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Especially recently, becoming your own boss can be glamourous. But not everyone who’s forged their independent professional path is happy they did.

Sam Schreim has been his own boss for nearly 20 years. He’s opened his own consultancy firm, launched multiple start-ups and advised high-net-worth clients as an independent consultant. But if the 54-year-old could go back, he may never have taken the plunge.

“If I’d had a crystal ball, I would’ve never made that jump,” says Boston-based Schreim. “I regret it all the time. I look back, and by now I would’ve consistently been making seven figures as a management consultant had I stayed working with the large firms.”

Quitting work to become your own boss has rarely been more popular. In 2022, for instance, new US business applications spiked to their highest levels since 2004, with more than 5 million new firms starting. But as evidenced by the collapse of Silicon Valley Bank in March, which left many small firms without access to their essential accounts, being a founder comes with big risks and responsibilities – and leads some people to regret ever giving up their day jobs. 

Schreim learned this the hard way in 2008, when Great Recession struck. He was forced to pay salaries to a team of 15 out of his savings. He racked up sleepless nights and huge amounts of debt. The start-ups he later launched all ultimately failed. And even now, as a solopreneur, combining freelance consultancy with writing books and developing information-based products, he often looks back with regret at not simply sticking with his job at a large management consultancy in Beirut.

“My friends envy me,” he says. “But they don’t know what I go through. Every entrepreneur is a risk taker, and the world needs them, but it's not an easy lifestyle."

It isn’t uncommon for the realities of running your own business to clash with expectations, says UK-based careers coach Ayesha Murray. “As business owners, we want to succeed, but we often have unrealistic expectations from the outset around sales numbers, income or work-life boundaries,” she points out. “If you've had a successful career before starting out on your own, there could be an assumption that whatever you try next will also work out.”

Added to this is the risk of comparing the gritty reality of your experience as an entrepreneur with the seemingly thriving experiences others share online.

That was the case for Catherine Warrilow, who first set up her own PR agency in 2006, having found she struggled with the hierarchy of a traditional workplace. From the outside, it looked like a positive move. The agency grew into a successful business, with seven staff and top clients.

“But I never switched off,” says Warrilow. “I felt overwhelmed and anxious all the time. Nothing ever felt good enough.”

The stress turned her into “a complete control freak”, always micro-managing her team. It wasn’t what the now 43-year-old from Oxford, UK, had imagined. “My biggest misconception was that being my own business equalled freedom, that you could come and go as you pleased and set your own hours,” she says. The reality was life had to fit around work, with clients expecting her to be constantly available.

That’s why, in 2015, having been offered a job by one of her prospective clients, the mother of two decided to give up the company. “The day I decided not to carry on being self-employed was probably one of the best days of my professional life,” she says. “It felt like a massive weight had lifted.”

Now managing director at travel company daysout.com, she says she enjoys many of the freedoms she’d hoped would come hand-in-hand with entrepreneurism. She’s able to pop out for appointments and finish early some days to meet a friend for coffee.

As for Schreim, he will stay his own boss for now. Though he tried working full-time for a large firm as recently as 2017, he just couldn’t make the transition.

“I found myself despising having a boss over my head, having to report to work and having to deal with admin tasks,” he says. He says, though, these elements may not have bothered him if he’d simply never become his own boss in the first place.

Of course, there are plenty of success stories, and many people who hang their own shingles would never look back. Still, Schreim is cautious about encouraging anyone else to follow in his footsteps: “Anybody who wants to make that jump into entrepreneurism needs to be aware of the ups and downs.”