What I Wish Someone Had Told Me in My Early 20s

Lessons from an eventful decade

Jack Krier
6 min readMar 6


Photo by Charlotte Karlsen on Unsplash

A few weeks ago, I entered the last year of my twenties.

The past nine years were full of wins, failures, and countless lessons. And that’s what your 20s should be.

Your 20s are a period of self-discovery and experimentation.

Of course, you can do all of that in your 30s. But most of us build the foundation for our future in our 20s.

When I entered my 20s, I pictured a straight road ahead. I will go to college, get a degree, pass the bar exam, and become a finance lawyer.

Five years later, I had gotten my degree, passed the bar exam, and quit my job as a finance lawyer. Another three years later, I had visited 70 countries and built an online business, and become debt-free.

Conversely, I had also spent all my savings, and my income fluctuated between living wage, high earner, and penniless student.

My 20s weren’t a quiet period — to put it mildly. But there is nothing to regret, just wins to enjoy and mistakes not to repeat.

On this basis, here’s what I wish someone had told me in my early 20s.

Fail more often

During the first half of my 20s, I played it safe.

I did what society expected and got a degree from a reputable university. I then worked my ass off in a job that looked good on business cards. I was driving the right car and living in the right sort of condo.

It was all marvelous. Except it wasn’t.

When I was 24, a massive tragedy struck my family, and we all started to question our life choices.

At this point, I realized a simple truth: your 20s are short, and it’s the best period to take risks and try novel challenges.

If you’re in your early 20s, you have one massive asset. It’s not your talent, looks, or background. It’s time.

Thinking about building that app your drunk friend came up with at 3 am? Do it. Want to travel around the world while being broke? Do it. Got a few online business ideas that sound ridiculous but have a 20% chance of succeeding? Go for it.



Jack Krier

Writer. Photographer. Nomad. I write about entrepreneurship, remote work, and personal growth | All of my links: https://linktr.ee/jackroaming