Work for Yourself: Can You Afford to Make the Switch?

When people find out that I’ve been working from home for years, they often respond with both envy and fear: “I’d like to do that myself…but I can’t afford to give up my paycheck. How could I possibly get started in a web work career? How do you get started on something like that?”

While there’s no magic formula, there are things you can do that make it more possible to move successfully from a 9-to-5 office career to a freelance web worker one. In the past we’ve covered some of the things that help web workers be successful after they get going. Today, I’ll offer some advice on actually making the transition.

Line up work in advance – You should know where your first job is coming from before you hang out your shingle. Better yet, you should know where your first several jobs will be coming from. I don’t know what industry you’re in, but in software development it’s not all that hard to find potential clients. Build up your personal brand, let people know that you’ll soon be available, take opportunities to establish your expertise and professionalism, and sooner or later someone will ask for a price quote. Be sure not to poach clients from your current employer (unless you’re fond of being on the receiving end of messy lawsuits). Yes, this means you’ll be selling yourself before you’re selling any services or receiving any money; it’s an investment in your future.

Pick the right transition style – There’s one big decision to make up front: do you take the plunge, quit your job, and go full-time into independent work, or do you start out with some nights-and-weekends side jobs to figure out if you can make a go of it? I took the former route, and while it worked out for me, I was young and without family responsibilities at the time (and there were some weeks of living on ramen, with peanut butter crackers as an occasional gourmet treat). A gradual transition provides more financial security, but it has other drawbacks. First, you’ll work longer hours because you’ll be working two jobs. Second, you run the risk of alienating your current employer if you’re perceived as a direct competitor, and perhaps even getting fired.

Have some money in the bank – Whatever strategy you use to move from office work to web work, you need to recognize that the checks won’t come rolling in immediately. Three months’ living expenses in your savings account is good. Six months’ is better. No savings account? If you can’t even buy ramen, you’re not ready to take the plunge.

Downsize your expenses – Moving from one career (or one form of career) to another is an excellent time to take a look at your budget and expenses and try to figure out whether there are any big savings to be had. While some folks go in for coupon-clipping and skipping that one latte per day on the theory that little things add up (and they do, if you put enough little things together), I’d look for big things first. Premium cable TV plan? Planned Vegas vacation? Eating out every Wednesday and Saturday? Every new Wii game as it comes out? Belt-tightening is never any fun, but just how much did you say you wanted to work for yourself? If you’re successful, you’ll be able to add the goodies back in later.

Control your debt – If, like too many of us, you piled up four or five figures of credit card debt when credit cards were easy to come by, chop ’em up and put all of that into a payment plan through a reputable credit counseling agency. This is actually a subheading of “downsize your expenses,” as you’ll find that you can chop your monthly interest payment by a huge amount when you do this. The tradeoff is that you won’t find it so easy to get and abuse easy credit for a few years, but again, what is being your own boss worth to you?

Don’t be afraid to negotiate terms – Just because you’re new at web work doesn’t mean that you have to allow yourself to be taken advantage of. If your first potential client doesn’t offer you a reasonable rate, ask for more. If they want you to sign their contract, have your lawyer review it (sadly, paying a lawyer is one of those expenses you just can’t afford to skimp on) and propose changes if necessary. If you need some cash to prime the pump, suggest billing every two weeks instead of once a month – often you can get this approved in the context of a more agile development cycle.


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