Everything I learned in art school has become valuable lessons in how I approached my professional craft as a software designer in tech. The parallels between art and software is not only the craft of making but how we approach the work. In this issue, I remember the lesson of making bold strokes.

My studies focused on multi-disciplinary art. However, my love was oil painting. I recall taking watercolor as one of my electives. I assumed that it would be a walk in the park because of my love for painting—quite the contrary. I struggled with watercolor painting. My comfort zone was oil painting; a medium which you could spend an eternity manipulating the paint.

Watercolor required precision with paint that would constantly remain wet, and when you let it dry, you can’t layer it as aggressively as oils, resulting in the paint re-wetting and becoming a puddle of paint.

One day, my professor noticed how close I was keeping my hands to the brush while making tiny strokes in hopes to control the water. “You need to take bold strokes,” she said to me, while adjusting my hand position on the brush. Instead of taking a bunch of small brush strokes, I took one big one across the entire paper.

It worked. The bold strokes gave me control over what I wanted to do on the paper. With this new approach, I was able to build a lot of layers on top of the aforementioned strokes. The metaphor of bold stokes carried me through as an entrepreneur, designer, and now a leader of orgs.

Lesson 1: Intention is crucial
Even in abstract art, everything is intentional. Before taking bold strokes, you need to know what you want to do. Set the intention of what you want to create, and the rest will be much easier to achieve. Sketching is the fastest way to capture intention. Whether it’s an idea for a concept or planning the week out, I to-this-day sketch everything out. Sketching and storyboarding oconcepts is

Lesson 2: Don’t stop in the middle of an action
There is a Japanese phrase I live by, ichi-go ichi-ei, which roughly translates to, “One encounter, one opportunity.” This means every moment is unique in itself, no matter how repetitive each breath you take is. Life in every breath. When you put your brush down on the paper, there is no going back. You must follow through with the stroke you plan to make; hesitation makes it worse.

One cannot stop in the middle of an iteration. This is how I approach any sprint cycle or iteration of design work. Stopping midway makes it worse. See it through, then iterate.

Lesson 3: Look ahead
When you’re serving food and bringing people coffee, they teach you to look at the table you’re heading to instead of what’s in your hands. The moment you look at the items, your hands begin shaking and there is higher risk of messing something up. Race horses wear blinders so they’re only running ahead.

Making bold strokes is looking ahead and entrusting your technique will get you there. When work gets a bit chaotic, I’m still looking ahead on what needs to get done. Looking only in what’s immediately ahead will keep you in the mindset of operating that way. Even as I stare at a looming deadline, I take a breather and look at what we need to achieve next month, next quarter, next year. This ensures you continue heading the right direction.

Lesson 4: Build up layers
The way I learned to build layers in watercolor is only on top of the bold strokes; allotting the time to let it dry. Focus on the bold stroke and once you’re done with it, only then can you take another pass at it. The litany of bold strokes all build on top of each other as elegant layers.

As you learn from one stroke, you can apply the learning to the next one. This is the spirit of retrospectives in sprint cycles. As you continue more iterations, you continuously improve and increase the mastery you hope to achieve.

Craft requires bold strokes

The beauty of our craft is most of the time we get multiple chances to iterate from what we learn through failure; something not many other industries have the pleasure affording. Whatever you embarck on next, remember to make bold strokes without hesitation. If you mess up, take another bold stroke.