Four Reasons I Freelance

It’s April, which means it’s my second freelance-a-versary.

When I marked this occasion last year, I felt pride in what I’d accomplished—but also a deep anxiety about what lay ahead in Year Two. I’d just let my clients know I was expecting my second child. I needed to spend the next five months working as hard and as fast as I could to afford a maternity leave. I wondered if my little business could weather three months off to adjust to my new role as Mom of Two. I feared that few, if any, clients would be there when I came back in January.

Yet when the calendar turned to 2023, my little business still stood. Not only were my previous clients ready to re-engage, but I also had a handful of new ones interested in exploring partnerships. In those conversations, one question came up repeatedly: “Why did you decide to become a freelancer?”

I think that’s a great prompt to meditate on as I enter my third (!) year on my own.

Why did I become a freelancer?

My practical answer is this: I left a full-time, in-house position and didn’t have another one to step into right away.

My deeper answer is this: I wanted to try a path that would fulfill me professionally while providing me with the logistical and mental flexibility to take care of my family.

I considered becoming a full-time freelancer almost two and a half years before I officially made the switch. Shortly after my son was born, I hired a career counselor to help me navigate the postpartum professional malaise I was feeling. In our conversations, it became clear that there wasn’t a job description out there that ticked off all the boxes I wanted. My counselor asked me: “Why don’t you make your own job description—and accept it?”

Thanks to COVID, my decision to say “yes” to freelancing took longer than originally intended. But here we are.

What do I love about freelancing?

So many things! But I’ll narrow it down to four for the purposes of this post:

Freelancing offers control.

When you’re a freelancer, you work when you want to. That’s not to say you’ve got license to be lazy. I’ve found the opposite to be true: When you work for yourself, you often work more than you do when you work in-house. But you largely get to decide when and where you do that work.

Want to only take meetings between 10 a.m. and 3 p.m., Tuesday through Thursday? Do it. Want to work four 10-hour days instead of five 8-hour days? Do it. Need to work at night for a while because your kids are home sick from school? Do it. Want to take a three-week work break in the summer to take care of your kids while they’re out of school? Do it. There’s nobody to tell you not to.

With great freedom comes great responsibility, though. You need to be skilled at managing your time and communicating with clients to make a non-traditional schedule work. Thankfully, there are a lot of strategies and tools out there to help you do this. (That’s a conversation for another post!)

Freelancing offers variety.

I became a freelancer after working in universities for more than a decade. In higher ed communications work, you do roughly the same thing every quarter, semester, or year. After you go through that cycle once or twice, you find yourself bored and/or butting up against stiff resistance to change (unless you’re at a college with some super progressive leadership).

When you’re a freelancer, you can work cyclically if you prefer—or you can never work on the same project twice. You can accept only projects you want, whether they have anything to do with one another or not. For example, at one point last year, I was working on:

  • Fundraising communications strategy for an Ivy League law school
  • Refreshed marketing copy for the engineering and science college of a top technology-focused university
  • Regular blog and thought leadership pieces for two health care companies
  • Brand and messaging research for a prestigious PK-9 independent school.

It’s true: Having such a diverse array of projects means you have to be very on-the-ball, organization-wise. But it also means you’ll rarely find yourself bored.

Freelancing offers continual learning opportunities.

I used to joke that working in communications for Johns Hopkins University and Medicine was like getting a very broad general knowledge master’s degree. I talked to faculty, researchers, students, and alumni in fields ranging from economics to neuroscience, learning a little about a lot along the way. As a freelancer, I’ve taken a similar path.

One of my biggest clients is a health care marketing firm. Working with them, I’ve learned a ton about the American health care system and the challenges it faces today. I’ve also taken a veritable crash course in artificial intelligence and machine learning and learned how those technologies are optimizing processes in hospitals.

Another regular client is a university alumni magazine. In writing profiles of their alumni, faculty, and students, I’ve learned about topics like transportation asset management and its importance to the American economy, or the ways venture capital is involved in the discovery of new green energy sources.

Not every project I take involves a scintillating topic. But I can’t help but feel a little bit smarter after each one, thanks to the clients I work with.

Freelancing offers confidence.

When I worked in-house, I often felt helpless. Even when I tried getting extra training, going the extra mile on a. project, expressing concern about poor treatment from a colleague—so much felt futile. I’d ask myself, Am I doing what I’m supposed to do to get promoted? Why isn’t my work being recognized? Am I even worthy of being here?

Working for yourself is challenging in other ways: There’s no boss to coach you, no team to back you up, no one else to help shoulder blame when things go wrong. I’ve struggled in each of these areas, but those struggles have made me more capable than ever.

I’ve learned to properly price my work, write effective proposals, negotiate contracts, enforce scope boundaries, nag (kindly) about past-due payments, speak up for myself to disrespectful clients, and say “no” when my gut tells me to. If I still worked for someone else, I don’t know that I’d ever have grown that backbone. Freelancing has forced me to, and it’s made a world of difference for my confidence—personally and professionally.

Roll on Year 3!

So far, Year 3 of my freelance career is looking pretty bright. I’ve got work under way for several longtime clients and leads for new projects that sound interesting and fulfilling (and capable of paying the bills!).

Will the waters continue to be this calm? Almost certainly not. But with any luck, my little business-that-could will still be standing come next year’s freelance-a-versary—and the challenges will give me some good lessons to share.

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