Career as a Canvas

Stop climbing, start painting.

We typically think of a career as a ladder, where each rung represents a defined milestone. Climbing the proverbial corporate ladder means starting from the bottom rung (like an assistant or intern) and climbing up to the top rung (like a CEO or partner). Each time you get a promotion, you gain permission to climb one rung.

This act of leveling up mirrors those role-playing games where you start by choosing a basic job class, boost your skills, and progress to a more advanced job class. The difference is that real life does not grant as much control. The ladder is a linear path with clear winners and losers. Many attempt to climb it but few rise to the top.

This zero-sum view of the world looks grim until you realize that it is outdated. The ground has shifted beneath our feet. We no longer live in a world of scarcity. The information revolution has ushered in an age of abundance — where freelance gigs, online influencers, and passion projects abound. It calls for a new model.

Throwing out the ladder

There was one metaphor that kept coming back to me time and again whenever I reflected on the zigzag swings of my career experiences — seeing a career as a canvas.

Let me spell out why I find this to be a more helpful way of framing.

A canvas is a surface made of strong cloth that artists paint on. In this model, you are a painter and every career move you make is a layer of paint on that canvas. The goal is not to climb towards a set destination, but to paint a picture closest to your creative vision.

On a canvas, you do not have to start at a predefined point. Whether it’s top or bottom, left or right, you are free to begin painting anywhere on the canvas. The canvas allows you to explore and make mistakes. You can approach your vision from different angles.

On a ladder, you constantly worry about whether you’ve climbed the right or wrong one. There is a fear of missing out, an opportunity cost that comes with choosing one path over another.

On a canvas, every stroke contributes to the finished painting in some way, shape, or form. Even if you do not know it yet at that time, you can just keep painting and connect the dots later on. Even if your vision for the painting changes while you’re at it, you can still pivot by adding a new layer of paint on top of a richer base.

This liberates you from constantly second-guessing whether you are where you’re supposed to be or just wasting time. You bring the painting to life layer by layer. Most people start with the university major as the base, then a first job as the layer right on top, then the next venture, side projects, professional network, certificates… they all combine to form a rich tapestry of strokes and colors unique to you.

Every stroke can get you closer to your vision, and it’s all within your control. As long as you keep painting, you are free to experiment with a diverse set of experiences without taking a linear path. You can even mix and match a relatively linear path like medicine or law with more offbeat side hustles like video production or yoga instruction. Blurring the line between hobby and career can make your painting more interesting.

Finding harmony

On a ladder, you win by jostling for space as you climb up the rungs. You either push or you get pushed. On a canvas, you win by getting as close as you can to your creative vision and earning an audience who appreciates your art.

Everyone appreciates beauty, so you have a large enough market to address. You just have to focus on painting it as best as you can, one stroke at a time. Sequence matters less than on a ladder, but harmony is key.

You may paint with any colors you want, but you’ll increase your chances of a beautiful painting if the colors match. You will want the colors and strokes that create synergy and surfaces an underlying coherence. From a career perspective, this means that you increase your chances of success by tying together a coherent narrative out of your diverse experiences.

Applying that to myself, I recognize that my career so far is a salad bowl that mixes strategy, marketing, product management, and business development across a range of companies in different locales. I did not know it at that time, but when I connect the dots now I find that the common thread tying all of them together is the theme of digital finance and my passion to synthesize and simplify information.

In my 20s, I freely painted on my canvas without putting much thought on what I was painting. Now that I’m a little older and the painting on my canvas is starting to take shape, I‘ve also grown more mindful about where to paint and which colors and strokes help spruce up my painting.

If I suddenly switch to an operations job at a beverage company tomorrow, it will probably be akin to splashing random blobs of paint on my canvas. I might as well paint a whole new layer on top. On the other hand, if I picked up an adjacent skill such as UI design, programming, or even a CFA, it will almost certainly add more vibrance and depth to my existing painting.

Being the only

Nevertheless, serendipity always has a role to play. You may be surprised by how a set of mismatched strokes and colors here and there can produce accidental harmony that lets your painting be more than the sum of its parts.

Cartoonist Scott Adams’ advice resonates here: “Every new skill you acquire doubles your odds of success.” Here’s someone who sits at the unlikely intersection of business and drawing, and ended up creating the wildly successful office-themed cartoon Dilbert.

This underpins another nugget of wisdom from Adams on how to achieve success. You either become the best (top 1%) at one specific thing, or become very good (top 25%) at two or more things. The first strategy is nearly impossible but the second one is fairly achievable. It gives hope that ordinary folks also have a shot at being exceptional. Why elbow for space in an existing category when you can create your own and monopolize that unexplored intersection?

On a ladder, it’s all about being the best. On a canvas, it’s all about being the only. Once you find the audience who can appreciate the unique combination of layers and colors on your canvas, you’re on your way to creating a masterpiece that no one else can compete with.