The companies that grow fastest treat failed experiments as valuable lessons, not mistakes.

Ezra Bailey | Getty images

Key Takeaways Assumptions are often wrong. Even well-funded, highly confident marketing campaigns can fail, while unexpected ideas can succeed, making testing essential. Innovation requires psychological safety. Teams are more willing to experiment and uncover winning strategies when failure is met with curiosity and learning rather than blame.

There’s an old sailor’s proverb: “You can’t control the wind, but you can adjust your sails.” This wisdom applies in business, too. The companies winning right now aren’t the ones with crystal balls or perfect five-year plans. They’re the ones who’ve built organizational muscle for rapid but measured adaptation.

Running an insurtech company in the specialty jewelry and wedding space, I think about uncertainty constantly. Insurance is, at its core, the business of managing risk. We price risk, anticipate what might happen, and prepare for scenarios we hope never occur. That mindset has shaped how I build teams, and it’s become increasingly relevant as AI and technology reshape entire industries overnight.

The truth is, there’s no guaranteed roadmap anymore. You have to build your own. For some people, that’s terrifying. For others, it’s genuinely fun. Knowing which type you have on your team makes all the difference.

Failure is just data in disguise.

What I tell every new hire at BriteCo is: We’re not afraid to fail here. When things are uncertain, it’s almost a certainty that not everything you try is going to work. Some people call that failure. I don’t. I call it trying and learning that particular approach didn’t work, so you try something else until it does.

This distinction matters more than it might seem. If your team is afraid to fail, you’re stuck in quicksand. Nobody moves. Nobody tests. Nobody learns. The organization becomes paralyzed precisely when it needs to be most agile.

At BriteCo, for example, we’ve put a lot of money behind marketing campaigns that we swore were going to succeed, and they fell flat on their faces. Other campaigns we launched despite some serious doubts, and they worked. We wouldn’t have known what approach would draw customers without a willingness to learn from the flops and take chances on the unconventional.

Building a culture where failure is treated as useful information rather than a career-limiting event requires intention. You have to make testing and pivoting feel rewarding, not risky. Nobody should be afraid that they’re going to get in trouble or looked down upon for trying something that doesn’t work. Instead, the response should be curiosity about what we learned and what we’ll try next.

Get the right people in the boat.

You can have the best strategy in the world, but if you don’t have the right people rowing, you’re going nowhere fast. You need folks who aren’t inherently afraid to test, try, fail and try again. Some people genuinely thrive in ambiguity. Others need clear, predictable paths to do their best work. Neither type is wrong, but only one belongs on a team that needs to adapt quickly.

Once you have the right people, leadership’s job is to steer the boat, demonstrate an openness to ideas and create space for them to do their best work. That means listening to feedback constantly.

A lot of the technology changes that we make and the features we add come from listening to our customers and actually taking action to address their concerns. As the people on your team are talking on the phone, responding to customer emails and analyzing chats, they’re sorting out which feedback is giving strong signals and which is just noise. The best feedback is valuable, real-time intelligence about what’s working and what isn’t. If you, as a leader, aren’t accepting, understanding and acting on that feedback, you’re flying blind.

Tools matter as much as mindset.

Some companies hire great people, build a supportive culture and then neglect to give their teams the resources they need to actually execute. If your team has the right mindset and you’ve built the right environment, but they don’t have the tools to act on feedback quickly, none of it matters.

In insurance, we take a data-driven approach to managing uncertainty. We gather as much information as possible, form hypotheses about what we think will happen, then test those predictions against reality. When the data tells us we were wrong, we revise and try again. It’s a continuous process of tweaking the plan based on what we’re actually seeing.

This same approach works across any business function. It’s not a one-time exercise. It’s a forever process of pivoting and constantly refining your hypotheses.

The companies that will thrive in 2026 and beyond aren’t the ones predicting the future with perfect accuracy. They’re the ones building teams that can adapt calmly when predictions prove wrong. They’re hiring people who see ambiguity as an opportunity. They’re creating cultures where trying something that doesn’t work is just another step toward finding what does. And they’re investing in the tools and processes that let their people move quickly without breaking things along the way.

Uncertainty isn’t going away. The question is whether your team sees it as a threat or as the environment where they do their best work.

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