Not All Who Drift Are Lost
The first time someone asked me where I saw myself in five years, I told them I'd like to be ruling the world. I got the job.
It was a deflection, and I knew it at the time. What was actually happening was a small, genuine panic at having been asked a question my brain had no mechanism to answer. Not because I lacked ambition. But because I don't think in straight lines projected forward through time, and the five-year plan question assumes exactly that. It assumes you can stand in the present, look down a corridor into the future, and describe what you see at the end of it.
I couldn't see anything. The corridor wasn't there.
You do not need a five-year corridor to have a real compass.
What I eventually had to reckon with was that this wasn't a gap I could fix with better planning skills. It was something more fundamental about how I navigate. I wasn't failing to plan. I was doing something else entirely, and I needed to figure out what that was.
What I was doing, it turned out, was making decisions by feel, but not arbitrarily. There was a consistency to the choices I made, a pattern visible in hindsight even when it hadn't been visible in the moment. Every time I moved toward something, it was because it offered one or both of two things: the chance to learn something I didn't know yet, or the genuine prospect of enjoying the doing of it. Every time I moved away from something, it was because one or both of those things had gone missing.
I didn't name this for a long time. It was just how I operated. But eventually I distilled it into two questions that I now use as a compass whenever I'm trying to figure out what to do next, or when something feels stuck, or when a decision is sitting in front of me and I can't work out which way to go. Am I learning? Am I having fun?
They sound simple. They are simple. That's not a weakness.
What they're actually doing is replacing a time-based planning framework with a values-based one. The five-year plan asks where you want to be. These questions ask whether where you are, or where you're heading, is aligned with what actually matters to you. One optimises for destination. The other optimises for the quality of the journey, which sounds like a greeting card sentiment until you consider that the journey is, in fact, most of your life.
The questions are mine. Yours might be different. Maybe you have one question, or five. Maybe learning and fun aren't the right words for what you're optimising for, maybe it's connection, or contribution, or craft, or challenge. The specific questions matter less than the decision to use questions at all, to navigate by values rather than by milestones, to treat your own compass as a legitimate instrument even when everyone around you is looking at maps.
What I also came to understand was that neither question operates as a simple yes or no. They're more like levels than switches. I knew I couldn't sustain pure enjoyment without growth, and I knew that learning without any satisfaction in the doing was a kind of grind I wasn't willing to settle into for long. What I was managing, without having language for it at the time, was a balance between two tanks, and the signal to move wasn't a single moment of dissatisfaction but a slow, accumulating awareness that one or both had been running low for too long, or that the balance between them had tipped too far in one direction and wasn't correcting itself.
That distinction matters. A hard period inside something that is still fundamentally right doesn't drain the tanks, it's friction, not depletion. The signal worth paying attention to is quieter and more persistent: the thing that used to replenish you isn't doing that anymore, and hasn't been for a while, and you've been telling yourself it will come back.
It doesn't always come back. Sometimes that's the information.
Direction can be real even when the route is not linear.
The career this system produces doesn't look linear from outside. It isn't linear. Mine has moved across integration development and business analysis, product management and civic tech, campaign management and event production, but those labels describe the containers, not the contents. What the containers held, consistently, was people. Teams I built and watched grow. Stakeholders with completely different mental models of the same problem who needed someone to find the shared ground between them. Communities who needed data made legible enough to act on. Colleagues who needed enough safety to experiment, to be wrong without consequence, to try things that might not work. The work changed shape. The core of it didn't.
Some of the most meaningful things I've done happened not through my own output but through building conditions for someone else's. Watching a team member find their footing and exceed what either of us thought they were capable of feeds both tanks in ways that individual achievement doesn't quite replicate. The learning is real, you learn as much about people and systems from leading them as from any formal training. And there is a specific, irreplaceable kind of enjoyment in a team that is genuinely functioning well, that trusts itself enough to disagree productively, that moves with both rigour and lightness. When that's present you know it. When it's absent you feel it in the tanks.
This is where the site you're reading gets its name. Genetic drift, in evolutionary biology, describes change that accumulates not through selection pressure, not because a trait is better suited to the environment, but through the random accumulation of small events over time. It's change without a plan. Change that produces real and meaningful difference, that can result in something entirely new, without anyone having directed it toward a destination.
I find this a more honest model for how some careers actually work than anything the five-year plan assumes. Not random, the decisions are real and considered, but not directed toward a fixed point either. Accumulating. Coherent in retrospect in ways that weren't always legible in the moment.
The best decisions I never made made me. The Musical Theatre degree I didn't take led me to Information Science, which led me to middleware, which led me to understand that I had always been a translator, of language, of systems, of the space between technical teams and the humans they build for. That thread runs through all of it, including the teams I built and the people I worked alongside. The corridor I couldn't see down turned out to be less important than the doors that kept appearing to the side of it. I walked through the ones that looked interesting. Most of them were.
What this system doesn't give you is certainty. It doesn't give you a clean narrative to offer at interviews, or a clear answer to where you see yourself in five years, or the reassurance of a plan you can point to and say: I am on track. Those things have value, and I'm not dismissing them for people who can genuinely produce them. But for people who can't, who experience the five-year plan question as a request to describe a corridor they simply cannot see, the alternative is not failure. It is a different instrument.
The instrument works. The career it produces is not a consolation prize for people who couldn't plan. It is, in many cases, richer and more responsive and more genuinely aligned with who the person actually is than the alternative would have been, precisely because each decision was made on internal grounds rather than external ones. You are not optimising for what looks good. You are optimising for what is good, for you, now, with enough awareness of your own tanks to know when the balance has shifted and it's time to move.
The reassurance I want to offer is not that everything will work out. I don't know that and neither does anyone else. It is that navigating this way is a legitimate choice, that the coherence is real even when it isn't visible, and that the two questions, or whatever your equivalent turns out to be, are a more honest compass than a destination you chose before you knew what you were choosing.
You don't have to be able to see the corridor. You just have to know which way is north.