Looking Back, Planning Ahead
December brings a natural moment for reflection, and this year offers plenty to consider. With hiring season on the horizon, it's a good time to assess where you are and where you want to go. The average person will spend roughly 90,000 hours—a third of their waking life—working. That time outranks almost every other activity except sleep, so it's no wonder there's pressure to make those hours count.
Kylie Poppen, a Design Lead at Google working on Gmail and Chat, recently faced this exercise herself while writing a professional bio. The result looked like a clean, linear path: from Stanford studies in Symbolic Systems with a focus on Human-Computer Interaction, through startups, and into Google. But that tidy narrative obscures the messy reality of career-building. When we talk about our professional lives, we tend to frame them as trend lines—looking back from the present and connecting the relevant points into a coherent story. The danger is forgetting that trend lines only exist after the data is collected. We actually live in scatterplots, jumping between interests and roles without knowing which dots will eventually matter. That uncertainty is why choosing a next step feels so intimidating: we want to make a move that reinforces a line we can't yet see.
Finding the Intersections
One way to make sense of the chaos is to look for overlaps between your disparate interests. Great work often emerges from unexpected combinations, and the logical starting point is a Venn diagram of what you actually enjoy.
Poppen's own story illustrates this well. As a kid, she used CorelDRAW—installed from a box of some 50 floppy disks—to design posters for everything from requesting ice cream to student council campaigns. That hobby fell by the wayside during college, when design felt out of reach compared to peers who had dedicated themselves to the craft early on. Instead, she interned across recruiting, marketing, engineering, and project management. It wasn't until a patient designer gave her constructive feedback and built her confidence that she gave design a serious try. Looking back, the connection was obvious: technology plus storytelling plus people equals a career in product design.
The lesson is that your hobbies aren't just fun—they're data points. Rediscovering an old passion could unlock a career you haven't considered or give you the confidence to pursue one you've been eyeing. Instead of resigning yourself to a life where hobbies and work occupy separate corners, ask what emerges at the intersection.
Setting the Variables
Interest overlaps are only half the equation. Careers unfold alongside life decisions: home ownership, city living, family plans, adventure, remote work, health benefits, proximity to loved ones—everyone's list looks different. Money often seems like the obvious solvent for all these variables, but it's only a store of value. There are many paths to the same outcome.
Consider the high school friend who abandoned the conventional office track to manage restaurants in the mountains and work with the Boy Scouts in the desert. That path gave him the time to motorcyle around Indonesia and sail across the Atlantic. Most of us know a version of that person—someone we admire and perhaps envy for rewriting the rulebook. That feeling is a signal to revisit your own variables. Are your current choices serving the life you want, or the life you think you should want?
A useful practice is maintaining a list of needs versus nice-to-haves. You don't have to solve for every variable today, but you should return to that list whenever facing a significant decision. The combination of your interests and your constraints will guide you through the difficult choices ahead.
The Power of Slope
Starting position can feel decisive, especially when you're surrounded by people who seem ahead. In an early college programming class, Poppen watched peers demo polished websites while she struggled with basic layout. She nearly dropped the course. But the professor offered a different frame: a little bit of slope makes up for a lot of y-intercept.
Mathematically, it's simple—given enough time, a line with greater slope will always overtake one that started higher but progresses more slowly. The same holds for careers: rate of learning and dedication matter more than initial advantages. That less experienced candidate who works hard and absorbs quickly will outpace the one who started ahead but stalled. This principle applies whether you're interviewing, considering a new field, or training for a race.
Persistence pays off even in creative work with long iteration times. Leonard Cohen famously told Bob Dylan he'd written Hallelujah in two years; in reality, it was closer to five. He ultimately wrote 80 stanzas, trimmed to 15 for the final version, and continued revising verses in live performances through the 1980s and '90s. The song has since been covered by hundreds of artists and became one of the most celebrated compositions of its era. What if he'd given up at the third failed draft?
The Point of the Exercise
If you periodically revisit your interests and variables, you'll find the right answers—but that framing undersells how hard the process is. The equation for a life only resolves at the end, when the 90,000 hours are done. In the meantime, the value is in returning to the math regularly: check whether your current trajectory still reflects what you care about, and give yourself permission to adjust.
Your story isn't predetermined by the dots you've already plotted. If you have tens of thousands of hours left to work, that's plenty of time to rewrite the trajectory. For additional frameworks, Designing Your Life by Bill Burnett and Dave Evans, as well as Elle Luna's essay "The Crossroads of Should and Must", offer practical starting points.
