from programmer to painter

May 9, 2020

I’m a coder who makes art. day job: startup founder (currently CTO @

An Art Hobby Develops

Painting started as a hobby, way to unwind. during previous startup, URX: IC->manager transition

oil painting of Whistler statue at sunset oil painting of Paris riverbanks 1,2

experimenting with my “modes” of work

formerly fun code projects now had deadlines paintings were a safe place for “scope creep”


Painting people was tough, but friends’ reactions were worth it

self teaching, starting to practice drawing people (friends’ reactions sometimes get remixed into new art!)


Found a new means of expression for stuff I hadn’t known to share

Reflecting on my own experience sharing ideas/emotions that had never had an outlet: sarcasm, wonder, irony


unexpected burden

big ambitious ML paintings

Painting sessions had become high-pressure, focusing on the end result

finished oil painting based on Deepdream algorithm output oil painting based on Deepdream algorithm output 1, 2

”premeditated art” - trust the process

surprising source of joy: making stuff for friends

My big complicated paintings weren’t as fulfilling for me as I thought they were.

Truly fulfilling: Making spontaneous creations and hearing reactions from friends and family.

ipad painting of jackson sharpie drawing of a dog on discarded amazon package

1, 2

Making Art Fun Again

Progress over Perfection

Around this point in my artist story, I started carrying a sketchbook everywhere I went. My intention was to focus on practice and enjoyment rather than impressive end results. I found that this was much more fun when I focused solely on filling sketchbooks rather than making them perfect.

process-oneline-journal-face process-oneline-journal-scene

Focus on Process, Not Product

In my engineering work, judging a day as good or bad based on amount of focused input directed to what I care about most - not whether a specific milestone is complete (because bugs happen and learning takes time).

oneline-process-diagram oneline-process-reflection

Daily Sketchbook: Quantity over Quality

Extending this idea to my sketchbooks was liberating. In my experience, intentionally drawing with a focus on quantity over quality of drawings has lead to some interesting discoveries, if only out of haste and randomness.

The more sketches you draw, the more chances there are that you'll produce good drawings.

An easy rule of thumb for beginners is that one out of each ten ideas you generate will be good. (And this applies to sketches, stories, videos, or anything you make as well.)

For instance, my skill as a writer or sketcher influences my ratio of good-to-bad stories or drawings.

Of course, this ratio might be lower or higher depending on the field you are in and your level of expertise.

Experts manage to bring that ratio down when they reach proficiency at whatever it is they do. Still, they know there will always be bad ideas among the ones they generate.

The good thing is that, apart from lowering the good-to-bad ratio, skill and expertise let you judge your own ideas to better identify the good ones and discard the bad ones.

Work on What's Hardest

I always had trouble with lines in my paintings.

Drawing in pen was especially hard for me, cause I couldn’t easily shade areas the way I did with pencil. I realized that as a painter, I had inadvertently trained my mind to look for shapes and intensity of color. I decided to jump into the deep end - stopped carrying around a pencil, started carrying a pen everywhere with my sketchbook(s).

Remembering my Past Drawing Exercises

Contour drawing exercises came back into my life when I found some scratch drawings I had saved from a Life Drawing class I had taken.

I was fascinated by how they work to train your muscle memory and build confidence by trying to short-cut the part of the mind that overthinks what we're trying to draw. For example:

don’t look at the paper (trains direct eye->hand movement, skip left-brain processing) look at the paper and don’t lift your pen off the paper (trains intentional economy of line, working with constraint)

Don't Lift Your Pen

When I stumbled upon continuous line drawings, they were exactly what I was looking for:

  • fast
  • challenging
  • repetitive
  • simple
  • subtle
  • nuanced

Just One Line

Extracting a single expressive contour in an attempt capture the essence and personality of a subject seemed like an appealing area to practice.

Both because it was intrinsically interesting, and I figured it would eventually yield dividends in my painting abilities if I was able to approach them with a newfound boldness and speed in my movements.

Eventually it became a habit, and it continues to be a source of joy for me.

Online original

Oneline taking the leap

The speed and repetition of single-line drawing got me past some creative blocks.

Eventually it got easier to try a lot of new things and not be upset if any one output doesn’t come out well.

My daily practice has taught me to trust that a steady flow of new drawings is on its way.

Single-lines make great gifts now

The speed makes it fast to try out new creations.

while the immediacy and expressiveness seems to delight friends.

Zoom dance

Dog and flowers

This has been the most fulfilling part of my art practice.

polaroid-AR (Augmented reality Polaroid single line)

maskface-bandana (Single line face bandana)