The picture of me on the left was taken when I was 21 years old. I was on a Meditation retreat with 12 other college students in the mountains of Colorado.
The picture of me on the right was taken when I was 29 years old. I was in Mexico for a month with my girlfriend, working and running my first company remotely.
Today, I turn 30 years old.
When I think about “who I was” at 20, I can hardly remember what it felt like to be me, then. I can remember the facts:
- I had just gotten back from canoeing 320 miles in Florida on a drug rehabilitation retreat with a bunch of other guys.
- I had just returned to the University of Missouri for a semester, before deciding to transfer to Columbia College Chicago to study creative writing.
- I had just started getting into meditation.
- I had just bought my first real gym membership, to the Sport across the street from my college dorm downtown Chicago.
- Etc. Etc. Etc.
My twenties were full of a lot of “firsts.”
But turning 30, a lot of those firsts have come and gone.
I’m writing my 4th book.
I’m starting a second company.
And that’s not to say life has become boring, or mundane, or unexciting. In fact, I feel the opposite: life has transitioned into a phase where I feel my choices are more intentional. I know what I like and don’t like. I know what motivates me and doesn’t motivate me. I know what I want to work on in myself. I know what discomfort I need to experience in order to grow.
Everyone says turning 30 is when you experience a mid-life crisis.
And who knows, maybe I’ll feel that too.
But the dominant feeling I feel isn’t anxiety. Or regret.
What I feel is appreciation.
I remember how lost I felt in my early twenties. I remember how insecure I was, and afraid of what people were going to think of me. I remember wanting so badly to “make my dreams happen,” and at the same time having absolutely no idea how. I remember struggling, a lot, accepting myself for who I was—and figuring out a way to move forward regardless.
Twenty to thirty was a massive decade of growth (as I’m sure it is for most people). It was a process of figuring out how to get from who I was then, to who I wanted to be today.
These are the 30 things I’ve learned about life, and myself, throughout that process.
1. Slow and steady consistency is the most powerful driver of growth.
When I reflect on every meaningful chapter from the past 10 years, anytime I grew significantly (and quickly), I was disciplined.
I grew the most in the gym when I ate, lifted, and rested, every single day, 7 days per week. I grew the most on Quora by writing every single day. I grew the most making music when I practiced every single day. I grew the most building my first company by pouring my heart and soul into it every single day.
1 single year of consistent, disciplined practice ALWAYS brought 10x the results to short, infrequent attempts at quick achievements.
2. When you’re younger, you want “things.” As you get older, you just feel thankful for friends and family.
I remember when I was 20, all I wanted was a new desktop computer.
I ended up working the 5 a.m. shift at ArgoTea to buy myself that computer for my birthday—along with two studio monitors and a bunch of music production sounds. And at the time, these physical gifts to myself felt like the greatest presents in the world (especially because I had bought them with my own hard-earned money).
Turning 30, I can’t think of any “things” I want. I mean, I could make a list if I really tried, but nothing immediately comes to mind. I have my basic needs met. I have a wonderful partner, an amazing dog, and a modest apartment. My girlfriend keeps asking me what I want to “do” for my birthday, and I don’t really have an answer.
I don’t really want or need to “do” anything.
I’m just happy I have the friends I do, the family I do, and that I get to live a life doing the things I love.
3. Achievements can fool you. How you live your life and treat your craft is all that matters.
When I first moved to LA, one of the first guys I met was a very, very successful sales copywriter. This is a guy who has made tens of millions of dollars.
We grabbed lunch together, and immediately shared a connection over writing.
He started inviting me to events at his house—exclusive dinners, big parties, etc. And for a long time, I would attend and ask myself, “Why am I here?” Everyone else there was either insanely successful, wealthy, or famous. I was just this guy who had found some modest success writing on a website nobody knew about, called Quora.
What I realized after a while, however, was that even though I felt like there was a lot I could learn from this guy, he also felt like he could learn something from me. It wasn’t my achievements or status in society he cared about. It was the way I treated the craft of writing—and he was humble enough to realize maybe there was something I could teach him.
Observing that dynamic in our relationship has had a profound impact on me.
4. Material rewards are both amazing and short-lived.
I will never forget the day I bought my first car: a metallic white BMW 430i.
I had just quit my 9–5 job. I had gone out on my own as a freelance writer and ghostwriter. I was making real money for the first time in my life. And I went to the BMW dealership with my dad—the salesman handing me the keys to my brand new whip.
I drove off the lot feeling both terrified I was going to somehow wreck this gorgeous car, and so, so excited for the light to turn green so I could floor it down the street.
That feeling lasted a few months. Until I moved to LA, pulled up to Soho House in West Hollywood next to a bright red Ferrari 488 and thought to myself, “Wow, I want that car instead.”
That was the moment I realized the chase never ends—and how destructive of a cycle that can become when left unchecked.
5. You don’t break down in a day. You break down little by little, day by day, week by week, month by month, year by year.
One of the hardest lessons I learned in my 20s was that a single destructive habit, repeated day after day, can impact your entire life.
While I was building my first company, I really stopped taking care of myself.
- I stopped meditating.
- I stopped journaling as often.
- I stopped going to the gym.
And at first, I thought, “It’s fine. I’m working like crazy now, so it will all pay off later.”
The problem is, when is “later?” At what point is enough ever enough?
I went on this way more for than 2 years, and it impacted every aspect of my life. I ended up in the hospital with shingles from being so stressed. My relationship suffered. I stopped writing. Everything in my life except work took a backseat, and I ended up having to climb my way back to a sense of normalcy—when what I should have done was just take care of myself, little by little, along the way.
6. Not everyone has to want to be their own boss.
When I was 25 years old, and hungry (so, so hungry) to work for myself, I had a strong opinion that everyone should want to work for themselves too.
I’ve since learned that’s a very flawed belief.
When I was younger, I thought there was a sort of weakness in working for someone else. I thought it meant you didn’t have enough ambition to do anything on your own. But the reality is, not everyone can or should take that path through life. They might be dramatically more effective being given a structure to be successful within—the same way that I am more effective when I’m the one creating the structure for myself.
What’s far more important than “going your own way” in life is knowing which way you need to go, for you.
7. You can’t know how things will turn out. You can only know whether or not you’re game for the adventure.
I only had one full-time job in my 20s.
When I got out of college, my first and only job was as a copywriter for an advertising agency. My boss became a very close mentor to me, and he watched me struggle to “figure out” who I wanted to be in my early 20s.
He called it “twenty-something syndrome.”
I would talk to him for hours and hours about all the things I thought I wanted to do, or thought I could do, or wondered how certain decisions of mine would play out. And over and over again, he would just keep saying to me, “Imagine how much more you would know if you spent all that time doing instead of thinking.”
He was right.
8. Anything meaningful in life requires a long-term investment.
Relationships. Companies. Artistic projects. Self-realizations.
All these things take time.
If there’s one thing I wish I had learned sooner, it’s that shortcuts are always longer roads in disguise.
9. The most valuable thing you can offer someone else is a genuine connection.
When I first moved to LA, I was 27 years old.
I had just started my first company, and we were growing like crazy. My first month here, I met a very successful entrepreneur and angel investor, and he invited me to his house up in Hollywood Hills—a house that looked like Iron Man would be living there.
As I was driving up the winding hills, excited and nervous, I called one of my closest friends. I told him where I was going, and how intimidated I felt, and he reminded me, “Everyone just wants to be seen. All of us want a genuine connection.”
When I stepped into his house, I felt how two paths were presented in front of me. I could either try to pretend like I was something, or someone, I wasn’t. Or, I could be myself, be vulnerable and open, and offer a genuine connection.
We ended up becoming great friends. He invested in my company. And I consider him a great mentor to me today.
10. In every difficult situation, you have to try to find “the root of the root.”
It’s very easy to be upset.
It’s easy to get angry, blame someone else, and assume the problem is outside of yourself.
At some point in my 20s, I came up with this phrase, “The root of the root.” It was my way of trying to understand the real, real reason I felt a certain way—not just accepting the surface-level emotion that revealed itself in the moment.
The root of the root will always tell you the truth.
And the truth is, the real issue is usually buried somewhere deep within you.
11. In the beginning, you create selfishly. As you progress, you create for other people. And in the end, you aim to do both at the same time.
When I first started writing seriously in my early 20s, I didn’t consider the reader.
I wrote only for myself—and as a result, it was a largely selfish pursuit.
As I got older, and started trying to figure out how to turn my craft into a career, I intuitively aimed my pursuits externally. I wanted to learn how to write things other people wanted to read, because that meant I was “successful.”
It wasn’t until I had achieved that goal (by accumulating tens of millions of views on my writing online) that I slowly started to realize, if you purely create for the external, you lose a part of yourself. And if you only create for yourself, then you aren’t giving enough to the reader.
Masters of their craft do both at the same time.
12. Who you are is more important than what you do.
Investors invest in people they trust.
People do business with people they like.
Employees work for people they respect.
Team members stand alongside people they know care about them in return.
All throughout my early, mid, and even late 20s, I thought I needed to “become” someone in order to be taken seriously. I thought I needed a credential, a title, a certain amount of money—something I could point to as “proof” that I was WORTH investing in, working with, or believing in.
It hasn’t been until very recently that I’ve fully internalized how much that is not the case.
Sure, external success markers help. But they aren’t “the root of the root.”
13. Your healing will trigger those around you—and their reactions can hurt.
I realized, at a very young age, that I held a tremendous amount of resentment toward my family, my peers, and the town I grew up in.
The only way I knew how to work through that resentment was to write. For four years, from ages 22 to 26, I worked on my first book called Confessions of a Teenage Gamer. The book was about my becoming one of the highest-ranked World of Warcraft players in North America as a teenager—but it was really about the difficult process of finding your identity when you’re young, and how it feels to be misunderstood when all you want is to fit in.
By the time I finished writing, and re-writing, and re-writing that book, I had grown into a different person. Chapters penned down in front of me had helped me better understand why I had felt the way I had growing up. But when I shared the book with my family, my healing held up a mirror for things they hadn’t confronted yet in themselves.
And it hurt.
I’ve come to realize the reason why I chose to start my first company wasn’t just because I wanted to explore my potential and become an entrepreneur. It was also because I had become terrified of writing, and experiencing rejection like that again. I wanted to work myself to death, and not think about my feelings anymore. I wanted to stop growing—because growth was painful.
It wasn’t until I took a trip to Mexico when I was 29, and started journaling on a daily basis again, that I realized how long I’d been running from myself.
And it was time to start healing again.
14. Becoming a millionaire isn’t all it's cracked up to be.
When I was 27, I became a millionaire “on paper.”
My company had crossed multi-millions in revenue (of which I owned 40%). I had invested in Ethereum very early, and the crypto boom of 2017 had turned my $10,000 investment into $183,000.
I vividly remember browsing homes on Zillow and thinking to myself, “If this keeps up, I’ll have my infinity pool in no time.”
Then, the crypto market tanked. A third of our clients (who were crypto startups, which had contributed to our massive growth rate as a company) vanished. And, because I believed long-term in the technology, I didn’t sell any of my Ethereum holdings.
In a span of 3 months, I went from being a “millionaire” and back down again—and nothing in my life had actually changed.
That’s when I learned there is a massive difference between being a millionaire “on paper,” and having a million dollars in cash.
15. Confidence is a reflection of how much you trust yourself.
I think everyone growing up thinks, on some level, that confidence is something you express outwardly.
It’s a posture—a way you can convey your power to the world.
Nothing has beaten this belief out of me like entrepreneurship. Running a company humbled the absolute shit out of me. It made me realize that confidence isn’t a posture or a pose, a title you wear or a status you hold. Confidence is, quite literally, who you are when things don’t go according to plan. Confidence is a front-row seat to the relationship you have with yourself.
In a sense, I think that’s why insanely successful people in LA show up in flip flops and a $15 t-shirt, while people who desperately want to be seen as successful show up as if they’re attending a black-tie event. The former, who have walked through fire, have an enormous amount of trust within themselves. The latter, who haven’t yet gone to war (in whatever industry they’re in), haven’t really tested themselves yet—and it shows.
16. The more successful you become, the more opportunities you will be offered—and the more you’ll have to say, “No.”
A mentor of mine called this, “The burden of opportunity.”
When you’re great at something, a lot of people are going to want to work with you. The problem is, if you say “Yes” to every opportunity that comes your way, you’ll lose sight of what it is you really want to do. Your days will become filled with helping other people achieve their goals—instead of you prioritizing what it is you truly want to do.
17. People who speak in complicated terms don’t typically know what they’re talking about.
This was a big professional lesson for me.
When people use industry jargon, buzzwords, or overly complicated explanations, it’s usually because they don’t actually know what they’re talking about. Meanwhile, it’s the people who can somehow explain complicated ideas or perspectives in extremely simple, immediately-understandable terms who are speaking from experience.
18. Who you are is already enough—and the more you can lean into who you truly are, the more “attractive” you will be.
I spent most of my early years trying to be someone other than who I already was.
I thought by trying to be what other people wanted me to be, I would be liked. I would be loved. I would be appreciated. I would be respected.
What I ended up learning (the hard way) was that, yes, you can change “who you are.” Yes, you can change the people you attract in your life. But are you attracting what you truly want? You’re putting forth all this energy, but is it actually the energy you want to receive back?
Years of working on myself, making my art, going through therapy, setting new goals and accomplishing them and realizing the trophy at the end didn’t solve all my problems, eventually made me realize who I already was, was enough. And the more I allowed my most authentic self to just BE, the more I attracted other people who appreciated me for me—and the more my life started to be a reflection of the things I truly valued.
19. Anyone “further along” on the path was once exactly where you are.
I’ve always been fascinated with this idea of not knowing where any one of us sits on our path of personal growth.
I was a hardcore gamer growing up, and in video games, the game always told you exactly where you were. If you were Level 7, you knew you needed 1,300 experience points in order to reach Level 8. But in real life, we don’t have that same sort of objective feedback. We pick up hobbies, we start down career paths, and for the most part, we never really know where we “are.” The only way we know is by seeing who is “behind” us (less experienced) and who is “ahead” of us (more experienced).
But it’s important to remember that anyone you see on the path as being “more” experienced, “more” successful, “more” accomplished, isn’t necessarily smarter or fundamentally different than you. They’ve just been at it longer. Or they’ve been fortunate and found teachers and mentors that accelerated their growth. Or their resources have allowed them to move faster. But again, that doesn’t mean you can’t get to where they are.
The way I remind myself of this is by attaching an arbitrary number to someone else’s accomplishments. If I see someone I want to “be like,” I think to myself, “Imagine it took them 5,000 or 10,000 hours to get to that level.”
I now have a more actionable path forward.
In order for me to reach their skill level, I need to invest say 5,000 hours into my craft, career, or path. And I can either invest an hour a week, and stretch that 5,000-hour journey across an entire lifetime, or I can put my head down, focus, and gain those 5,000 hours of knowledge in the next 4 years.
We all have this choice.
Sometimes we just forget, because we don’t “know” where we are on the journey, right now.
20. The “perfect time” never comes. Every day is the perfect time.
For years, my girlfriend has asked me if we could get a dog.
I said, “Absolutely not,” up until very recently.
Nothing had really changed in my life that made it a “better” time to get a dog. I wasn’t any more or less financially stable. I wasn’t any more or less busy. I also didn’t consider myself any more or less “mature” or “ready” for that sort of responsibility.
One day, she convinced me to go to a dog adoption event. And I saw this white Border Collie mix with a brown face like a little bear, and it was game over. I held her. She licked my face. We took her for a walk, and she was driving home with us an hour later.
Now, the first few days we had her, I definitely said to my girlfriend, “We can still give her back, can’t we?” It was an overwhelming transition to have a puppy in our apartment running around, destroying clothes, barking at random sounds, waking us up in the middle of the night, etc. But after a few weeks, and then a few months, we all became a family. And now, I couldn’t imagine not having her. Even the thought makes me incredibly sad.
There’s never a perfect time to adopt a dog.
There’s never a perfect time to start a company.
There’s never a perfect time to make a big life decision.
Today is as good of a day as any.
21. You’re never too old for things you loved to do as a kid.
Growing up, I thought there was an age where you sort of had to “let go” of what it meant to be a child in the world.
And I feared the day that would come.
But through my late 20s, and especially after taking on the responsibility that comes with employing other people, or caring for a girlfriend and a dog, I’ve really seen how that’s a choice. Sure, there is something to be said for letting go of childish behaviors, but you should never let go of living life as a child—that is to say, openly, curiously, excitedly, energetically, passionately, unapologetically, and so on.
22. You have to stop measuring success over the course of a day or a week, and start measuring over the course of a month, three months, six months, and a year.
There’s a nuance here I want to clarify.
I firmly believe that success on the daily level, or even the hourly level, is what ultimately defines success over the yearly level. Home runs don’t just “happen.” Home runs happen as the result of practicing day in, and day out.
Now, that said, as you get older it becomes much harder to measure true success in the short term because vision get bigger, projects get bigger, goals get bigger, and so on. As your vision widens and your goals grow taller, you have to reframe your expectations for the timeline required for those goals.
- Big leaps forward in skill don’t happen in a day—they happen over months.
- Companies don’t just grow and exit in weeks—that happens over the course of a year, two years, five years, etc.
- Relationships and trust isn’t built in an hour—it’s built over months and years of consistent nurturing.
This is why “patience is a virtue.”
You can’t just wake up tomorrow and expect your life to be dramatically different.
23. The true meaning of love is the ability to grow together.
When you first meet someone, it’s all heart-eyes.
What defines whether or not that relationship remains intact isn’t the stability of that feeling of complete and total infatuation. It’s the stability of the feeling of connectedness, even if sometimes those feelings hurt.
My mom said to me, many years ago, that “love is the ability to grow together.”
And I never really understood that in my previous relationships, because they had never lasted more than a year. But in a relationship that stretches across several years, I have started to see just how true that really is.
24. Friends can be made in a wide variety of ways. The question is, do you want friends who make you better? Or friends who are just… there.
All of my friends, for my entire life, have always been people I’ve met through a shared passion or interest.
- When I was a teenager, all my friends lived inside the computer and played World of Warcraft.
- When I got into bodybuilding in college, all my friends were other bodybuilders and powerlifters at my gym.
- When I started my first company, all my friends were other entrepreneurs.
I chose where I wanted to go in life—and then I made friends with people who were on that same path with me.
As a result, I ended up having to deprioritize a lot of other friendships in my life. That’s not to say these relationships can’t remain, in some capacity. But I have always been someone who cared too much about my own direction in life, and wanting to be surrounded by people who I not only connected with, but could also help me on the path I’d chosen for myself—and vice versa.
Either way, friends present themselves. When you move to a new town, or you pick up a new hobby, or start a new job, people naturally emerge as potential comrades on your journey.
The question is: are you choosing your friends intentionally?
Or are they just… there?
25. Patterns always repeat themselves. Your job is to catch them, and if you want a different result, change the pattern.
We are a reflection of the choices we make in our lives.
If we don’t like the direction we’re headed, all we have to do is change the pattern. This means questioning who we’re spending time with, what projects we’re investing in, what habits are holding us back, etc.
Once you see a pattern repeat itself several times, you better believe it will continue to repeat itself until you acknowledge “the root of the root.”
26. In a world becoming more digitally connected, “focus” is becoming each person’s greatest competitive advantage.
The older I get, the harder I work to be less digitally connected.
I try to keep my phone on silent and on the other side of the room as often as possible.
I practice not spam-refreshing my email every 5 minutes.
I only use social media for my writing, and try to not get sucked into hours and hours of scrolling.
In a world where these tools are only becoming easier and easier to abuse, it’s the people who are able to maintain a level of clearheadedness and focus who will achieve the most, create the most, and provide the most value to society. They’re the ones who will define the game, opposed to being trapped within it.
27. Most people stop reading as they get older—and that’s a shame.
Whenever I talk to someone, catch up with someone, or meet someone, one of the questions I love asking is, “Read any good books lately?”
As a writer, I’m always curious.
Unfortunately, most people don’t respond with an exciting answer. In fact, the usual response is, “Oh wow, I haven’t read a book in a long time.” The argument here is that we’re moving to a world of Netflix shows and podcasts. And no matter how informative or interesting those mediums are, they are still very new. Books, on the other hand, house centuries and centuries of knowledge—much of which has yet to be “converted” into today’s more entertaining mediums.
But reading does something very different for the mind, and the soul, than watching a Netflix series or listening to a podcast does. And I find the more often I read, the sharper I am, the more creative I feel, and the more in touch with my feelings and awareness I become.
Don’t stop reading.
28. Destinations don’t exist. All that matters is how you feel in this moment.
I’m not sure when, but somewhere throughout my 20s I realized the goal wasn’t to become a billionaire and have all the money in the world (although, that’s still a “tangible” goal of mine).
Instead, I realized the real goal was to just be happy and have fun along the way.
Every time I’ve tried to tell myself the trophy at the end would solve all my problems, I’ve been motivated, I’ve achieved the goal, I’ve gotten the trophy, and then I’ve ultimately realized the trophy didn’t mean a thing—and what I valued much more were the friendships I’d made along the way.
Today, whenever I start a new project, or set a new goal for myself, the first thing I try to optimize for is the experience of it. I want to work with people I love working with. If I’m going to pour my heart and soul into a pursuit, I want to do it with people I know will make the path more enjoyable. If I’m going to do something difficult, I want to find ways to make it fun.
I want to set harder and harder goals for myself, but I also want to remember the whole point of life is to enjoy the journey.
29. Everyone is on their own path, and it’s not your job to tell other people how to live.
In fact, it’s a massive waste of your own time.
Some people want to live purposeful lives. Some don’t.
Some want to set big, audacious goals for themselves. Some won’t.
It’s not your job to try to get everyone around you to see life the way you see it. All you can do is go in the direction you know is best for you, and see who is moving in that same direction. The energy you expend trying to convert people to your way of life is never worth it. You only end up distracting yourself.
I would actually argue that by trying to “change” other people, what you’re really doing (the root of the root) is avoiding doing the hard work you know you need to do within.
It’s much easier to try to change someone else than change yourself.
30. Ten years is a very long time.
When I was 19, 20 years old, I wanted to be a rapper.
When I was 21, 22, 23, I wanted to be a bodybuilder.
When I was 24, 25, 26, I wanted to be a creative director at a huge advertising agency.
When I was 27, 28, 29, I wanted to be an entrepreneur.
And from age 17 to 29, I’ve wanted to be a writer.
In my 20s, I got to live 4 completely different lives. I immersed myself in 4 different industries, learned entire tool kits of different skills, made different friends, explored different paths, and ultimately became different versions of myself.
And every one of those pursuits made me who I am “today.”
If I was able to live that many different lives in those ten years, then I can only imagine what 30 to 40 will look like, and how many different lives I may be able to live again.
Ten years is a long time. And the older you get, the more knowledge you accumulate, the more resources you have, and the more freedom in front of you to become whatever it is you want to become.
I don’t feel old at 30.
I feel like I’m just getting started.
If you enjoy my writing style, and want to learn how to become a better writer yourself, check out my weekly “How I Wrote This” newsletter on Substack.