10 Life Lessons I Learned from Surviving My 20s

My 20s certainly were dramatic. Here are some of the life lessons I learned.

13 minute readProductivity

On my 20th birthday, I got drunk and peed on some old ladies’ front lawn. A cop saw me and stopped me. Fortunately, I talked my way out of going to jail that night. I already had an arrest record, but he didn’t bother to check. My 20s started out with a bang.

At the time, I was aimless. I had just dropped out of music school and cut my long, tangly hair. I wanted to move out of Texas but didn’t know how or where. I would sometimes lecture people about the spiritual aspect of consciousness and had a number of half-baked ideas about the theory of relativity and whether the universe actually existed or not.

I was smart and audacious and arrogant and really annoying.

Three days from now, I will be turning 30 years old. I will be in Las Vegas and probably completely out of my mind when it happens. But I’m happy to report that I’m far more responsible and far less pretentious these days. I’ve changed a lot in these 10 years. I don’t get arrested anymore and I don’t pee on people’s lawns anymore. I’ve built businesses, been around the world multiple times, and managed to create a career for myself as a writer — something I never could have predicted.

In our instant gratification culture, it’s easy to forget that most personal change does not occur as a single static event in time, but rather as a long, gradual evolution where we’re hardly aware of it as it’s happening. We rarely wake up one day and suddenly notice wild, life-altering changes in ourselves. No, our identities slowly shift, like sea sand getting pushed around by the ocean, slowly accumulating into new contours and forms over the passage of time.

It’s only when we stop years or decades later and look back that we can notice all of the dramatic changes that have taken place. My 20s certainly were dramatic. Here are some of the things I learned:

1. Fail early and often; time is your best asset

When you are young, your greatest asset is not your talent, not your ideas, not your experience, but your time. Time grants you the opportunity to take big risks and make big mistakes. Dropping everything and traveling the world for six years or starting some company to build this crazy app you and your friends came up with when you got high one night, or randomly packing up all (four) of your belongings and moving to another city on a whim to work and live with your cousin, you can only get away with these things when you’re young, when you have nothing to lose. The difference between an unemployed 22-year-old with debt and no serious work experience and an unemployed 25-year-old with debt and no work experience is basically negligible in the long run.

Chances are you aren’t strapped by all of the financial responsibilities that come with later adulthood: mortgage payments, car payments, daycare for your kids, life insurance and so on. This is the time in your life where you have the least amount to lose by taking some long-shot risks, so you should take them. Because it’s the disastrous failures of these years — that crazy love affair with the Taiwanese dancer that made your mother lose her hair, or the entrepreneurial joint venture some guy in Starbucks talked you into that turned out to be an elaborate pyramid scheme — it’s these failures that will set you up for your life successes down the line. They are the best lessons of your life. Get learning.

2. You can’t force friendships

There are two types of friends in life: the kind that when you go away for a long time and come back, it feels like nothing’s changed, and the kind that when you go away for a long time and come back, it feels like everything’s changed.

I’ve spent the majority of the last five years living in a number of different countries. Unfortunately, that means that I’ve left a lot of friends behind in various places. What I’ve discovered over this time is that you can’t force a friendship with someone. Either it’s there or it’s not, and whatever “it” is, is so ephemeral and magical that neither one of you could even name it if you tried to. You both just know.

What I’ve also found is that you can rarely predict which friends will stick with you and which ones won’t. I left Boston in the Fall of 2009 and came back eight months later to spend the Summer of 2010 there. Many of the people I was closest to when I left could hardly even be bothered to call me back when I returned. Yet, some of my more casual acquaintances slowly became the closest friends in my life. It’s not that those other people were bad people or bad friends. It’s nobody fault. It’s just life.

3. You’re not supposed to accomplish all of your goals

Spending the first two decades of our life in school conditions us to have an intense results-oriented focus about everything. You set out to do X, Y or Z and either you accomplish them or you don’t. If you do, you’re great. If you don’t, you fail.

But in my 20s I’ve learned that life doesn’t actually work that way all the time. Sure, it’s nice to always have goals and have something to work towards, but I’ve found that actually attaining all of those goals is beside the point.

When I was 24, I sat down and wrote down a list of goals I wanted to accomplish by my 30th birthday. The goals were ambitious and I took this list very seriously, at least for the first few years. Today, I’ve accomplished about 1/3 of those goals. I’ve made significant progress on another 1/3. And I’ve basically done nothing about the last 1/3.

But I’m actually really happy about them. As I’ve grown, I’ve discovered that some of the life goals I set for myself were not things I actually wanted, and setting those goals taught me what was not important to me in my life. With some other goals, while I didn’t attain them, the act of working towards them for the past six years has taught me so much that I’m still pleased with the outcome anyway.

I’m firmly convinced that the whole point of goals is 80% to get us off our asses and 20% to hit some arbitrary benchmark. The value in any endeavor almost always comes from the process of failing and trying, not in achieving.

4. No one actually knows what the hell they’re doing

There’s a lot of pressure on kids in high school and college to know exactly what they’re doing with their lives. It starts with choosing and getting into a university. Then it becomes choosing a career and landing that first job. Then it becomes having a clear path to climb up that career ladder, getting as close to the top as possible. Then it’s getting married and having kids. If at any point you don’t know what you’re doing or you get distracted or fail a few times, you’re made to feel as if you’re screwing up your entire life and you’re destined for a life of panhandling and drinking vodka on park benches at 8AM.

But the truth is, almost nobody has any idea what they’re doing in their 20s, and I’m fairly certain that continues further into adulthood. Everyone is just working off of their current best guess.

Out of the dozens of people I’ve kept in touch with from high school and college (and by “keep in touch” I really mean “stalked on Facebook”), I can’t think of more than a couple that have not changed jobs, careers, industry, families, sexual orientation or who their favorite power ranger is at least once in their 20s. For example, good friend of mine was dead-set when he was 23 of climbing the corporate hierarchy in his industry. He had a big head-start and was already kicking ass and making good money. Last year, at age 28, he just went and bailed. Another friend of mine went from the Navy to selling surf equipment, to getting a masters in education. Another friend of mine just picked up and took her career to Hong Kong. Another friend stopped working as an environmental scientist and is now a DJ.

I rarely had any clue what I was doing. I get emails all the time from people wanting to know how I built my business, when I decided to become a writer, what my initial business plan was. The truth is I never knew any of those things. They just happened. I paid attention to opportunities and acted on them. Most of those opportunities failed drastically. But I was young and could afford those failures. Eventually, I was fortunate enough to work my way to do something I liked and do it well.

5. Most people in the world basically want the same things.

In hindsight, I’ve had a pretty rollicking 20s. I started a business in a bizarre industry that took me to some interesting places and allowed me to meet interesting people. I’ve been all over the world, having spent time in over 50 countries. I’ve learned a few languages, and rubbed elbows with some of the rich and famous and the poor and downtrodden, in both the first and third worlds.

And what I’ve discovered is that from a broad perspective, people are basically the same. Everyone spends most of their time worrying about food, money, their job and their family — even people who are rich and well fed. Everyone wants to look cool and feel important — even people who are already cool and important. Everyone is proud of where they come from. Everyone has insecurities and anxieties that plague them, regardless of how successful they are. Everybody is afraid of failure and looking stupid. Everyone loves their friends and family yet also gets the most irritated by them.

Humans are, by and large, the same. It’s just the details that get shuffled around. This homeland for that homeland. This corrupt government for that corrupt government. This religion for that religion. This social practice for that social practice. Most of the differences that we hold to be so significant are accidental byproducts of geography and history. They’re superficial — merely different cultural flavors of the same overarching, candy-coated humanity.

I’ve learned to judge people not by who they are, but by what they do. Some of the kindest and most gracious people I’ve met were people who did not have to be kind or gracious to me. Some of the most obnoxious asshats have been people who had no business being obnoxious asshats to me. The world makes all kinds. And you don’t know who you’re dealing with until you spend enough time with a person to see what they do, not what they look like, or where they’re from or what gender they are or whatever.

6. The world doesn’t care about you

The thought that is so frightening at first glance — “No one cares about me!?” — becomes so liberating when one actually processes its true meaning. As David Foster Wallace put it, “You’ll stop worrying what others think about you when you realize how seldom they do.”

You, me, and everything we do, will one day be forgotten. It will be as if we never existed, even though we did. Nobody will care. Just like right now, almost nobody cares what you actually say or do with your life.

And this is actually really good news: it means you can get away with a lot of stupid shit and people will forget and forgive you for it. It means that there’s absolutely no reason to not be the person that you want to be. The pain of un-inhibiting yourself will be fleeting and the reward will last a lifetime.

7. Pop culture is full of extremes, practice moderation

My life immediately got about 542% better when I realized that the information you consume online is predominantly made up of the 5% of each extreme view and that 90% of life actually occurs in the silent middle-ground where most of the population actually lives. If one reads the internet enough, one is liable to start thinking that World War III is imminent, that corporations rule the world through some conspiracy, that all men are rapists (or at the very least, complicit in rape), that all women are lying, hypergamous whores, that white people are victims of reverse racism, that there’s a war on Christmas, that all poor people are lazy and destroying the government, and on and on.

It’s important to sometimes retreat to that quiet 90% and remind oneself: life is simple, people are good, and the chasms that appear to separate us are often just cracks.

8. The sum of the little things matter much more than the big things

I remember reading an interview of Dustin Moskovitz, the co-founder of Facebook and Mark Zuckerberg’s college roommate. The interviewer asked Dustin what it felt like to be part of Facebook’s “overnight success.” His answer was something like this, “If by ‘overnight success’ you mean staying up and coding all night, every night for six years straight, then it felt really tiring and stressful.”

We have a propensity to assume things just happen as they are. As outside observers, we tend to only see the result of things and not the arduous process (and all of the failures) that went into producing the result. I think when we’re young, we have this idea that we have to do just this one big thing that is going to completely change the world, top to bottom. We dream so big because we don’t yet realize — we’re too young to realize — that those “one big things” are actually composed of hundreds and thousands of daily small things that must be silently and unceremoniously maintained over long periods of time with little fanfare. Welcome to life.

9. The world is not a scary place out to get you

This gets said all the time, but it’s basically true. I’ve been to a fair amount of dangerous shit holes both inside and outside the US. And when given the opportunity, the majority of people are kind and helpful. If there’s one piece of practical advice I would give every 20-year-old, regardless of circumstance, it is this: find a way to travel, and when in doubt, talk to people, ask them about themselves, get to know them. There’s little to no downside and huge, major upsides, especially when you’re still young and impressionable.

10. Your parents are people too

And finally, perhaps the most disillusioning realization of your 20s: seeing mom and dad not as the all-knowing protectors like you did as a child, and not as the obnoxious and totally uncool authoritarians like you did as a teenager, but as peers, as just two flawed, vulnerable, struggling people doing their best despite often not knowing what the hell they’re doing (see number 5).

Chances are your parents screwed some things up during your childhood. Pretty much all of them do (as my mom always likes to say, “Kids aren’t born with instruction manuals.”) And chances are, you will start to notice all of these screw-ups while you are in your 20s. Growing up and maturing to the extent that one can recognize this is always a painful process. It can kick up a lot of bitterness and regret.

But perhaps the first duty of adulthood — true adulthood, not just taxed adulthood — is the acknowledgment, acceptance, and (perhaps) forgiveness of one’s parent’s flaws. They’re people too. They’re doing their best, even though they don’t always know what the best is.