This September, my partner and I will be celebrating 10 years of having our own business. I’ve learned about a million things in that time. Some of them were hard lessons. Others taught me a lot about my abilities. All of it has raised my self confidence and skills to new levels. Taking the plunge into self employment has been the single most frightening and rewarding thing I’ve done in my 20+ year career.

A lot of people are terrified of going into business for themselves. Fom my experience, a big part of that fear is the uncertainty of not having a steady paycheque.

I’ll be blunt. You have good reason to be afraid. There’s a common misconception that starting your own company is easy. You just peruse your LinkedIn contacts, go to a few networking events and before you know it you’re swimming in money and projects. The truth is, this very rarely happens. In fact, you may go months before you see your first contract. And even if you get one, you may work for months before seeing any money at all. And once you do get that first, big, juicy cheque? By the time you pay the bills you couldn’t pay because you were waiting on a cheque, rent, insurance, and that kid you got to help you set up your web site, your paycheque is much less than it was originally (if you have any money left at all!)

But all is not lost. There are solutions to this conundrum.

Don’t Give Up Your Day Job

When Jen and I first started Jester Creative, we both had jobs. She worked in television and I worked in high tech. We didn’t just up and quit our jobs. Nope, in fact, I kept working for 5 more years, and Jen worked AND had a couple of babies!

What did that mean? It meant that we spent a lot of evenings and weekends and time between diaper changes and feedings working on our business. I’d put in an 8 or 9 hour day at work, run home, grab some dinner, and head to Jen’s place for the evening. We would work until 11 or midnight, and I’d get up and do it all again the next day.

That work not only helped us to define our business and what we wanted to achieve, but it allowed us to land our first contracts. Those contracts were intregral to us. They didn’t make us a pile of money, but they did win us valuable contacts (some of whom we still work with 10 years later), and gave us some all-important portfolio pieces.

Were we tired? You bet. But our work was energizing. And we knew it was a means to an end. In 2006, I gave up my full time job for the last time. Though I wasn’t totally in the black yet (and couldn’t have done it without my husband’s support), I was smart in keeping my job as long as I did.

Get a Haircut, and Get a Real Job

While I eventually took the important step of breaking the chains of the workaday world, I wasn’t out of the woods yet. In fact, it was quite a struggle for a while. Living on one income, for me and my husband, was tough. There came a point when I had to make a decision. Go back to work full time, or find some sort of part time way to make extra money until the business starts to pay off in a more reliable way.

I thought about the things I was good at. I could become a waitress again. Good money and flexible hours, but I totally sucked at it the first time around.

Then someone said to me one day (I forget who), “Why not teach? You’ve always been good at it.” I hightailed it down to the local community college and talked to an old classmate who still happened to work there. I walked out with a part time job.

Not only has teaching done well to fill the in-between paycheque gaps, it’s opened up a whole new passion for me. I’ve developed curricula, coordinated programs, and given numerous (paid!) talks on technology and education. What started out as some extra cash has taken my career on a course I completely didn’t expect.

If you’re considering taking the plunge into self employment, I say DO IT! But do it with some thought into how you’re going to make the transition. Find a way to supplement your income while you grow, either by figuring out how to work it into your existing job, or by finding something to do part time, like teaching. If the college isn’t hiring, go to a community centre. I have a friend who is a multimedia designer, teaches AquaFit and is a professional stand up comic! There are some fun part time jobs out there. Look at some of the things you do well outside your main job. Find something that fits, and pays.

Most importantly, don’t give up your dream because you’re afraid of not having enough money at first. Don’t worry, you won’t have enough money at first. Find ways to make up the difference until you don’t need to anymore, and you’ll be just fine.


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