Space for serendipity: how to embrace the unknown in product planning

Why a little chaos is a very good thing

If you're reading this, you've likely figured out that our "Roadmap Randomiser™" announcement was our April Fools' joke for 2025. We aren’t launching a moon phase driven prioritisation algorithm—yet.

Today, let’s explore some genuine insights about product strategy that inspired our fictional product.

When "chaos" leads to innovation

While we don't advocate throwing darts at a feature list, there's real value in bringing some chaotic energy to your product thinking:

Value from surprising places

Ever heard of Tiny Spec? No? How about Slack? The Tiny Spec team set out to build a multiplayer game and ended up creating a world-beating communication tool. They noticed when they’d made something valuable—even if it wasn’t what they intended.

Turbo-charged creativity

Companies like Spotify run “hack weeks” where teams work on passion projects. These events regularly lead to breakthroughs that traditional prioritisation would never uncover. Discover Weekly? Yup, that was a hack week baby.

Tinkering space

Google famously dedicated 20% of employee time to “work on things you think will make Google better,” leading to world-changing products like AdSense and Google News. Even the humble Post-It Note—beloved by Product folk—came out of unstructured innovation like this.

So how can we make space for serendipity in our product roadmaps?

Agility means admitting we don’t know enough

In the complex systems we navigate, we simply don’t have enough insight to plan far in advance.

As Melissa Perri explains: don’t try. Be agile. Anchor your product strategy in a long-term vision, then focus only on the next step that gets you closer. When you get there, the world will likely have changed—so reassess and choose the next step from that new vantage point.

Get comfortable with an unclear path. A little wandering is part of the journey.

Explore the future you want to achieve

Try using the Cone of Possibilities to map today’s insights forward—exploring possible, likely, probable, and preferred futures.

It’s a fantastic team exercise that helps you define a strong long-term vision while also surfacing emerging risks that could affect your product’s trajectory.

For example, where might your product land in a world with tighter regulation, emerging competitors, or AI-first user expectations?

Bring that future to life

Use a product vision artifact—like a storyboard, press release, concept video, clickable prototype, or narrative—to help your team and stakeholders experience your preferred future. Whatever format you choose, make sure it triggers emotional buy-in as well as intellectual. A great example comes from AirBnB - they used the tale of Snow White for storyboard vision inspiration. When people can see and feel where you're headed, they can create and innovate toward that destination, even without a fixed roadmap.

Set a clear North Star Metric to define success. Then map out leading indicator metrics that tell you which user behaviours you need to shift to get there. When everyone knows the goal and the early signals, they’re empowered to experiment and contribute—without rigid plans slowing them down.

Celebrate failure and encourage risk-taking

We never innovate if we only commit to ideas we think will succeed.

Great product companies bake experimentation into their DNA. Jeff Bezos once called Amazon “the best place in the world to fail at.” The key is funnelling your bets so you’re testing early and investing effort in the ones most likely to succeed.

Test broadly. Fail fast. Fail cheap.

If you want to build your team’s idea validation muscles, Itamar Gilad’s Confidence Meter and GIST planning frameworks are excellent places to start.

Systems that make space for the unexpected

The most successful product leaders balance rigour with room for the unpredictable. They create systems that support both structured prioritisation and serendipitous discovery.

Because you never know when the butterfly effect might hit your roadmap.

Your roadmap randomiser moments

Have you stumbled into product gold through serendipity or surprise? We’d love to feature your story.

Reply to this email and tell us how chaos sparked innovation in your team. It might just show up in an upcoming post.

Until next time (when we'll be back to our regularly scheduled, non-April Fools programming),

The Product Breaks Team