Freelancing isn’t for everyone

Last week at SXSW I was on a panel called, “Boss Lady.” At the end of that panel a young woman approached me with the question of how to start her own company. At the moment she was working full time, had a really busy life and a family that depended on her to keep those two things going.

I offered her the idea of treating her new business as a part-time evening gig; working after all her other things had been taken care of. Her face squinted up at this. This, she said, seemed a little hard because she was already busy. I gently explained that working on your own is one if the hardest things you can do – especially at first. The effort, sacrifice and bravery required are often more than when you start a job with a company that has everything laid out for you. The cushion of a 40-hour work week with weekends off, sick benefits and coworkers to tag team with does not exist. Her face squinted more because she didn’t like the sound of all that work; that’s not what her idea of being self-employed was.

She had the “9-5 grass is greener” syndrome. The one in which you imagine that if you were on your own, everything would be easy peasy or at least easier. You’d have freedom, creativity, total control, late mornings, time off, possibility. And while you do get to have these things, there is a price to pay for it and that price is not for everyone.

So I suggested that perhaps she wasn’t made to be an entrepreneur and I could tell she didn’t like that answer because she was not happy where she was. And the opposite of unhappy is happy so the opposite of corporate must be freelance, right? Wrong.

I know a lot of people who work for corporations, company’s and star ups that are extraordinarily happy because they have found the right fit and the right company. These people know how they work, what they want to do and then target companies and other people that match their values, ideas and work ethic. And these people who go to offices each day are happy office people – they’re sometimes happier than a lot of self-employed people who struggle every day.

I asked the woman if she liked the company she worked for. No, she said. I asked if she even liked the role within the company. No, she said. I asked her if she had thought of defining who she was, what she could do and then taking that to a company that matched and she said no. She hadn’t thought of going to a different company with a different job. She had believed (as I once had), that every job would be the same. Every office would be the same. And the only solution to cubicle hell would be to leave.

It was the answer for me at the time, but it’s not the answer for everyone. Especially someone like her who really needed financial security to meet so many responsibilities and who also did not want to really work all that hard on something else. But when the idea of finding a different company in a different area and taking on a different career came to her, she smiled and shook her head “yes” for the first time in our conversation.

Sometimes when a person isn’t satisfied with something they tend to daydream about the total opposite – if you’re single you think being married would make you happy. If you have children that are driving you crazy you think about being childless. If you’re in a job you hate you think about going on your own. But I don’t think swinging to extremes is ever a really good idea because it’s usually just you reacting and not really thinking. You’ll end up with the same issues (perhaps more) if you just go to the opposite instead of figuring out what would really work best.

There are great things about working for someone else just as there are great things to working on your own. If you’re deciding weather or not to become an entrepreneur, writer or artist, you need to be honest about the amount of work that you’ll have to put into it without outside help – especially until you can afford to hire an assistant, a manager, an accountant or land an agent. You’ll have to ask if you’re prepared to work more than 40hours a week (and it’s true, you’ll be working in an area you love so perhaps it won’t feel like work, but then you run the risk of blurring the line between work and play. Burn out can be a problem). You’ll need to ask yourself if you require financial stability which can be hard to come by, especially when you’re first starting out. And you’ll have to understand how you work – because no one will be handing you work and giving you yearly reviews. You’re your own boss.

If you need freedom, creativity, the need to be of service, be independent, run your own ship but can’t quite make the leap to freelancer, see how you can rearrange your current life. Can you switch to another job within your company, can you go to a different company, can you work 4 10-hr days and have Friday off, can you go part-time, can you work in an entirely different area, can you work for an entrepreneur or a start-up to gain experience?

Going out on my own was the right thing for me to do at the time and it’s worked out extraordinarily well. All the challenges have been so completely worth it because the rewards were more than I expected. But it’s not for everyone. I think we all want to do work that we love and feel good about it at the end of the day. And for some working on their own is the way to do it whilst for others it’ll be nothing but a miserable time. Vice versa for working for someone else. The trick is just to be truthful about what you need, how you work, and what you are willing to do. Maybe that’s starting your own company or maybe it’s working for someone else.

Neither is better than the other – it’s just a question of what works for you.

(For another perspective, read Summer Pierre’s Artist in the Office series.)

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