Grid of every drawing so far (January 1 through May 27, 2018)

Drawing Every Day

Published on

Halfway through 2017, I transitioned from employee to partner at Cloud Four. The change has been really positive: It’s a privilege to lead an organization that truly believes in the web.

But big changes have a way of destabilizing one’s work-life balance. This became especially clear to me when, later that year, I returned to my sketchbook after an unintentionally long absence.

Drawing was a struggle. Nothing came out right. Glaring down my nose at the page, a slow sense of panic set in. I’d spent thirty years drawing nearly every day… had I really squandered all that in only a month or two away?

Skills Can Atrophy

A lot of people scoff when I tell them anyone can draw with enough practice. “I can barely draw a stick figure,” they reply. “I could practice every day and I’d never improve.”

But they’re wrong. Talent may be a factor, but I know it’s mostly practice.

I know because when I stop practicing, I get worse at it.

It isn’t like riding a bike. It’s like trying to write with the wrong hand. You know how the words are supposed to look, you remember how they’re written, but your digits are clumsy and uncooperative.

Drawing’s been my most direct form of self-expression for as long as I can remember. It’s the starting point of every website, app, game, icon or presentation I’ve ever made. To pick up a pen or pencil after months away and feel that sense of disconnect between my thoughts and gestures was truly alarming.

Luckily, I had an idea for how to fix it.

Discipline Restored

Erika Lee Sears is a painter based here in Portland. She also helps her husband and I manage the business aspects of Backabit. And she’s been sharing a new oil painting every day for the past four years!

I decided to follow her example, and the basic rules she set for herself:

  1. Make art every day, no matter how big or small. Any medium counts. Even if I draw a stick person or just snap a blurry photo, the point is just to make art.
  2. I am not allowed to give up. This is very important.
  3. I am not allowed to throw away any artwork or rip out any pages in my sketch book. I am allowed to start over. I am not allowed to start painting over canvases or ripping out pages in my sketchbook.

I started on January 1 of this year. It’s nearly 150 days later and I’m still going strong!

"Do. Or do not. There is no try." Yoda felt like an appropriate start to the project.

Thoughts So Far

The experience has been incredibly rewarding. I feel a renewed sense of confidence in my ability. My speed has improved. And I feel it’s had a positive impact on my mental wellbeing and my overall creative output. (I’m not just drawing more… I’m writing more, too!)

Occasionally the daily requirement will feel confining, but more often I find that it lowers the pressure. No matter how wonky or slap-dash today’s drawing may be, there’s always another chance tomorrow!

Sharing the work has been crucial. As silly as it sounds, sometimes a “like” or supportive comment from the previous day’s drawing can carry you through the next.

I can never predict which drawings will be well-received, so I try not to worry about it. Anyone but me liking them is just a nice bonus!

Drawing of a happy duck

Questions I’ve Been Asked

How do you find time?

Most of the drawings I share take a half-hour or less, though it can range from a few minutes to a few hours. I try to pick subjects I know I can finish in whatever time I have. Artists will be able to spot the corners I’m cutting pretty easily (partial figures, no backgrounds, etc.).

It probably helps that I’ve always admired illustrators who can speak volumes with very few lines.

This screen recording of one of my early digital drawings has been shortened from a couple of hours to a couple of minutes. I think I'd finish this one faster today!

What tools do you use?

Digitally, I draw in Photoshop using a Wacom Intuos tablet. Otherwise, I usually draw in a Canon Mix Media sketchbook with my trusty Pentel Twist-Erase 0.9mm pencil, Faber-Castell pens and Prismacolor markers.

But I try not to sweat the tools I’m using too much. I’ve shared drawings in my Moleskine, on sticky notes, in ballpoint pen. Sometimes I don’t have time to scan a drawing so I’ll just snap a quick photo. The process is more important than the result.

Do you have a favorite drawing so far?

As of this writing, I still like the simple, gestural lines of the Wonder Woman profile I drew on March 8:

Drawing of Wonder Woman's face in profile

June and Beyond

I’ve got seven more months till I meet my goal! Unless I get around to adding a sketchbook section to, you can find my latest drawings on Instagram, Tumblr, Twitter or Facebook.

If you’re thinking of starting a daily art project, I say “do it!” It’s a fun and challenging way to freshen your creative synapses.