Things I Learned On The Way To 27


Last year I wrote a short piece: 25 Rules For Living From A (Semi-)Successful 26 Year Old. I didn’t expect it to be controversial but it was. To me, cutting around slow, indecisive people in line doesn’t exactly register as a mortal sin. Neither did saying Frequent Flyer Miles are for people whose time is worthless. But to others I guess it was.

What I was trying to do in that post was explain some of the things I’d learned as a young person stumbling around trying to find my way in life. They were my tricks and heuristics for life and for getting stuff done. Anyway, Gawker called the piece “insufferable” and got all outraged, which tells me I was probably more right than wrong. Whatever choices and priorities contribute to dooming someone to work there—I generally want to run very far from.

So this year, a year older, I thought I would follow up. It was a big year. I bought a house. Got engaged. Put out a book. Those are the visible accomplishments. Beneath them are the lessons, a lot of which came the hard way.

Between 26 and 27 I learned a lot. I was humbled. I was gratified. I was scared shitless a couple times. I lost things. I made a lot of money. I lost some on bad decisions. I definitely made mistakes. I also happily turn another year old, well on my way to undoing several of those mistakes and heading in the right direction.

Many of you may disagree with my advice but in any case, you can’t argue it isn’t sincere or that it wasn’t hard won. Hopefully the rest of you get something out of it. I can only share what I’ve learned. What you choose to do with it is up to you.

[*] Some habits that have saved me a lot of money and only mildly inconvenienced me: fly coach, don’t drink much alcohol, don’t pay for premium cable, drive an older car… when I look at friends who make a lot more money than me and wonder where it all goes, I assume it’s these things.

[*] Listen to your spouse or significant other. Like really listen to them. Their happiness determines your happiness.

[*] Sometimes you have to be a dick. Don’t waver when the time comes for it. Just push through it and move on.

[*] Pay for professional help. There’s that saying: if you think pros are expensive, try hiring an amateur. That saying is true as fuck.

[*] Yes, it’s true that money is better spent on experiences than material possessions. But, I will say that just because an experience presents itself doesn’t mean you have to feel obligated to do it. Sometimes you’ve had too many “experiences” and staying home is nice.

[*] It doesn’t matter how well things are going or how good a handle you think you have on things. We could all use a little therapy.

[*] You don’t have to live in New York or some other stressful city.

[*] If you’re unhappy with situation or people in your life, do something about it.

[*] Consider whatever it costs to make that happen well worth it. Dr. Dre walked away from Death Row Records and left everything behind. Now he can claim he’s hip hop’s first billionaire.

[*] You don’t control the results, only the effort.

[*] Try to be cool to strangers. It makes you feel better than being angry or annoyed with them.

[*] Physical exercise is a must. Everyday. Forget rest days.

[*] Walking is not physical exercise. It’s a mental health requirement. You have to do that in addition to physical exercise.

[*] Pets are a reflection of their owners.

[*] Be wary of what you get outraged about online. Save those emotions for real life.

[*] We all have our own sicknesses. Don’t fight people on theirs. You’re better off just trying to understand it.

[*] If you’re someone who goes out to eat a lot, try to avoid $$$ restaurants on Yelp—especially the new ones. They are usually way overrated and pretty much all the same. So when you go out, really go out ($$$$) or eat something cheap but awesome (East Side King, Chipotle, Shake Shake, whatever). You’ll have more fun.

[*] Fire clients that suck. Quit jobs that suck. Don’t be an entitled asshole who can’t take a little heat or unpleasantness, but don’t put up indefinitely with work that drains your soul. Besides, there is probably a better client out there you were too busy to pursue.

[*] I never would have thought this but dinner parties—hosting them even—are fun. And an important part of life.

[*] Always be reading. Never drift too far from philosophy.

[*] It doesn’t matter what age you are or how healthy you are: people die.They die unexpectedly. They die tragically. Sometimes they die violently. Never let this drift too far from your mind.

[*] Having Apple TV or Chromecast is better than having regular TV not because it’s cheaper but because you have to be deliberate about what you watch. And when there isn’t anything good you have to do something else instead of re-watching Law & Order. Plus, to watch sports you’ll leave the house.

[*] The more you patch things up with your parents, the better you might feel as a person. And weirdly, the more other seemingly unrelated areas of your life improve.

[*] James Altucher wrote something this year that helped me as a writer. He said to write/create the things you are afraid for other people to see. This kind of honesty is scary but it works.

[*] The hyper successful are, in addition to their genius, often messed up in some way. There is some pathology that’s a blessing but behind the scenes also a curse. I’ve started to come to understand that I might lack that pathology. And instead of feeling like this will deprive me of certain successes I once coveted, I feel lucky.

[*] People are often just as afraid of you (or of conflict) as you are of them. Remember this when you have to have unpleasant conversations. I keep forgetting this.

[*] We all have limits. No one can take on an unlimited, endless amount of work and stress. Not even me. Respect those limits.

[*] This doesn’t say anything about you as a person. This doesn’t say anything about you as a person. Nobody is paying attention like you think they are.

[*] Be direct about what you want and need. Even if you think it might hurt someone’s feelings. It’s better than resentment or stewing in anger.

[*] At the end of last year, I bought all the books I had on my Amazon wishlist, thinking it would be cool to just pick one up right after another. It actually had the opposite effect. I think what I learned is that letting curiosity take you where it leads you is important. Don’t plan everything out. It deprives you of the crucial elements of surprise and fun.

[*] I never thought I would care about taking care of a lawn or running to Home Depot for some house project, but I do now…and I like it. These things are relaxing, welcome distractions. I get it now. I regret mocking it so much when I was younger.

So that’s a year of learning, give or take. I’m sure there were plenty of other lessons I should have learned—but apparently the consequences or the morals weren’t clear enough. And now this year or next year or maybe far, far down the line I’ll have to learn it again.

Or maybe I’ll forget some of these. The point is you have to keep trying. You have to keep trying to get better and squirrel away little bits of wisdom from every experience and every person that you meet.

I hope these help you.