7 “Stupid” Things I Did In My 20s That I’m Thankful For (And Why)

They helped me transform my success.

Anthony J. Yeung
Apr 14 · 6 min read

hen you’re young, you sometimes do “stupid” things. Call it inexperience, bravado, or just not giving a damn, youngsters can sometimes make bizarre decisions.

In my 20s, I definitely had my share of so-called “stupid” choices. But thankfully, a few of them were some of the best decisions I ever made. And only by making them and looking back did I realize they were really blessings in disguise.

I’ll share seven “stupid” things I did in my 20s that actually had powerful benefits for my future. I’ll also explain the common themes behind them so you can make better decisions for the long-term—regardless of how they might seem right now.

1. Getting Banned From Google Adwords

When I was 22, I followed the steps in the Four Hour Work Week by Tim Ferriss to test a business idea. I would never do those same steps today (they’re pretty bad, honestly), but I didn’t know any better — so I spent a month building a site and bought ads from Google.

Shortly after, however, Google suspended my account and permanently banned me.


But even though I failed, I’m thankful for it because I actually took action and tried something bold. I had no experience; all I had was a lot of passion and courage, which are two things essential for success. Most people, however, don’t fail enough. But that’s exactly how you succeed: Taking action toward your dreams, making mistakes, learning, and trying again until you win.

“You’re thinking of failure as the enemy of success. But it isn’t at all… you can be discouraged by failure or you can learn from it. So go ahead and make mistakes. Make all you can. Because, remember that’s where you’ll find success. On the far side.”

— Thomas J. Watson, Sr.

(I eventually got my ban lifted, by the way.)

2. Becoming a Janitor

After I decided to be a fitness trainer, I did an internship at one of the top gyms in the US. When I finished, I wanted to work there full-time, but they had no openings. Instead, they offered to hire me as a janitor because they always “hire from within” first—so once there’s an opening, I’d get it because I’d be working there.

So I took it.

It probably wasn’t a smart choice. (Looking back on it, they were probably bullshitting me and just didn’t want to hire me.) But it was a renowned gym and I thought it would be great for my career as a 23-year-old to keep learning from them.

I’m proud of my choice—given what I knew—because it proved to me that I was willing to do whatever it took to become successful. It showed I had a dedication few people had. And it showed I was willing to learn from the best, no matter what I had to do.

It also humbled me. I wasn’t “cocky,” but it was important to pay my dues and “start from the bottom.” It teaches you humility and it makes you appreciate how hard some people work without others ever noticing.

3. Moving 6,000 Miles Away From Home

In 2009, I graduated from university, but even with a great GPA, I couldn’t get a finance job because the industry was in flames. The “smart” thing to do would’ve been to stay in school, get real experience in my career field, or go to law school like some of my classmates.

Instead, I moved to a country where I didn’t speak the language (South Korea) to do something I never did before (teach English).

To this day, it’s easily one of the best decisions of my life. Every day challenged me and taught me something new. It changed everything I thought was possible and gave me a passion for travel. And because I moved abroad once, it was far easier to do it again, which eventually did many, many times.

A lot of people talk about it, but few people actually do it; yet once you do, you’re free. And by doing something that bold, you’ll completely alter your future because you’ll experience infinitely more things—and you can never go back to who you were before.

4. Putting All My Eggs in One Basket

When I was in college, I opened a Roth IRA and put all my money into Apple.

Conventional wisdom, however, says that’s pretty damn stupid: It’s unwise and unsafe to not diversify your portfolio. (Hey, I was 20; cut me some slack.)

But I’m thankful for it because I actually invested money in my youth, picked a “good” company, and held onto it. I thought Apple was a solid stock: All I had to do was look inside any class to see that 99% of kids had an Apple product so I “put two and two together” and invested.

Needless to say, that move single-handedly transformed my net worth.

5. Getting Earrings

I got earrings in my early-20s, and many people would probably say that was “stupid.” Back then, most style gurus were against piercings for men. (For them, unless you looked like you were on a Brooks Brothers catalog, you had no fashion.)

To this day, I still wear my earrings and I’m glad I have them. The biggest reason why is that I never have to wonder, “What if?” Many people would think about something—a new haircut, tattoo, or style—for years without trying. Instead, I debated the pros and cons (I even bought magnetic earrings just to see how they would look) and eventually pulled the trigger.

I’m also grateful I weighed the long-term implications. How would it look professionally? How would it affect my perception? I also reminded myself if I stop liking them, I could take them off (as opposed to something I could never take off). And those are always important things to consider.

6. Getting Rid of 90% of My Possessions

When I was 22, I decided to get rid of almost all of my stuff in one night—I raided my closet, stuffed two large garbage bags full of my clothes, and donated them.

People sometimes look at me crazy when they see how few clothes and things I own. But I love it—I have so much freedom and I don’t feel possessed by my possessions. Instead, I can move at a moment’s notice, I have far fewer worries and stresses, and I feel so much lighter.

Even now as I’m traveling around Europe, I live out of a tiny carry-on suitcase and wear the same clothes constantly. But it’s a small price to pay for less physical (and mental) overhead—and I wouldn’t have it any other way.

7. Quitting My Job Without a Backup Plan

When I hit 25, I had worked a job I hated for 16 months and couldn’t do it any longer—so I wrote my resignation letter and never went back.

Conventional wisdom says you should have a “backup plan” before you quit. (i.e. Find another job first and then leave.) But I couldn’t wait. Every morning, I woke up feeling like shit, wondering how I could skip work, and I was miserable all day. For my own sanity, I had to leave and use that newfound freedom and energy to improve my life.

Thank God I did.

One year of your life is no fucking joke. I know I was young, but I couldn’t spend more time doing something that was crushing me inside. If anything, I was compounding my mistake by holding onto my shitty job.

I’m not saying you should quit your job and sit on your ass and not do anything; I’m saying, by quitting your job, you have a ton of free time and energy to work harder than you’ve ever worked before to get what you want.

“What if I don’t have a backup plan?” you might ask.

That’s the wrong question to ask because you’re trying to solve a problem with the same mindset that got you that shitty job in the first place.

Take action and go for what you want.

Be confident in your resourcefulness.

Enjoy the power of serendipity.

And if all else fails, sometimes it helps to know that your true friends will love you, no matter what you do.

Sure, I’m not “mega-successful” or anything: I don’t own a multi-million-dollar company or I don’t have a private jet.

But I have made mistakes.

And that counts too.

It’s your life, baby.

Use it.

Ready to upgrade your success? I’ve created 5 free life hacks that will boost your results. If you use them, your life could change very quickly.

Get your 5 Life Hacks here.

The Ascent

Aspire to something greater.

Anthony J. Yeung

Written by

Featured in Esquire & GQ. Founder. Full-time traveler. Ready to upgrade your life? Get my 5 life hacks to boost your results here → https://bit.ly/2IDx15y

The Ascent

The Ascent is a community of storytellers documenting the journey to a happier and healthier way of living. Join thousands of others making the climb on one of the top publications on Medium.

Anthony J. Yeung

Written by

Featured in Esquire & GQ. Founder. Full-time traveler. Ready to upgrade your life? Get my 5 life hacks to boost your results here → https://bit.ly/2IDx15y

The Ascent

The Ascent is a community of storytellers documenting the journey to a happier and healthier way of living. Join thousands of others making the climb on one of the top publications on Medium.

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