Your Roadmap is a Lie (And That’s OK)
How continuous planning and trust can outperform any long-term roadmap.
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Read time: 6 minutes
If you're a product manager, the word "roadmap" might make you feel a bit queasy. There's this persistent, almost romantic idea that product roadmaps should be stable, linear paths guiding us to success, but what we end up with often looks more like a winding rollercoaster with surprise twists from market changes, CEO whims, and customer demands. Yet, somehow, as PMs, we keep hoping for calm seas in a business world that's practically a hurricane every other week.
Look, I get it. I've been there, religiously following every piece of advice from Marty Cagan's "Inspired", devouring every product newsletter on Substack, and meticulously crafting those beautiful roadmap views in Productboard or Notion. We've all done it. The PM world has sold us this dream of perfect quarterly plans and neat execution frameworks. It's like trying to build a sandcastle during a tidal wave.
When frameworks fail
I used to be a framework junkie. RICE scoring? Check. Opportunity solution trees? You bet. Value vs. Complexity quadrants? Had them plastered on my wall. Then, I joined a hypergrowth startup where our biggest competitor would ship major features every other week. Suddenly, all those frameworks felt like bringing a protractor to a street fight.
Don't get me wrong - frameworks are useful thinking tools. But somewhere along the way, we started treating them like gospel. It's the product management equivalent of thinking following a workout plan perfectly matters more than actually getting stronger.
The brutal truth about market changes
Here's a fun story: In my last startup, our team spent a few weeks meticulously planning a major platform upgrade. The roadmap was perfect, stakeholders aligned, and everything groomed and ready. Then, our biggest competitor launched a game-changing feature, our partners changed their developer API terms & conditions, and our top customer threatened to leave over a performance issue.
Just another Tuesday in tech, right?
The reality is, market speed has fundamentally changed. Your competitors aren't waiting for your quarterly planning cycle. Customers aren't organizing their needs around your sprint schedule. And that shiny new technology you're planning to adopt? It'll probably be outdated by the time your long-term roadmap "completes."
Finding balance: The six-week cycle
After years of quarterly planning PTSD, I realized I needed a different approach—something more adaptable and realistic. That's when I stumbled onto something that actually works: six-week cycles, inspired by Basecamp's Shape Up method and adapted to fit our needs. Not sprints, not quarters - cycles. Here's why:
Long enough to build something meaningful
Short enough to change course without massive waste
Natural breakpoints for reflection and adjustment
Maps well to human energy levels (try staying excited about the same initiative for 3 months)
But here's what makes it really work: continuous strategy. Each cycle isn't just about delivery - it's a chance to reassess, realign, and readjust based on what's actually happening in your market. Think of it as strategic planning in perpetual motion.
Recharge with a cooldown week
The secret sauce? Week six is a cooldown week. Not a planning week, not a catch-up week - a cooldown week.
The main benefit? It gives everyone time to recharge and invest in future growth, which ultimately boosts productivity in the long run.
During this time:
Engineers can tackle that technical debt they've been eyeing
PMs can do deep discovery work without delivery pressure
Designers can explore new patterns and ideas
It's a deliberate break to recharge and refocus every six weeks, ensuring teams stay fresh and motivated. And surprisingly, it makes the other five weeks way more productive.
Trust over roadmaps
Here's the real kicker - our obsession with detailed long-term roadmaps often masks a trust problem. When executives demand to see the next 12 months mapped out, they're usually saying, "Prove to me you know what you're doing." When PMs resist changing plans, we're often saying, "Trust that we did our homework."
I learned this the hard way at my last company. Instead of fighting for roadmap stability, I started spending more time building trust through small wins and transparent communication. By consistently delivering small, valuable increments and being open about our process, we replaced the need for detailed roadmaps. The funny thing? Once trust was established, nobody cared much about long-term roadmaps anymore.
Rethinking success
The mindset shift that changed everything for me was moving from "What can we finish?" to "What do we care about finishing?"
It sounds subtle, but it changes everything:
Instead of cramming features into arbitrary time boxes, you focus on impact
Instead of measuring velocity, you measure value delivered
Instead of following a static plan, you follow market signals
When we made this shift, our team started shipping better features faster - not because we planned better, but because we stopped letting the plan get in the way of progress.
Facing the reality of product management
Let's be honest with ourselves:
That 12-month roadmap? It'll change by month 2
Those precise story point estimates? Creative fiction
The perfectly groomed backlog? A security blanket
Instead of pretending we can predict the future, what if we got really good at:
Shipping small, valuable changes frequently
Building trust through consistent delivery
Staying close enough to users and the market to spot shifts early
Making decisions quickly with incomplete information
Reality isn't as tidy as we'd like, but adapting fast is the superpower we need.
Staying focused with a North Star metric
But wait - doesn't all this flexibility mean we'll lose sight of our long-term goals? It's a valid concern. The answer is no, and that's where your North Star metric comes in.
Every cycle ties back to your North Star (I talked about this in a previous post). If it's reducing cart abandonment, every six weeks you're tackling a piece of that puzzle - whether it's performance, UX issues, or missing features. The path might zigzag, but the destination stays constant.
Adaptability: The only real truth in product management
The best PMs I know don't have the prettiest roadmaps - they have the fastest learning cycles. They're more like rapid-response teams than long-term planners.
Think of it this way: If product management was a sport, would you rather be really good at creating game plans or really good at reading the field and adapting in real time?
Stop beating yourself up about changing plans. The market doesn't care about your roadmap. Your users don't care about your process. They care about getting value, consistently and reliably.
Your roadmap is a lie, and that's OK. The truth is in what you ship.
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— Sam ✌️