Sam Shrem has been his own boss for nearly 20 years.
Throughout his career, he has opened his own consulting firm, launched several startups and advised high net worth clients as an independent consultant.
But if the 54-year-old entrepreneur could go back in time, he might not have made the move to become a self-employed entrepreneur.
“If I had a crystal ball, I wouldn’t have made that leap,” says Shrem, who lives in Boston.
“I regret it all the time. I look back now and I would have made seven figures consistently as a management consultant if I had continued to work with big companies.”
Going off work to become your own boss has become a very popular option.
In 2022, for example, applications to open a new business in the United States rose to their highest levels since 2004, with more than 5 million new businesses registered.
But as the March collapse of the US Silicon Valley bank showed, leaving many small businesses without access to their accounts, being a founder comes with great risks and responsibilities, and makes some regrets about leaving their jobs as corporate employees.
Shrem learned this the hard way in the Great Recession of 2008.
So he had to pay stipends from his savings to a team of 15. He had accumulated sleepless nights and huge debts.
The startups he launched recently have failed, and even now, as an entrepreneur who combines freelance consulting with writing books and developing data-driven products, he often looks back with regret at not continuing his work. In Beirut, Lebanon.
“My friends envy me,” he says.
“But they don’t know what I’ve been through. Every businessman takes risks, and the world needs them, but it’s not an easy lifestyle.”
It’s not uncommon for the reality of running your own business to clash with expectations, says British employment consultant Aisha Murray.
“As business owners, we want to be successful, but we often have unrealistic expectations early on in terms of sales numbers, revenue, or time spent,” he says.
“If you had a successful career before starting a business on your own, you might think that anything you try to do after that will work, too.”
Added to this belief is the danger of comparing the harsh reality of your own experience as an entrepreneur to the seemingly thriving experiences we see on social media.
Such was the case for Kathryn Warrilow, who set up her own PR agency in 2006 after becoming disillusioned with the traditional workplace hierarchy.
From the outside it looked like he had moved in the right direction.
The agency has become a successful business, with seven employees and major clients.
“But I never shut down,” says Warrilow, 43.
“I felt exhausted and anxious all the time. I never felt like things were good enough.”
The stress has made her a “total control freak”, always running her team.
This was not what he had imagined.
“My biggest misconception was the belief that being my boss would give me freedom, that you could come and go whenever you wanted and set your own hours,” he says.
The truth was that life had to adjust to work, and clients expected her to be constantly available.
So in 2015, after one of her potential clients offered her a job, this mom of two decided to leave the company.
“The day I decided not to be self-employed anymore was probably one of the best days of my career,” he says.
“I felt like a huge weight had been lifted off my shoulders.”
Now the managing director of travel company daysout.com, she says she has many of the freedoms she’d come to expect from entrepreneurship.
You can manage your time better and end up early some days to meet a friend for coffee.
As for Shrem, he will remain his own boss for the time being.
Although she tried to work full-time at a large company in 2017, she just couldn’t make the transition.
“All of a sudden, I found myself hating having a boss over me, having to show up for work and having to deal with administrative tasks,” he says.
However, he claims that these items might never have bothered him if he hadn’t been his own boss before.
Of course, there are many success stories, and many people will never look back.
Still, Shrem is wary of encouraging anyone else to follow in his footsteps: “Anyone who wants to take that leap into entrepreneurship has to be aware of the ups and downs.”
*If you would like to read the original BBC Worklife article, click here.
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