I’ve crushed my first ever Inktober drawing challenge. Here’s what I learned:

Jonathan Shamir
ART + marketing
Published in
4 min readNov 1, 2016

I’ve been drawing since I was six. I’ve always loved it. It sat well with my introspective/introverted nature as well as my ever growing fondness for escapism. I’ve never been very good (at least in my eyes) but it was almost always fun.

My problem was that I was good at copying but not very patient when it came to using reference or settling into a personal visual style. I always prefered copying other artists, which, in retrospect, never got me out of my comfort zone and allowed me to grow as an artist myself.

I was also getting frustrated very easily, dumping my sketchpad whenever a line didn’t come out right. Producing works I was (semi) proud of became a rare occasion and after I dropped out of design school I stopped drawing altogether.

10 years went by before I finally settled into a career as a graphic designer, yet I almost didn’t draw at all. I was constantly missing it, though. Always fantasizing about buying an expensive Wacom Cintiq (OMG, so sexy), like that would be the thing that would put me back in the zone. Obviously, I never bought one.

8 more years passed.

A kick in the butt

About a month ago, David Tintner from HackingUI wrote an inspiring post about his passion for writing and how he wanted to write more and be better at it (read it! It worked on me). Here’s what I commented on his post and his answer:

We had a short Twitter chat and I got to a spot where I said:

David outed me in public right away:

That was on September 30th. The Inktober challenge just happened to start the very next day.

No pressure.

And so it began

My very first Inktober drawing

I racked my brain every day for ideas and got down to sketching one when my kids went to bed. Most of the sketches were bad but some were actually worse. I still had no personal visual style (nor would I acquire one by the end of the challenge), but I was producing one drawing every day, and publishing it, no matter how bad I thought it was!

Glass bottom boat in Malta

I went and bought some good technical pens and a new, bigger sketch pad and kept on keeping on, even during a family vacation with in Malta. Anything around me was becoming an inspiration for the evening drawing session. I honestly didn’t know where all this drive was coming from. The sketches were not that good, but I felt good knowing I completed one every day.

And I wasn’t missing days.

I began to feel more patient doing the work, less frustrated when my hand wasn’t doing what my brain and eyes were telling it to, I looked for and used reference and seemingly just like that, I found that old joy again.

If you dare, you can check out the rest of my fugly artwork in my Instagram account.

So where was the motivation coming from?

I figured it out only last night when I finished my last drawing. In the past 2.5 years I have become quite good at willing myself to do stuff:

  1. I started running to get in shape and lose weight (got 3 half-marathons under my belt).
  2. When weight-loss plateaued, I changed my diet to the very strict Ketogenic diet (still keto after 7 months).
  3. I Started lifting weights 3 months ago. Didn’t know that could be fun at all.
  4. 2 years ago I changed creative direction from advertising to become a UX designer.

So, there’s a pattern here. A pattern revolving around taking control of my life and steering it in the direction I want.

However, sometimes, one does need a kick in the butt, and for that I thank you, Mr. Tintner :)

Thanks for reading.

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Jonathan Shamir
ART + marketing

Full stack designer with emphasis on product design. Aspiring #Illustrator. Looking for work: www.hyperstoic.co