3 Freelance Tips From My Worst Year That Boosted My Career

Written by Tim Beyers on February 5, 2018

Odds are, this isn’t the first freelance tips article you’ve read. I’ve been a solo operator for 14 years, and I’ve read thousands. Most are aspirational, chock-full of how-tos for “getting your life back” or “working the way you want to.” This isn’t that type of article. These freelance tips are aimed at helping you avoid the trouble I got into eight years ago.

For many, 2009 was the year we finally started to see relief from a historic housing crisis and economic meltdown. For me, it was a year of self-inflicted wounds as a freelancer. Not only had I taken on too much low-paying work, but I’d failed to project just how much my income would decline while pursuing writing for big-name magazines. By summer, I’d landed my first feature story in a national magazine — and nearly broken my finances. But the experience of trying new things has been a boon to my career in other ways: I can adjust to new work more easily, I’m comfortable pivoting and, most importantly, I know how fleeting work can be.

Let’s tackle these ideas one at a time, first by telling you what happened, then by explaining what I learned and, finally, what I do differently now.

Adjust to New Work

Earlier in the year, I was cranking out high volumes of work for a particular website that I still write for. This was still true by spring, but I’d also co-founded an online Twitter chat with other freelancers and some big-name editors. I convinced myself that it was a good idea to contribute to other sites where I wouldn’t be paid unless my work generated huge volumes of traffic. I also started pitching the big-name editors for work on the theory that writing for a big-name newspaper or magazine would land me big checks. Neither dream came true; I’d spent months pushing a boulder up my own personal Everest, barely reaching even the first base camp (which was that assignment in the national glossy, which did come with a four-figure check).

The lesson: What seems like a good idea often isn’t, and I no longer take on work without first digging into the data. If it’s a big project or would require reframing my schedule, I wait at least a few days and get some advice before booking it. As a freelancer, the worst thing you can do is rush into a bad contract you’ll have to spend months unwinding.

Get Comfortable With Pivoting

By the time my worst year of freelancing came around, I’d forgotten what it was like to pivot from one type of work to another. Earlier in my career, this wasn’t a problem: I’d been consulting with companies on marketing and branding, and writing under my byline when the work was there. By 2009, I’d been writing full time for four years, seven days a week just to make ends meet — except I wasn’t making ends meet. Instead of running the numbers and going back to what I’d done well, I tried graduating into the higher ranks of professional freelance writing without considering the cost of doing so. I’d forgotten that freelancing is as much a dance as it is a business.

The lesson: Your schedule is finite and needs to be treated that way. Consider every hour you’re “on” precious and salable, and then seek to maximize by getting the best contracts. Now I aim for retainer work when I can get it (predictability is important when you’re a freelancer with a family, like me) and group similar types of work so pivoting from writing to marketing rarely happens during a single day but rather a few times a week.

Freelance Work Is Fleeting

Betting everything on one client was bad enough, but trying to win a steady stream of assignments from big-name magazine editors was a nightmare. I wasn’t prepared for the volatility, even though I’d been warned over and over to expect difficulty building sustainable relationships. Also, I had no backup. Aiming for the higher echelons of “freelancedom” would have been great if I’d built my business in a way that I could live on a fraction of the work I was doing. That way, my upward push would have been for growth. Instead, I was flailing about like a fish out of water, pushing furiously but going nowhere fast.

The lesson: The best time to pitch new business is always. Let me say that again, because it’s important: The best time to pitch new business is always. You don’t know when the work you have is going away, and you won’t know if your dream project is out there if you don’t pitch for it. This is why I make time every month to check in with potential clients.

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