Just as cubicle drones envy their freelancer friends who make their own hours and seemingly take vacations at will, self-employed folks sometimes long for the regular paycheck and built-in benefits of a day job.

Personal Dividends examines the dark side of self-employment and notes the travails of being your own boss.

Among the drawbacks of the lifestyle:

*Having to pay quarterly taxes. Freelancers have to be disciplined enough to sock away a sizable chunk of their income to feed the IRS beast every few months. Forget to do so and you could get financially maimed during tax season, potentially having to pay penalties or interest on missed quarterly payments.

*Vacations are unpaid and guilt-ridden. When the self-employed take time off, the money stops rolling in. This means you’ll either be forced to take your work with you to the beach, or just leave it at home and forsake the potential income — which is tough to do when you’re blowing funds on a trip.

*You never clock out. If your workload carries you away, you could long for the calm rigidity of a 9-to-5 schedule. Deadlines have a way of keeping you up late into the night and ruining your weekends.

If you’re a freelancer, what boundaries do you set to keep your life manageable?

The Dark Side of Being Self-Employed [Personal Dividends]

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