Stuck Following a Plan? The Best Leaders Pave Their Own Path

When Lewis and Clark set out from St. Louis in 1804, their main mission was to chart a water route across the continent and reach the Pacific Ocean. Beyond that, almost everything was uncertain. Existing maps of the American West were mostly blank space, filled only with speculation and hearsay. No one in their party knew what they’d encounter once they left.

In the end, the expedition never found the fabled Northwest Passage. But ultimately, it didn’t matter. Over the course of two years, they cataloged hundreds of species unknown to science, forged relationships with Indigenous tribes and mapped terrain no outsider had ever seen. Their journey didn’t follow a prescribed route, because there was no route — and in that lay its value.

Business is no different. Leaders tend to love roadmaps because they create the illusion of clarity and control. But in uncharted territory, following such a map can be more dangerous than helpful. Imagine if Lewis and Clark had narrowed their goal to finding that water route, blinding themselves to the other wonders and opportunities that filled their expedition. They would have declared the mission a failure instead of bringing back invaluable knowledge that reshaped the nation’s understanding of the West.

My take? Entrepreneurs should treat the unknown in the same way as Lewis and Clark: not as an objective to be conquered, but an opportunity to explore.

The explorer mindset

Every big idea, whether it’s a business or a product, should solve a problem in a novel way. That was true before AI became the disruptive force that it is, and it’s even more true now. Think of AI as the Wild West. As a leader, it’s your job to discover the possibilities that exist in the vast unknown.

But this isn’t to say that you shouldn’t lay the necessary groundwork before your expedition. Just because Lewis and Clark didn’t have a roadmap didn’t mean they were setting off unprepared. Lewis, a former Army captain, studied medicine, botany, astronomy and zoology, in addition to analyzing existing maps, accounts and any other information on the region he could find. Clark, for his part, was a mapmaker and former soldier, and together they assembled the Corps of Discovery — nearly four dozen men skilled in hunting, building and survival. They may not have known what they’d encounter, but they were prepared in every possible way for whatever they’d find.

The same philosophy should be applied to running a business. You don’t have to know exactly where you’re going, but you’d do well to be prepared. Study your competition. Read blog posts, watch videos and listen to podcasts about the latest trends in your industry. Equip yourself and your team, if you have one, with the skills and tools you need to adapt when the unexpected appears.

Because it will. Markets shift, technologies evolve, customer needs change — and no roadmap can predict all of it. What matters is having the foundation to endure uncertainty and the curiosity to see possibilities where others see only risks.

The problem with roadmaps

Roadmaps aren’t just ineffective — they can also be bad for business.

Why? Because as soon as you publish a roadmap, you’ve created expectations. That might sound like a positive, but it’s actually not. If the idea you’ve plotted does come to fruition, there’s no reason for users to be excited, since it was what they already anticipated.

And that’s the best-case scenario. If you don’t deliver on your promise, it sows mistrust and can lead to anger. Elon Musk, for example, started promising in 2016 that Tesla’s total self-driving capabilities would be available in just two years; eight years later, the functionality he promised — “a complete full self-driving car” — has yet to materialize. Instead of delighting users with surprise progress, Tesla has faced the opposite: customers frustrated by delays and critics quick to point out broken promises. The roadmap itself became a liability.

Public roadmaps also drain motivation from leaders. Making goals generates positive feelings, but the trick is that in order for these emotions to be motivational until our goals are realized, the reward has to be time-released, writes neuroscientist Marwa Azab. Publicizing our intentions (or in this case, our roadmap) gives us all our dopamine at once. “The more others admire our goals, the more dopamine rush we get, and the less likely we are to execute the future necessary actions to implement them,” Azab says.

Roadmaps limit discovery. If your goal is to chart new territory and build something truly useful, preparation matters — but so do curiosity and adaptability. Equip yourself for the journey, then let go of the roadmap. The most valuable opportunities will reveal themselves along the way.

When Lewis and Clark set out from St. Louis in 1804, their main mission was to chart a water route across the continent and reach the Pacific Ocean. Beyond that, almost everything was uncertain. Existing maps of the American West were mostly blank space, filled only with speculation and hearsay. No one in their party knew what they’d encounter once they left.

In the end, the expedition never found the fabled Northwest Passage. But ultimately, it didn’t matter. Over the course of two years, they cataloged hundreds of species unknown to science, forged relationships with Indigenous tribes and mapped terrain no outsider had ever seen. Their journey didn’t follow a prescribed route, because there was no route — and in that lay its value.