I Became My Own Boss Because I Had To–Here’s What It’s Taught Me

Over a third of freelancers don’t choose self-employment. Here’s how these accidental “solopreneurs” found success after layoffs, startup failure, and loss.

I Became My Own Boss Because I Had To–Here’s What It’s Taught Me
[Photo: spukkato/iStock]

Some people dip their toes into self-employment slowly. They take their time. They plan it out–for years, even–before finally quitting their day jobs to work for themselves. But while steadily, deliberately building your solo portfolio or startup idea on the side can make the transition easier, some people do it much more abruptly. Many first-time “solopreneurs” are simply people who’ve been fired, laid off, or have to deal with an illness–whether their own or in their families–and that can sharply dial up the pressure on learning how to support yourself.


After getting fired, Jen Remsik spent eight months hunting for a job. Finally, she decided to start her own event-planning business, but it felt like her hand was forced. While bootstrapping the company, Remsik struggled with imposter syndrome, feeling like a risk-averse newbie who had to prove herself. Ultimately, she overcame these hurdles and got her new company on firm footing–where it still is today. But Remsik isn’t alone. One recent study by Upwork estimates that 37% of freelance workers feel they don’t have a choice when they start working for themselves.

Here’s how many figure out how to make it work anyway.

Related: Why These Freelancers Ditched Cities For Rural America

Cherrypick From Your Existing Skill Set

Adam Calihman found himself unemployed after his startup foundered. The company’s biggest client pulled out, so Calihman had to lay off most of his staff and eventually wound the business down. Then he hit the job market.

Having spent years as a generalist and product manager as his startup’s COO, Calihman struggled to find jobs that fit his broad skills. He’d poured his life savings and a good deal of credit into the startup, so he needed income fast. While Calihman was a skilled business strategist, he knew he’d need more focus; picking a tangible skill would help him make money fast as a freelancer.

Web development was just one area Calihman had had a hand in with his startup, but he’d never formally learned to code. But as he puts it, “Necessity is the mother of income.” So night after night, he sat at his kitchen table hacking away on websites. Just a few months later, while discussing his fate over a beer with a friend, he landed his first web-development client, and before long a new business was born.


Looking back, he says, being “open-minded, receptive, and not afraid to be uncomfortable” were what saved him after getting pushed into working for himself.

Dig Into Whatever You’re Doing To Distract Yourself

Unhappy and questioning his career, digital designer and writer James Greig found himself sinking into depression. He drained his savings account and took a trip around the world, hoping it would give him some clarity and shift his perspective. It didn’t.

Instead, things got worse. He ran out of money and had to move back in with his parents. Greig felt totally destroyed. To distract himself, he started taking photos of people with their bikes, then posting them on Instagram. Before long, it turned into a full-blown project, called CycleLove, a popular blog and newsletter celebrating cycling culture.

Creating something on his own terms instead helped Greig come out of his shell. Before long, he started picking up graphic design projects, and somewhere along the way, the depression lifted. Five years later, Greig still works for himself and sees this difficult period as an important career shift.

If you’re facing burnout or a mental health challenge, James says, “Don’t pressure yourself, it’s going to be a slow process of rebuilding your life. It’s exciting when you have complete freedom,” he adds, “but you’ve got to be patient. Explore all the things you can be. Explore different avenues for yourself.”


Related: How My Cycling Obsession Has Made Me A Better Entrepreneur

Focus On Your Future, Not The Past

Lizz Spano had a similar experience to Greig’s. Before being laid off, she’d been in the habit of posting photos on Instagram from restaurants she liked–something lots of people do just for fun. For Spano, too, it just felt like a hobby, and she worried whether she had enough valuable skills to reset her career path.

Like Greig, Spano turned to her Instagram feed to distract herself in the meantime. She started learning how to take higher-quality shots and picked up some baseline knowledge about influencer marketing on social media. Soon her Instagram feed had over 25,000 followers, and brands like Postmates and Business Insider took notice; Spano started landing new clients, eventually starting a company that offers social media management, food photography, and influencer marketing services as well as restaurant consulting.

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Her advice in retrospect? Keep looking forward. “Don’t let a job loss or any other failure set you back for too long. You can always change your career and start a business with next to nothing,” she says. Her experience is proof that “it doesn’t take a ton of money, it takes knowing you can do it.”

But Spano would always have doubted that if circumstances hadn’t pushed her to try. “I never would have pursued building my Instagram feed if I hadn’t lost my job. Instead, losing my job led me to find the right market and build my business.”


Look For Opportunity In Loss

Erin Pickard was ending a long-term relationship and feeling uncertain about her career when her father suddenly died, leaving her a 2,500 acre farm. Despite her grief and knowing nothing about either farming or running a business, she decided to keep the land, becoming a business owner overnight. Out of sheer necessity, Pickard channeled her grief into learning on the fly. She dug into the minutiae of crop insurance and managing tenants, figuring out how to tend the property her father had left her, and allowing it to transform her in the process.

Working for herself expanded what Pickard thought she could do and gave her confidence she didn’t have before. The first time she wrote a big check, she says, her hand shook and the room started spinning, but it got easier with time. When facing an unplanned–and probably frightening–career shift, Pickard says, “You just have to buckle down and get through it. There’s opportunity in hard places.”

In some ways, these accidental solopreneurs were lucky. They each figured out how to handle an unexpected career change without it letting it get the better of them. As their experiences show, it’s not always easy to let go of the past, but once you’ve managed to look ahead, you can usually find a foothold to steady you, then another, and another–even if you didn’t choose this path yourself, or when to start running down it.