To make a career change, first answer this question
Why the typical approach leads us astray and how to define what's next
Welcome to The Reset. This isn’t your average career advice column promising quick tips and tricks. It’s your ally in designing meaningful life and work, and that means asking you to confront the deeper, more challenging questions.
Fortunately, you aren’t the average career advice reader. Over the past few months, I’ve had the pleasure of speaking to dozens of you about your career transitions. You’re not just looking for another job; you’re searching for your life’s work— something that is fulfilling and matters to you, that engages your best gifts.
If there’s something important missing in your work, if you’re afraid of the uncertainty that comes with a big change, if you’re feeling a little lost and unsure of where to start — this post is for you.
We’ll explore how people typically approach career transitions and why this method is flawed. We’ll then dive into a crucial exercise at the end of this post. Let’s get started.
The default strategy for career transition
I’ve noticed a common approach among high achieving career switchers.
Step One: They first set an anchor in their current job. Where am I now? What industry am I in? What skills and experiences do I have?
Step Two: Next, they map alternative options within a certain radius of their current job. For most, the radius is low. They don’t dare venture far. For example, an investment banker may consider tangential roles in financial services: moving to a different investment bank, or jumping into private equity, venture capital, or hedge funds. They may broaden their radius slightly: moving to corporate development, becoming an angel investor, or working for a fintech company. They will look around at their peers who’ve left their jobs and make a list of where it seems safe to go.
Step Three: They then eliminate the options that don’t meet their baseline criteria or seem out of reach. Often, the process of elimination is haphazard— driven more by fear and luck than by a clear understanding of desire and viability. Perhaps they speak with a recruiter, get feedback that their background doesn’t fit what the company is looking for, and abandon an entire path altogether. Or they look at an opportunity and say “I’m way behind everyone else in that industry; I could never get the skills to do that.”
One by one, they dim the lights on what’s possible until they’re left with a small palmful of options that feel safe, certain, and viable.
Why this approach limits us
While straightforward, this approach employs fallacies:
Local optimization: When we use our current job to dictate the universe of opportunities, we’re more likely to pick something that’s incrementally shinier than what we have now, and miss the leaps that will bring true fulfillment.
Irrelevance of authority: Under this default strategy, we’re more likely to make decisions based on the opinions of authoritative others in our immediate orbit— our mentors, managers, parents, respected leaders in our current industry. The problem: While we admire and respect these people, we’re the ones making the change, not them.
False assumptions: We’re apt to make a lot of assumptions under this strategy— what opportunities are possible given our backgrounds, what path does or doesn’t meet our criteria. We generalize singular data points. We give into hearsay, black-and-white thinking, and misinformation. We fail to even name our assumptions, let alone test them methodically.
Solutions without a purpose: I’ve spent the past decade of my career as a product manager in tech startups. A cardinal sin of product management is committing to a solution without a vision— yet that’s exactly what most high achievers do when confronted with a career change. We apply frantically to new roles without reflecting on what we’re solving for at this stage of our careers. Visions are challenging to nail down; they start out murky and require real reflection to shape into something tractable. It’s easier to throw résumé spaghetti at the wall and get a false but satisfying sense of progress. And so, we keep ourselves busy by browsing LinkedIn job postings and attending networking events— all to avoid the deeper questions that beg to be asked.
When we’ve been deep into a particular career path for years, it can be hard to imagine options beyond the periphery of our direct experience. We forget that there’s a whole archipelago, an expansive ocean, entire continents to be voyaged beyond the island we’ve been standing on.
We end up choosing among options that are not too different from the job we just left. And when we arrive in a new team, in a new office, we gradually realize that this grass is only one shade greener and still missing the liveliness and lushness we were seeking.
“The attempt to create a complex professional identity most often buries us in layers of insulation through which it is impossible to touch our best gifts,” writes David Whyte in Crossing the Unknown Sea. “The day may be full, we may be incredibly busy, but we have forgotten who is busy and why we are busy. We lose the conversation, we lose our calling…”
The essential question to ask ourselves
To make a better decision, first anchor in purpose: What am I yearning for in my work?
If this sounds “woo woo,” if you’re feeling impatient for quick answers, if you’re hungry to start networking and dropping your resume right now— take a moment to consider this question: What am I yearning for in my work?
For many of us, this is an uncomfortable inquiry. We’re not used to listening to our own wishes. It’s more convenient and less petrifying to receive the perspectives of wise others and wear them as our own truths. Perhaps that is how we ended up here in the first place, feeling disconnected from our work and a desire to pursue “something else.”
Now is the time to start listening. What am I yearning for in my work?
Change is uncomfortable and scary. Our mammalian brains don’t like significant changes— and so when we’re itching for it, that’s a big deal. It means there is a profound desire that exceeds the preciousness of consistency and safety. It would be a waste not to listen and realize what that is.
"One doesn't discover new lands without consenting to lose sight of the shore for a very long time." — André Gide
From my conversations with you, I identified 19 common yearnings of work:
Authenticity - to express who you truly are, and be seen and valued for it
Teaching - to provide guidance that helps others learn and grow
Imagination - to dream up and envision what's possible
Autonomy - to have agency in deciding how to approach to work and life; to own your destiny
Teamwork - to work toward a shared purpose/goal; to count on each other and achieve something together
Creativity - to put things together in ways that haven't been done before and see them come to life
Service - to have a positive impact on the well-being of others
Awe - to experience beauty, transcendence, amazement, and/or something unexplainably beyond ourselves
Challenge - to encounter high stakes difficulty and be given the chance to overcome it, not knowing fully if you will succeed or fail
Security - to feel safe physically and financially, so you can live other aspects of life more fully
Learning - to satisfy one's curiosity, acquire new knowledge and insight, and experience the joy of learning purely for the sake of learning
Play - to have fun and explore what's whimsical, quirky, hilarious, or off the beaten path; to experience the joy of amusing yourself and others
Beauty - to immerse yourself in what's aesthetically pleasing to the senses
Peace - to simply live and let that be enough; to experience calm, tranquility, and lack of striving
Craft - to carry something out with skill, devotion, and mastery; to make something high quality that you're proud of
Community - to feel fellowship and belonging in a mutually supportive group
Order - to bring structure, predictability, and order to what's chaotic, messy, and disorderly
Pioneering - to be at the frontier of what's new; to experience the thrill and risk of trailblazing
Competition - to have a rival; to experience the thrill of battling and pursuing victory
Consider these the “jobs to be done” of our careers. How would we like our work to engage us? Our yearnings will change from time to time. What’s true during one season of life might shift in the next.
You might notice certain yearnings missing from the list: growth, success, happiness, fulfillment, self-confidence. I tried to stay away from naming the elements of self-actualization that we all want, and instead focus on the “how”— the underlying desire that becomes the vehicle for our desired state.
I also tried, as much as possible, to stay away from buzzwords like “leadership” and “achievement” that are catnip for high achievers like us. We might be too tempted to select those simply because we feel we have to.
Exercise: Identify your yearnings
Clone and complete this Notion worksheet. If you’d like, reply and share it with me. Alternatively, share it with a trusted friend or mentor.
If things feel unresolved after exploring these questions, remember this: To produce satisfying answers, we first need to ask questions that turn the soil. In doing so, you have created a more fertile foundation for growth— even if your mind may feel messier and even more impatient than before.
Now that we know what we’re yearning for, how do we begin to understand the universe of options? We’ll explore this in the next few posts.
Who writes The Reset?
I’m Mindy, a leadership coach at Throughline. I've spent the past decade as a product leader at multi-billion dollar tech companies. I helped Dropbox scale from 200 to 2,000 employees and led the NYC Product team. Most recently, I was Director of Product at Oscar Health, leading a cross-functional team of 50+.
Amidst the pandemic, I uprooted my life and career so that I could prioritize my values. I now coach high achievers who grew up with a traditional notion of success to define what they want, shed limiting beliefs, and design meaningful lives and work. Learn more about me.
A huge thank you to Ben, Amber, Thomas, Cameron, Anindya, Russell, Katherine, Jay, Ashwin, Thi, Muhammad, Alex, and Foster for their feedback 🙏