How to progress when your career path isn’t linear

The Jump #5

Welcome to The Jump: a bi-monthly newsletter for Millenials in the midst of a career transition. The genesis of this newsletter began with a question I had when I was in between jobs: what is the relationship between career change and personal growth?

This issue’s tl;dr:

Your career path will most likely be nonlinear. Nonlinear career paths mean that your progression looks more like mastering your craft and less like climbing the corporate ladder. Let’s recognize this and be less hard on ourselves.

To stay motivated, people need to feel a sense of progress. And because career paths today rarely look like climbing the corporate ladder, we need to be proactive about visualizing our own progress. 

Career progression was easy to conceptualize twenty years ago. You start your first job after graduating from college. You work hard to get a promotion, receiving an increase in salary and “senior” in your title as a result. Your next promotion gives you people to “manage”, a nice P&L, and another increase in salary. Eventually, you earn a spot in the C-suite.

Progression in the old world of work is tangible: more pay, more people under you, the corner office, more budget, sexier title. 

In today’s world of work, progression is less tangible. Smaller companies don’t have a corporate ladder (if they do, it probably should be a red flag to you). And if you work in a large company, you’re likely going to leave in three years. Three years isn’t enough time to reap the tangible outputs of progression.

In conversations I have with my peers* about career goals, I hear two statements consistently:

  1. “I have no idea what I want to do with my life.”

  2. “What do you want to do?”

*this doesn’t include business owners. You all are an unrivaled breed—unconcerned with silly millennial existential crises due to the necessary focus required of you to run a solid business.

This has never made sense to me. We don’t have ten-year plans ourselves, yet we ask our peers what theirs are.

The good news is, no one needs a ten-year plan. 

A friend and mentor of mine, Jordan Husney, once told me something wise that I’m about to paraphrase because my poor memory can’t remember it word for word:

“Instead of a clear ten-year plan, I’d rather be more clear on my purpose and immediate next step and less clear on what my ten-year plan looks like.”


Jordan’s point stuck with me. Unless you’re an aspiring doctor, lawyer, or professor, it’s more practical to be certain of your purpose and next step than to have a certain ten-year plan. Just how we see the danger of a long-term plan for companies, we’re seeing how dangerous a long-term plan is for our own career paths. Believing our plans lead us to fulfillment, they leave us unfulfilled, wondering what to do next.

How do I know if I’m progressing?

A nonlinear career path leaves us a big question: How do I know I’m progressing?

I made the point earlier that people need to feel progress to remain motivated about what they’re doing. So it’s worth answering this question.

I think there are three ways to think about this:

  1. Skills & mastery (getting better at your craft is progress)

  2. Portfolio & outcomes of your work (the work you produce is progress)

  3. Teaching & mentoring (the people who learn from you is progress)

Each point deserves its own newsletter rather than a few hand-wavey paragraphs. For the purposes of (hopefully) giving the point what it deserves, we’ll focus this issue on skills & mastery.

Skills & mastery

To understand mastery, let’s look at two personas: the artisan and the athlete.

The Artisan

The artisan is the shoemaker, the blacksmith, and the chef. The artisan’s work is a craft. The artisan’s main priority is to create something beautiful, delicious, or inspiring. The artisan is not satisfied if their work isn’t beautiful, delicious, or inspiring.

To the artisan, progress is making something even more beautiful, delicious, or inspiring than their previous thing made. 

If we think about career progression in the way an artisan thinks about mastery, I think we’ll benefit. What makes an artisan fulfilled is the craft itself, rather than the number of people who work for them or what their salary is.

The Athlete

The athlete is the person who wakes up in their running clothes and runs along the river just as the sun rises. The person who’s first to be on the court and the last to leave.

The athlete aims to improve the breadth and depth of their skills. How do I improve my three-point percentage? How can I increase the number of miles I’m able to run?

The athlete is obsessed with deliberate practice. The only thing they think about after winning a game is when the next practice is. The practice schedule is constricting to the casual exerciser but freeing to the athlete.

Athletes teach us that today’s career progression can be more about how we improve our craft.

Today’s career progression is mastery

The beautiful irony is that the future of career progression can be found in an age-old idea: mastery. Pursuing excellence in our craft and finding fulfillment in the pursuit itself.

Millennials, don’t be hard on yourself if you feel like your progression is stalled.

You have a craft. Improve your craft and witness the progress you’ll make.

More reads on mastery and work

ShuHaRi | Martin Fowler

ShuHaRi is the most simple way of thinking about learning a technique. Here’s the idea:

  • Shu = follow the teaching

  • Ha = branch from the teaching

  • Ri = innovate the teaching

Simple and applicable.

The Strategist’s maturity matrix | Clay Parker Jones

I decided to re-read Clay’s piece after starting my new job at Sanctuary. It’s a great take on what the progression of a Strategist looks like. I’m sure I’ll be revisiting this when we think more deeply about the kind of development we hope to see from Product Strategists at our company.

Product Management Skills self-assessment | Whitmaan

More skills matrices, yay! As statistician George Box would say, “All models are false, but some are useful.” If you’re a fellow product person, hold back your instinct to poke holes in this framework and try this yourself. I found it helpful.

Spidey-sense | Rands in Repose

“Spidey-sense is a feeling. You might be hesitant to heed it because you can’t tell where it came from. You might attempt to ignore it because the difference between a feeling inspired by hard-earned wisdom and one inspired by an irrational emotion feel the same. They aren’t, but the only way you’re going to learn the difference is by first listening then acting.”

The Working Pair | Rachel Yaeger

Six couples. All New Yorkers. All knowledge workers. The Working Pair might be inspiring any of you who a) are in a relationship and/or b) worry that being in a relationship somehow holds you back from pursuing your career. Beautiful site, even more beautiful stories.

In transition with you,

–tim

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