From Failure to Fortune: How I Learned to Fail Forward

I’ve got a confession to make: I used to be terrified of failure. Like, sweat-dripping, stomach-knotting, “Oh no, they’re going to laugh at me” terrified. And, honestly, who isn’t? No one dreams of fumbling the ball in life, right? But let me tell you how I went from living in fear of failure to practically inviting it over for coffee—and why it’s the best thing that ever happened to me.

It all started with my brilliant idea for a business. I decided to start a custom T-shirt company in my early twenties, convinced I’d be the next big thing in fashion. Armed with a basic screen-printing kit, a questionable logo (thanks, Microsoft Paint), and a budget of $300, I was ready to conquer the world. Spoiler alert: I didn’t.

Crash and Burn
My first sale was to my mom. Classic, right? But after that, crickets. My Instagram page had five followers, one of whom was my dog’s account (he was a better influencer than me). A month in, I realized my designs were… let’s say, “niche.” Nobody wanted a shirt that said, “I’m Late But It’s Fine” except me.

Then came the expenses I didn’t anticipate—like shipping, printing mistakes, and that one time I accidentally ordered 200 blank T-shirts in the wrong size. My bank account hit rock bottom faster than you could say “Oops.”

Naturally, I gave up. I was convinced I wasn’t cut out for entrepreneurship. Failure: 1, Me: 0.

The Lightbulb Moment
A few months later, I was scrolling through YouTube (because who doesn’t procrastinate by watching cat videos?) when I stumbled upon a clip of Sara Blakely, the founder of Spanx. She said her dad used to ask her every week: “What did you fail at this week?” He wasn’t looking for success stories—he wanted to know what risks she had taken and what lessons she learned.

I sat there, mind blown. Failure wasn’t the enemy; fear of failure was. If I wanted to succeed, I had to stop treating failure like a dead end and start seeing it as a detour.

My Comeback
With this newfound mindset, I decided to give business another shot—this time with a better plan. I started small, selling handmade journals on Etsy. My first batch? A disaster. The binding fell apart, the designs smudged, and one customer left a review saying, “Nice try, but no thanks.” Ouch.

But this time, I didn’t quit. Instead, I asked for feedback, watched tutorials, and, most importantly, let myself experiment without worrying about perfection. Slowly but surely, my skills improved. Orders trickled in, then poured in. Within a year, I had a thriving little business—and way more confidence than I’d ever had before.

Failure: The Ultimate Teacher
Here’s what I learned: failure isn’t a roadblock; it’s a signpost. Every mistake I made taught me something valuable, whether it was about customer service, product design, or the importance of triple-checking my inventory (seriously, don’t skip that step).

Now, I embrace failure like an old friend. When I launched my next venture—an online course teaching others how to start small businesses—I wasn’t afraid to mess up. And guess what? I did mess up. But I also learned, grew, and eventually built something even better.

Why Failure is Your Secret Weapon
Here’s the thing: nobody succeeds without failing first. J.K. Rowling was rejected by 12 publishers. Steve Jobs was fired from his own company. Oprah was told she wasn’t fit for television. The difference between them and everyone else? They didn’t let failure define them—they let it refine them.

So if you’re staring down a failure right now, take it from me: it’s not the end of the road. It’s just a pit stop. Grab a coffee, reflect, and get back on track. Because fortune favors the bold—and the bold know how to fail forward.

And hey, if all else fails, you can always make T-shirts. Just maybe skip the “I’m Late But It’s Fine” design.