Entrepreneurs reveal the true cost of playing it safe

“What if I fail?”

“Can I afford this?”

“I have people counting on me.”

These thoughts often occupy the minds of aspiring entrepreneurs as they brace for the unknown. Forgoing steady income and taking a chance on a big idea can be all at once exhilarating and frightening. 

Still, the desire to pursue entrepreneurship is strong. In fact, 62% of U.S. adults would rather be their own boss than work for someone else. However, only 36% are willing to take on a fair amount of financial risk to make that happen. Even those who already own businesses share this concern, with 40% citing financial risk as their biggest worry.

But what do you risk by not starting your own business? What’s worse: a failed attempt or the regret of never trying? For many, the positive impacts to mental health, independence, and flexibility far outweigh the potential risks. 

Both Sonja Detrinidad and Toby Gutteridge were at this crossroads. The emotional debt of accepting the status quo weighed them down. These two founders faced risk head on, building new businesses that changed their lives for the better.

Banking on blooms

Sonja worked in mortgage lending for 16 years. And she was good at it. By the time she left the industry in 2019, she was financially comfortable. “We didn’t even have a car payment,” she says.

But it wasn’t always this way. When she was a single mother of two, Sonja says her goal in those years was to get to zero. “If I didn't owe anybody, I was already ahead,” she says. She couponed and scrimped to get by. “I could make that Costco chicken last for five frickin’ days.”

Paying off debt and eventually gaining financial freedom was a big win for Sonja. But other costs were piling up: “I found myself curled up in a fetal position, crying and drinking vodka underneath my table,” she says. And, the industry didn’t love her back—she found herself hustling to reach goals imposed on her by her employer. 

“I'm only as good as what I did last month,” Sonja says. “And the relationships felt very disposable.”

That’s when Sonja turned to a new hobby. As she was building out the garden of her California home, she was learning about native species that would reduce her water bill. Her interest was piqued. A fledgling green thumb turned that hobby into a personal shopping service as others sought out her plant sourcing skills. 

Sonja created a TikTok account to document her journey. She was an instant hit. Her humor and candid approach to content gained her a loyal audience on the platform. This is when she asked herself: does this thing have legs?

In 2019, Sonja took a risk. She quit the industry she’d worked in for almost two decades, telling her husband, “I need to try this for six months. If this doesn't work in six months, I'll go back.” She launched Partly Sunny Projects, selling plants online to her newfound fanbase.

Partly Sunny is now in its fifth year of business, bolstered by a pandemic-borne plant craze. 

While having a financially successful business means the risk paid off, it’s the other benefits of entrepreneurship that stick with Sonja. “Having control over my value, my worth, how much income I'm going to make is really rewarding,” she says. “If I need to take a break, I take a break. And I don't have to answer to anyone to be able to do that.”

The ultimate comeback

Like Sonja, Toby was never one to be held back by risk. He threw himself into extreme sports and pursued work in the UK Special Forces. But when Toby was injured in active duty, his career and hobby came to halt—he was paralyzed from the neck down.

“It took me a long time to accept my new reality,” he says. “But once I had gotten through that grievance cycle, I started thinking, ‘I wanna do something.’” 

The extreme sports lifestyle still had a hold on Toby. He returned to school for business and started a brand that let him stay in that world. While he was still young, not tied down by family or financial obligations, the risk of starting his own business was low. But the risk of not starting was much higher. “Without purpose you can find yourself in bad places mentally,” Toby says. 

It was this sense of purpose that helped Toby start the next phase of his life. He launched Bravery, a gear and apparel brand for extreme sport enthusiasts. It’s his love letter to the brave and the bold. The business has kept Toby connected to his passion and helped him spread his message of perseverance.

“I firmly believe you've just got to go for it because the risk of not doing it will just eat you up over time,” he says. “You'll always be thinking, ‘What if?’”

In 2023, Bravery expanded its online brand into the physical realm, opening a hybrid retail store and café. The space is a community hub, with one morning a month dedicated to veterans. Being able to give back is another reward for Toby’s fearlessness.

These days, Toby says he approaches risk a little differently. Financial stability is something he needs to consider now that he has a team and a family. “I've got people to think about so I’m a bit more conservative,” he says. But the same Toby that hurled himself into extreme sports lives within his entrepreneur self. “I still like to challenge myself. I do take risks. Sometimes it pays off, sometimes it doesn't.”

And when it doesn’t, Toby can sleep at night knowing he’s not wondering “what if?”

Risk today or regret tomorrow

Nothing in life comes without risk. Even if you do put off your dreams in favor of a reliable paycheck, there’s no guarantee you won’t lose your job—or your ability to do the work. While starting a business comes with its own set of unique risks, ultimately you’re in control of the outcome. 

Financial risk and lack of startup funding pose some of the biggest barriers to entrepreneurship. But there’s good news. Equitable funding opportunities are emerging every day. And for Shopify merchants, more than $5.1 billion in funding has been distributed through Shopify Capital since 2016.

When it comes to taking a risk versus playing it safe, the choice is obvious for Sonja. “At the end of the day, which one are you going to regret more?” she says. “I don't think you're ever going to say ‘I really wish I would have spent way more time at the office.’”

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*Shopify partnered with Gallup on an entrepreneur poll based on responses from a survey of 46,993 U.S. adults (18+ years old) conducted online May 1-14, 2024. All participants are members of Gallup’s probability-based, nationally representative panel.