Reflections From 12 Months On the Wind

Or: How this whole freelance thing is going.

Hello, dear readers. I hope you'll forgive a bit of unfiltered personal retrospective this week, as this marks 12 months since my time at CNET came to an end, a year since I decided to strike out on my own and give freelancing a try.

In the spirit of full transparency, I had no idea what the heck I wanted to do with myself 12 months ago. I had conversations with many very talented people who I respect greatly. I pondered everything from jumping over to join my friends on the PR side of things, trying to embrace my love of metrics to become an analyst, and even going back to the software career I shrugged off about 13 years ago.

At first, going full-time freelance wasn't a conscious choice. It was just me having a fundamental need to be working. In my time between jobs in the past I've practically driven myself insane finding things to do. This time, I told myself I wouldn't jump at the first job offer that came along.

However, I knew if I didn't do something I'd be again on a path to mania.

So, I started writing, started chasing exclusives, started putting myself out there, and very uneasily started coming to the realization that maybe I could do this as a living.

To be fair I didn't jump into this blind. I've had plenty of practice over the years. My first freelance assignment came my way back in 1997, when I was still in college. Back then, I didn’t even know what the term “freelance writer” meant. I didn’t even know that was a thing, never mind a career path.

I've freelanced on and off since then, writing on everything from enterprise software best practices to high-end Swedish axes, and I've always loved the opportunity to dabble in this and that, but never has it been my sole source of income.

For the last 12 months it has been, and this has been my most prolific year of writing in my life. I've written over 250,000 words worth of assignments in the past year, enough to fill about four novels, written for dozens of outlets that I've respected and read for years. 

It's honestly been a real honor, but it's also been an education. Here are a few key things I've learned.

---

Organization is Key

For me, every pitch, assignment, due date, invoice, and payment has to be tracked. If I don't immediately note this stuff it gets forgotten. After evaluating a lot of options, I ultimately built a system in Notion to track and cross-reference everything. It's worked really well for me. 

Big Travel is Practically Mandatory

In the automotive game, you need to go where the cars are, and many drive opportunities, including most of the biggest ones, happen in faraway places. If you're not willing to get on a plane you may struggle to find work. I'm lucky that I don't mind travel, but when you have a life and people you love at home, being away from it feels like putting that life on pause. 

I've spent 84 days on the road so far in 2023. I've had my passport stamped in 16 countries in the last eight months. That's too much. 

Keep Your Editor Happy

As an editor I already knew this one, but it's a good reminder to other freelancers out there. You need to keep your PR contacts engaged and you need to keep your readers in love. But, if you're not making your editors’ lives as easy as possible, you're not going to go far in this game.

Momentum is Key

Opportunities lead to assignments. Assignments lead to opportunities. 

Balance is a Struggle

When I finally decided to really give the freelance life a go, I thought the flexibility would be great. I thought that I could just bug out whenever I needed a day off. In reality, I've hardly had a break, taking a few days off here and there, feeling guilty all the while. I bought a season pass for snowboarding last year and didn't use it once. Every time I've tried to take a little vacation it's been blown up by some assignment or another. 

---

I'm still working on that last one. I literally haven't figured out how to take an effective vacation without an overwhelming sense of dread and shame. I'm still at a point in my career where I feel like missing opportunities will stall my momentum. Maybe in the coming year I'll figure that out a little better. That should come with confidence, and confidence has never been my forte.

But, where before I always strived for a rigid divide between "work" and "life," where before I felt aggrieved whenever a meeting crept past business hours, those things bother me less now. 

I think that's because this career is, for me, extremely personally fulfilling. I get a huge rush when I see my work published and shared at all these outlets who've graced me with assignments. I feel great satisfaction building and solidifying connections with people in the industry. I feel amazing when someone takes the time to write or comment or share and say that something I wrote was worth their time. All of that now feels like a meaningful extension to my life, not just a source of funding.

That's a good thing, because the sum of that funding is significantly less than it was 12 months ago. Alas, maybe that's a topic for another day.

Anyhow, that's enough retrospective and personal rambling for one year. Mostly, I wanted to write this because I'm feeling thankful. Thankful for every assignment, thankful for every publication, and, as ever, thankful for you who took the time to read this far.