IT Career JumpStart

Aug 22 2011   4:50PM GMT

Resisting the Ineffable Allure of IT Freelancing

Ed Tittel Ed Tittel Profile: Ed Tittel

Saw a great blog from Susan Harkins on freelancing this morning over at TechRepublic. It’s entitled “10 things you shouldn’t believe about freelancing” and its various bullet points not only struck home (and occasionally also, my funnybone) they also go me to thinking about what’s involved in launching a self-directed career as a freelancer, especially in today’s dicey economic climate.



Tech Republic logo and headline

Tech Republic logo and headline

 Here are Harkins’ 10 points with my own reactions to them, which I’ll follow with additional input and advice to those who may be pondering the leap from working for “the man” to working for themselves:

1. Freelancers make the big bucks: You may occasionally make more per hour freelancing than you make on salary, but you will often make a lot less. When you’re self-employed the paying work has to fund your overhead, and most people have at least one day of overhead time per working week.
2. Freelancers can specialize: Yes and no. Yes, in the sense that you’ll always tend to take on work you know how to do properly and well; no, in the sense that any work is better than no work when you’re trying to keep the cashflow going.
3. Freelancers are their own bosses: Again, yes and no. Sure you may run the firm of me, myself, and I, but I agree wholeheartedly with Harkins that every customer is your boss when you’re a freelancer, and that you should bend over backwards to keep all of those bosses happy.
4. Freelancers accomplish more: Here, too, Harkins point that freelancers get more done because they spend more time working is right on the money. In good times, you work to meet deadlines and get the job done; in bad times, when you’re not working for whatever income you can generate thereby, you’re out hustling for new work.
5. Freelancers are happier because they’re doing what they love: I’m not entirely in Harkins’ boat on this point, but it is true that freelancing involves doing what you’re good at and what pays. As you get better at it (and better known), however, you will have more opportunities to be choosy about what work you take on.
6. Freelancers work in their pajamas: They can if they want to but most of us don’t. FWIW, it’s not an option to me because I don’t wear pajamas…ever!
7. Freelancers have more freedom: Yes and no: you can decide when and if you want to work, but you must work or you won’t get paid. For most of use this means most waking hours during the week are spent working, even if we do get to decide when those hours might occur.
8. Freelancers have less stress: I don’t buy into Harkins’ thought that “people with real jobs get unemployment benefits, and freelancers don’t” because unemployment benefits are largely terrible, and because everybody who works deals with stress as part of the job (and then, of course, there’s the rest of your life, which comes with its own stresses, too). We all cope as best we can, whether employed full-time, freelancing, or doing something else.
9. You need a Web site: Harkins opines one really isn’t necessary because hers hasn’t brought in any new business. Like most Internet phenomena, this is clearly a case of YMMV (your mileage may vary). Mine has brought me plenty of business, but only at odd intervals. If you want to create a personal brand, or are thinking about starting a company, building a Web site will teach you stuff that will come in handy someday, if not right away. Your call!
10. Freelancers can sleep in: Only if they make up for getting up late by working late. But if you work with customers (and who else is gonna pay you), you’ll work when your customers work because that’s when they’re going to want to work with you.

Other thoughts I had while chewing on this material included the idea that you shouldn’t go freelance without at least 3 months worth of cash flow available to you. It always takes a while to fill up your pipeline, and for that pipeline to start pouring cash into your bank account. Be sure you can cover your costs while you’re waiting for invoice payments to start appearing (and in these times, if your terms are net 30, adding 30-45 days to this is a good idea because many customers will be slow to pay). You should also be sure you’ve got some initial business lined up before you take the freelance plunge, because while it’s always a good idea to keep marketing and actively soliciting work, if you have none and can find none, your brilliant freelance career can’t last very long!

And finally, here’s the most valuable lesson I’ve learned in my 17-plus years of freelancing: if you have to choose between sitting idle and taking on work that’s going to lose you money, keep sitting. If you’re going to lose money anyway, why not do it looking for new work, instead of knocking yourself out working on something that’s going to bring you financial losses when all is said and done. This is a tough lesson, though: I have to relearn this one myself at about 5-7 year intervals when the work flow slows to a crawl. I hope I don’t have to learn it again, ever!

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