The 5 Best Mistakes I Made in My 20s
Embarrassing mistakes that I would absolutely make again
I wasted no time in making tons of mistakes after high school, many in my 20s. Mistakes that, if I had to do it all over, I would absolutely make again.
No hesitation. No questions asked.
Two decades removed and these mistakes continue to feed me insights, fulfillment, and drive. It’s not too overreaching to say that, in a very real sense, these mistakes made me who I am today.
I’ve messed up many times in my life in ways that I would change, given the chance. Then there are those beautiful mixups, messes, and mistakes that shaped me.
Here are the five best mistakes I made in my 20s.
I lived “homeless” for half a year
In my second year at university, a dorm fire left me and hundreds of other college students homeless. Many relocated to new living quarters.
I never did.
I couch-surfed between friends for half a year. Now, I know that’s not the traditional definition of “homeless”. I wasn’t living on the street.
But I still felt “homeless.” I didn’t have a home.
I slept on literal couches or recliners. If you’ve never had that experience, it comes with waves of anxiety and uncertainty. You never feel settled, which can dramatically impact your mental and emotional health.
However, I wouldn’t change it.
Homelessness taught me resilience, friendship, and flexible living. Human beings are incredible at adapting — I learned that I possessed inner resources capable of dealing with harsh life lessons.
This inner strength carried me through many of life’s difficult ups and downs since college.
I dated my future ex-wife
Long story short, I met my ex-wife in college. The marriage lasted 15 years, a decade and a half that I would love to reclaim. After going through a divorce two years ago, I’m happier than at any other time in my life.
Still, divorce is sometimes a kind of relationship failure. I never intended on divorce. It’s embarrassing even though it shouldn’t be at all.
So, why in the world is dating my ex-wife on this list?
She is the mother of my two children — a boy and a girl. If I could get them without the marriage, I would take that offer in a heartbeat. She is not the problem; the marriage was the problem.
Even so, the marriage provided a cauldron for my personal growth.
The painful, personal experience of the drama-filled relationship and eventual divorce imprinted “what not to do in a relationship” on my soul. I will never make those mistakes ever again.
And my marriage gifted me with my kids.
To get my kids, I would trade a million decades. They are everything to me. Children change you in ways that no one can really describe or prepare you for in advance.
Children are magic.
I lost my religion
In college, I signed up for a mission trip to Bello Horizonte, Brazil. What was supposed to be the best two months of my life turned into a complete nightmare.
One long airplane trip later, we touched down in Brazil. It took me 0.3 seconds to fall in love with the country.
I loved the warm weather, the Brazilian food, but mostly I fell in love with the beautiful people. One beautiful person, in particular, caught my attention. Typically this wouldn’t be a problem.
However, the mission trip team leaders strictly forbid any kind of fraternization or dating. We were there to share a loving message not fall in love.
Despite the rules, Ines and I snuck off into the woods for some illegal fraternization. We promptly got caught and I was sent home a month early from my trip.
Again, not a big deal until you realize that my friends and family had helped pay for my trip. Also, I legitimately wanted to fulfill the loving intention of my mission trip. My faith has always mattered to me — and still does.
Instead, I slinked home to face disappointment, failure, and shame.
For the next few years of college, I completely lost my spiritual footing. I partied, experimented with drugs, and made a series of unhealthy decisions that challenged everything I had previously believed.
But, I would do it all over again.
“I wasn’t searching for something or someone….I was searching for me.” — Carrie Bradshaw
I don’t regret exploring my beliefs, testing out new ideas, and trying on new behaviors.
I learned more about myself in those last two years of college than in the prior 20 years. I now know my flaws, my secret corners, my skeletons.
In a very real sense, losing my religion helped me find my faith.
I failed at crappy jobs
Oh, man. I failed miserably at so many jobs. Let me recount the embarrassing ways.
First, I tried working at a call center trying to squeeze money from alumni. I hated it and quit weeks later. Then there was the dumpster fire of working at the National Boyscout Museum.
The job itself was not the problem. My boss — who thought I could rewire the entire building like a team of professional electricians — was the problem.
Next, I experimented with being a nighttime security guard, but it left me sleep-deprived and missing classes. I cut my hours until I finally surrendered to the fact that I’m not a night person.
From a short-lived job at Hardee's, I jumped into an assistant supervisor role at a shoe store. I lasted a month before getting the boot for not vibing with upper management.
Honestly, it’s embarrassing to admit how often I failed at jobs back then. But I wouldn’t change it. Those failed jobs taught me what kind of positions didn’t work for me.
Conversely, I know to find the positions where I naturally excel.
I’ve never worked the night-shift again. I would if I needed to, but it’s my last choice. I’m not at my peak performance late at night (hence why I’m writing this article at 6:19 am on a Friday morning).
Also, before taking a job, I know to ask about management style, expectations, and training.
I embraced purposelessness
Lastly, I graduated college without a clue as to what kind of career I wanted to pursue. All I knew is that I loved writing.
I embraced purposelessness for the entirety of my 20s. I tried different types of jobs (using the info gleaned the hard way during college). I embraced not knowing where I was headed or how to get there.
I wrote a variety of short stories, articles, novels, and nonfiction books.
I experimented in every area of my life — meditation practices, different churches, hobbies, fitness routines. By constantly testing new things, I accelerated my personal growth.
“It takes courage….to endure the sharp pains of self-discovery rather than choose to take the dull pain of unconsciousness that would last the rest of our lives.” — Marianne Williamson
Personal growth led to results that I repeated, expanded, and leveraged to get promotions, raises, and new opportunities.
Some of my friends seemed just as lost but they felt helpless and hopeless. They resisted not having a purpose. They refused to go through a series of tests.
They chose a purpose just to have one — with predictable poor results.
I chose to embrace purposelessness, and it’s a choice I would make again. It gave me permission to explore every facet of my life and being. Once again, I learned so much about myself that continues to inform my decisions daily.
Final thoughts and takeaways
There is a beautiful simplicity to admitting embarrassing mistakes.
I hope you won’t judge me too harshly. I’ve failed a lot. My blunders caused me and others a ton of unnecessary pain.
But they also shaped me as a person, father, friend, and man.
Here are the major takeaways:
- Don’t be afraid to “lose yourself”.
- Explore and experiment with your beliefs.
- Try out different types of jobs to find positions that best fit you.
- Get comfortable with discomfort.
- Embrace uncertainty. It’s ok not to know what you want or where you are headed.
By reading my mistakes, I hope that you will gain some relief. I hope that you give yourself permission to fail miserably over and over again.
Mostly, I hope you make some mistakes of your own. Mistakes that you’ll look back on 20 years from now with a smile and say, “Yeah, I would do that again.”
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