The tagline for Brendan Leonard’s website, semi-rad, is “humor, essays, adventure.” If you sneak in the addition of “drawings”, it would perfectly sum up his content. Leonard is a remarkably consistent creator who has for years been adding personality and levity to his writing through the use of simple drawings and charts.

I first found his writing through the article, The Life-Changing Magic of Ignoring the Ratings, and have been thoroughly enjoying everything he puts out since (you can grab his newsletter at bottom of his website to never miss new posts).

His best drawings from 2020 are a great primer to his visual style.

His drawings largely deal with real-life relatable situations:

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. 

From there, I started to do more and more, until in 2016, I bought myself an iPad to try to make digital files of my drawings. And then I started posting lots of them to Instagram, which over the years became the place I have my biggest following. 

What tools do you like to use for creation and publishing? 

I use a 2016 iPad Pro and an app called Procreate, and I honestly use about 2% of the real capability of Procreate—I have one brush I use, and my stuff is very, very basic, compared to what the app can do in the hands of someone who is more of a “real” artist.  

Is there one image you are particularly proud of?

Near the end of 2020, I asked people on Instagram about the things they did to get through our very weird year, and I got about 500 responses. I put as many of them as I could into a big digital drawing that I put on my website and on Instagram.

That took a ton of work for something I knew was not going to be relevant for very long, and also was very hard to present online, so it was probably kind of foolish, but felt important at the time. 

Are there any creators who work at the intersection of writing and art that inspire and motivate you?

Off the top of my head: Adam Kurtz, Ellis Rosen, Mona Chalabi, and my friend Anna Brones. 

What advice would you give anyone who wants to start (or continue) adding visual creativity to their work?

I think most of us have a really hard time giving ourselves permission to try something, like we think our stuff needs to be way better before we put it out there. The more you try, the more your stuff is going to improve, and you are always going to look back on what you did three years ago and think it sucks compared to what you can do now, so you might as well get started.