The Perils of Full Time Freelancing

freelance workIf you are new to freelancing full time or are about to make the leap, you’re probably wondering what to expect–what’s lurking around the corner waiting to jump out at you? Fortunately, there is plenty you can anticipate and avoid if you know it’s coming.

Experienced freelancers know all of these by rote, but if you’re just starting out, these are often lessons of the “learn by doing” variety. If you’re an experienced freelancer trying to help out someone new in the biz, this list of “must avoids” will be quite handy as an in-writing reference.

Freelance assignments pile up all at once when you’re pressed for time, and mysteriously vanish when you’ve got plenty of time to spare. It sounds like a truism, but this a lot closer to reality than cliche. Prepare for this reality and you’ll be plenty busy during the good times, but you won’t fret as much in the lean ones.

You’ll work longer hours than you did in your day job. It’s amazing how motivational having to hustle for your own paycheck can be. But you’ll also feel the guilts for taking half days off–don’t give in to those guilty feelings. Taking days off when you need them is one of the perks of being a freelancer. You’ve earned it.

Clients will try to take advantage. Sometimes they don’t mean to be selfish, but the blog owner I worked for who asked me “Can you post on Christmas day?” was told in no uncertain terms there’d be no work done on the 25th, thanks. You CAN tell them no when you need to. It won’t hurt your career a bit.


You’ll lose sleep in the early days until you learn how to generate work when you need it. Try not to lose TOO MUCH sleep–even though stressing out over the freelance game is par for the course when you’re still learning the game. Remember that it IS a game, the way life is a game. Nothing’s worth sacrificing your health over long term. Just be persistent and don’t give up. You’ll do fine.

Keep careful records. Make a record of EVERYTHING in your first two years from how many hours you worked that day to how many miles you drove on the job. After two years you’ll have an excellent idea of what to record and what is already being recorded for you by your bank or the credit card company. Until then, write it all down.

Do not delay in filing your taxes. In fact, if you prepare your taxes long before April 15 you may find you need to take some extra deductions in order to avoid a massive tax bill. You can do that by contributing to an SE IRA before April 15th. Ask a tax pro about this one, but you won’t be able to take this deduction past the April deadline–so learn how much you need to contribute to the IRA long before April rolls around.

Keep your tax information straight. Your personal deductions are subject to different rules than your business deductions. Make sure you ask your tax preparer about how to take and calculate both personal and business deductions so you don’t miss the chance to get the legal tax breaks you deserve.

Ask a more experienced freelancer to evaluate your personal marketing and branding strategy. Are you missing the boat in a way only an experienced freelancer could catch? Are you sending the wrong signals to an editor or client? Ask someone you trust and make the tweaks they suggest. You could find your career turning a big corner with a few minor adjustments.