Tag Archives: joyfully jobless

The Freelance Switch: Being scared and doing it anyway

Working from home, legs up on deskI’m no stranger to freelancing. I’ve been moonlighting as a freelance book indexer and writer for the past 11 years. And it has always been mostly manageable. Up until now, that is.

I recently made the decision to leave a stable, comfortable and well-paying role in communications to focus on my freelance work. Trying to be kick-ass in two careers was getting too challenging, and I decided the time was right to choose the path that was the best fit for my strengths, skills and passion. Today marks the two-week countdown to owning my days.

The people in my network who know about my moonlighting side say it’s about time. I have wanted to strike out on my own for as long as I can remember. For years I have been gobbling up books like My So-Called Freelance Life, The Anti 9 to 5 Guide, Making a Living Without a Job, and the $100 Start-up. (PS: If you know someone with as much love for the “joyfully jobless” life, tell them to connect with me on LinkedIn, because I’d love to hear their story.)

I expected to hear a lot of negative remarks from my friends and family. Instead, I got the opposite: most comments consisted of variations on “I’m so jealous” and “You’re so brave.” The ones who are jealous probably think that working from home means I’ll be enjoying long lunches and coffee breaks with the PVR, luxuriating in impromptu naptimes, and writing dazzling prose while reclining in the La-Z-Boy. Those people probably also think that Sex in the City realistically depicts a writer’s life.

The ones who said I was brave have a more realistic view of the freelance life—the ups and downs, the lack of a support system, the isolation, the uncertainty, the potential drop in personal hygiene standards. True, there are many benefits to being the captain of your own work-at-home ship, but I am still pretty anxious.

Here are the kinds of things keeping me up at night:

  • Will I forget how to act in polite company? I will probably swear a lot more than I do now.
  • Will I go a little stir-crazy? Granted, I already talk to my cats when I’m on a deadline, but what if they start talking back?
  • Will my lazy side turn out to be my dominant side? I confess to already being a champion napper, and it is very easy for me to be busy doing absolutely nothing.
  • Will easy access to the fridge make even my comfiest yoga pants feel tight? Note that said fridge is often filled with tasty pastries, sauces made with real butter, and puh-lenty of carbs. (My husband is a pastry chef. Do not envy me.)
  • Will I be able to motivate myself to be successful? Every decision will be my own, and success or failure will be up to me.

Despite all these fears and anxieties, some more serious than others, I am still making the leap. Interested in hearing how it turns out? Watch for more posts to come with the scoop on what it’s like to make the freelance switch.



Filed under Freelancing, Starting up