Successful yet miserable? Here's how to get unstuck
Hoards of people from almost every professional field are trapped in temporary careers that became permanent. Some thoughts on why this happens, and how to break free.
"Everybody worships. The only choice we get is what to worship. And the compelling reason for maybe choosing some sort of god or spiritual-type thing to worship — be it JC or Allah, be it YHWH or the Wiccan Mother Goddess, or the Four Noble Truths, or some inviolable set of ethical principles — is that pretty much anything else you worship will eat you alive." — David Foster Wallace
Every profession has heroes — the people who reached the top in their craft owing to a combination of wits and luck. Out of the depths of their hard-earned wisdom often comes the desire to teach and level up others.
In product management, Lenny Rachitsky, Shreyas Doshi, and Marty Cagan are such people. They have made it their mission to help product managers level up to the Top 1%. According to them, a distinct combination of skills, habits, and practices sets apart the cream of the crop of PMs. You, too, can build those skills, develop habits, and learn the practices.
It's a fine message because career and financial results will follow with enough effort. It's good to remember, however, that the pursuit of professional excellence doesn't guarantee happiness. Often, it's the contrary: a single-minded focus on professional mastery means tying your self-worth to an external measure of success.
I know that because I've been there. For years I've been so obsessed with professional growth that I would start and finish my waking hours learning product management instead of spending time with the dearest people in my life. It made me more than a decent PM, but it also made me miserable. I couldn't even hold a conversation that didn't revolve around work.
How exactly did we end up here?
Many PMs I know started doing it as a stepping stone toward something else. Some wanted more business impact, and software engineering didn't allow that. Others were like me and aspired to become founders. To them, Product was the best way to learn the ropes and to have a go at end-to-end influence on the business.
In all cases, a special something made us move into Product. However, as we grew in skills and ranks, our professional journeys took a more traditional turn: to get promoted, we needed to build strategy skills, growth skills, and technical skills. We mastered stakeholder management and learned to communicate under pressure.
The further we went along in our product careers, the further we moved away from why we started those careers in the first place. The abundance of accessible professional education gave us easy goals: take this course, sign up for that newsletter, and definitely earn this certification. The cycle of learning, doing, learning, doing, learning, doing was made so easy that we forgot to ask: Learning — what for? Doing — what for?
Somehow, we forgot the intrinsic goals that brought us into Product and swapped them for extrinsic goals of beefing up our expertise and climbing the career ladder.
Of course, product managers aren't the only ones suffering from this. Hoards of people from almost every professional field are stuck in temporary careers that became permanent. Unsurprisingly, many are secretly miserable in their jobs. Multiple studies of motivation and wellness show that people who pursue goals imposed by social or professional expectations have low well-being and life satisfaction. This is true for all goals: short, medium, and long-term.
In other words: if you're honing your skills on an auto-pilot because that's expected of you as a top performer, you may not be doing so well — regardless of the size of your paycheck.
There's a way to change this
Remember how you used to believe that anything in life was possible? Then you started making choices and narrowing down options, resulting in a decent life, but probably not what you were hoping for.
This happened because when making compromises, you might have focused on something that was expected of you over something else that was important to you. You then justified that and adopted those goals as your own. And here you are.
But you're not stuck, and there's a way to switch to another track. Doing that is as simple as getting back to your core values. Many techniques exist for that, but I especially like the one from a book called Designing Your Life (see below).
Creating your new life plans
Your task is to create three alternative life plans for the next five years. Each of those plans must be progressively divergent from your current path:
Plan One must focus on your current life plan. It's good to bring in bold ideas and goals you may already have.
Plan Two must explore your life if Plan One is not an option. Imagine that the thing you do now simply doesn't exist anymore. If you're a product manager, assume that ChatGPT is doing your job and tech companies don't need PMs anymore. You can't make a living in your old field of work and industry. What's your new domain? What does your life look like?
Plan Three is the wildest. In it, you must describe the life you could live if money or status weren't a problem. If you knew you could support yourself regardless of what you do — what would you do? What would your life be like?
I made a Google Doc template for this exercise: Three Life Plans - Template.
If that's too much work, you can do a simple freewriting exercise to unlock your thought process. Try this reflection prompt: If you couldn't do your job anymore, what would you do instead?
Image credit: absurd.design
Research reference: Self-Determination Theory: Basic Psychological Needs in Motivation, Development, and Wellness; Richard M. Ryan and Edward L. Deci