People often asked me how I made the decision to take the leap into freelancing. I am—as I have noted in this space countless times—a fairly risk-averse person. That makes it kind of odd that I’m a freelancer, actually.
My answer to the question is always the same: I didn’t enter this path in the conventional sense of weighing the pros and cons and deciding to take the plunge. In my case, I was unemployed, had come off a series of demoralizing office jobs I’d hated, and in many ways felt I had hit career bottom. From my perspective, I had nothing left to lose by trying freelancing. These days I regularly give thanks for that horrible set of depressing circumstances, because I doubt I would’ve come to it any other way; if life had been okay, I never would’ve taken the risk.
But most people do come from acceptable career circumstances, by choice, and have to figure out if freelancing is really right for them. And there are countless resources available on the Internet to help you decide.
Today I want to draw your attention to an invaluable pair of articles, because together they do an incredible job of illustrating exactly what you need to consider on both sides of the equation.
On April 19th, Webdesigner Depot published 20 Reasons You Shouldn’t Be a Freelancer, and let me just warn you, it’s kind of brutal. In a good way. It makes no bones about the down side of being your own boss, and you may not think it the right thing to read if you’re just starting out (or thinking of starting out). But you should read it, because it’s full of important stuff. And furthermore…
… a few weeks later, they went ahead and published How to overcome 20 Reasons Not to Become a Freelancer. You’ll get the most out of the second article if you read them both, I think.
It’s funny… the thing I tend to latch on to when people ask about the biggest challenge or thing to watch out for is the insurance issue. Webdesigner Depot gives some very practical tips on how to find group insurance rates as a freelancer, bu then it’s not as funny when I make my standard crack about having married my husband for his health insurance. Hmph. Personally, I think that if you’re in a couple, one of the best ways to mitigate the risk of freelancing is to have one freelancing person and one salaried person; it sort of splits the difference when it comes to all of the standard worries about paid vacations and economy downturns and, yes, health insurance. I mean, yes, obviously that’s not an option for everyone, but I’m just saying.
But the best part, I think, of the two pieces comes in at lucky number seven. From the first piece:
7. You Don’t Love Your Work
So many people who work the usual 9-to-5 don’t really love their jobs. They don’t wake up in the morning looking forward to going to work. But they do it in order to earn a paycheck and put food on the table. Sometimes this is because of the work environment itself, but others times it’s because they don’t really enjoy the work they’re doing.
If you don’t love what you’re doing, you’re probably not going to love it any more once you’re freelancing. Freelancing is hard work, and if you’re already struggling to find the motivation to get your job done, you’ll probably struggle even harder once there’s no boss there to motivate you.
And then from the second:
7. You Don’t Love Your Work
If you don’t love your work, or at least enjoy it, you’re going to find it hard to stay motivated to complete things, even if you’re normally a very motivated person. The best advice here is to find something you do love and then start freelancing in that field instead.
in many ways, this seems so self-explanatory as to be inane to even need mentioning. But it really does need to be said. Freelancing only works when you love what you’re doing. Otherwise you’re putting in more work and getting less security for… what?
So now my question when folks come to me to ask about whether they should or shouldn’t will be this: Do you really love it? If the answer is no, well, then, you have your answer. If the answer is yes, then you can figure out the rest.