• Optimistic Thom

How to be a Failure in Your Twenties

Updated: May 15

“The path to whatever your notion of success is will likely not be linear. Just because you’re older doesn’t necessarily mean you’re wiser. Your 20s will be full of failures — let them happen and learn as you go.” — Holden Desalles

When I was graduating high school, I thought I would have everything in my life figured out by the ripe age of 25. This meant my finances, my relationship, and my career would be causing me zero stress. I held it as an assurance that, by this time, the uncertainties in my life would be gone.

Reading that expectation now, I cannot really put into words how utterly wrong I was. It’s honestly hysterical what eighteen-year-old me expected of older Thom. I by no means have it all figured out, and the amount of failure I have been exposed too in my twenties seems unprecedented.

You don’t have to wind the clock back far to find this failure.

Last year I had awful experience in where my internship didn’t pan out, and I had to move home from Toronto, back in with my Dad. From there, I found a genuinely terrible, cold-calling job while in the same month, my long term relationship had just ended. On top of all of this, I had also stopped going to the gym and lost all care about my health.

These failures all happened within a couple of months, and it’s hard to think of one thing that was going right in my life at the time. So, I began spending hours on end playing video games and getting too drunk on weekends. I was doing anything to give me short-term happiness to avoid my situation.

Being twenty-four at the time, I was a failure.

I’m not alone thinking this about myself, as everyone in their twenties believes they are a failure in one way or another, and frankly, some people are. I certainly was.

What really made me a failure back then may not be what you’re thinking, and in this article, I’m going to explain why.


Our Twenties are Riddled With Conventional Failures

One thing that makes our twenties more unique than any other decade is it’s the first time we don’t have a hard and fast norm to follow.

Up until around eighteen, we go through a standardized school system, usually followed by a college or university degree of some kind. During this time, we are running a very paint by numbers life, and therefore never have to question that we are on the right path.

Once we finish school, however, the path splits into ten thousand different directions. Where we live, who we spend our time with, and our careers are suddenly our own decisions. Likewise, the only consequences of each choice are our own.

No one has the same path, but each one of those paths will have failure involved. Maybe you’re less financially stable, perhaps you have a tough time meeting someone, or possibly you’re miserable at your job. We are all facing these failures individually and they are catered to our own path.

The problem here is, thanks to the nature of social media, all we see is their success. We endure our own failures and look over to the perfect path of our friends who seemingly have chosen the ideal route for their life.

We convince ourselves that we have fundamentally failed in our choices, where, in reality, no one is completely confident in what they are doing.

Everyone has serious doubts about their career, everyone messes up taking adventurous risks, and everyone goes through relationship highs and lows.

These are conventional failures, and they do not set us apart. Our twenties are filled to the brim with these failures. They are not what defines us.

The Truth of Failing In Your Twenties

When I was going through a rough spot last year, and basically everything about my life was going wrong, I was a failure. However, it wasn’t because everything for me had gone astray.

No, as I said, this failure is commonplace in your twenties and dealt with by everyone.

I was a failure last year because I stopped pushing. I went through hell, and for a while there, I had given up completely. I couldn’t face how poorly my life was going, so I turned to short-term solutions to be happy.

I gave up on my ambitions and success for partying and video games. That’s right, there is the true mark of failing in our twenties, and it’s much more in your control than you think.

Imagine your life is a race. Many people mistakenly think it’s a sprint. People think the first one to get a good-paying job or the first one to get married, wins. Every time something goes wrong that slows us down to achieving these goals, we stop to believe we are a failure.

Life isn’t a sprint, though, it’s a marathon and the only way to fail in a marathon is to give up. Because of this, it doesn’t matter how many setbacks you have or how many times people pass you, all that matters is if you finish or not.

But if you give up, stop trying or get comfortable in not meeting your goals, then sorry, you’re an actual failure.


My life was at an all-time low, and because of that, I gave up. Now, one year later, I’m probably in one of the best places I’ve ever been in my life. I’m starting this fantastic new job, I’m dating someone I am completely crazy about, and I’m genuinely making strides in a fulfilling passion.

I’m frankly just really stoked about everything, and it feels great.

Just because you’re a failure now, doesn’t mean it’s a permanent label. Once you realize how much control you have in your persistence, your success becomes incredibly autonomous, as long as you keep pushing.

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