Freelancing: Then and Now

Although I still have a few paychecks coming from my old job, I have no further work responsibilities — those ended June 30 — so I’ve now officially been a freelancer for two weeks. While I’ve always dabbled a little, with side hustles ranging from a few hundred to a few thousand dollars a year, I haven’t been fully freelance since I returned to grad school at age 26. I’m now 39, so that’s 13 years of steady paychecks. (Brief pause while I bemoan how little financial progress I made during that time.)

During the four years between college and graduate school, I was a full-time employee for only one year, and a freelancer for three. Those three years were a wild ride in many, many ways. I often wonder what my life would have looked like if I’d spent them in, say, law school, or if I’d continued with the job I started right out of college (it wasn’t the right job for me, so I’ve always been pretty glad I didn’t continue with it, despite my weird life path since.)

I’ve been thinking a lot over the past two months about what it was like to freelance then, comparing it to “now.” Here are some preliminary thoughts — though I’ll probably have more in six months or so.

In my early 20s I looked for, and took, every kind of work that would have me. Ultimately, I let my freelance career be led by others: the kind of work I was getting the most of, which was a little random, led to more work in that field, and about 1.5 years into full-time freelancing I was making enough doing that so that I just did that. I started to specialize. But if events had fallen out differently I might have pursued a different angle. I was really being driven by who was offering me money rather than by my interests. And especially during that first 1.5 years I said yes to the most random stuff, because I desperately needed money. I spent a lot of time on craigslist looking for small gigs, and got a few more other things via word of mouth. I remember one gig where I held a dog on a leash outside NBC for a couple of hours (it was a publicity thing). I think that officially qualifies as the most random!

Also, I was just generally afraid to go on vacation, or leave town for any reason, or not pick up my phone. I did lose gigs sometimes because they simply went to the first person who picked up. But sometimes I would arrange my schedule around something that just never materialized — I remember one month I really wanted to be out of the city for financial and social reasons, but I was supposed to start work on a new project so…. And it just didn’t happen. Sigh.

I definitely feel some of that same reluctance to say “no” now. A kind of professional FOMO. I might not be that interested in the specific job…but if I turn it down, what if I never get offered anything again? I think I will probably end up saying yes to pretty much anyone offering me work in my price range this year.

That’s a big difference though: I have a price range! I’ve set a minimum amount I’ll accept per hour and I’m determined not to undercut that rate.

I can do this now, when I could not do it then, for two reasons, one of which is much more important than the other. The less important one is that I am much better networked now than I was then, and am confident that if I turn down work that isn’t worth it, I will get other work from other sources. The more important one is that unlike then, when I typically had an average of zero dollars in my bank account, I now have an absurdly large cash reserve. I ballpark that at my current (granted, quite low) spending level it’s about three years’ worth. So I just don’t feel compelled to undercut my rates.

Another difference is that, while I am open to work that involves being on-site, most of the work I’m looking for now is remote. That will help a lot with the vacation problem I had in my early 20s, when virtually everything I did required me to show up in person. I’m not planning major international travel that will take me out of reach of my email for more than a day, and there’s no reason why I can’t go hang out in my friends’ living rooms and edit or research/write.

A third difference: health insurance. I just straight-up didn’t have it for several years in my 20s. I’m basically a very healthy person, so I really only need coverage in case of catastrophe. However, I am going to get that coverage now: because the ACA has made insurance available in a way it wasn’t in my 20s; because I am older and the likelihood of a catastrophe has gone up; and because I can afford the premiums now, when I simply couldn’t spare a dollar at age 23.

So: do I feel better or worse about freelancing at this point, vs then? I sort of don’t know. Financially I definitely feel much more confident, and that’s a vast improvement. It also affects me psychologically on a day to day basis. I used to worry so much about money that I didn’t really take advantage of the many days I had “off” from work (read: nobody had hired me.) Sometimes I read or went for walks or went to free events, but I didn’t do a lot of civic engagement or self-improvement, which is one of the things I regret when I look back at that period of my life. Now, since I am not concerned about my finances, I feel much more able to take on unpaid projects on days I don’t have paid work to do. That’s a good thing, especially since much of the point of this “freelance” year is really to volunteer.

On the other hand, I have to admit that I feel a bit weird about becoming a freelancer again at age 39 — when I am also not FI. At 23 it felt kind of normal to be working a bunch of oddish jobs. And I also had a fairly clear career path in mind, though ultimately I turned away from that too and went back to grad school. At this time of life it feels much less conventional to pause full-time work. Not totally unheard of or anything, but certainly kind of weird. I do want to go back to full-time work eventually, whether it’s a year or three years from now, and I worry that when I want to, I’ll have trouble finding a job I really want to do. On the other hand, maybe taking this period of 1-3 years will ultimately be a good thing for my career. It’s just difficult to know from this vantage point. Managing feelings of uncertainty: that’s a full-time job in itself!

5 thoughts on “Freelancing: Then and Now

  1. I feel different about it too, knowing I have a large cash reserve (although too, not FI). I’m going to be spending more time putting contracts into place and making it more official so that I hopefully can avoid some of the pain points I experienced before. But, and maybe surprisingly, I’m not tied to staying freelance. In a lot of ways it can be a big pain in the you know what! But I have some time to figure it out. Good luck to you!!

    1. thesingledollar says:

      Yes, I also want to go back to full-time! I figure it’ll take a year or two and I’m happy to freelance that long. But I will miss health insurance, 401ks, and the steadiness of having not only a paycheck but an organization to contribute to. I like teamwork.

  2. First, I love your blog. It’s so well written.

    Second, I can’t wait to follow along on this freelancing journey. It sounds like you’ve set up your business in a very thoughtful and careful way. I LOVE that you are taking on only those jobs that pay you what you deserve.

    1. thesingledollar says:

      Thanks! I am a good natural writer, but I don’t work on my blog as much as many people do, so I always appreciate it when people like my quirky topic choices anyway.

      I don’t think I’m going to want to freelance for more than a couple of years, but I am hoping that it works out well for the time being. So far so good.

  3. Megan says:

    I am very interested in this, mostly because while I currently have employer-based insurance, one of the most tempting things about trying to go freelance for me is that the ACA makes it possible to decouple health insurance from a specific employer. I’m very curious how the ACA aspect of it works out for you. Looking forward to more updates!

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