The Pitfalls of Freelancing

Image use Creative Commons license via Flickr: http://www.flickr.com/photos/frielp/2661943/

If you’ve made the jump from a full-time employee to an overtime self-employed freelance position, you’ve undoubtedly found that there is no shortage of criticism for the freelance lifestyle. Hundreds of articles and blogs will tell you that, frankly, freelancing is harder than working 9-to-5 and that for every perk there is a pitfall – you will find that “freedom” means the freedom to work long hours, that “opportunity” means opportunities to brush up your accounting and other paperwork skills, and that “working in your pajamas” means staying up until the wee hours of the morning to beat a looming deadline.

I’m not going to detail such pitfalls here, because I know that intelligent strategy and perseverance lead to successful freelance careers that actually do afford you the freedom, growth and financial stability you’re so passionately seeking.

Instead of languishing over the woes that every new business owner faces, let’s talk about the pitfalls of a successful freelance career. Imagine yourself, two years from now, working smarter instead of harder, having acquired the ability and willingness to delegate, with a steady stream of well-paying clients coming through your door. You can take vacations at-will because your assistant can run your business better than you can, you’re pushing your way in to a higher tax bracket, and your Second Life avatar’s personal life is blooming for all the free time you have to nurture it.

What could possibly go wrong? Let’s examine:

Loneliness – You might be a successful freelancer who can knock off at noon, but your friends will still be hard at it until the late afternoon. Or maybe you don’t go in until noon, preferring to spend your evenings cavorting in the clubs. Either way, you’re going to spend a lot of time alone. That is, unless the seniors at the park let you in the chess game or you strike up friendships with the college kids who always smell funny.

Family – Of course, the only thing that will disrupt your loneliness is your family, and I’m not talking about those you hold near and dear but the ones you go well out of your way to avoid. They will find you. They need favors. “Oh,” they’ll say. “I heard you can design websites. I was thinking about getting a website, how neat!” What they really mean, of course, is “I need a website and since you’re my favorite cousin I haven’t spoken to since I let you take the heat for breaking Grandma’s lamp I expect you to do it pro bono.”

Relationships – Some think a successful freelance career means you’ll get to spend tons of fun-loving time with your spouse or significant other. Let me just say that there is a reason retirees go back to work.

Paranoia – On a business level, you will constantly be paranoid that you’re going to lose it all. You’ll become distrustful of your employees and that distrust will be compounded exponentially in proportion to the amount of time you spend away from the office. Combined with the previous pitfalls, you’ll find reasons to be locked back in your office.

The next time someone says you have it easy, remind them that working 9-to-5 isn’t all bad. They get job security, an escape from family and relationships, and the opportunity to connect with new friends with shared interests. After all, everyone hates the boss.

  • http://www.johnguzman.com John Guzman

    Great article – been doing full time freelance for several long stretches over the last 10 years. You hit the nail on the head. Still trying to find that vacation though, that never quite happened :)

  • Brian

    Thanks John, and nice portfolio site! Vacations can definitely be tricky to come by… but I’ll assume that since you’ve been at it for a decade you can’t find time for vacation because you’re so busy, not because you can’t get work. Kudos!

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