General Writing

The Leap into Freelancing

One of the conventional bits of wisdom about freelance work is that it is chancy. Never quit your steady job, experts often insist, unless you have six months of contracts lined up, or a hundred thousand in the bank. It’s sensible advice, except for one small detail: I have never met anyone who followed it, including me. All of us seem to have reached a point where we had enough of the nine to five grind, and took a leap into the unknown.

I still remember my own leap. I was consulting, and making heavy weather of my consulting work as a marketing and technical writer. I had just come off being an executive in two start ups, and was having trouble being just an employee. I was used to responsibility, and I was seeing too many decisions I believed that I could make better. At one gig, the CEO whose office I shared was honestly baffled that he had a morale problem when he had cut a quarter of the staff, including several key hires required to keep the company operating. At a second, the CEO had a habit of arriving at meetings two hours late and drunk, and unilaterally undoing all the decisions already made. Increasingly, I was fed up.

At the second gig, I was part of a team working long hours in a hot summer. Things hit bottom when the company decided to reward the team with an evening at a night club. However, nobody signed up. We were tired, and the last thing any of us wanted was more of each other’s company. When the company changed the evening to an afternoon event, nobody came. The human resources manager was reduced to flushing employees out of washrooms and closets, and from under desks, and herding them over to the club. There we sat, barely chatting, using our free drink tickets, and then, at exactly 5pm, leaving without bothering to make excuses.

The next week was spent doing last minute cleanup on the project. Still shaking my head over the afternoon at the night club, one day I went for a walk along the sea wall in Vancouver’s Coal Harbour. I was weary, and realized that I no longer took even a professional’s pride in doing good work. I gazed up at the North Shore mountains, wishing I were there –or anywhere, really — and reflecting that the mountains would still be there, even if my development missed the final deadline but a few days. I had had enough.

I worked out the final days of my contract, and turned down an offer to renew the contract, despite my misgivings and the internalized voice of my upbringing telling me to be sensible and play it safe.. In the past year, I had done occasional articles for Linux.com, then the online newspaper of free and open source software. In my search for an income, I begged Linux.com’s editor, Robin “roblimo” Miller for a regular position. He said he would take a chance on me as a contributor, but that I would need to write twelve articles a month –over 15,000 words.

I was nervous about only being a contributor rather than an employee. I was even more nervous about researching and writing more than I had ever written in a month, and doing it month after month. But no other source of income turned up immediately, so I decided I could write for Linux.com until more steady work turned up.

I was still there a few years later when the Linux.com URL was sold to the Linux Foundation. In fact, I had found other sites and magazines to make regular contributions to as well. Moreover, when Linux.com closed down, I replaced my lost income in a matter of hours. Since then, I have done the same several more times.

Undoubtedly, I was lucky. Still, looking back, I realize the conventional advice about waiting until I could freelance safely is like the advice to take a regular job and write in your spare time: if I had listened, I never would have made a career out of writing.

I learned, too, that, far from being precarious, in some ways freelancing can be far more secure than regular work. With regular work, I had only one job to depend on. When I lost it, I lost my income and at times my self-respect. By contrast, as a freelancer, I could arrange my finances so that they depended on several sources. Lose one, and I still had an income. Moreover, because I developed a reputation for writing grammatical copy and meeting deadlines, I could almost always replace one lost source of income with another.

I’m not saying that anyone should rush blindly into freelancing. However, I am saying that freelancing is a calculated risk, and a moment may come in your working life when you can take that calculated risk. In fact, a moment may come when the calculated risk of freelancing is no greater than the calculated risk of taking a steady job. Rather than listening to the conventional voices of reason, consider your own circumstances, and whether it’s time to believe in yourself and take your own leap of faith.

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