The Best Life Advice You Haven't Heard: 27 lessons in 27 years
Practical, non-obvious lessons from reading a thousand books, traveling the world, and never having all the answers.
I’m not big on birthdays, but I also don’t dread aging. Many of my friends view 30 like a Rubicon — the death of youth, a fast lane to marriage, kids, and oblivion.
Here I am turning 27 this week, and I'm happier and more at peace than ever. I get to write for a living, I love the people around me, and I have more control over my life compared to any other age.
When you’re young, it’s hard to figure out who you are while also establishing the relationships, work, and habits that make you eager to wake up every morning. As you get older, responsibilities pile up, but so does freedom of choice — the autonomy to build the life you want to live.
Striking a balance doesn’t exactly get easier each birthday. But getting older does mean you have a little more wisdom behind every decision, which hopefully means you’re better at being who you want to be.
In no particular order, here are 27 lessons I’ve learned in 27 years.
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1. You only get good at things you do for a long time
Unless you dedicate years to a skill, there’s very little chance you will be above average at it. Most A-list actors have dozens of films or shows under their belt before their first hit, and most writers write a million words in obscurity before anyone notices.
The only way you will become a skilled photographer, programmer, or speaker is if you’re more committed to consistent action than the idea of success.
New skills seem scary at first, but fear shrinks in direct proportion to competence.
2. Happiness lies in the most boring parts of life
It's easy to feel happy when you first fall in love, just like it's easy to be happy on a tropical vacation. But notable events or passion-fueled moments don’t resemble day-to-day life. We chase the extraordinary even though it's rare and hard to replicate.
Being satisfied with work, a routine, and the people and things you have in your life already is harder, but it's more realistic and sustainable.
Plus, when tragedy or hardship strikes, all we want is a mundane, normal moment.
Tim Urban has a great post titled “How to Pick Your Life Partner,” and he says a lot of people end up in unhappy relationships because their expectations of romance actually have nothing to do with a life partnership: “If we want to find a happy marriage, we need to think small — we need to look at a marriage up close and see that it’s not built out of anything poetic, but out of 20,000 mundane Wednesdays.”
3. Don’t postpone being the person you want to be
Annie Dillard said how we spend our days is how we spend our lives. “Flipping a switch” into adulthood is a myth. Habits are hard to break, particularly when you impose an arbitrary deadline on them (i.e. I’ll stop smoking when I have kids, I’ll start working out when I turn 30, I’ll start saving money when I get my next job).
Maturity is a skill, and you get better at it the more you practice. Professionally or romantically, if you spend your time fooling around, you just get better at fooling around.
4. It takes time for your skills to catch up to your ambitions
I’ve always wanted to be a world-class writer, but for years, most of what I wrote was shit, and I knew it. Reading good books meant I could recognize a good story, but that’s not the same thing as being able to recreate one myself.
It took a long time for the quality of my work to catch up to my vision. Even now I have a ways to go. I started this website when I was 22, and it's only recently started to gain the traction I anticipated hitting years ago.
Being the best at something largely comes down to outlasting everyone else. Most people lose patience before hitting their potential.
5. The longer something takes to build, the more staying power it has
If you grew up speaking a second language, you know it takes a long time for it to disappear, even after years of neglect. The same is true for long-standing habits, projects, and relationships. A long history can prevent two incompatible people from leaving a toxic relationship, for example. It can also prevent good partners from splitting over one bad fight.
6. “You should never be at home”
That’s according to Professor Scott Galloway, who says there’s an inverse relationship between the amount of time spent at home and how successful you become.
In one sense, if you spend most of your time home, it doesn’t matter how smart, charismatic, or talented you are because no one’s there to see it. Positive energy in a vacuum is meaningless, and it can’t compound over time.
Who we become, personally and professionally, is largely determined by how we exist in relation to others. Putting yourself around people and spending time in inspiring environments generates forward momentum that sitting at home can’t replicate.
7. If you try to create something for everyone, you end up with something for no one
Whether it's a newsletter or baked goods or a sex toy, “Earth” cannot be your target audience. Too broad an aim leads to a vague and impersonal product or service.
If you can’t narrow your focus, consult your own interests. Write the book you want to read. Record the podcast you want to listen to. Use yourself as your ideal audience.
8. Focus is a superpower
With smartphones and social media, our attention is splintered more than ever before. Most of what we consume is garbage, and we forget almost all of it after a minute. News articles and books are getting shorter, and video trends from TikTok have made it to the big screen too. Hollywood producers know to make films that include more cuts per scene, decreased shot durations, and more motion.
The least productive stretches of my life are when I juggle six projects and hold dozens of meetings a week. Those times feel productive, but very little of my efforts move the needle. It's unfocused and chaotic, with most of my tasks being prioritized by urgency rather than importance.
Ideally, that balance is flipped, with urgent matters being tackled in bulk or delegated so you can focus on one important project at a time. The most successful people I’ve met are those who operate above the noise.
9. One-sided relationships take a long time to wither
Especially for people who have known each other for a long time. The one who gives more feels resentful because there’s no reciprocation, and one who doesn’t try can feel resentful because the other person is too blind, dumb, or nostalgic to get the message.
There’s a saying, plants die more from overwatering than underwatering. The same is true for humans.
10. Pursue enjoyment, be wary of pleasure
Think of everything you like to do, then see which of these two buckets they fall into.
Pleasure is cheap and fast dopamine, the stuff you get without earning: TikTok videos, sugary foods, pornography, video games, one-night stands.
Enjoyment takes intention and time and there's a higher barrier to entry. It’s earned dopamine: the satisfaction after a workout, quality time with loved ones, reading a good book, grappling with work you care about, nurturing a relationship.
Pleasure isn't evil or bad, but recognizing when you are chasing it can be helpful in determining whether you're playing long-term or short-term games.
11. Bad things happen way faster than good things
Making money, for example, requires time for compounding. Losing it does not. Building a reputation as a detail-oriented, hard worker can take years, but it could dissolve on one bad rumor.
I always liked the answer one of Hemingway's characters gave when describing how he went bankrupt: “Two ways. Gradually, then suddenly.”
12. There’s no such thing as the right time
To move cities, change jobs, or start a relationship. You’ll usually know when you have to do something, but you’ll rationalize like hell against changing the status quo. Whatever the reason for hesitation, it's best to take action before you're ready (since you'll never "feel" ready).
And, the longer you wait, the more negative consequences tend to balloon.
13. Experiment widely and never stop iterating
This applies to jobs, relationships, college majors, personal projects — let your curiosity guide you. Experimenting reminds you that you can be more than one thing in life, and allow you to continuously reinvent yourself. Most people who end up doing what they love get there by iterating over and over until they find a niche or figure out what they're best at.
It's not just good for figuring out what you love — casting a wide net is also the most effective way to discover what you hate.
14. Don't pursue your passion — build obvious advantages
There's something romantic about telling people you're pursuing your passions, though saying is easier than doing. Especially for creative disciplines like art or music, a passion-fueled interest can be incredibly competitive and difficult to scale.
Pursuing what you're already good at is a more sustainable place to start. Double-down on one or two specific, in-demand skills, and you give yourself obvious advantages. Confidence that's rooted in some pretense about passion evaporates quickly, but when it's grounded in genuine skill acquisition and competence, it can take you far.
If you do get good enough at something for it to become an obvious advantage, odds are you'll gain satisfaction from it anyway.
Passion isn't necessarily innate — it blooms from mastery.
The ones who are able to turn a passion into a livelihood aren't those who wake up one day and quit their job on a whim so they finally have time to write their novel. No, it's the person who has been honing their craft for years, and has completed enough reps to have a proof of concept that is marketable and has an audience.
15. Always leave wiggle room
The idea of “room for error” is popular in the investing world, with money managers leaving themselves enough margin to be wrong so their portfolios don’t go to zero.
I try to apply this to everything, from parallel parking and hedging a bet at the poker table to lifting weights. Giving yourself wiggle room sometimes means limiting immediate returns, but it allows you to keep showing up for the long run. You keep yourself in the game.
Wiggle room also implies not playing "Russia Roulette" stakes. Even if something has favorable odds, if there’s a chance of being wiped out completely then it’s a bad bet. You don’t want to lose when things go mostly right, but not perfect.
16. If you agree 100% with a single political party or ideology, you likely haven’t thought deeply enough about your own values
The world is not black and white (or red and blue). Mostly, it’s gray. I’ve met very smart people who are so gripped by politics that they stop asking themselves what they believe, and instead prioritize how to best align with a group or ideology. The people I admire most interrogate their own beliefs without double-checking party lines.
Aligning with a group or party is an easy short-term game that anyone can win, but a long-term trap everyone will lose.
17. There’s nothing wrong with a 9-to-5 job
There’s also nothing wrong with founding a company or being an entrepreneur, but it shouldn’t be done because it’s “trendy.” There’s wisdom in securing a steady income before building something on your own, as it grants you the safety net to fail and experiment.
To that point, criticizing someone who's building a side hustle while working a day job is akin to shaming ambition.
18. Time passes even if you don’t make the most of it
You can postpone a profession, degree, relationship, or side hustle all you want, but the years won’t slow down. Maybe you don’t want to write a book because it’ll take you five years, or you don't want to sign up for a marathon because it'll take you 12 months to train.
Well, that time goes by anyway.
19. Complainers are the loudest and least productive
Social media has minimized the consequences of whining and amplified those who have the most to complain about. There seems to be an inverse correlation between the amount someone complains and the amount of actual work someone accomplishes.
Writers, for example, who pour their energy into complaining about the rise of ChatGPT are going to fall far behind those who put their head down and focus on their craft.
20. The internet presents a massive opportunity
Putting yourself out there has never been easier and there have never been more hungry eyeballs. I’ve had job offers come from random people who stumbled upon my online writing. Starting a blog, podcast, or YouTube channel is free. Just like in the physical world, if you show up with great work and honest intentions, you attract good opportunities and better people.
(This is the digital version of the idea, "You should never be at home.")
21. Consciously work to eliminate knee-jerk reactions
I’m not saying you should not care deeply about things. But the less control you have over your emotions, the less effective your communication and the less power you have over your own mind in that moment. Usually, a knee-jerk reaction stems from some insecurity or ideology or a buried emotion.
Define it to master it.
22. What if everyone did it?
I’ve found great wisdom in this question when I’m not sure what to do. It’s rooted in the German philosopher Immanuel Kant's writing. He believed that for something to be good, it had to be universal. Loosely put, you shouldn’t do something unless you believe it would be good if everyone did it.
I don’t think this works 100% of the time, but I do think it offers a helpful perspective if you’re stuck at a crossroads.
23. Pick today's suffering over tomorrow's
Everything has a price, and I've found paying it up front to be faster, more productive, and more respectable than pushing it to some vague tomorrow. This goes for prioritizing work on a day to day basis, or even footing the bill for a gym membership now so you don't deal with health issues down the line.
Indeed, I’ll be the first to admit writing at night and on weekends for years while keeping a day job sometimes sucks. But I’d feel far more regret if I instead postponed or skipped this work and passed the time doing something easier.
Malcolm Gladwell put it like this: “Hard work is a prison sentence only if it does not have meaning.”
24. Your values aren’t real until your actions reflect them
The easiest way to find out whether someone is honest about who they say they are.
You can say you value reading, but if you read one book every seven months then it isn't true. You can say you value your health, but if you get drunk every weekend and don't make exercise a priority, that’s not true either.
25. Keep a journal
You will forget most of what happens in your life. When you make a habit of writing about conversations and people and happenings, you become more observant, more grateful, and more aware of the life you lead.
Daily or weekly both work wonders. Your current self will thank you for better mental health, and your future self will thank you for the writing skills and autobiography.
26. Advocate for yourself more than you think you should
Tell your boss about your wins. Share your ideas and work on social media. Don’t be shy about building something in public. It's uncomfortable at first, but the more you do it the more natural it feels.
The most successful people I know have never hesitated to be their own cheerleader. That's not a coincidence.
(Say, have you ordered a copy of my latest book?)
27. You will never hear someone who's doing better than you speak negatively about you
The people who spread rumors, talk smack, and try to shame you on the internet aren't worth your time. People who lack competence, confidence, work ethic or aim for low-hanging fruit usually gain pleasure in bringing others down to their level, while those who have done more than you are usually extremely generous with mentorship and teaching those who are interested in getting better.
Bonus: Don't sweat the small stuff.
(It's all small stuff.)
Thanks for reading.