There are perks to being your own boss and setting your own schedule.
“Being an entrepreneur is great. It’s awesome,” confirmed Alex Yale, who quit corporate America to launch an e-commerce business. “But the grass is green wherever you water it. It takes a lot of hard work, and it takes a lot of time and energy.”
Success in its most basic form — keeping the lights on — is far from guaranteed, he added: “There’s a huge graveyard of failed entrepreneurs.”
And if you do happen to make it, don’t expect it to be stress-free.
“As an entrepreneur, you take things really to heart. It’s your product, your baby, your brand — and when something goes wrong, you lose sleep over it,” said Yale, who owns and operates cleaning brand Uncle Todd’s and Flip-It! Cap, a company that sells bottle-emptying kits.
“You lose dollars over it. In the corporate world, your boss might be upset or your performance review might not be stellar, but you’re getting the same paycheck.”
PTO looks different — and may be nonexistent — especially if you’re running a lean operation.
“Everything is on me. I can’t just disconnect and put an out of office up, because if I’m not there to solve it or reply to it or what have you, the buck stops with me,” he said. “There are some serious differences between being a W2 employee and not — and some of them are great and some of them aren’t.”
For Yale, whose brands both do seven-figures in revenue on Amazon, the pros outweigh the cons.
Long-time entrepreneur Kyle Goguen, who launched his first e-commerce business right out of college, feels similarly.
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“There’s far more risk associated and a ton more upside with starting your own business,” said Goguen, who runs a pickleball brand, CRBN, with his childhood friend Garrett Gosselin. “And it just depends on your risk tolerance. Garrett and I both have a lot of friends who have awesome careers. Neither Garrett nor I would want to trade positions with them, but they actually wouldn’t want to trade places with us either. They like having stability for themselves and their family.”
Leaving behind a W2 job often means leaving behind employer-based health insurance and retirement plans. In some cases, it also means leaving behind a team of coworkers.
That’s what Drink Wholesome founder Jack Schrupp misses the most about his former job. As a French teacher at a boarding school, he lived on campus and was surrounded by other teachers and students.
“That was my community. That’s what grounded me and made sense to me,” he said.
Now, as the owner of a small business with one employee — his sister, who works remotely from the opposite side of the country — he spends most days by himself.
Schrupp works from his home in Hanover, and while he considers his schedule “pretty relaxed,” there’s a trade-off. “It’s professionally lonely.”
Running your own business can feel isolating, “especially if it’s a hard journey, which it often is,” he said. “You feel like you are doing it alone with no one to turn to for help or advice. So, I wouldn’t say that entrepreneurship is like a hack or should be the ultimate goal for everyone.”
He’s found that it’s harder to set boundaries when you’re building a company versus working for an employer.
“I have the potential to work way more. I could probably work all day, every single day,” he said. “There’s no end to growing a business because it’s growing, right? It’s ever-evolving.”
That said, the millennial recognizes the perks, such as the freedom that comes with being your own boss: “I will say, it would be hard for me to start working for someone else, just because I do have almost unadulterated freedom. I’m accountable to no one.”
That’s how Gosselin feels. Before founding CRBN, he was a sommelier at a country club, often working nights and weekends.
He doesn’t sugarcoat the entrepreneur lifestyle, but he appreciates it.
“The first two years, we had a lot of ups and downs, and I’ve never been more stressed in my life,” he said. “I think I’ve learned to manage that. It comes with the territory, and once I kind of accepted that, I don’t think I would trade it for anything. To me, it’s worth it.”
His cofounder, Goguen, chimed in: “We just get to play pickleball and think about pickleball and talk about pickleball and get paid to do it. It’s a pretty great situation.”