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12 Years of Lessons Learned as a Freelancer

When I started freelancing a dozen years ago, it was meant to be a stopgap. The Web company I’d been working for had popped with the Internet bubble and freelancing seemed to be a good way to keep some revenue rolling in while I looked for my next job. I’d seen Elance open on a friend’s computer, joined and within a week had landed my first job. I picked up a second job a couple of days later and haven’t looked back since. I still work for that second client and my client base is now solid enough for me not to have to pitch for jobs or bid on projects. Work comes to me and the ten bucks a month I pay to Elance now functions as a kind of unemployment insurance, keeping my reviews, my ratings and my profile up to date just in case I need it. It’s been a long time since I have needed it.

Freelancing turned out to be my next job.

I have learned a few things over the last dozen years or so. These are the most important things I’ve picked up:

1.     You Don’t Sweat the Small Stuff

Spend any time in a workplace, and you’ll hear people criticizing management, expressing their incomprehension at decisions they have to follow and wondering why they’re not being listened to. When you work for yourself, those negative feelings disappear.

Sure, clients don’t always do what you think they should do. Projects disappear in weird directions and you wonder sometimes how a client will ever sell what she’s asked you to create. But it doesn’t matter. You finish the project. You collect the payment. You move on to the next job. Employees are stuck with their bosses. Freelancers get to change them.

2.     Freelancing Is More Stable Than It Looks

The biggest concern for new freelancers is the loss of a stable income. It’s true that no two months are ever the same but it’s also true that they don’t vary very much. Once you have a solid base of regular clients with predictable needs, you’ll find that income stays within a narrow band.

In practice, the biggest challenge isn’t that freelance income will drop too low but that you’ll struggle to keep pushing it up.

3.     Bad Times Don’t Last Long

That isn’t to say that there are never worrying dips in income. They can happen. A couple of years ago, when the recession was at its deepest, a couple of clients reduced their output and for the first time in a decade I found that days were actually long enough to complete everything I needed to do.

It was worrying while it lasted but it didn’t last long. A few job pitches later, my schedule was full, everything was back to normal and I was racing to get everything done in time again.

4.     You Never Have a Free Moment

Freelancing is a form of self-employment which means that you’re in control of every part of your business. Yes, you’ll be producing your designs or articles or code or whatever it may be, but you’ll also be reading professional literature, maintaining your website, emailing clients, collecting invoices, managing payments and sometimes marketing for new jobs.

Any moment you’re not doing one of those things is time that you’re not earning. (I find myself doing invoices in the evening in front of the television so that I don’t waste productive hours on paperwork.)

Freelancing allows you to set your schedule but it also gives every hour a value.

5.     People Think All Your Moments Are Free

On the other hand, because you’re working from home, and because you set your schedule, people around you tend to think that you time is more flexible than theirs. When there’s a chore to be done, a shirt to be collected from the dry cleaners or a kid to be taken to the doctor’s, it usually falls to the freelancer because they don’t have to ask the boss for permission.

You can just miss a deadline.

Freelancing does provide plenty of freedom… but not as much as people think.

6.     Change Is (Usually) Good

A base of regular clients will give you stability but it’s also restrictive and you can come to depend on the income even when you no longer enjoy the work. That’s always dangerous. It makes improving your career difficult and it means that the loss of a client can be more frightening than it should be.

Clients come and clients go, even clients you’ve served for years. What I’ve found though, is that at the end of every client relationship is an entirely new one — and usually it’s better than the one that just ended.

7.     I’m In Control of My Career

If there’s no point in complaining about my boss as a freelancer, it’s mostly because I have the power to change the direction of my career. If I want to write more books, about a different subject or earn more money, I have to work towards that direction myself.

That’s not easy. It requires planning, an understanding of the opportunities available and an awareness of the training I’d need to do and the connections I’d need to build to move my career in the direction I want it to go. Most importantly, it means that I have to know whether the kind of work I think I want to do is really the kind of work that would make me happiest.

8.     Freelancing Isn’t the Best Way to Work, But It’s the Best Way for Me

There are plenty of reasons not to freelance. A regular job would give me more company, perhaps some stock options, a clear career path, more stability. The benefits would be better and cheaper, and I’d have the same kind of routine that friends and family enjoy.

But freelancing suits me. I like the solitude. I like the control. I like the clients and I like the work, its variety and its challenges. I may have started freelancing temporarily but I’ve learned that I’m sticking with it permanently.



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