If you're weighing freelancing vs employment, I'd recommend doing medium term contracts instead. Look for the typical 3-12 month contracts and go from there. Yo

If you're weighing freelancing vs employment, I'd recommend doing medium term contracts instead. Look for the typical 3-12 month contracts and go from there. You'll get decent experience, have some stability, and it won't be terrifying financially. Keep focused on building up connections to clients, stay active in your local community (meetups, conferences, user groups, etc), market your services, and establish a business presence (LLC, business bank acct, office space, phones, website). But at the same time, your bread-and-butter financially can be your contracts, until you're able and comfortable moving to pure freelancing. You can also try to structure your contracts so that you're paid on a 1099 instead of a W-2 and that way you can start filing as self-employed and get the full deduction for health insurance and the assortment of other tax breaks (but get your own tax advice; this isn't it). Note that you should expect more money being paid on a 1099 since you pay self employment taxes (I usually discount W-2 work at 15%). But if clients want to control your work day, they'll be reluctant to pay you on a 1099 because of IRS rules. If you just jump right into freelancing, I'd worry you'll never get the opportunity to really see first-hand and in-depth how businesses are run and that you'll always lack something in terms of project, team, and management skills.