Major con of freelance life: Paying income tax in one big, brain-busting lump every spring. Pretend you work in a traditional office, in the "sitting at the desk, doing the work" way, and you'll reap the benefits; pretend you can forget about Uncle Sam like your salaried friends do, and you'll rue the day. According to this fun little financial-planning service called the IRS, "If you are filing as a sole proprietor, partner, S corporation shareholder, and/or a self-employed individual, you generally have to make estimated tax payments if you expect to owe tax of $1,000 or more when you file your return." Pay estimated taxes quarterly, and you'll thank yourself (and me—you're welcome!) in April.