The Work Escalator: Is it real?

For the past month, I've been part of Tad Hargrave's Point of View Marketing semester. The whole point of the course is to articulate my own take on why I think the people who come to me struggle—and what I believe is the best way to approach these challenges, whether they end up working with me or not.

The last newsletter was my first attempt at articulating what I think the path forward is. Today, I want to share why self-aware tech folks—or people in high-intensity jobs—often struggle during career transitions.

It boils down to this:

For the first time in their lives, there isn’t a “next obvious thing” to do in their career. What they desire no longer fits the conventional work story. They have to create the next step themselves—possibly for the first time ever.

For most of us, our work story follows a script. It defaults to the next obvious thing as we follow a pre-set path shaped by the industrial revolution, which was designed to produce efficient workers. We go to school, progressing from grade to grade. We pick an area of interest and pursue a degree in it, hoping to land a good job. Based on our degree and school, there’s a standard set of “good jobs” at “good companies” to apply to. Then we work our way up—from junior to senior to manager—within the same basic story, until we’re promoted just beyond our actual competency. Job changes happen, but the story stays the same.

Like the relationship escalator, the work escalator isn’t inherently bad—as long as we choose it consciously. But the work escalator doesn’t account for unconventional paths or detours. It also doesn’t teach us how to ask ourselves meaningful questions or how to experiment which are essential skills in designing a work life. .

I realized this earlier than most, mostly through the example of my parents. The work escalator didn’t exist for them—not with the choices they made. My father stepped off his crown attorney path when he and my mom decided to move to Canada. He took landscaping jobs, managed the Polish cultural center, and eventually went back to school for accounting. Now, he runs his own business. My mother started her own flower design business shortly after we moved, picking up other jobs in between. Their work stories weren’t linear, but they were grounded in their values: making enough money to live, and spending time with me and my sisters.

I also didn’t really follow the work escalator—partly because of the degree I chose: Knowledge Integration. It asked me to design my own path, and while that was a challenge, it taught me to make choices based on what I want and to experiment to test my assumptions.

I did try to do the work escalator thing. I got what I thought was my dream job at a financial consulting agency, complete with a fancy office and work trips to New York. But I quickly realized that it wasn’t my dream. It might be someone else’s, but it wasn’t mine. I stepped off, took time to rethink what I wanted, and began walking an unconventional path: starting my own coaching business. That path has been equally non-linear—with pauses, blocks, tangents, and reboots as my life has evolved. But what’s stayed constant is my commitment to walking a path I create, guided by mentors, my needs, and what I believe the world needs.

I love collecting stories of unconventional paths. One recent example: I visited Tulip Valley Farms for the Tulip Festival in Mount Vernon, Washington. We had a “tulip talk” with Farmer Andrew—who turned out to be Fake-Farmer Andrew. He wasn’t a farmer at all, but a lawyer who started this farm after seeing a need and opportunity in the community where he grew up. He chose to focus on the tulip experience and isn't following any of the traditional rules of tulip farming. Now he’s being asked to speak at tulip conferences because of his unorthodox approach. He credits his success to his many Dutch “uncles”—mentors who have guided him in the tulip business, both encouraging and challenging him along the way.

A lot of finding our path involves guidance from others who have done something that resonates with our own dreams, and then laying down our unique path piece by piece.

So—what’s your work story? How did you end up where you are? Do you believe in the work escalator? Have you walked down or witnessed any unconventional paths?

I'd love to hear about them.

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If you're anywhere on the path of trying to figure out your quirky relationship both to work and projects overall, my friends and I are running Give Your Gift in early June 2025. It's a two week online program about discovering a new, joyful, energizing relationship to work and projects. It’s focused on fun service projects, a practical approach to iteratively discovering what you enjoy, what you excel at, and how you can benefit the world.

Check out more details (what a fun service project is, who this program is for, and how it works) here: https://serviceguild.fun/give-your-gift/