Rethinking the 10-Year Plan: Why Destination-First Career Thinking Is Holding You Back
Ask anyone “Where do you see yourself in 10 years?” and odds are, they have a polished, ready answer prepared. Most people have crafted a detailed master plan that ends at an impressive pre-defined career milestone. If you don’t have such a plan already, you’ve almost certainly internalized that you should have one one. After all, this is the conventional wisdom we’ve all absorbed: plotting a clear long-term path is the most strategic, reliable way to build a successful career.
But if you feel stuck, unfulfilled, or disconnected from your work — even after checking every box you were told to check — it’s very likely that this rigid, destination-first 10-year planning framework isn’t helping you; it’s holding you back. This traditional, outcome-obsessed approach to career building is failing us.
The conventional model works like this: first, lock in what you want your life and career to look like, build a 10-year roadmap to that end goal, then work backward to map out the most strategic starting point. It is built around climbing fixed ladders and following linear, pre-determined career tracks. The unwritten rule is simple: you have to know exactly where you’re going, and exactly how to get there, before you even start living and experiencing your career. In short, it teaches us to prioritize the end destination above all else as the surest path to success and fulfillment — it teaches us to live destinationally.
On paper, Destinational Living sounds like a sensible, ideal framework. It’s an idea we desperately want to be true, which is why it’s remained the dominant cultural norm for so long. It’s incredibly comforting to believe that our lives, our futures, and the world around us are stable enough to map out in advance, as long as we put in the work to plan carefully. The idea that we have full control over our outcomes is incredibly seductive. If only that were how life actually works.
The hard truth is, we cannot reverse-engineer our lives — at least not in a way that leaves us feeling authentic and fulfilled long-term. The first critical flaw of the destination-first approach is that we are terrible at picking end goals that actually align with who we are and bring us lasting fulfillment — and that alignment is the entire foundation a 10-year plan relies on. Our ability to pick a viable end goal is severely limited by one simple fact: we cannot predict the future. We have no way of knowing what the world will look like in a decade, let alone what we’ll value, be interested in, or feel inspired by at that point.
Destinational Living and 10-year plans both operate on the assumption that the future is knowable, fixed, and at the very least reasonably predictable. But if the past 25 years, and especially the COVID-19 pandemic, have taught us anything, it’s that the so-called surefire paths to success are anything but guaranteed. The destinations we were traveling toward can vanish overnight, if they were ever real to begin with. We were told commercial real estate would always be extremely lucrative — until a global pandemic kept us locked in our homes and upended the traditional office model. We were told jobs in legacy media would always be stable — until the open internet flipped the entire journalism industry on its head. We were told a computer science degree would always guarantee a high-paying, in-demand career — until the rise of AI (and whatever comes next) shifted the landscape entirely. The examples go on and on. When you look at how much the world can shift in just a few years, it’s harder and harder to imagine how any 10-year plan — even a 2-year plan — could possibly stay relevant or effective.
Even if you do manage to reach your pre-planned destination — say, landing the CEO role at your current company — there’s zero guarantee you’ll actually want that role, or feel satisfied once you get there. After all, you picked that narrow, arbitrary destination years earlier, before you grew and changed as a person. More likely than not, you’ll fall prey to what positive psychology researcher Dr. Tal Ben-Shahar calls the “arrival fallacy”: once you arrive, the destination doesn’t feel anything like what you imagined. You’ll end up disillusioned, stuck, and still searching for fulfillment, even though you checked off every goal you set out to achieve. As the old saying goes, often there’s no “there” there when you finally arrive.
What’s more, when we’re fixated on reaching that one pre-determined end goal, we end up cruising through life on autopilot, and miss unexpected opportunities that pop up along the way. What if you weren’t meant to be CEO of your current company at all? What if you were meant to found and lead your own company — possibly in an entirely different industry? You might never notice that calling, because you’re too busy sticking rigidly to your original plan, and writing off any deviation as a distraction. Or what if the CEO role is a terrible fit for you, but a COO or CMO role would play perfectly to your strengths? You could miss that far better path entirely, because you’re too busy grinding toward CEO and shaping your resume to fit that one specific role.
Destinational thinking and rigid 10-year plans don’t let us adapt to our constantly changing worlds — both the external world around us, and the internal evolution of who we are. That’s because they’re built on a fundamental falsehood: that the world, and we ourselves, stay static and unchanging forever.
Rethinking the 10-Year Plan: Why Destination-First Career Thinking Is Holding You Back
