Why Freelancing Isn’t For The Faint Of Heart

These days everyone wants to be their own CEO. But do they really want the risk that comes with it?

Why Freelancing Isn’t For The Faint Of Heart
[Image: Flickr user Powerslide]

The first week in January is the busiest of the year for divorce lawyers and job sites. One U.K. poll showed that 42% of Britons plan to look for a new job this month. An increasing number of them will dream of starting a company or jacking it all in to become a yoga teacher. Forbes recently published a breathless article following lawyers and bankers who are quitting their highly paid jobs to launch startups. LearnVest discovered last year that CEO (36%) and entrepreneur (28%) were the most aspirational job titles of 2013, the new face of the American Dream.


It’s no longer enough to just make lots of money, even as a CEO; you must also do “meaningful work,” to quote Forbes. But is starting a company or making a radical career change really the route to work nirvana?

“I would love to start my own business.”

After 10 years of working as a programmer in various startups in the Bay Area, Sonia Connolly had a revelation. “I was sitting at my desk one day, and had the profound sense that I had lost my path so badly that I didn’t know which way to turn to get closer to it,” she says. After some soul-searching Connolly took bodywork classes and opened her own practice two years later.

“I took part-time computer contracts as they came along,” she says, “always thinking this would be the last one, but my practice never grew beyond half-time. I didn’t know how hard it is to be a successful solo business owner. I figured if I tried hard enough and did the right things it would all work out.”

Faced with a dwindling savings account, Connolly eventually took a permanent, part-time programming gig a year ago. “I still say the corporate environment doesn’t suit me, but I have a different perspective on it, and part-time makes a big difference. I’m grateful for the steady income, the learning opportunities, and the ability to continue contributing to the world with bodywork.”

Connolly loves the way bodywork makes a tangible difference in people’s lives, and the best thing about starting her own business was the sense of possibility and openness it offered in contrast to the predictability of a 9-5 job, but that unpredictability was also the main downside. “The worst thing is the financial instability and sense of failure, “ she says. “The number of clients varies wildly from month to month, which would be okay if the average income is high enough, but mine never was. Even that has its upside. I don’t take corporate benefits for granted, and I understand the inequities in our society a lot better.”

“It’s great that you are doing what you love.”

This writer never planned to become a journalist. After being laid off from my tech job and and then running out of unemployment benefits, I was left with no other option but creating my own job. I had been writing for fun for several years and started to write for profit.


More than a decade previously, I started working for tech startups, then more prosaically referred to as small tech companies. While there are many things I enjoy about both startups and writing, and I’m certainly rarely bored, I’m far from starry-eyed about either as a career move.

In contrast, friends who are still comfortably installed in corporate jobs tend to have romantic notions about both startups and “creative” careers, of which they refuse to be disabused, no matter how many times I mention that most months my income doesn’t cover my bills. They are amazed when I point out that I have never said that writing was what I love. It’s as if the prevailing meme of “doing what you love” overrides the reality of any individual story.

One friend, who is a corporate lawyer, trained as a personal trainer and nutritionist on the side with a view to eventually practicing full-time. Once she realized that she would never make anything near her current salary in her new career, the project was quietly shelved. She would have suffered the same the loss in status and income, which has been the most difficult adjustment for me.

Like Connolly, I can now appreciate the structure and other benefits my permanent jobs gave me, although I might have complained about the accompanying restrictions. I’m still not sure I will ever go back to a regular job, but if I do I’ll certainly be wiser than before.

“I knew you would be a success.”

Last year, two months after the birth of his first child, Neil Murray quit his job as a commercial manager at a FTSE 100 company in London and moved to Copenhagen. He started doing freelance sales work with startups and then created a platform to connect freelance sales people with companies who are looking for flexible sales staff.

“Considering I knew no one when I came and am now considered an active member of the Copenhagen tech startup community,” says Murray, “I feel that this year has been a big success. However, in terms of finances, it has been near disastrous. It depends what you consider success, and whether you are looking short- or long-term.”


Murray loves the freedom that comes with being his own boss. “I have found out that you don’t have to live your life working a 9-5 in a job and earn a stable wage just because society tells you to,” he says, “and that you will be happier earning less doing something you love rather than earning more doing something you hate. I wish more people would take the chance in discovering this.”

In spite of his conviction that he is on the right track, Murray still struggles with his own and other peoples’ ideas about success and failure. “People tend to consider you a success because you have set out on your own,” he says, “when in fact I feel I am a long way from success, as I am not even sure what that looks like at this point. I feel like I am simultaneously heading toward success and failure, and I have no idea what will come first.”