As you’ll see in the interview below, Leonard has been hard at work building an audience over many years, and he was generous enough to share some of the secrets to the artistic side of his content.
Tell us about the creative projects you work on.
I’ve been writing a blog post every Thursday on my site at Semi-Rad.com since February 2011, and I have a biweekly column on OutsideOnline.com. Over the years, I’ve written for more than a dozen publications in the adventure world, including Outside, Adventure Journal, Alpinist, Climbing, Backpacker, Trail Runner, Runner’s World, and others. I’ve been directing short films since 2014, and my films have toured internationally and won several awards (my most recent film, How to Run 100 Miles, is probably the most widely-viewed).
I’ve also been doing hand-drawn illustrations and charts since about 2013, at first just for my website and Instagram, but in recent years for editorial and commercial clients (Strava, Arc’teryx, La Sportiva, Tuft & Needle, Smartwool, and others). I’ve also written a dozen books, and my illustrations appear in some of those, including my newest book, I Hate Running and You Can Too. I also do a lot of public speaking and I teach a writing and creativity workshop every year through the Freeflow Institute.
How long have you been visually creative?
Wow, on my current professional trajectory, not that long, maybe since 2015, but I guess I’ve been drawing stuff off and on since I was a kid, and I did get some graphic design experience designing newspaper pages early in my career, from 2003 to 2008.
What went into the decision to start including original visuals with your work?
I actually just drew a very scrappy flow chart on a piece of printer paper as a joke for my blog one week back in 2013, and the response to it showed me how much people react to easy-to-read, simplified ideas.