The 8 Biggest Life Mistakes You Can Make in Your 20s

by Alexander Heyne · 61 comments

Let’s face it, many people tell you that your 20’s are for making mistakes, right?

Others have told me that “your 20’s are your wealth building years.”

Yet another person has told me that “your 20’s is your last chance to be sexually promiscuous and participate in orgies to dionysus.”  (Thanks…. )

But very few people have told me there are some life-changing mistakes you can make in your 20’s when you don’t have shit figured out.

These are the top ones I’ve seen. Where do I see them? I literally am referring to many of my closest friends and other acquaintances I’ve met on my travels.  These “mistakes” are ubiquitous. Some you can fix. Some you can’t — and they may alter the course of your life, forever.

So — from looking at the mistakes I’ve made, as well as those of my friends, these are the worst mistakes you can make:

The Not-So Obvious:

1) Avoiding Asking Yourself the Hard Questions

Except for being the perpetually lost demographic, we 20 somethings are also famous for avoiding our problems.

Some of us, a small percentage, actually continue to put off life… indefinitely.

And you know why that is?

It’s not because we’re slackers.

Its not because we’re lazy.

It’s not because we don’t know what we want (even though that’s true too).

It’s because resistance has beaten us, and we are too fucking scared to ask ourselves the hard questions. We’re afraid of the answers that might bubble up.

You’ll be sitting on a beach in Thailand talking to one of these people and they’ll go on some long diatribe about how “it’s bullshit how the world is run” or how “money is everything back in my country” or how “I’m trying to live a spiritual life.”

But in reality many of them are cowards. It’s easier to get fucked up 4 nights a week than stay sober and face the reality of your life.

Guess what. Lots of other people hate their jobs. You’re not special. But only a small percentage do something about it. They take the courses, they read the books, they learn the skills, they make the network, then they make a change.

So what are the hard questions you need to ask yourself? 

If you’re lost, just admit it, we all are. You’re not alone.

If you really don’t want to go back home to live in the 9 to 5 grind, there are other ways around it. But you need to have the emotional maturity and the cojones to admit that and know that the road may be long and difficult. But that road is always more fulfilling than living on some beach in southeast Asia, retreating, and just cultivating your little plot of land.

Somehow we all know what our path is, but many of us choose to ignore it for one reason or another. It’s time to stop being afraid, and ask yourself the hard questions. What do you really want to do?

2) Living Someone Else’s Life

By far, and I mean by far, the #1 reason you see many adults (your parents) freak out and join the half-life crisis club, is because they spent their youth doing things they should have done, instead of things they wanted to do.

They spent that time becoming a New York City finance guy instead of backpacking in Thailand.

They spent that time stuck as a corporate rat despite the fact that their inner entrepreneur was trying to claw its way out.

They became a lawyer even though they always wanted to be a school teacher — because dad said you could never make enough money as a schoolteacher.

And guess what happens when you “wisen up” and “get logical” and “act realistic?”  You harden up. You stop giving a shit about childish things like dreams, you think long-term travel is for hippies that live in Thailand and do drugs.

You think that “pursuing your passion” and “living your dream” is for douchebag college 20 somethings – not for mature, grown up, adults.

But the worst part – and I mean, by far the worst part – is that somewhere down the road, maybe 2 years, or 5, or 25, this creeping dissatisfaction with life enters your world.

“What the fuck am I doing all this for?” 

Whether that’s at 25, or 50, those little stirrings of discontent show up. First in your job, then in your life. Your relationships start going haywire. You start going haywire. Your life goes through a new incarnation.

And it was all because you ignored your gut.  So I don’t really know what else to tell you other than this: You already know what you want, you just have to go for it. It will be one of the hardest things you ever do in your life. But it will be the single, most worthwhile thing you ever do.

There will be a hundred and one reasons to be swayed by someone else and go into a life you don’t want.  There will be your parents who want you to grow up and be a successful, contributing member of society.

There will be your friends who want you go off and do what you want.

There will be acquaintances that tell you to hustle now and stack that cheese, and you can retire early – maybe as early as 40.

But only you know what you really want to do, and at the end of the day you’re only looking yourself in the mirror.

3) Thinking You’ll “Figure it All Out” And Then go do Something.

Guess what. Most people live their entire lives without figuring it all out, and they don’t end up doing shit.

You’ve heard this a million times before, but there is almost never a perfect time.

Yeah I’ll admit some of us get lucky. We get that sweet business introduction. We get a scholarship to live abroad. We get a hook up from mommy and daddy.

For the rest of us? The more time you spend thinking, the more time you spend screwing yourself over. Grow some big-boy balls and take action.

I recently talked about how thinking is one of the major causes of unhappiness.

The same is true about “figuring your life out.” Trying to think it through is the absolute worst idea. I can tell you this because I’ve done it myself and it didn’t get me any closer to figuring out shit – and that’s when I learned that it’s fundamentally flawed.  You truly don’t know something until you’ve done it. So go do it.

“Which one will I like more? Being a doctor, lawyer, or teaching English in Korea?”

Here’s what you do:

Shadow a doctor. Shadow a lawyer. Talk to a family friend who is a doctor. Talk to a friend who is a lawyer. Go teach in Korea.

Yay! In 1.5 years you’ve answered the question you would’ve guessed about for the next 40 years.

4) Making Expensive Financial Decisions When You Don’t Have a Clue What You’re Doing.


This is the “caveat” part of #2. Doing something is more important than trying to think it through.

However – doing something  (when you don’t know what you’re doing) that costs $100,000, like grad school or an MBA, is one of the biggest mistakes you can make.

Just my 2 cents of course.

But “I’ll see how I like psychology” is not the same as enrolling in a PhD program in clinical psyche.

If you want to know if you’d like a PhD program or would like being a psychologist, how about shadowing one first? Go into an office and actually talk to one. Creep around their place of work. See what they actually do all day. Sometimes it’s a lot less glamarous than you’d think. Also talk to PhD candidates and shadow them, because you’ll be one of them.

That’s one of the reasons I opted-out of being a doctor. It looks great on the outside – I love medicine, love biology, love helping people.

But when I did some research, guess what I found?  You spend 5 minutes with a patient. You don’t even let them talk and say “So what’s bothering you?”  You are confronted by sales reps of pharmaceuticals all the time. JAMA/NEJM and the other major research journals are filled with full-page pharmaceutical ads.

Even the good physicians complain about the system.

Not what I signed up for.

Go with the minimum viable product methodology – find a way to see what it’s like before committing. And no, attending med school is not “seeing what it’s like.” That’s called “an easy way to burn 100k” and “being a dumbass.”

5) Being Dissatisfied in a Job But Doing Nothing About it

Why do I consider this such a sin? Such a life mistake?

I consider it a big mistake to stay in a situation you’re unhappy with (when you’re young) because it’s one of the only times in your life when you can be uber-selfish and just go do whatever the hell you want on a whim.

That means you can quit 10 jobs and still have a safety net. You don’t have to worry about a spouse or kids.

The only things holding you back then are….

  • Fear of the unknown
  • Laziness – looks tough; I’ll pass.
  • Lack of information (You tell yourself, but it’s a lie, it’s actually laziness. There’s no such thing as lack of info in the internet age. It’s lack of action.)
  • Not knowing what you want (and feeling like you need all the info before you act)

Well guess what. I say this a lot but I’ll say it again: your work occupies a shit ton of your waking hours. And when your work sucks, your life sucks pretty hardcore.

Spending 7 am to 6 pm thinking about your work in some way, shape or form?  Awesome when your work is good; terrible when it’s bad.

If you DO want to go into business for yourself, I wrote an overly simplified guide here.

If you don’t — and you just want more pay in your job, more freedom, or just more fun, then you’ve gotta do more research.

Check out this ultimate guide here to finding “Your work” in life.

And check out the ultimate guide to flow-testing.

This may be the last time in your life you can start or quit 10 different jobs, or businesses without losing much.  What’s holding you back?

When you get married or have kids you have 1/2 the time, and 5x the responsibility. There will never be an easier or better time to quit a million jobs until you find one you like, or go into business for yourself.

6) Getting too comfortable.

Guess what? When you die, your coffin will be really comfortable – lots of nice padding in there.

Many of us looooove comfort. We love sitting down with half a box of krispy-kremes to a nice movie on the couch.

Many of us would rather write about (or read about) interesting lives, than go do it ourselves.

It’s like this epidemic of 20 something male wannabe MMA fighters. They watch MMA all day, and then start weight lifting.

3 months later they think they can take out anyone on the street. Wake up. 

This is a big gripe I have with many bloggers talking about living “big lives” and breaking the mold. Many of them live ordinary lives and they just write about the life they wish they could be living.

The problem with comfort is that it’s boring. You don’t acquire life experience through comfort and familiarity.

You know that thing called Flow that I’ve talked about a lot? It happens when you get slightly uncomfortable.

It’s like when you’re learning a new language and you show up to class sweating through your clothes. You have no idea how to say the words in the new language, so it’s nerve wracking. But 6 months later you have some basic skills.

That’s how LIFE IS.  When you start doing things that make you uncomfortable you grow.  If you want to know the secret to getting good at just about anything, it’s this - as soon as you get comfortable, find a way to make yourself uncomfortable again.

Choose growth.

We are happy when we’re growing.

7) Settling & Giving Up

Settling, rather than being a “mistake” is pretty much the path that the vast majority of people take.

We decide to make a bargain with life.

“Alright, I’ll get the job that I may or may not like, you pay me, I live a quiet life, get drunk friday and saturday, and then suck it up. I’ll meet a nice girl and marry her, and then we’ll have some kids, I’ll play with those kids for 20 years, spend 20 years in retirement, then die a quiet death.”

The people that stop fighting have unfortunately believed the lie that it’s time to “get realistic.” So what do they do? They hunker down, get a job, and get a life.

Unfortunately, I’ve received 100’s of emails from just these kinds of folks who woke up one day and said “Shit, this is not the life I wanted.”

They tell me that life went like this:

College (+ debt), work (to pay off debt and “be realistic”), get married, have a family, buy a new car, stay in debt and continue to work.  And then around 40-50 that creeping feeling that they haven’t done anything with their life other than purchase things.

I recently knew someone that died from cancer in his late 30’s — and one of the things he just could not shake was this one thing he kept telling me over and over:

“I spent my entire life buying stuff. Buying a nice apartment, filling my nice apartment with nice stuff. Buying nice clothes. Not even going on vacation. And now I find it ironic that I’m giving it all away to friends because none of it matters. So what else do I have to show for my life? Nothing. I spent 30 years accumulating nothing.”

It was scary to me. And unfortunately that’s where I find most of my friends who have “given up.”  They just settle in and buy all the trappings of a comfortable but boring life.

8) Believing in the Retirement Lifestyle

This might sound funny – believing in retirement, a mistake?

Yeah, and here’s why: believing in retirement (and acting accordingly) is a totally different way of life.

If you ask me, the entire idea of stacking cheese today so you can save it for tomorrow is flawed. Yeah of course you need to save money. Yeah of course you need to plan for tomorrow.

But deferring your happiness for 40 years and then start living?

I’ve got friends that got jobs right out of college, and being “settlers” they settled down into comfortable but boring lives. 4 or 5 years later, they’re still doing that. Some of them are still dreaming about starting businesses or traveling. They fantasize about waking up without an alarm. They wish they could work on stuff they love.

But unfortunately, the idea of “deferred” gratification is so built into our society I know that very few of them will escape. They’ll get so stuck into their work that 28, 29, 30 roll around, and they’ll get married – and then they get really stuck.

One of my friends finally decided that he wast tired of it and wanted to make a change, so he asked me when the perfect time was.

So I told him this:

For many of us the stars never align, the clouds never part, and the sun never shines. You just have to pick a day when you’re in a good-fucking mood for an adventure, and go for it.

You can’t store up happiness. You can’t store up life stories and experience. A lost day is a lost day. One day putting off your dream is just another day you’re getting further away and losing time.

You and I both know that “one day” never ever happens. One day becomes 40 years. Ask your parents. Ask them what dreams they’ve put off. One day becomes 40 years very, very quickly.

What About You?

Would you add anything to this list? What’s the biggest mistake you’ve made (in your 20’s or otherwise). What other advice would you give to 20 somethings?

Images: Road, Lantern Things, I hate my job,Never Give up, Retirement

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