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How Freelancing Leads To Insecurity—And How You Can Build More Confidence


The greatest cost of freelancing is insecurity. Well, that and no maternity leave. Also, no healthcare. And clients who don’t pay. Okay, maybe freelancing is kind of expensive. And while most freelancers I asked said that their insecurities spring from a lack of financial stability, there are other causes, as well. For me, as a freelancer, I sometimes find myself plagued by emotional insecurity.

The Problem Of Other People

I’m a neurotic human, and I care far too much what other people think. On the other hand, not caring what people think is sociopathic, in my opinion. We live in a society. It matters what people think! And for the first few years I worked as a freelancer, what the people in my life thought is that I didn’t have a job. That was in part because of how I phrased it—I had quit my tech job and moved back in with my parents to do stand-up open mics every day. So, yes, I can see how they got there.

In time, however, I began to make money as a freelancer. I had a job that looked similar to my friends in many ways; I was paid money in exchange for doing specific tasks, many of which I hated doing. That’s the definition of a job, I believe. Look it up.

Still, it took a long time for anyone to accept that I might be busy during the day. To this day, I bristle when anyone suggests I have a wide open schedule or assumes I’m always free. How often has a friend asked “what I’m up to” on a Wednesday morning. I’m up to emails, Nancy. Wednesday mornings are for emails. How often a friend has texted me saying, “I randomly took the day off work—want to get lunch?” No, I’m not free to take the subway 45 minutes to lunch, as I’m busy, and also, why do I have so many friends who randomly skip work? Plus, I eat lunch at 10 a.m. like a normal work-from-homer.

The Problem Of Myself

But my insecurity about freelancing isn’t entirely because of other people. It comes from me, too. I live in a way that doesn’t match my own idea of a “real” adult. I often take naps (power or otherwise), sometimes as early as 10 a.m. (on days when I’m having a late lunch). For my mental health, I go on walks without my phone, but some of these walks take up my entire afternoon (without my phone, I have no idea how much time has elapsed—duh). I convince myself it’s fine—I work most nights doing stand up, and some of my best writing gets done on the weekends when I don’t have to balance the day-to-day tasks of my current social media jobs, so of course I should take off the random Wednesday afternoon. Of course.

And still, I worry I’m in this period of arrested development. That I’m living like I did in college, even though I haven’t had a twin bed since I was 27, which was, too be fair, far too old for a twin bed. I worry that I won’t be able to adjust to the rigors of a “real” job, if I get one again. I had a part-time job at a non-profit last year, and I once had such bad menstrual cramps that I locked myself in an office and lay on the floor for half an hour. This office was not mine, although, to be fair, it wasn’t anyone else’s, either—the company paid so little that there was near-constant turnover. When I stood up, I was struck with deep shame. I’m not fit to rejoin the workforce. I can’t do it. I was also struck with even worse menstrual cramps; being a woman is honestly unethical.

Letting Go Of Shame

Except, of course, I was a member of the workforce. I was working at an office, and I’d taken a break without getting in any sort of trouble. So really, it was in my head. Clearly, I needed to work on letting go of this shame that I don’t have a “real” job. It’s inaccurate, as I work over 40 hours per week and make a decent amount of money each year. But that almost misses the point, too. What if I didn’t? What if I worked fewer than 40 hours per week, and made less than the minimum wage? Would that be a reason not to respect myself?

In a way, a freelancer’s insecurity about not being part of the traditional workforce is a microcosm of our collective insecurities over not succeeding at capitalism. At not always having more, at not thriving in the exact way we’re taught to thrive. I can’t snap my fingers and eliminate insecurity from my life. If I could, I’d write one killer self-help book and never have to work again! Instead, all I can do is choose not to act on it. I must continue to pursue the career I want, despite what the voices inside and outside my head tell me.





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