4 Ways Failure Led Me to Become a Solopreneur

December 9, 2020
feature image

I used to crack jokes about being the black sheep of my business school in college. Mingling with corporate recruiters, relentless internship hunting, networking events that were more awkward than an eighth-grade dance—none of them were quite my forte. “What am I even doing here?” I’d ask friends with a sheepish grin, in between classes where I wrestled to keep my focus. Under the jokes, however, there was a gnawing fear that I wasn’t good enough.

Me and failure? Oh, yeah. We go way back.

We’re old pals, really. Between wiping tears on the sleeve of my Ann Taylor suit (that I loathed) after career fairs and feeling like I got punched after yet another job rejection, we’ve gotten to know each other painfully well. What I didn’t know back then was that failure had a secret agenda the entire time: To align me in a direction congruent with who I really am.

Two-and-a-half years, one self-designed career, and 40+ countries later, I couldn’t be more grateful for my so-called failures. Without them, I’d probably still be taking lunch break naps in my car at an office job. Here’s how each blunder and botch catapulted me into becoming a solopreneur.

1. Each rejection prodded me to try something new.

Early in college, I chased big-name corporate internships. I never received a single offer. Taking everything far too personally at age 19, I’d stew in the sullen sting of failure, agonizing over why I didn’t make the cut.

After moving on to pursue advertising agencies, I was beside myself that I had ever attempted working in corporate America. My personality wasn’t suited for a “normal” office, I thought. I should work somewhere with colorful bean bag chairs, a place where people swear in their emails, I convinced myself. While it was comparatively better, the agency world offered little improvement when it came to freedom. Not even all of the Friday office beers in the world could make up for that. As fate would have it, none of my job prospects materialized anyway.

With each perceived screw-up, I gained insights about what would actually make me happy. It wasn’t freedom within the office—it was freedom from the office. I wanted to travel the world like a crazy vagabond, not spend 97% of the year daydreaming of a meager 10-day vacation. That revelation was scarier than any rejection, as I knew it would be much harder to achieve.

2. I learned exactly what I didn’t want for my career—much faster.

A fancy name tag, gargantuan skyscraper office views, glossy high heels that echoed in hallways… I used to think I needed these things to be successful. It turns out that was only what other people around me wanted at the time. Failure bopped me on the head like a Whack-A-Mole, time and time again, saying you don’t want any of that anyway. I lusted after their approval, mirroring others’ dreams that weren’t suited for me. I can only imagine how much longer this realization would have taken had I not gotten turned down from the start. 

In a last-ditch effort to get a job that provided some semblance of freedom, I applied to be a flight attendant. I wanted to try freelancing while flying for a living, hoping I could figure out self-employment while on-the-go. I made it to the third round of the interview process and never got a callback. I sobbed at the news, thinking I had officially lost all chance at freedom in my career. Little did I know that crushing letdown would later lead me to take a leap into freelancing full-time, something I’d later look back on with immense gratitude.

3. It made me a more resilient and courageous person.

Reminiscent of first heartbreak, those initial flops in your professional life can leave you feeling like you got dumped on Valentine’s Day. To make matters even worse, there probably isn’t any leftover chocolate laying around either. I used to put so much emotional stock into each application, meeting, and interview — forming lofty attachments that would only come back to bite me. As the years passed, I eventually learned to peel myself out of the pity zone a bit faster. 

Don’t get me wrong: Sometimes I still feel heart-sinking pangs of disappointment when things don’t go how I’d like. I’m only human, after all. The difference nowadays is that mishaps feel less apocalyptic; resilience has taken the stage. I started to accept (and even embrace) the unknown. Risk-taking became commonplace when I realized I wouldn’t get high rewards by staying comfortable. Failure is the devious cousin of risk, and you have to invite ‘em both unless you want your party to be painfully boring.

4. Without other options, failure forced me to try that one “crazy idea.”

Jobless as a fresh graduate, I couldn’t find a single reason to hold back. Without these bumps in the road, I would’ve never hopped on a one-way flight to Vietnam in pursuit of building my own location-independent career. I would have never felt the goosebump-raising thrill of building something that felt so authentically me in all ways. And I certainly wouldn’t have been able to manage the tumultuous roller coaster that comes with paving your own way as a solopreneur. 

Had I “succeeded” in my past endeavors, I’d probably be sitting in a corporate office racking my brain over some superfluous comment my boss made in our morning meeting. 

Like a friend dishing out tough love after a breakup, failure yanked my hand and swung me exactly where I needed to be. And while we’ve come a long way, this is a lifelong journey.

About the Author: Sarah Lempa is a writer, entrepreneur, and creative media strategist covering the joys (and challenges) of freelancing, travel, and solopreneurship. Her work has appeared in Business Insider, Fodor’s, and SUITCASE Magazine, among others. Currently based in Indonesia, she’s called multiple countries home and has ventured across 6 continents along the way. When she’s not chipping away at a piece, you’ll find her jamming out to groovy beats or riding a motorcycle. Keep up with her on Instagram @travelempa.

MORE ON THE BLOG

Return Policy

All sales are FINAL. No refunds on purchases, no exceptions. By completing this purchase from Create & Cultivate, you agree to this policy.

Terms of Service

By completing this purchase from Create & Cultivate, you agree to our Terms of Use and forfeit your right to dispute charges.

Privacy Policy

By completing this purchase from Create & Cultivate, you agree to the terms of our Privacy Policy.

Small Business, Big Influence.
Order Summary
The HR Bundle
$29.99
$22.49
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Venture Capital Bundle
$24.99
$18.74
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Bootstrapping & Budgeting Bundle
$24.99
$18.74
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Marketing Bundle
$24.99
$18.74
Billing Address
Review your information and purchase when you're ready.
Order Summary
The PR Bundle
$14.99
$11.24
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Branding Bundle
$24.99
$18.74
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Launch Your Business Bundle
$24.99
$18.74
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Grow Your Instagram Bundle
$29.99
$22.49
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Podclass VIP Download
$399.00
$199.50
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Growth Hacking Bundle
$17.99
$13.49
Billing Address
Review your information and purchase when you're ready.
Order Summary
The WFH Bundle
$14.99
$11.24
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Job Hunting Bundle
$14.99
$11.24
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Grow Your Email List Download
$9.99
$7.49
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Career-Boost Bundle
$14.99
$11.24
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Podclass Download
$299.00
$149.50
Billing Address
Review your information and purchase when you're ready.
Order Summary
The Self-Care Bundle 2.0
$29.99
$22.49
Billing Address
Review your information and purchase when you're ready.