Does Not Work Well with Others, or: Why Freelancing Is Never What You Expect

introvertAround the time I first joined Toastmasters, the club president gave a speech about leadership.

In Toastmasters, members typically work their way through a Competent Communicator manual, and often neglect the other manual they receive upon signing up: the Competent Leadership manual. Our president spoke of the importance of working on leadership, and urged us all to start making time for our leadership manuals.

There was a Q+A afterward. Being the pain-in-the-ass brat I am, I asked:

“Why should I work on leadership if, as a full-time, work-at-home freelancer, I aspire to avoid all leadership roles?”

Little did I know how much things would change in just a year.

Before going full-time freelance, I struggled to fit into the corporate work environment. I preferred working on my own. I didn’t trust others to get the job done right, and I was easily ruffled when others failed to take my advice. It made me feel devalued. As an introvert, I was also not as aggressive as it seemed I should be. In meetings, for instance, I never felt compelled to contribute. Rather, I sat back and listened, took time to digest the information I’d gleaned from the meeting, and then finally felt prepared to offer my own feedback. Most times, anyway, the meetings felt like wastes of time: people boasting about the things they’d accomplished vs. actually establishing actionable plans for the future. And on top of it all, I had no interest in working my way up any sort of ladder. I didn’t want to manage anyone. I just wanted to create.

This past fall, a regular client of mine recommended me for a permalance position managing and creating online content for a professional organization. I thought I might be getting in over my head, but the idea of a steady paycheck appealed to me, especially considering how slow 2013 had been for me income-wise. So I went all in.

Suddenly, I was managing an editorial board and liaising with a web development team in order to help create a brand new website, envision and create a new version of the organization’s monthly newsletter, and launch a blog. And on top of all this communicating and coordinating, I was conducting interviews and creating content.

Suddenly, I had more power and influence than I’d ever had before and, being unused to it, I felt unsettled. I had a team of people who were supposed to respect my judgment, and I didn’t even respect myself. I was constantly second-guessing myself.

Over the past five or six months, my emotions regarding this job have seesawed back and forth. On some days, I feel that I’m not cut out for this. I’m not qualified. I’m a lone wolf. I should run far, far away.

Then, maybe two days later, I’ll somehow manage to diffuse some conflict or avert some disaster and, perplexing as this is, I’ll think: Hey. Maybe this is good for me.

When I first started freelancing, my primary values were:

  • flexibility
  • independence / autonomy
  • personal fulfillment
  • enough money to pay the bills

But in finally getting to a place that felt easy and comfortable over the course of six or seven years, I also became bored.

I always thought that getting the chance to be a full-time freelancer would be about being that lone wolf. Not having to work with others. Not having to manage anyone but myself.

But this new position is suddenly fulfilling other values I didn’t know I had, such as:

  • being challenged
  • being valued
  • having power and authority (or at least feeling as if my input matters)
  • experiencing a sense of accomplishment

The other week, I taught an e-course in a week-long series created by Cassie Boorn during which I told students that, in the process of reevaluating their careers, they should also be reevaluating the values that are most important to them. Questioning whether their dreams are still the same or whether they’ve shifted. Learning to be okay with that shift.

What has surprised you most about this freelance life? How have things shifted for you in a direction you never planned for?

(image via)


  1. Sarah Schmidt says:

    Hi Steph! I’m happy to hear you have taken on such an exciting project. It sounds like you are doing great. I work as a content editor and team up with a lot of marketing managers who do very similar tasks — such as redesigning websites, creating content, running blogs etc. I think a lot of them learn as they go, so you are not alone in dealing with that kind of challenge! I think the key is gathering a great team of people around you, asking the right questions and trusting your own judgment. Good luck. I hope you enjoy it.

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