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Welcome to the thirteenth issue of The Featured Image newsletter, a place where writing meets art. As a reminder, the goal here is to add visual creativity to our work and gain inspiration from those already doing it.
The more I dig into the realm of writers/creators who draw, the more unbelievably cool people I find. Brendan Leonard featured below is no exception.
Creator Interview: The Very-Rad Visuals of Brendan Leonard
Drawing of success stairs. Can't see anything? Turn on visuals.
Drawing by Brendan Leonard

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:

A little too relatable
And humorous reflections on adventure/running:
Drawing of graph. Can't see anything? Turn on images.
Another favorite of mine.

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 since February 2011, and I have a biweekly column on 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. 

Picture of hand-drawn chart. Can't see anything? Turn on images.
Can't beat a poop chart as origin story

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 KurtzEllis RosenMona 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.

Read the full interview online
Take aways: I love seeing the success that Brendan Leonard has had with combining fun visuals with his writing. It's a creative path not explored nearly enough. I've been enjoying adding visuals to Twitter, but Leonard's success with Instagram has helped me decide to start posting there as well. I just need to decide if I want to create a new account or not.

Another lesson is that you really don't need anything fancy. Leonard fully admits to keeping things "very, very basic." Again, it's more about creativity and expression than setting your sights on an MFA! And of course, lastly, the part about keeping it going and trying over and over really spoke to me.

Links to keep the creative juices flowing:

Sketching on a banana. Pretty wild and imaginative. 

From Harvard Business Review, Visualizations that Really Work.

Learn how to letter.

Be sure to really explore Brendan Leonard's semi-rad and his column at Outside, which both have an incredible amount of inspiring and great reads. 

Ok, that's it for this week. Be sure to create something cool and share it with someone.

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