Why you should throw out your 10-year plan

Where do you see yourself in ten years? My guess is you know exactly how to answer this question. You probably have a carefully crafted master plan with an impressive destination in mind at the end of it. If you don’t have one, you’re well aware that you “should.” After all, this is what we’ve all been taught is the best, most strategic way to navigate a career successfully. But if you’re feeling stagnant, unfulfilled, or disconnected in your work, even when you did everything you were “supposed to” do, then it’s very likely that the ten-year-plan, Destinational approach is holding you back, not helping you out.

This traditional outcome-oriented approach to career is failing us. It says, “Decide what you want your life to look like, come up with a ten-year plan, and then work backward to determine the most advantageous place from which to start.” It consists of climbing ladders and linear, predetermined career paths. You must know, it instructs, exactly where you are going in your career and life and how you will get there, before you can even begin to experience living it. In short, it teaches us to prioritize the destination as the most secure path to success and fulfillment—to live destinationally.

In the abstract, Destinational Living is a lovely idea, and one we so badly want to be real. There’s a reason why it’s persisted as the dominant cultural paradigm for so long. It’s incredibly comforting to believe that the world and our futures are so reliable and predictable that we can plot it all out in advance—we just have to put our minds to it. How seductive to think that we have the utmost control over the world around us. If only it were true. The problem is that, as it turns out, we cannot reverse engineer our lives, or at least not with any measure of authenticity and fulfillment.

The first problem with the Destinational approach is that we’re not very good at picking aligned and fulfilling destinations for ourselves, on which the entire success of a ten-year-plan depends. Our capacity to select destinations is severely limited by the fact that we can’t predict the future. We simply have no idea what’s going to transpire and what the world is going to look like in ten years, let alone what we are going to be interested in, care about and inspired by at that point.

Ten-year plan, Destinational Living assumes that the future is knowable and fixed, or at least reasonably predictable. And yet, if this quarter of a century and especially the COVID-19 pandemic has taught us anything, it’s that the supposedly surefire paths to success may not be such sure things after all, and the very destinations to which we were en route suddenly no longer existed, if they ever existed at all. Commercial real estate would always be highly lucrative, they said . . . until we didn’t leave our houses or return to offices. Traditional media jobs would always be secure . . . until the internet became widely available and flipped journalism on its head. A computer science degree would always be lucrative and in demand . . . until AI (or something else) came along. The list goes on. Given all this, It’s increasingly hard to see how your ten-year plan—or just your two-year plan—could possibly be effective.

Let’s say you are able to land at your stated destination—say, CEO of your current company—and it is, in fact, there to welcome you. There’s no guarantee that you’ll actually want to be there or be satisfied in that role because you picked an arbitrary and narrow destination that was never meant for you in the first place. It’s very likely that you’ll be confronted by what Dr. Tal Ben-Shahar has called the “arrival fallacy”— when you arrive, the destination won’t feel like what you thought it would, and you’ll find yourself disillusioned, stuck, and still longing for fulfillment, even though you achieved everything you set out to achieve. Often, there is no “there” there, as the saying goes.

Furthermore, when we’re hell-bent on that one predetermined destination in our plan, we end up moving through life on autopilot and miss out on opportunities that emerge along the way. What if you’re not meant to be CEO of your current company because you’re meant to be CEO and founder of your own company — maybe even one in a completely different sector? You may completely miss that inclination because you’re so diligently following your original path and see anything that threatens that as a distraction. Or, what if CEO is actually a terrible role for you, but COO or CMO is a role that is much better suited for you, but you’re so busy gunning for CEO and trying to craft your resume into a CEO resume that you miss that redirection? Destinational thinking and ten-year plans don’t allow us to be responsive to our real and ever-changing environments — internal and external — since they’re predicated on the falsehood that the world, and we ourselves, are static and fixed.

As a result, this approach also means outsourcing our decision-making. What is impressive, what is valuable—these are defined not by what matters to us personally but, rather, by what matters to others and which ways of life, which checkboxes, the collective has deemed “worthy.” We’re incentivized to defer to sources outside ourselves for guidance on what counts, what to do next, by when, and in what order. It takes all the you-ness out of the equation. We, as individuals, barely factor in. The Destinational approach leaves no room for authenticity or individuation. In effect, we’re “life plagiarizing,” and we don’t even realize it. We’re essentially taking someone else’s life trajectory and imitating it, maybe changing a few words or details along the way. It’s attempting to copy something—a life—that is meant to be proprietary. It’s asking, “What did that person do to achieve such success?” and then turning around and saying, “Okay, got it. Copy, paste. I’ll have what she’s having.” What the logic of Destinational Living neglects is that success isn’t arbitrary or generic; it is deeply personal. One size does not fit all.

So, what do we do instead? If you want to create a fulfilling career and find a sense of your Something Bigger, throw out the belief your “best life” is a destination waiting for you at the end of that sacred ten-year plan and the Destinational thinking that we’ve all been so reliant upon, and adopt a Directional approach instead—one where you focus on moving iteratively in your own personal right direction without needing to know the precise destination. Instead of asking, “Where do I need to end up?” ask, “Is this single next step Directionally right?” Directional Living looks a lot like the “launch and iterate” approach used in the tech world. You don’t launch a new product with the expectation that it’s the final version and that you’re going to “set it and forget it.” You launch with the minimum viable product (MVP)—the best you can build with what you know today—and you expect to continue iterating as you go. Think of the constantly pushed updates on our phones and devices. The goal is not to get it “right” or perfect on the first try or even, necessarily, to adhere to the original plan at all. Rather, the idea is to evolve and fine-tune over time by being alert and responsive to the changing needs and desires of users and markets. The only way to fail is to refuse to iterate and adjust. We’ve been stuck in an expired “set it and forget it” mentality where we decide the job we want to retire from at 65 when we’re just starting out. We instead want to take the launch-and-iterate approach to life.

The old Destinational approach would look like deciding at twenty-two that you want to be a CEO, and maybe even the CEO of a specific company in a specific industry (that may or may not exist down the line), then strategizing on what role you think will expedite your CEO agenda, and landing in an enterprise sales role you hate because someone told you that every great CEO has global sales experience. You believe that the fact that you’re miserable is irrelevant and the end (CEO) will justify the means (all the dissatisfaction you feel on the way there).

Instead, in the Directional approach, you simply select the next job role that you’d like to experience now. Maybe what intrigues you the most is a product marketing role that sends you on a CMO trajectory. You end up getting to the C-level in half the time because it’s particularly well-suited to your talents. When we stop needing to predict exactly where we are going, opportunities emerge. New options that were once inconceivable to us present themselves when we interact with the world as it is, as opposed to how we anticipate it will be. Counterintuitively, the less you focus on the outcome, the better—the more fulfilling, innovative and impactful—the outcome (not to mention the process!) will be.

The Directional approach requires you to work forward, not backward. It asks you to live into the questions “What is my work and my life about?” and “What is my Something Bigger?” These are questions we simply can’t figure this out by sitting at our desks with our spreadsheets and journals and plotting out life maps.

Excerpted with permission from Directional Living: A Transformational Guide to Fulfillment in Work and Life (Penguin Life) by Megan Hellerer.