Welcome to The Jump, a newsletter for millennials in the midst of a career transition.
As I was in the midst of my own career switch, the idea of this newsletter started with a question I couldn’t get out of my head:
What’s the relationship between career change and personal growth?
I found out about a book called Working Identity by Herminia Ibarra and read it to help me answer this question. I heard about Working Identity from a Bill Simmons podcast with David Epstein (sidebar: David’s Range is also a book I've been meaning to read).
First off, I do consume content that isn’t career/work/org/psychology/product-related, contrary to what many of you work nerds think. It’s usually NBA analysis though, so I’m not as cultured as I sound. As I indulged in my regular reading of non-work-related stuff (which is only NBA analysis), I stumbled on a gem that ultimately inspired a work-related newsletter.
My struggle to expand my taste in content beyond work/product/psychology is beside the point.
Ibarra’s thesis is this:
To bring your ideal next career move into reality, we must test & learn possibilities, rather than predict what might make us happy and execute against that prediction.
As I was in the midst of my own transition, Working Identity deeply resonated with me for two reasons:
Testing & learning transforms organizations. As someone who’s spent the last three years helping organizations test-and-learn, I’ve seen this approach unlock more meaningful change than creating a 100-page deck that outlines a grand change plan.
Testing & learning defines my career trajectory:
I tested the idea of studying computer engineering and learned that I wanted to study how people can thrive. After nearly failing my Java class in the summer of 2013, I wanted to try something different. I always enjoyed reading about how to build better habits and was curious about what that would look like professionally. So I switched my major to psychology.
I tested the idea of grad school and learned that I wanted to be a practitioner. My plan was to pursue a PhD in Org Psychology, so I led a research lab and published an academic paper (PhD programs love applicants who’ve published). At the same time, I was freelance writing for a consultancy and wondered the possibilities of working full-time for them. With a lot of luck, I started working for them.
I tested the idea of building my people and process skills and learned that I wanted to gain more skills in product. I loved the opportunity to work on process- and people-related problems. And, I found out myself itching to work on product-related problems. Thus, my recent endeavor as a Product Strategist at Sanctuary Computer began two weeks ago.
I lied. Ibarra’s book resonated with me for two reasons and three longwinded sub-reasons.
It’s worth noting that Working Identity is written for the mid-career-changer. Think the 38-year-old financial services leader who’s curious about cryptocurrency, but doesn’t know how to build a career around that. Or the 45-year-old schoolteacher who wants to start their own organizational behavior practice but worries about losing financial stability. I felt Ibarra’s insights applied to me as equally as it did to her target audience.
Hence, the genesis of The Jump.
Needless to say, I want to acknowledge how much harder it must be to go through a career change later than earlier in our career. The Jump readers are in a much more fortunate position than Working Identity readers.
But again, the insights from this book also apply to the early career millennial.
Here’s five.
“There are two types of people. Some are always jumping. Some never jump—they settle down too easily and get stuck.” (1/5)
True. Settling down is comfy, tho. And the more settled down you are, the harder it is to make The Jump. This is why we need explicit strategies to help us do so.
“Almost no one gets change right on the first try. Forget about moving in a straight line.” (2/5)
Amen. Building a meaningful career is less a linear process than it was before. We’re overdue to outgrow this mental model.
“Becoming our own person, breaking free from our ‘ought selves’—the identity molded by important people in our lives—is at the heart of the transition process.” (3/5)
This. So much this. Two things I want to unpack here.
Change is letting go of what we ought to be in service of becoming who we want to become. As I’m new to the product/tech world, I’ve been slowly letting go of my “ought” org design self in service of being a better product strategist.
This “ought self” is likely influenced by people important to us: our spouse, family, and friends. Maybe your parents wanted you to be an engineer, so 18-year-old you decided it as your destiny. When you feel stuck and ask your parents for advice, they’ll likely say, “Well, your experience is in mechanical engineering, so look for mechanical engineering positions.”
Which is a good segue:
“Reason and consistency—what Susan Fontaine, the M.B.A. who jumped from one corporate job to another, called the ‘relentless logic of a post-M.B.A. CV’—keep people from thinking outside the box.” (4/5)
Being “completely logical” rarely serves The Jump. Logic tells us to work in a role or at a company that would impress our parents’ friends. In addition to your reasoning, your instincts are also a source of information. Remain attentive to your instincts.
“We learn who we are—in practice, not in theory—by testing reality, not by looking inside. We discover the true possibilities by doing—trying out new activities, reaching out to new groups, finding new role models, and reworking our story as we tell it to those around us.” (5/5)
If there’s any quote that you take away from this slightly strange edition of The Jump, it’s this one.
Introspecting our way into our dream career won’t work because we’re terrible at predicting what makes us happy. Psychologist Dan Gilbert talks about this idea of affective forecasting: we predict how we feel once we reach a future state, and we’re often wrong about our predictions. Anyone who says “I want to be a lawyer/doctor/engineer when I grow up” is making an affective forecast.
Don’t get it twisted, I’m all for hypothesizing a career we think would make us happy. What I’m not for is treating this hypothesis as an absolute truth and/or a static plan.
It’s best to assume we’ll be wrong about what will make us happy. To truly make The Jump, we must disprove our views that stem from our “ought self” as quickly as possible.
Work with people in spaces you think you’re interested in and see if you want to keep working in that space. Start coaching others for free and see if you want to keep coaching. Build software and see if you want to keep developing.
Let’s stop assuming our career plans are 100% infallible. Let’s test what we assume may be a career move that makes us more fulfilled.
If we do this, we’ll be much happier.
At least, according to Ibarra, my working identity assumes so.