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 preoccupy aspiring entrepreneurs as they prepare for the unknown. Giving up a steady income and taking a risk on a big idea can be exhilarating and scary at the same time.

Still, the desire to pursue entrepreneurship is strong. In fact, 62% of adults in the US would rather be their own boss than work for someone else. However, only 36% are willing to take an appropriate financial risk to do so. Even those who already own businesses share this concern: 40% cite financial risk as their top concern.

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

Both Sonja Detrinidad and Toby Gutteridge found themselves at this crossroads. The emotional guilt of accepting the status quo weighed on her. These two founders faced risk head-on and created new companies that changed their lives for the better.

Set on flowers

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

But that wasn’t always the case. As a single mother of two children, Sonja says her goal back then was to get to zero. “If I didn’t owe anyone anything, I was already ahead,” she says. She bought vouchers and saved to make ends meet. “I could make that Costco chicken last five damn days.”

For Sonja, paying off her debts and finally achieving financial freedom was a huge win. But other costs also piled up: “I was curled up in the fetal position, crying and drinking vodka under my table,” she says. And the industry didn’t love her – she had to rush to achieve the goals imposed on her by her employer.

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

Then Sonja turned to a new hobby. As she was planting the garden at her home in California, she learned about native species that would lower her water bill. Her interest was piqued. A newly green thumb turned this hobby into a personal shopping service, while others sought their skills in the plant sourcing business.

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

In 2019, Sonja took a risk. Leaving the industry she had worked in for nearly two decades, she told her husband, “I have to try this for six months. If this doesn’t work in six months, I’ll go back.” She founded Partly Sunny Projects and sold plants online to her newfound fan base.

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

While a financially successful business means the risk paid off, it’s the other benefits of entrepreneurship that stick in Sonja’s mind. “Having control over my value, worth and income is truly rewarding,” she says. “When I need a break, I take a break. And I don’t have to answer to anyone for that.”

The ultimate comeback

Like Sonja, Toby was never one to let risks hold him back. He was involved in extreme sports and worked in the British special forces. But when Toby was injured on active duty, his career and hobby came to a halt – he was paralyzed from the neck down.

“It took me a long time to accept my new reality,” he says. “But once I got through that cycle of complaining, I started thinking, ‘I want to do something.'”

The extreme sports lifestyle still had a hold on Toby. He returned to school for business and created a brand that allowed him to stay in this world. When he was young and had no family or financial obligations, the risk of starting his own business was low. But the risk of not The start was much higher. “Without intention, you can find yourself in a bad place mentally,” says Toby.

It was this determination that helped Toby begin the next phase of his life. He founded Bravery, an equipment and clothing brand for extreme athletes. It is his love letter to the brave and courageous. The company kept Toby connected to his passion and helped him spread his message of perseverance.

“I’m a firm believer in just doing it, because the risk of not doing it will just eat you up over time,” he says. “You’ll always think, ‘What if?'”

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

These days, Toby says, he approaches risk a little differently. Now that he has a team and a family, he needs to think about financial stability. “I have people to think about, so I’m a little more conservative,” he says. But the same Toby who threw himself into extreme sports lives in his entrepreneurial self. “I still like to challenge myself. I take risks. Sometimes it pays off, sometimes it doesn’t.”

And if not, Toby can sleep at night knowing he isn’t wondering, “What if?”

Risk today or regret tomorrow

Nothing in life comes without risk. Even if you 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. Although starting a business comes with its own set of risks, ultimately you are in control of the outcome.

Financial risks and lack of start-up capital funding are among the biggest obstacles to entrepreneurship. But there is good news. Fair financing options emerge 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 or playing it safe, for Sonja the choice is obvious. “What will you regret more at the end of the day?” she says. “I don’t think you’ll ever say, ‘I really wish I had spent a lot more time in the office.'”

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*Shopify conducted a business survey with Gallup based on responses to an online survey of 46,993 U.S. adults (18 years of age and older) conducted online May 1-14, 2024. All participants are members of Gallup’s probability-based, nationally representative panel.