10 crazy facts that you wish you knew earlier


Regrets can eat at you like mosquitoes by the lake at dusk. They’re a kind of emotional debt owed to you — a kind that can’t be repaid, only written off. They’re demons that can’t be defeated, only outrun. Put simply, you want to barrel through life with as few of them as possible. So if Doc Brown — or, for the kids, Rick — allowed me to travel back in time to when Outkast was king and Skrillex was still a parody name for high-end kitchenware, here are 10 things I’d tell myself; I’m telling them to you instead.


10. Your grades matter less than you think.

Things that matter more than you think: Relationships and activities. Talk to everyone you meet. Befriend professors, peers, fellow students, bosses, colleagues, bartenders, baristas, roommates, auto mechanics. Walk through every open door and kick down all the closed ones. Related: Paying through the nose to go to a prestigious university is way overrated. For you kids in the Northeast US, this will shock you, but state schools are where it’s at in the south and west.

9. Spend more — and spend on fewer things.

The road to financial ruin isn’t paved in splurging on a vacation or a music festival — it’s paved in repeated, habitual, autopilot spending on smaller, more regular things. At 25, my biggest monthly expense — after rent — was going out and blowing a hole in my wallet in energy drinks, coffee, Gatorade, bottled water, booze, drugs and cigarettes. Really. I nickel-and-dimed myself to death. Two energy drinks (to wake up), coffee (to stay awake), two bottles of Gatorade (to nurse off that hangover), a bottle of water (to stay hydrated), five beers (to loosen the fuck up), a dime-bag (to go to sleep) and a pack of cigarettes (because why not). In New York State, in 2007, that checks in at about $55 per day. Coulda stayed home for one week and bought a round-trip plane ticket to Miami (and bought all those things in South Beach instead).

8. Take more calculated risks.

“Seems to me like all the world gets high when you take a dare.” — Red Hot Chili Peppers

Risks are the great inspiring adrenaline rush of life. They motivate you and attract others. If you don’t think you can climb that mountain, finish that marathon or win that battle of the bands, but want to tackle it anyway, you should. Nearly all the greatest stories you tell, all of the things you’ll be most proud of, involve some element of risk.

7. It’s okay to be weird.

Look at this goddamned car. That was mine from 2009–2010. It’s a 1985 BMW 745i. I bought it for $800 as a reclamation project and did a lot of the work on it myself. It had heated seats. A moonroof. A V8 engine. And all the controls were written in German. It didn’t even have a working speedometer. (OfficerDo you know how fast you were going? Me: Zero, sir. Zero.) It’s completely impractical and handled like a shopping cart in the winter. And it’s my favorite car I’ve ever owned. If something feels like you but is a little different from the norm, it’s perfectly fine to lean into it.

6. Boundaries are important.

If you find someone who sets your soul on fire, by all means, chase them. But don’t be relentless. Space is crucial for growth, and for developing a sense of longing. You don’t want someone you do everything with. You want someone who complements you and gives you the space to become the thing you want to be. A lack of established boundaries paves a superhighway toward a codependent relationship … which is the surest way to secure a life of misery and resentment.

5. That said, maybe hang out with your friends more.

The people in your life will be your greatest assets and your greatest strength. It’s crucially important to endear yourselves to each other at a workable, metered pace. The best times in your life will be the ones you remember with people all around you, where you felt like you were part of a collective whole that’s greater than your individual parts. I have a group of friends from that era who I remain in touch with, and we travel the country together just tearing up whatever city we happen to be in. Would’ve never happened if we didn’t put in the foundation early, when we were all broke and had nowhere else to go except each other’s houses.

4. Break more rules.

They were usually created by other humans — imperfect other humans who also break rules. People who follow every rule probably don’t take a lot of calculated risks — again, the adrenaline rush of life and the superhighway toward fulfillment — and probably value grades over relationships, saving over spending, norms over self-expression, and things like shoulds and oughts. You can be a rule follower if you want to, but be prepared to be very average, and — if you’re the type of person who does a lot of thinking — prepare to experience a lot of unpleasant cognitive dissonance … the precursor to regret.

3. Go outside.

The sun is fucking magical. So are trees. So are mountains. So is the beach. So are other cities. You know where you can create lasting memories that make your heart warm and full? Anywhere you can work up a good sweat. Outside your comfort zone. In motion. Be an explorer; be a navigator; be an athlete. It’s a big world and there’s plenty of places to go to find inner peace or embark on a spiritual quest. Find them. You don’t have as long as you think.

2. 90% of talking is listening.

People think they need to develop impressive oratory skills to become a gifted conversationalist … this is reverse engineering. I’ll provide an unrelated example. Let’s talk about sex, baby. You don’t become a great lover by practicing “moves” (really wish there was a better term for that) or learning positions. No. That’s *part* of it, but the ROI is much lower. You become great by learning what your partner likes, doing it over and over, mastering it and then exploring other related concepts. This is how a great conversation should flow. Pay attention. Understand. Remember. Ask questions. Follow up. Build off what they like to talk about. Discover their sense of humor and play to it. No matter how many people share a room with you, whoever you’re talking to should feel like the only person in it.

1. The road to success is paved in failure.

I grew up in an environment where failures were chastised as character deficits, or signs I was pursuing the wrong things, and not as stepping stones or opportunities for growth. And the fear of failure, and a resentment of success, were (in some cases) literally beaten into me for as long as I could remember. Failure, and avoidance of it, became the central focus of my mind. I became pathologically scared of rejection and other people’s perceptions of me. I started to say yes to everyone who wanted me: people I am comfortable around but not really chasing. I became self-conscious, stilted and awkward in situations where things are on the line — dates, job interviews. I waited to pursue anything until I felt sufficiently comfortable in my own skin and confident in my own worthiness and abilities. I waited to feel fully prepared. That moment never really arrives. In fact, failure is not just instructive, but empowering. I learned through failing later in life that it was through these experiences I gained my greatest strength. The more you embrace failure, the more comfortable you become immersing yourself in it, the more likely you are to find greater success earlier. And that’s the greatest life lesson I can give you.

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