of your interests for 5 years

Starting a business is hard. You need to be willing to give up a massive chunk of your life. You will have to put down other passions. You likely won’t have time to think about other areas of your life. You’ll need tunnel vision to get it done. 

When I founded Universal Dialect with Sean in 2018, I knew it would be hard. And I was ready to grind. But I wasn’t ready for the entirety of the sacrifice. I wasn’t ready to stop thinking and growing in other areas of my life—relationships, my understanding of the world, my mental health, and my love for other social issues.

So over the last couple of years, we decided to downshift our business. We turned it into a project. Our mission continues, but I no longer view it as a viable career.

As Hugh Jackman put it, “if you start a business—it could be a pizzeria, it could be a bar, restaurant, anything—you have to give it seven days a week for five years.”

18. Old problems require old solutions

Old problem, old solution. New problem, new solution.

If I’m trying to work through health, wealth, and happiness, read ancient philosophy—not self-help books. Intelligent humans have been around since the Cognitive Revolution 70,000 years ago. Read about what has been making humans happy and healthy throughout history—not just the latest fads.

If I’m trying to learn about economic policy, that’s a fairly new concept in the grand scheme of history. So it’s okay to read recent books and articles to figure it out and make informed decisions.

19. Instead of thinking about the type of person you want to be, just take actions

Philosopher Terry Patten writes, “Life satisfaction is the by-product of moving from seeker—to want a certain lifestyle—to practitioner—actually live that lifestyle”

So it’s a simple shift: don’t just think about who you want to be. Go take action and become that person. You want to be a kind, fit, and intelligent human? Go out of your way for people, exercise, and read each day. Make those activities habits.

20. your whole world shifts when you temper expectations and desires

I think this is an idea from Tony Robbins.

In order to feel fulfilled, you have two options: 1) continue to desire more and then get more. Or 2) lower your expectations, needs, wants, desires. Option 1 isn’t salient because you’ll never “get enough”—you’ll endlessly desire more.

Instead, if you tame your desires—and remove your unrealistic expectations—you will have “enough.” You’ll need less money, so you can afford to work fewer hours. And then you’ll be able to fill your free time with the things that are virtuous and things that make you more fulfilled.

21. If you want to become a better person, get a dog

You’ll start saying “no” to the right things. You’ll feel more grounded. And you’ll learn how to take care of something. You effectively get your head out of your ass.

22. Use money to remove negatives from your life—instead of adding positives

Anytime you’re considering a purchase, ask yourself; is this removing a negative from my life?

Pete Adeney (Mr. Money Mustache) has some great thoughts on this:

“It’s pretty well studied that happiness is not very much affected by adding positives to your life. Especially in a rich world environment like we live, it’s mostly accomplished by removing things that are a strong negative to every day. So getting myself a remote control photography drone is unlikely to make me happier because my life doesn’t currently suck due to the absence of a photography drone...

Whereas if there’s something that every day I’m like, dammit, I just wish I didn’t always trip over this broken dishwasher or whatever. Then replacing your dishwasher is probably going to be a happiness-boosting proposition.”

23. You must love the place you live

Topophilia means love of place. And to be truly satisfied or happy, you must love—or at least have admiration for—the place you live. Life’s too short to constantly feel negative about the place you live. And, if you actually love your city or town, you are more likely to get involved. To meet people. To volunteer. To help those in need.

Consider where you live carefully.

This is why my partner and I decided to move to Burlington, Vermont. And we favor living directly in the center of town—to walk everywhere instead of taking the car. And to build community right in town. There’s something magical about walking over to a close friend’s house on a weeknight.

24. Be a local celebrity

Last year, without much effort, I built a following of over 3,000 people on Twitter. But then I realized that’s not what I want. Instead, I want to be there for people locally. In person. 

Brad Stulberg writes, “As far as I can tell, it is exponentially more fulfilling to be deeply involved, to be a celebrity in your local community rather than a celebrity on the internet.”

25. Think, write, and spend time in nature

Ryan Holiday wrote, “To paraphrase Epicurus, the good life is about being reflective, responsible and moderate, and relaxing in nature. Compare that to Aristotle’s description of the lives of slaves, ‘Work, punishment, and food.’”

Modern society feels more like Aristotle’s description of the lives of slaves. But you can live the good life that Epicurus described by prioritizing writing, reading, moderate work, and nature.

26. Pulling everything together

Desire less. Spend less. Consume less.

It’s funny how most of the philosophies here can come together so effortlessly.

If you desire less, you’ll spend and consume less.

You’ll become financially independent much quicker. So you won’t have to work a job that you hate—and you can spend much more time doing the things that you love.

Spend time with loved ones. Exercise more. Think more. Write more. Your physical, mental, and spiritual health increases. More time for stillness, education, health, and love. More time for thinking and writing and relationships helps you understand yourself.

You won’t be pulled with desires like cars and vacations, so you can instead live in a town/city center where you can walk and ride your bike everywhere—to your job, to the gym, to your friends’ houses, to the grocery store. Spend plenty of time outside and stay fit.

And you have less of a negative impact on the planet since you'll create less waste.

It’s a simple change to “desire less.” But also the most profound.

27. Rapid-fire learnings

Cliche, but if you’re not embarrassed by your understanding of the world a year ago, you haven’t learned enough in a year.

There are few things better than nature. Optimize your days to be outside.

Mental health, though gaining momentum, is the most underappreciated area of study in modern history.

There is no “end.” where you’ll be satisfied. You must focus on enjoying the process—99% of life is process.

Routines make us strong, healthy, and happy. Stick to one and lean on it during difficult times. But then break it once in a while for fun. Zig, zig, zig, ZAG.


There you have it. I'll likely create a new list in 2022. But for now, this serves as my current life philosophy. Hope you enjoyed, and cheers to a happy, healthy, and thoughtful 2022!