I’m on day 66 of 365 days of learning how to draw

A few months ago I went to a training session as a coach for The Future Project. We were asked to bring a “piece of purpose,” an artifact (like a notebook of our poetry) that’s of particular importance to us because it explains our dreams and–by association–us. I didn’t bring my item, because I picked my computer. Why? My computer–by making it possible for me to design–is what has allowed me to believe myself to be an artist even though the extent of my drawing ability has always maxed out at these (arguably adorable) stick figures:

Stick figure demonstrating the extent of my drawing ability Stick figure demonstrating the extent of my drawing ability
These may have been drawn not more than two weeks ago.

Needless to say, I have always, always wanted to learn how to draw.

“Don’t Break The Chain”

I read a lot of articles on maximizing productivity and setting/achieving goals. Sometime last year, I stumbled across a productivity framework that, no kidding, changed my life — or rather, has allowed me to slowly but surely change my own life by helping me to finally get around to doing a ton of things I have always wanted to do.

Like drawing.

The idea is this: you spend some amount of time every single day doing something that gets you closer to your goal.  Every day that you do, you mark a big X on a calendar, and pretty soon you’ll have a chain of X’s that you won’t want to break.

Most famously, Jerry Seinfeld wrote jokes using this method. Karen Cheng of “I Learned To Dance In A Year” used this method.

Since I discovered this, I’ve used it to develop several habits I’ve always known I should have, like exercising everyday and eating healthily (I now enjoy both running… and salads!).

I also used it to catalogue 100+ ed tech companies as a means of getting to know the ed tech landscape, to learn how to design a responsive website, and to get six-pack abs (just kidding – still working on this one…).

So now, I am using it to learn how to draw. The idea is to draw one thing every day for 365 days, and then at the end of the year to see if I can put on an exhibit of my drawings somehow, somewhere. I’m on day #66.

Practically, I’m hoping it will help me become a better designer — specifically, a better illustrator.

More broadly, I’m yearning to master something. And I’m curious if doing something, anything, every day for a year will get me even in the general vicinity of mastery.

So this is how I’ve been doing thus far.  Coaching and/or feedback most welcome!

Is there anything you’ve always wanted to do that you think “Don’t Break The Chain” can help you with? I’d love to know.

(For a full catalog, see: 365 Days To Learn How To Draw)

Day 7

Day #7: Lesson 1 of Mark Kistler's 'You Can Learn To Draw In 30 Days'

Day 12

Day #12: Lesson 3 (Bonus) of Mark Kistler's 'You Can Learn To Draw In 30 Days'

Day 21

Day #21: Lesson 8 in Mark Kistler's 'You Can Draw In 30 Days'

Day 33

Day #33: Lesson 14 in Mark Kistler's 'You Can Draw In 30 Days'

Day 50

Day #50: Lesson 21 in Mark Kistler's 'You Can Draw In 30 Days'

Day 62

Day #62: Lesson 29 (Bonus) in Mark Kistler's 'You Can Draw In 30 Days'

Day 66

Day #66: Lesson 30 (Bonus) in Mark Kistler's 'You Can Draw In 30 Days'

The fantastic drawing book I’ve been following per Karen’s recommendation:
You Can Draw In 30 Days by Mark Kistler

Follow along to track my progress:
365 Days To Learn How To Draw

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  • Stevan Petrov


    I’ve just seen your 365 days challenge and I am amazed by the progress you’ve made! I am on the last day of reading Kistler’s book on learning how to draw in 30 days (I saw it on Karen’s website) and I’d like to continue improving my drawings skills after finishing it. So, I’d like to ask you: what have you been doing after finishing the book? How do you come up with new challenges? Do you follow another book on drawing?

    Thank you! :)