The TripTik Method: Why Your Long-Term Plans Need Better Wayfinding
A case for productive meandering in careers and products
Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.
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My sister and I would pass them around the backseat like sacred scrolls. Those spiral-bound AAA TripTiks, with their narrow strips of highlighted highway and hand-circled rest stops. This was 1990s, and we were driving from Maryland to Disney World. No GPS. No smartphones. Just these custom-made guidebooks that showed you one thing: how to get from here to there, with just enough detail to make the journey interesting.
The binding cracked when you folded back each page. In the margins, the AAA agent had written cryptic notes in blue ballpoint: "Good BBQ here" or "Clean restrooms" or "Skip - tourist trap." Each page revealed maybe 50 miles of road. You couldn't jump ahead to see the whole route. You had to trust the process.
I've been thinking about those TripTiks lately, especially during planning season — when product teams lock in multi-month roadmaps, professionals chart career plans, and everyone asks AI to optimize their path forward. We've all fallen for the same delusion: that we can algorithmically plan our way. Now we're doubling down, asking machines to be even more precise about predictions that were already fiction.
The TripTik understood something we've forgotten. The best journeys — products or careers — aren't about perfect navigation. They're about having just enough structure to move forward confidently while staying flexible enough to discover something better along the way.
When Perfect Plans Make You Sick
Here's what nobody talks about during planning season: that tension in your shoulders when the board asks about Q4 deliverables in January. The knot in your stomach when you're asked for your five-year career plan.
Your body knows what your spreadsheet won't admit: you're lying to yourself.
A little anxiety sharpens focus — remember taking the AP Calculus exam? But constant anxiety about controlling the uncontrollable creates paralysis. You spend so much energy maintaining the fiction of certainty that you have none left for the actual journey.
My friend Sarah learned this the hard way. Stanford CS degree, Google APM program, fast-track promotions. By 32, she was Head of Product at a unicorn startup, exactly where her life plan said she'd be.
I met her for coffee last year. She looked exhausted. "I'm in a meeting about optimizing ad revenue," she said, "and I realize I don't care. Not even a little bit. I'm building features for metrics I don't believe in, for users I've never met. But this was supposed to be the dream job." Her Sunday night panic attacks had gotten so bad she'd started taking Mondays off.
The same thing happens with product roadmaps. I've watched teams commit to features in Q1 for Q4 delivery, then spend the next nine months defending decisions that stopped making sense by Q2. They ship what they promised, not what users actually need. The roadmap becomes a prison, not a guide.
The Lost Art of Waypoint Planning
The TripTik's genius was its waypoints. Not a rigid route, but suggestions. A scenic overlook here. A famous diner there. Each page showed just 50 miles — enough to move forward, not so much you couldn't adapt.
Compare that to how we plan now. Career paths become ladder-climbing exercises: Senior PM by 28, Director by 32, VP by 35. Product roadmaps become feature factories: Authentication in Q1, Payments in Q2, Analytics in Q3. We're so focused on destinations we miss the actual journey.
The irony? At our best, we understand this principle with AI tools. You wouldn't ask Claude to 'write me the perfect app' without any context. You'd start with your specific problem, iterate on solutions, and build up complexity gradually. But somehow when it comes to career or product planning, we reach for tools to input our constraints and get back the optimal path. We're asking the wrong questions of ourselves.
Good waypoints are different. They're about capabilities and experiences, not checkpoints:
For careers: "I want to see a product scale from 10 to 10 million users" beats "I want to be a Director." One teaches you something. The other just changes your email signature.
For products: "We need to understand user retention deeply" beats "Ship analytics dashboard." One creates learning. The other creates features that might miss the mark.
The Art of Productive Meandering
Let me tell you about my best career detour. In 2018, I joined Casper — it was a detour from my other roles. To this day, it always registers the most questions from future employers, "Tell me about your decision to join Casper." If you were to put all of the logos from companies I've worked on a sheet of paper and ask someone to circle the one that doesn't belong, 10/10 they'd pick Casper. It's the only D2C company and the only company with a physical product. It's a company where I was sometimes referred to as working in the IT department.
So whenever I'm asked I always give the same response — I look them in the eye deadpanned and say, "Because I wanted to sell mattresses." I try to hold it together for a few seconds before cracking a smile. No, selling mattresses wasn't the my career goal. It was a detour. I wanted to push myself to scale my impact through others — to refine my leadership skills. You know what isn't important to do that? The tech stack. You know what is? Support from your manager, partners, and team to grow, try, fail, rinse, and repeat.
What that detour gave me was depth. I already knew the theory of leadership — create conditions for others to succeed, focus on the team, build people who build products. But knowing something and living it are different. At Casper, with the tech stack out of the way, I could spend all my mental energy on the nuanced work of actually leading.
When I returned to more traditional tech product work, I wasn't just applying leadership principles, I was applying battle-tested instincts I'd developed through focused practice.
Was it optimal for reaching VP? No. Did it make me better at leading others? Absolutely.
The discomfort of not knowing exactly where you'll be isn't a bug — it's a feature. It means you're navigating reality, not a fantasy.
Building Your Own TripTik
Whether you're planning a career or a product roadmap, here's how to think like a TripTik instead of an algorithm:
Start with direction, not destination. "Build products that make work more humane" beats "VP of Product at a public company." "Help small businesses succeed online" beats "Process 1M transactions monthly." Directions flex. Destinations break.
Identify must-see experiences. What would you regret missing? Working at an early-stage startup? Shipping something your mom would use? Building a team from scratch? These are your waypoints. For products: What capabilities must you build? What user problems must you solve? What technical foundations can't be skipped?
Plan in 50-mile chunks. The TripTik showed one segment at a time. Plan the next quarter in detail, the following quarter in themes, everything else in directions. For careers, focus on the next role deeply, the one after that loosely, and let the rest be directional.
Build in rest stops. The TripTik always showed where to pause. Your plans need these too. Regular retrospectives. Time to ask: Are we still headed where we want to go? Is this still the right direction?
Reading the Road Signs
How do you know if you're productively meandering or genuinely lost?
You're on track when:
You're learning something that changes how you work
Each experience connects to your larger direction
The discomfort feels like growth, not drowning
You can explain why this detour matters
You're lost when:
You're only there for the title or metrics
You can't connect current work to larger purpose
You're executing without learning
The anxiety feels paralyzing, not energizing
Your Journey, Your Rules
We create rigid plans not because they work better, but because choosing from infinite options feels terrifying. Black and white is simpler than navigating infinite grays. So we build detailed roadmaps, chart exact career paths, and now ask AI to make these fictions even more precise — as if higher resolution could somehow make uncertainty disappear. But that rigidity is what's making you sick, literally. The tension in your shoulders, the Sunday night dread, the defensive roadmap reviews where you justify outdated decisions.
We kept those TripTiks for years in the seat back pocket of our Jeep Cherokee. Sometimes I'd pull them out and trace the route, remembering not just where we went but what we discovered.
Years after that Disney pilgrimage my family moved to Savannah, GA — a city we discovered on the journey.
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What waypoints guide your planning? How do you balance structure with flexibility? I'd love to hear about the detours that taught you more than any straight path could.