Can I Safely Retire from Corporate Work to Become a Freelancer?

Question: I’m a corporate been-there-done-that person. After trying mid-level management, I retreated to the world of individual contributors, which makes better sense for me. In a few years, I’ll be able to afford to leave the rat race. But since I’ll still have many working years left, I’m thinking about becoming a contract or freelance application programmer. It’s a field where requirements usually are well defined and there seems to be plenty of opportunities. I’ve done some graduate coursework in the field, and my plan is to pick up more expertise in the next few years and find part-time programming work to hone my skills. Then, after I leave my current job, I’ll have the option to move anywhere and find work. Is this a sound plan? Are there drawbacks I should be aware of?

– Irene, Naperville, Ill.

Irene: It’s too bad every early retiree isn’t as well prepared as you (assuming you truly enjoy programming and aren’t doing it strictly for the money, in which case you’ll become unhappy quickly). Perhaps the most important issue to remember is that when you’re the boss of your own venture, you’re responsible for both doing the work and generating the business. That means becoming a salesperson willing to toot your own horn shamelessly to attract customers. Of course, you can bypass that chore by registering with a technical-placement firm that will find plenty of opportunities on your behalf, but will keep a share of the revenues for their efforts. For most new freelancers, it’s a fair trade-off until they become established.