Polka Dot Couture: The Steve Jobs Playbook For Fashioning A Custom Career

Alexandra Allen
4 min readOct 23, 2021

--

Photo sources: Feedly (left) & Harper’s Bazaar (right).

A young boy tinkers with machinery. Stationed at a workbench made by his dad, he pursues his curiosities as a form of play. His process becomes his passion, and through assembling radios and receivers, he learns the power of connection. This revelation guides his life, and he becomes the most influential businessman of our time.

Steve Jobs.

Jobs understood that one of life’s greatest riches is doing work that nourishes our curiosity. So he used his curiosity as a compass, based on this philosophy:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

So how can regular folks like you and me customize our careers based on our unique accumulation of dots?

We need to think of ourselves as fashion designers.

Imagine we’ve each been tasked with creating “Polka Dot Couture” for Paris Fashion Week. Our individual challenge is to figure out how to combine a bunch of unrelated dots (in different sizes and colours) in a way that captivates and inspires others.

Our approach to fashioning custom careers should be no different. It’s simply a creative endeavour in which we must combine our experiences into a sophisticated work strategy. One we can execute with a style that can’t be replicated.

Here’s how this worked for Steve Jobs: by “collecting and connecting dots” throughout his life, Jobs developed an innovation strategy that combined his great taste across industries. And with that, his signature style of cutting out “people, products, and systems that weren’t world-class” was born. This was his Polka Dot Couture. His career equivalent of small dots brought together to create a pattern that stood the test of time.

The table below maps Jobs’ curiosity-based experiences to applications, which (through Apple) have had profound impacts on the global consumer market.

Here’s hoping it sparks ideas as to how your own combination of experiences could lead you to the intersection of financial and creative success.

Source: This is a reformatted table from Simmons, Michael. (2015, January 15). The №1 Predictor Of Career Success According To Network Science. Forbes with the addition of Jobs’ Pixar experience.

“As a result of pursuing his curiosity in different fields throughout his life, Steve Jobs developed an extremely unique perspective, skillset, and network; one that no one else in the computer industry had. He turned these unique advantages into the largest company in the world by having a razor sharp focus.”— Michael Simmons

Jobs became a trailblazer commanding a career runway through uncharted territories.

Yet he didn’t pursue curiosity-based experiences with the intent of amassing a $260 billion company that would change the lives of people like you and me. He simply trusted in the idea that one day he would be able to connect the dots in a valuable way.

And there’s no reason you can’t do the same. Because chances are the dots you’re collecting based on your authentic curiosities, can be brought together into a Polka Dot Couture of your own.

Here’s how this works for me: I recently launched a freelance career based on my ability to connect a bunch of random dots of my own. Dots I acquired through pursuing my curiosites in different fields (such as training and gaming) and countries (such as Australia and France). And now my Polka Dot Couture is my ability to help clients create engaging and effective online learning experiences for diverse groups of students.

The table below maps how my curiosity-based experiences apply to my freelance success (which up until six weeks ago, I didn’t think I could achieve):

As you can tell from my experience, you don’t have to become a household name like Jobs to own your Polka Dot Couture. Because it’s not about being the star of the fashion show, it’s about being the star of your career runway. Whatever that looks like to you.

You are the common denominator across your variety of experiences. And that’s an advantage — even if it doesn’t seem like it. I mean, it took me eight years and ten jobs in four different countries to figure this out. So trust me when I say, regardless of how insignificant a curiosity-based experience seems to be, everything from assembling radios as a child to traveling the world as an adult, is a dot toward fashioning your Polka Dot Couture.

And you can start creating your career couture at any time (whether you’re on the cusp of beginning your career or someone who’s been around the block). You just need to prioritize collecting and connecting your dots with the same childlike wonder of a young Steve Jobs tinkering at his father’s workbench.

Thank you to Michael Simmons for not only inspiring this post but for helping me see my curiosity-based experiences as the assets they are. You can read his brilliant article on Steve Jobs in Forbes: Simmons, Michael. (2015, January 15). The №1 Predictor Of Career Success According To Network Science. Forbes.

Thank you for reading my article (it was originally published on Oct. 6). Please connect with me on Twitter or LinkedIn for similar content.

--

--