This article is for people who are still considering the jump. You’ve heard the
phrase about where the grass is greener, and some people romanticize
freelancing as a modern-day hired-gun adventure.

While daydreaming about nomadic wanderings through corporate America, you may
forget that working for someone else means you have a lot less to do. When
you’re on your own, sundries such as health insurance, paperwork, and
retirement are all up to you. There’s a lot of self in
self-employment.

A question you should ask yourself, then, is do I have what it takes?
Greed alone doesn’t guarantee long-standing affiliation with the Church of the
Billable Hour™. You should also consider the following:

1. Are you responsible?
   You’ll have to keep up with taxes, insurance, and any applicable licenses
   or certifications required for your industry. It’s easy to forget these
   details when you’re busy with a job (or gig, as the cool kids call
   it) and the only reminders you’ll get are late notices (or worse).

   Invest in a PDA to help compensate for an ailing memory. That’s the
   closest you’ll get to a human assistant for quite some time.

2. Do you manage your finances well?
   The upside of freelancing is that there’s potential for some hefty
   paychecks. The downside is that those checks aren’t from The 1st and the
   15th Club. Pay may come at irregular intervals, infrequently, or both.
   You must know your “floatability” — that is, how long you can go without a
   paycheck — at all times, and conduct yourself accordingly.

   If you already keep track of your personal finances, this is simple: divide
   your current bank balance (freelancer lingo: The Stash; or as
   we’re wont to call it, The Fund) and you know how long you can
   hold out without a paycheck.

   If you don’t track your finances, this would be a good time to start.

3. How well do you juggle?
   Running your own business means you are a one-man show (even the ladies):
   boss, receptionist, sales rep, and worker bee. It’s easy to get caught up
   in any one role and let the rest slide, at your detriment. Ella said
   Something’s Gotta Give and, at least in the near term, it may be a
   significant portion of your personal life. This goes double if you still
   hold your full-time job while getting setup.
4. Are you self-motivated?
   Once you get your business off the ground, you have to keep it running.
   Consider that you’ll always be working, even if you’re not on the
   clock with a client. You stand a fair chance of falling into a rut if you
   don’t crack your own whip.
5. Are you outgoing?
   Even freelancers in the Dot-Com era (our halcyon days of the mid-90’s) had
   to go out and find work, make connections, and so on. The chances of
   someone beating down your door looking for your services are slim.

   You don’t have to fit the stereotype of the slimy, cold-call salesman.
   Keeping in contact with colleagues is often a good foothold. (Let them be
   the slimy salesmen, if they’re of that ilk.)

6. Are you easily discouraged?
   Freelancing’s not too unlike the singles scene: you’re after someone
   (sometimes, anyone) but not everyone wants you. To some clients, people
   offering your services are a dime a dozen, and they won’t hesitate to tell
   you. (They might not be rude about it, but nor should you expect them to
   sugar-coat the facts.)

   For every yes, expect a few nos, and just accept that
   it’s part of the price of admission. Going back to our bar-scene singles
   analogy, you’ll have to be the persistent lad (or lass) who makes eye
   contact with anyone and everyone. Waste no time on rejection; just keep
   your game-face on and move to the next person foolish enough to glance past
   you. (If you don’t recognize such a person, it’s probably you. Congrats!)

It’s worth your time to be honest with yourself and know what you’re
getting into. A “no” or two don’t necessarily preclude you from the
freelance arena. Just realize that you have some extra hurdles to clear.