The Side Show: Q&A With Senior Strategist Alex Rakestraw

By Minda Smiley 

The deadline for submissions to The Side Show, a new awards program that’s only doling out prizes to creative endeavors done outside of work, is today. If you have a side hustle you want to show off, take a few minutes to submit yours today. Entries are $10 a pop.

We’re spotlighting some of this year’s entrants and their projects. Today we’re featuring an interview with Alex Rakestraw, a senior strategist at Deutsch New York and freelance fashion writer. His side hustle is Coatchecking, a site where he posts detailed reviews of outerwear.

“Jackets are wicked expensive. People want to make the right choice. But it’s an esoteric subject, and most reviews are more about extreme sports than ‘is this too warm for the subway.’ So I decided to fix that,” he wrote in his entry. “For the cost of a tripod and an annual Squarespace membership, I whipped up a site and got to side-projecting.”

According to Rakestraw, the site launched at the start of this year and has since attracted close to 10,000 users.

What do you love most about your side hustle?

It’s a chance to stretch every creative muscle. Agencies are full of enormously inspired people who use 20% of their talents they’re comparatively best at to pay rent. With Coatchecking, I get to write, shoot, edit and even do a bit of web dev. It’s a nice break from brand planning.

How has your side hustle made you a better creative/professional?

I have a much deeper appreciation for everything creative and production does to build out ideas, which hopefully makes me a better partner. There’s nothing like art directing a web page or retouching your own photos to realize how much you don’t know about your co-workers’ craft.

Has your side hustle helped you land a job? If so, how did that happen?

In adland? Not yet. But I have had brands DM me and offer to send me coats. So I’ve gotten more work, of sorts.

How do you draw the line between a healthy side hustle and always-on hustle culture? How do you prevent burnout?

It’s all about the put-down test. I’ve dove headfirst into past side hustles and ended up in a cave of burnout. What I realized was that if whatever I was doing—making T-shirts, playlisting, etc.—wasn’t something I could put down when work got busy and pick back up without feeling like I’d stunted its potential, it wasn’t going to end up in a healthy place. The hustle mentality is great for coding boot camps where there’s a defined stop and start, but resiliency over time is much more important for the rest of us.

Also, part of it is managing expectations—mostly your own, but also whoever you’re creating for. With Coatchecking, no one’s tuning in on Mondays at seven o’clock for a new review. I write when I have the energy for it and don’t when I don’t. The site has kept growing, and the world has kept spinning. It’s rather lovely, actually.

If you could turn your side hustle into a career, would you? Why or why not?

Absolutely would. I love the innovation and creativity of the jacket space, and think it’d be a ton of fun to become the Points Guy of performance outerwear. The dream: get recognized by title at an outdoor industry event, Abe Froman style.

What is your dream agency or brand-side advertising job?

Product marketing director for a premium apparel brand like Nike, The North Face or Rapha.

Anything else you’d like to share?

The only side projects worth doing are ones you intrinsically enjoy. Not to get all Marie Kondo, but if you don’t love it, just find something new. You’re crazy enough to be turning your fun, relaxing downtime into work. If it’s not fun, why bother?

To find out more about The Side Show and submit an entry, visit its website here