If you look at the dates on the posts here, you’ll notice a bit of a gap: I took the last couple of weeks off while I was on a trip to Oaxaca, Mexico. Normally I still do things like post blogs and whatnot when I travel, and I did still do a bit of work and a few other creative career type things during the trip. Unlike my usual working-on-the-road excursions, though, I wanted this trip to feel a smidge more like an actual vacation.

I struggle to take breaks as a rule, largely because I genuinely like to work. Having literally nothing to do is not my idea of a good time—I can handle it for a day or so, but more than that and I start to get antsy. This is a good thing for a freelancer most of the time, but it also makes me prone to epic burnout if I’m not careful about keeping my life in balance.

I’ve been relatively stationary in Pittsburgh for the first half of 2023 but I’ve got a couple of trips coming up in the next few months. My first trip of the year starts in a week, and it’s a new one for me: a visit to a national park (Yosemite) followed by a cross-country Amtrak excursion back to Pittsburgh.

I’ve done long road trips in the past, but typically the destinations have been urban areas—places I thought I could count on getting easy access to things like power and Wi-Fi. I didn’t always plan ahead properly, and as a result I learned:

• Outlets can be a hot commodity when you’re working out of coffee shops or other public spaces
• Just because a place offers free Wi-Fi doesn’t mean it works
• Long-distance Amtrak routes don’t have Wi-Fi, and Greyhound Wi-Fi is spotty

These things are annoyances for typical travelers, but can be huge sources of stress for working writers who have clients waiting for responses and assignments that need to be completed by a deadline. Being prepared for potential snags can save you a lot of headaches and wasted time, letting you actually enjoy your travels and keep up with your work at the same time.

I’m a sucker for a mailing list. Anytime I research new journals and presses to submit to, or go to a conference or bookfair, I end up subscribing to a plethora of new lists.

Of course, doing this, I’ve signed up for a bunch of newsletters that were…less than helpful. Inevitably, I’ll come to realize my inbox is getting inundated and embark on a purge. But there are newsletters I’m always excited to see pop up in my inbox, and a few I’ve come to anticipate, to the point I’ll go searching through my spam folder to double-check if I don’t see them.

I wrote a post a couple of weeks back about the skills you need to freelance, and honing those will certainly help you to succeed when you start a freelance career. Writing that post got me thinking about some other things that either helped me when I was starting out, or that I learned along the way and wish I’d known from the beginning.

Just for some context, I started freelancing mid-way through 2015. I’ve been doing it full-time ever since and it’s currently my only gig (though that hasn’t been the case the entire time). In those 7-ish years I’ve definitely made my share of mistakes and taken on some clients who were walking red flags in hindsight. Some of those missteps I think are an unavoidable part of venturing out as linguistic mercenary into the wild world of words for pay, but hopefully these tips can help other new freelancers make the transition a bit more smoothly.

Freelancing is arguably the easiest way to start writing for a living. Freelancer platforms certainly make it look appealing, and while you probably don’t need me to tell you most freelancers don’t work at beach or on a lakeside dock, these ads promote a more pervasive misperception, too—that if you can write well, you can be successful as a freelance writer.

The truth is more complicated. Yes, you do need to have a certain level of writing ability to be a freelancer, but you don’t need to be a “great writer” and having that kind of advanced mastery won’t guarantee you success. There are other skills that I’d argue are equally important if you want to turn freelance writing into a sustainable full-time career. Based on my experience, these are the most important.