Should You Freelance?

Last Updated Aug 9, 2009 10:34 AM EDT

Many people dream of going freelance. Few have what it takes to be successful.

Freelancers are a disciplined lot, able to impose organization upon themselves. They are also aggressive marketers, selling themselves as well as their work, often to strangers. They are bookkeepers, file clerks, office managers, IT departments and CEOs in their own business.

Does this sound like you? A tone of "it's not as easy as it looks" is what I like about Ariana Green's Is Freelancing Right For You? on Harvard Business Publishing.

Some questions from Ariana as you consider whether this is a career option:

  • Are you or your skills in demand?
  • Are you willing to work your way up the ladder?
  • Do you have financial resources to weather a start-up phase and dry spells?
Start with a conversation with yourself, Green says.
"To be a successful, happy freelancer, you should be honest with yourself about exactly what it is that most appeals to you. Maybe you want more freedom, flexibility or variety. You may want to explore your entrepreneurial passion, or perhaps you simply hate reporting to a boss or being part of a corporation. Rank the relative importance of your desires and aversions. How much do you value each when comparing them to a theoretically steady, salaried job? How much are you willing to endure for a freelancer's lifestyle?"
I tried freelancing for awhile and discovered, surprisingly, it wasn't for me. I liked the work but I missed the social networking at the office. Freelancing can be a somewhat lonely existence.

How about you? Have you tried freelancing? What turned you on or off about the lifestyle?

(Home office image by zak greant, CC 2.0)

  • Sean Silverthorne

    Sean Silverthorne is the editor of HBS Working Knowledge, which provides a first look at the research and ideas of Harvard Business School faculty. Working Knowledge, which won a Webby award in 2007, currently records 4 million unique visitors a year. He has been with HBS since 2001.

    Silverthorne has 28 years experience in print and online journalism. Before arriving at HBS, he was a senior editor at CNET and executive editor of ZDNET News. While at At Ziff-Davis, Silverthorne also worked on the daily technology TV show The Site, and was a senior editor at PC Week Inside, which chronicled the business of the technology industry. He has held several reporting and editing roles on a variety of newspapers, and was Investor Business Daily's first journalist based in Silicon Valley.