Ludomir Wanot, a Seattle real-estate investor and the cofounder of Evergreen Housing Network.
Courtesy of Ludomir Wanot
Running your own business comes with a unique set of challenges.Insider spoke with entrepreneurs about what they wish they’d known before leaving their 9-to-5s.One major challenge is finding good, affordable health insurance. This article is part of “Starting Up Your Small Business,” a series exploring steps small-business owners can take when starting out, transitioning, or scaling up.
Starting a business isn’t for the faint of heart. It can be a risky, stressful, and all-consuming career path.
“Entrepreneurship can get overglamorized,” said Tyler Wright, who left a sales job to build a personal finance brand and coaching business. “There are pros — you have flexibility and the ability to control how much you make — but there’s also a lot of extra work and time involved to get there.”
Wright and eight other entrepreneurs and small-business owners shared some of the major challenges that come with running a business and what to expect if you make the leap from corporate America to working for yourself.
They don’t share their challenges to deter prospective entrepreneurs. “I generally wish that more people would be willing to give it a try,” said Phil Thompson, a consultant turned artist. But it’s what they wish they’d known before leaving their nine-to-fives.
Lack of accountability
When you work for yourself, “you are now 100% accountable for everything,” Mike Gardon, a former banker and the creator of The Break Community, said.
You no longer have a boss to answer to or a team to follow through for, meaning you have to be more disciplined. “You have to manage yourself better and differently because you’re working a job and you’re trying to get something else off the ground, but you don’t have to do it.”
Wright experienced that while building his brand, Defining Wealth.
Tyler Wright, the founder of Defining Wealth.
Courtesy of Tyler Wright
“There is a level of baked-in accountability when you work for somebody because you have to go to work at a certain time. You have to show up to meetings on time,” he said. Whereas, if you’re your own boss, “it can be difficult because there are no rules necessarily. You have to make the rules and stick to them.”
While he likes the flexibility of being an entrepreneur, “it can be a double-edged sword at times,” he added. “With freedom sometimes comes more responsibility.”
You’re also fully responsible financially. If sales drop, for example, you’re the one who must figure out what went wrong and how to get back on track.
As Thompson put it, “When things are not doing well, there’s no one there to save you or buffer you.”
Navigating insurance and benefits
Being an employee typically comes with benefits like health insurance, retirement plans, and paid leave.
“Entrepreneurs, on the other hand, must set up these complex items all on their own,” said Ludomir Wanot, who quit a six-figure job at Amazon to build a real-estate-wholesaling business, Evergreen Housing Network. “I spent months figuring out the best and most affordable health-plan coverage.”
His current coverage is “not nearly as good as the healthcare I received at Amazon,” he admitted. Plus, “it’s quite a bit more expensive.”
Thompson said the No. 1 factor holding employees back from quitting and working for themselves is losing insurance and benefits.
Not only are you leaving a salary and a consistent paycheck, but “then you get hit with this quite substantial monthly bill for your health insurance,” he said. “It’s expensive and it goes up every year.”
Thompson’s wife, Katie Lauffenburger, also quit her corporate job to pursue a more artistic career creating ceramic homes. They now run Wonder City Studio together. They found a good insurance broker who helped them shop for plans, and they recommend other small-business owners do the same.
“When I first started, I remember having a really, really terrible health-insurance plan. It was a very high deductible but a very cheap monthly payment,” said Thompson. “But now we’re on kind of a classic Blue Cross standard plan and it’s expensive, but we trust our broker to have gotten us the best possible deal for what we needed. So I would say shop around with different brokers and find one that you really like who is responsive.”
Building out your team
Hiring team members is another task you’ll be responsible for as an entrepreneur, especially as you grow.
“The team around you is not automatic,” said Steph Gordon and Den Mathu, a couple in Toronto who quit their corporate jobs to become full-time online content creators. “You need to build that, and there are definitely growing pains.”
Steph Gordon and Den Mathu quit their day jobs in 2021 to focus on content creation full time.
Courtesy of Steph Gordon and Den Mathu
As content creators, Gordon and Mathu work with video editors, lawyers, and accountants. They prefer to find smart, capable professionals by asking other creators in their industry for referrals.
Hiring can be intimidating, “and you might get burned, but it’s probably not going to break you,” said Adah Fitzgerald, a former teacher who now owns and runs a small-town bookstore. “Learn from it, because you have to have people. A lot of business owners wait too long to hire someone.”
You wear multiple hats and the work never truly ends
Unlike corporate roles, which tend to be specialized, you’ll likely be juggling multiple roles as an entrepreneur.
“When I was in sales, I didn’t have to worry about posting content for my company or HR or accounting or leadership,” said Wright. “I just showed up and I did sales.”
Now, “I’m the CEO, I’m the CFO, I’m the head of content, I’m the head of accounting, I’m the head of everything,” he continued.
Lauffenburger had a similar experience, going from working on the design team at a software company and having specific tasks to doing everything herself as an artist. “When you’re working for yourself, you’re responsible for making the product, planning the product, marketing the product, maintaining your studio, training your assistant. You’re responsible for everything.”
She said the task list feels never-ending and ever-expanding.
If you’re transitioning to a more entrepreneurial career, don’t expect to work nine-to-five, added Katie McCarron, the founder of the family-run business Portland Pet Food Company. Running a business “is 24-7, but you need to carve out time for yourself and make sure that you take care of yourself.”
Income fluctuation
Income fluctuation is probably the biggest transition from the corporate world to entrepreneurship, and there’s no guarantee you’ll ever get used to it.
Phil Thompson and Katie Lauffenburger, the founders of Wonder City Studio.
Phil Thompson and Katie Lauffenburger
“With retail, there are seasonal ups and downs,” explained Lauffenburger. “And even though we’ve had this business for so long and expect it now, it’s still not comfortable. We never really get fully used to it.”
With experience, though, comes confidence that you can make it through a slow period.
The first drought can be “super depressing,” added Thompson. “It’s easy to just wallow and be like, ‘Well, I guess I’m never going to get sales,’ and you question the universe.”
But after some time, you start to realize you’re in control. “I can make a new product, I can do more marketing, I can send out an email newsletter,” he said. “I’m in the driver seat and I can just decide to do more.”