Freelancing Is A Journey—Treat It Like One

Improve your career by tacking


That time I finished a design project 1,300 miles from the nearest city (Honolulu).

Starting the day off on a creative foot is really important to me, so you can almost always find me at Creative Mornings Philadelphia every month. (Introduce yourself!)


Last October, Josh Goldblum spoke about his journey to starting his own business. I found myself relating to his career trajectory—he started out working at a pretty basic job, then tried a couple of other things for a while before settling in to freelancing. This eventually grew into his digital strategy company, Bluecadet.


When I asked him about his time freelancing, he described it using an analogy that I’ve started applying to my own career. Any sailor, he said, knows that tacking is often the only way to get where you’re going. The wind is almost never at your back, pushing you directly to where you want to go; rather, it’s coming at you from the side, or maybe almost straight at you. When making a beeline for your goal isn’t possible, the only way to make any progress is to zig this way then zag that way toward your destination. The total distance you travel may be longer, but each piece of the journey gets you closer.


Your career is just like this sailing trip. If you’re professionally unsatisfied, looking straight into the wind, you’re not alone. You just have to tack.


Try working on something different for a while, even if it’s not directly related to where you see yourself. Then shift gears—tack—and work on something else. That doesn’t have to lead right to your goal either. By adjusting your sails to capture the direction the wind happens to be blowing, you’ll get closer to your destination than you will by waiting for the wind to adjust to you. And sometimes, you may end up somewhere you couldn’t even predict.


This is essentially what Silicon Valley calls “pivoting.” But you don’t have to be a startup to make use of this excellent tactic on a much smaller scale.


How I’ve Been Tacking

If my ideal career was a meal, I think graphic design would be the main course, photography the side dish, and creative writing my dessert. So when I moved to Philadelphia to join a communications team that handles packaging, messaging, and photography for a national network of nonprofits, I felt like the perfect feast had been laid before me.


After realizing the organization was not a good cultural fit (and did not, in fact, live up to many of the values it espoused), I eventually quit. The ensuing job search was difficult, and similar positions were just not popping up, so when my accountabilibuddy sent me a digital photo archivist job listing, I thought it sounded like a great part-time gig to help me get through to the next thing. I like photography! I like Lightroom! I’m detail-oriented!


So I tacked. It wasn’t exactly the direction I wanted to go, but working as a photo archivist taught me Lightroom and Photoshop skills I will apply for the rest of my working life. I also learned about Flickr’s backend, which could prove useful as well.


When I stumbled upon a small studio in Philly that had just the sort of graphic design position I was looking for, I snapped it up, and began working there part-time as well. I felt like I was back on track!


But another tack was fast approaching. Work at the studio was drying up, and I needed other options. So I started more earnestly pursuing freelancing, something I had perviously only dabbled in. I spruced up my portfolio website, printed business cards, created Facebook and Instagram accounts, and started putting out feelers and work.


And in the last few months, I’ve tacked again! After moving to Philly, I quickly became enamored of its street art, and stickers in particular. Philly has such a vibrant street art scene that there’s an internationally-recognized blog dedicated to documenting it: Streets Dept. After going on the second-ever walking tour by the blog’s owner, Conrad Benner, I reached out to him to ask if there was anything he needed help with. It just felt like something I could contribute to.


We met up for coffee to talk about our needs, interests, and capabilities, and decided that we could be a good fit for each other. He needed more content for his blog and Instagram, and I had a flexible schedule that would allow me to go out and shoot whenever he needed. Last November, as a test run, I photographed two murals and interviewed Darkmeal, one of my favorite Philly sticker artists.


A year ago, I never thought I would be able to say: “I’m now working part-time as a street art photojournalist!” Nevertheless, I love it and I want to do more of it—while continuing to work on generating more design clients and, as always, figuring out what’s next.


I’m ready to tack.

©2020 Eric Dale Creative

freelance designer • freelance photographer • freelance writer • career coach