Are You Being Challenged By Your Career?


Why is it so darn tough to remain interested and engaged by a job after you’ve been there for four months?

I used to blame it on semester syndrome (we’ve been conditioned to expect that change after a semester’s length of time), but I’ve since become  convinced that it actually has more to do with the ways in which a job stops challenging you after you’ve been doing it for an extended period of time…the ways in which the newness wears off.

Are new challenges necessary in order to achieve career satisfaction? If so, freelancing definitely fits the bill for the ideal career path.

After the jump, the ways in which freelancing constantly challenges me:

Maintaining Self-Discipline:

Those still in the corporate world have got it all wrong. They think that we sit around in our fuzzy pants all day, watching A Double Shot at Love and playing Minesweeper. They think we’ve got it easy. And this causes them to underestimate us. The truth is, it’s really hard to put on real pants and keep the TV turned off and stop obsessively checking Twitter. That’s why I need to play tricks with my mind (I will reward me with five minutes on Google Reader if I can make it through this post) and keep multiple checklists littered about my desk.

Finding New Clients:

As much as I’d like to, I can’t keep my nose buried in my writing and hope that new writing assignments magically find their way to me. This is why mastering the art of self-marketing is so darn important. And publicist/marketer isn’t the only role you have to play when you go into business for yourself. Having to do it all (at least until you can afford to hire on employees or outsource the stuff that you loathe) ensures that you will constantly feel challenged by the day-to-day operations of your business.

Believing In Yourself:

My husband says that one of the toughest things about freelancing is having to continuously convince clients of your legitimacy as a service provider. Heck, I have trouble convincing myself and, for this reason, I’m always struggling over setting and quoting rates to new clients. Books like this one help, as do sites, such as Freelance Switch, with nifty rates calculators.

Feeling Secure:

I tend to prepare myself for risk-taking by having low expectations. Before I left full-time publishing to try my hand as a freelancer, I tried to convince my husband that there was a good chance that I would fail at this new endeavor, and that we should prepare ourselves for a lot of scrimping, saving, and struggling. We were both blown away when I ended up matching my former salary within six months. Still, I’ve never really felt secure because I know that, at any moment, a big client can disappear. Being able to live with that (without getting an ulcer) is a superhuman feat.

Trying New Things:

Back when reality television was still fairly new and groundbreaking, I used to wish that I could be on Road Rules, so that I could be forced into trying the things that scared me the most. This is why I’m a writer. It gives me an excuse to push myself…to try salsa-dancing so that I can do up a piece on couples workouts…to attend the sex party of that hostess I’m profiling…to sit for a nude portrait…to speak to the people who awe me despite my social anxiety. As long as I’m a writer, I know that — at the very least — I’ll never be bored.

I’m not the only one working through the daily challenges of freelancedom:

  • dossy of Dossy’s Blog has trouble “finding other talented freelancers to cooperate with.”
  • My husband (as mentioned before) finds that “constantly having to prove i’m a professional to clients can be challenging!”
  • Copywriter Alexis Rodrigo struggles to juggle her “client work” with her “personal projects — not 2 mention my personal life.” (Amen to that.)
  • Stacy Lipson longs for more writing outlets. I can’t blame her!
  • James Ryan Moreau of JR’s Not So Literal Logging agonizes over “focusing on delivering excellent product(s) and seeking out and effectively pitching all at the same time… marketing is hard!”
  • Kristin T. of Halfway to Normal is an extrovert: “I get energy and ideas from being around people, yet as a freelancer I’m almost always working alone.”
  • Chris Clark has trouble “staying motivated & on schedule day in and day out when working at home, alone. I only have myself to make me sit down & write.”
  • paperhurts of postings of a professional redhead writes: “When I was doing freelance webdesign, GETTING PAID ON TIME, followed by making sure the clients knew what they actually wanted.”

I’d love to hear more about the challenges you guys are facing, or whether you have any tips to share  on the ones above. Leave your stories in the comments!


  1. great article! really inspiring.

  2. margiewrites says:

    “My husband says that one of the toughest things about freelancing is having to continuously convince clients of your legitimacy as a service provider. Heck, I have trouble convincing myself…”

    This is so my story. I took about a year off of freelancing because I was so afraid. I was doing well for a while, then clients started to dry up. Now, I’m doing it out of necessity — but I did miss it! The challenge I’m struggling with is getting it in my head that it is possible to make a living doing what I’m best at. Once I can fully convince myself, I can convince others…

  3. This is not bad advice, unlike a lot I have come across.

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