4 Ways Failure Led Me to Become 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.” 

-Sarah Lempa, Writer, Entrepreneur, and Creative Media Strategist

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.

“I wanted to travel the world like a crazy vagabond, not spend 97% of the year daydreaming of a meager 10-day vacation.”

-Sarah Lempa, Writer, Entrepreneur, and Creative Media Strategist

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.

Photo: Courtesy of Sarah Lempa

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.

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5 Steps to Handling Professional Failures Like a Pro

Photo: Smith House Photography

It's our LEAST favorite “f” word: failure.

And yet, it happens to the best, most seasoned, and buttoned-up of us. When a deal goes wrong, we don't get the money we expected, when someone says “no,” or worse, when we get laid off or fired—it's all part of climbing the professional ladder. 

Such failures are rough. We doubt ourselves, our abilities, and what we are doing with our lives. So how do we take these bumps in the road in stride? Here are five ways to make sure that we can move forward in the face of career failure.

And remember, you have to fail to be great. 

1. Take a minute, or two. (A week if need be. As long as you get back up.) 

When something goes wrong in our personal lives we tend to give ourselves more wiggle room, fewer guilt trips. We aren't as hard on ourselves when we fight with a friend or end a relationship, but with work, when the only person we have to blame is ourselves, we tend to take it a little harder. So give it a minute (or a day, or a week). A time frame where you're allowed to feel "bad" about the loss, whatever it might be, and then move on to step number two. 

2. Look at the failure with a fresh set of eyes. 

Sometimes this means asking for someone else to assess what went wrong. Sometimes the time we take away from the issue at hand allows us to address the situation in a manner that's productive. Even though we're talking about failure, rejection doesn't actually mean that you've failed. It means that you need to find a new in-road. Or a new job.

There are very few successful business people where "failure" is not a part of their story. J.K. Rowling was penniless when writing Harry Potter. At thirty years old Steve Jobs was removed from the company he started—Apple. Oprah was fired after she was deemed not "suitable for television." They flopped and then they got back up. 

There's opportunity in defeat, but you need to be able to look at it with clarity. 

3. Talk to those who have failed before. 

OK, maybe you can't call up Oprah, but you most certainly know people who have lost money, who have been unceremoniously fired, and who have suffered professional embarrassments that probably trump what you're going through.

Here's what they'll tell you: you have survived every single one of your worst days so far and every time you've emerged stronger, more capable, and better prepared for the next ring around the non-rosy situation.

Lean on those who've gone through it, and then lean in (à la Sheryl Sandberg) to your next career move. 

4. Watch this TED Talk about being wrong. 

Kathryn Schulz is a writer and public speaker who claims to be "the world's leading wrongologist." She is also the author of Being Wrong: Adventures in the Margin of Error. Wrongness, according to Schulz, is the stuff of life.

In the talk, in regards to our mistakes, she reminds us: "The good news: Owning up to them and coping with them forces us to come up with new ideas and strategies that just might work… or not."

Which leads us to the final point...

5. Accept responsibility for where you went wrong, and then let it go. 

If you are unable to see what happened or take responsibility, return to step number one. Blaming your boss or your co-workers is not a step in the right direction. Let your failure refocus your directives. You will never move on without acceptance. 

Onward and upward we say!

This post was originally published on January 2, 2016, and has since been updated.

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Why This Emmy Winner Says You Should Flip Off Failure

Fearless and free. It’s a pretty good place to be when it comes to your career. Which is exactly what Emmy-award winning TV news producer and author Wendy Sachs writes about in her book, Fearless and Free, How Smart Women Pivot— and Relaunch Their Careers. 

In the book she discusses the self-imposed barriers that hold women back. The job market’s radical change in recent years. And how we can all take small steps that lead to massive growth. 

Here are our 5 favorite takeaways that you can apply to your career today. Free? Fearless? Right this way. 

1. “The only career goal you should be focusing on right now, is staying relevant.” 

In the book Wendy quotes Karen Shnek Lippman, a managing director at the Sloan-Koller Group. Lippman says, “There is no such thing as a career path now.” It’s scary to think about, but in the last decade we have seen industry change exponentially. Keeping yourself relevant, continuing to advance and develop your skills (ahem, learn new ones), and evolve with the times is a way to make sure you keep your job. 

2. Your sorry’s add up. 

Wendy references the Amy Schumer May 2015 sketch on Inside Amy Schumer, that documents the female tendency to apologize. It’s satire sure, but that means it’s biting. And it packs some truth. Think of how many times you say “sorry” when someone runs into you. Sorry! It’s innocuous enough in that moment, but the propensity to apologize adds up and seeps into our other behavior. 

We suggest testing out actively not saying sorry in instances that aren’t your fault. Someone runs into you? Look them in the eye and wait for their apology. See if it shifts your attitude and self-worth even a smidgen. Because smidgen's add up too. 

“Inertia is a confidence killer.There’s no time to get stuck.”

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3. Confidence is more important than competence. 

Wendy cites research from journalists Katty Kay and Claire Shipman and their book, The Confidence Code: The Science and Art of Self-Assurance, in which they found that we’re either hardwired for confidence or we’re not. “Like blue eyes,” Wendy writes, “this inheritable trait is something we are born with— imprinted in our genetic code. Kay and Shipman found that the correlation between genes and confidence may be as high as 50 percent and may be even more closely connected than the link between genes and IQ.” 

Did that make your heart stop? We’ve always been told that we can power pose our way to confidence! (Something Wendy also discusses in the book.) And these women are telling us, maybe not? “The key here,” says Wendy, “is that those with overconfidence weren’t faking it—it simply wasn’t bravado or bluster—they actually believed they were that good.” 

So what’s a woman not born with the confidence gene do with this research? We say, allow yourself off the hook for not getting the [insert anything you’ve ever beat yourself up about here] and then rewire your brain to become more confident. 

Wendy says, “While confidence may be partly genetic, the good news is that it is also very malleable. It’s like a muscle that can be strengthened.” 

She also says that “confidence creation is about taking risks.” So go ahead and make some risky moves. 

4. Get Up and Go After It 

If you’re making risky moves, you’re going to fail. You’re going to fall. Sometimes that means starting all over again. 

Wendy recounts the story of Jill Abramson, The New York Times’s first and only female executive editor, who was fired two and a half years into her job. “Some reported,” writes Wendy, “that Jill was ‘difficult,’ which for a female executive is a word loaded with gender double standards. It was also reported that Jill had hired a lawyer before she was fired to look into compensation issues, believing that she was not paid the equivalent to her male predecessor.” 

But Jill didn’t stay down. According to Wendy, “The morning after Jill was fired, she went to a session with her trainer that handed her pair of boxing gloves. She had never boxed before, but hitting the bag was intensely satisfying, Jill asked her trainer to take a picture of her with the gloves and she emailed it to her kids who were worried about her.” The pic went viral after her daughter Cornelia posted it to her Instagram. 

It’s a great reminder that no one fall is your end. Only you can decide your professional end. 

Which is why we love #5…

5. Flip off failure. 

Seriously. Process your failure and then give it the bird. (And the wings so that it may fly away.) You can’t become paralyzed because something doesn't work or survive in the marketplace. 

"Process your failure and then give it the bird. (And the wings so that it may fly away.)"

Tweet this. 

We’re reminded of this modern day biz facet the whole book through. And it’s a vital Wendy says, “Inertia is a confidence killer, and with the world today moving at the speed of social, there’s no time to get stuck.”

For more career advice and how to fail forward, check out Wendy’s book, available on Amazon here. 

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The 4 Rs You Need to Recover From a Mistake

Photo Credit: Musings of a Curvy Lady

By: Cassie Hughes & Gabrey Means, Grow Marketing

Anyone who has dared greatly, innovated or made things better has also known failure. When we first set out to create our own experiential agency, we may not have known what we were doing, but we were crystal clear on what we wanted. Neither of us came from an agency background but we knew what was important from the client’s perspective and that we had something different to offer than what we were seeing in the marketplace. We knew there would be a lot of mistakes along the way and rather than shying away, we faced them head on. 

"Anyone who has dared greatly, innovated or made things better has also known failure."

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Everyone makes mistakes. We’re only human. But how you learn and grow from them can help you better prepare for challenges ahead. Whether in your personal or professional life, here are a few tips to help you bounce back from a mistake and walk away stronger and smarter.

RECOGNIZE 

Early in the life of our agency we took on a project where there were red flags we didn’t pay attention to because we were so eager to prove ourselves as a new entity, even though we had a long track record of success in our careers. It was a huge national brand in a category we were dying to break into so while our intuitions were screaming no, our egos kept saying yes. The client was unrealistic but we thought we could turn her around. We couldn’t have been more wrong. In addition to grinding us on every budget and continually asking for new ideas (free of charge) eventually she actually became verbally abusive.  We got through the project and delivered but at a cost to ourselves and our team, who were left feeling deflated, unappreciated and exhausted.  

RECORD 

We are big believers in intention and writing things down. When we make mistakes we process them by writing down a list of what we learned and would do differently the next time. This was crucial to our process of avoiding bad project/client matches in the future. While it may sound intimidating to see your mistake recorded in black and white, it's actually quite liberating. When possible, sharing your list with a friend or partner who can keep you from being too hard or easy on yourself helps to keep the process honest and, therefore, most useful.

REPAIR 

If you want to create an environment where people are inspired to be their best, they have to feel safe to fail. If they don’t, they’ll engage in all kinds of unproductive behaviors that only compound the mistake, from covering up to placing blame on others. Meanwhile, time ticks away and the impacts are increased. Encouraging people to own their mistake and take an active part in the solution means resolution comes quicker and the individual is left with the empowered feeling of having helped to repair it versus the deflation of screwing up, which only makes people feel and think smaller. To repair the damage to our team from the verbally abusive client, we owned up to letting our eagerness override our instinct and shared how we would avoid such situations in the future.

"If you want to create an environment where people are inspired to be their best, they have to feel safe to fail."

Tweet this. 

RESOLVE 

One of the most important parts of recovering from a mistake is knowing when to take a deep breath and let it go. Continually reliving mistakes is unproductive and paralyzing. Once you have done the work to repair the mistake and can clearly articulate your learnings, you should trust you have learned what that mistake has to teach you, freeing you to move on.

The mindset of recovery and resolution is an important one to build. It allows people to continue to want to take on new challenges and find new ways of doing things-- which, are really powerful assets. A culture that rewards creativity and trying new things – without punishing the misses – fosters a team of savvy problem-solvers who can think on their feet and are energized, instead of paralyzed, by new challenges.

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