Roadmaps Are Unreliable

Forget Roadmaps—Think in Directions

Let’s be honest: most roadmaps are just PowerPoint fiction.

You know the ones. Color-coded quarters. Neatly stacked features. Arrows flowing like everything is linear, predictable, and tidy. And yet—every software team knows what actually happens: half the stuff gets pushed back, priorities shift, and three months later, the roadmap looks more like a list of broken promises than a plan.

We don’t lack planning. We lack honesty about what’s plan-worthy.

It’s time to rethink the roadmap.

The Further You Plan, the More You Guess

Imagine you’re planning a cross-country road trip. You map it all out in advance: every city, every meal, every bathroom break. But the second day in, a storm hits. A detour adds four hours. The hotel you booked closes down. Your perfect plan? Gone.

Software is like that. Except the storm is your CEO changing priorities, the detour is a new piece of tech debt, and the hotel is a third-party dependency that just deprecated their API.

The problem with roadmaps isn’t the idea of planning. It’s the illusion of predictability. The further out you go, the more variables you’re stacking—market shifts, customer feedback, technical unknowns, team bandwidth. Every month you extend the roadmap, the confidence in it should halve.

But that’s not how we treat them. We act like Q4 plans made in Q1 have divine authority.

Roadmaps as Expectation Debt

What starts as a flexible plan quickly becomes a contract—especially in organizations that crave certainty.

“We promised this to the board.”

“It’s in the roadmap, we need to deliver.”

“Marketing already has the campaign ready.”

Suddenly, you’re not solving problems—you’re delivering expectations. Expectations that were often based on incomplete information, outdated assumptions, or political expediency.

And here’s the kicker: when the plan doesn’t survive reality, teams get blamed. Not the roadmap.

The Alternative: Plan by Direction, Not Destination

There’s a better way: trade in fixed roadmaps for strategic directions.

Instead of saying:

“We’ll launch Feature X in July, then Feature Y in August, and complete System Z by Q4.”

Say:

“We’re focused on reducing churn by improving the first-week user experience. We’ll experiment with onboarding flows, review activation data weekly, and evolve our approach based on what works.”

That’s not vague. That’s agile in the original sense: responsive, iterative, grounded in reality.

Real-World Directional Thinking

Let’s say your company wants to improve payment reliability.

Roadmap thinking might say:

Q2: Migrate to Stripe Connect

Q3: Add PayPal support

Q4: Launch multi-currency handling

Directional thinking reframes this:

“Our direction is to increase payment success rate and reduce support tickets. We’ll validate which providers offer the most reliability in key markets, and invest in the integrations that offer the highest ROI.”

This lets you learn as you go. Maybe Stripe’s API isn’t the bottleneck—maybe your internal retry logic is. Maybe multi-currency isn’t the issue—maybe it’s card rejection due to address mismatches. A fixed roadmap would have you chasing the wrong solutions for three quarters.

“But Stakeholders Need to See a Plan”

Sure. But what they actually need is confidence, not certainty.

Instead of feeding them a fictional timeline, show them:

Themes (e.g. “Global expansion readiness”)

Problems you’re attacking (“Churn in week one,” “Failed payment retries”)

Signals of progress (“We’ll move to the next stage once success rate hits 98%”)

This creates transparency without overpromising. You still have goals. You still make decisions. But you’re not chaining yourself to guesses masquerading as guarantees.

Direction is Honest. Roadmaps are Theater.

Let’s not pretend we can predict the future. Let’s stop writing fiction to make other departments feel better. Let’s be honest about how teams really work best: by staying aligned on purpose, focused on outcomes, and free to adapt based on what they learn.

Roadmaps promise control. Directions offer clarity without constraint.

And in a world that changes faster than your quarterly deck, clarity will take you further.