Curiosity Wins

The other day I was having one of those rare, valuable, deep conversations with my son. He’s 15, which means he has that particular teenage confidence that does not always come with much appreciation for nuance. He’s also smart enough to make arguments that sound right on first listen, which is usually how people, adults included, get themselves into trouble.

I eventually realized I do not actually need to win every point with him. What I want is something simpler and harder. I want to teach him how to be wrong and how to recover from it without turning it into shame or a fight.

It is better to be right eventually than feel right right now.

That line is easy to agree with in theory. In practice, it runs into one of the strongest forces in leadership: the desire to be seen as certain. Executives are rewarded for conviction. People look to you for direction. Your name comes up when there’s an open board seat, a community issue, a tough call that needs a steady hand. Over time, it gets tempting to confuse being trusted with being correct.

If you’ve found any success, it’s also easy to start getting high on your own supply. You have pattern recognition. You have instincts that have paid off. You have stories you can tell about times you were right when everyone else hesitated. Those are real strengths. But they can quietly turn into a weakness if they make you less curious.

Curiosity is not asking more questions in meetings so you sound thoughtful. Curiosity is the willingness to look for what is true, even when it threatens what you already said out loud.

Hank Green, a science educator, talks about the difference between arguing like a lawyer and arguing like a scientist. A lawyer argues to win one case. If precedent is on their side, they lean on similarity. If it is not, they lean on differences. They show what helps them, and they keep the rest tucked away unless they are forced. They use opaque but often brilliant sounding rhetoric to confuse the point rather than elucidate it. A scientist argues because they think they are observing something real. They show their work. They invite critique. They try to simplify where possible. They want other smart people to stress test the idea, not because they enjoy being challenged, but because the goal is to arrive at what is right, not to win a single disagreement.

This is a useful mirror for leaders because most of us, under pressure, default to lawyer mode. We build a case. We select the facts that support the plan. We describe the outliers as exceptions. We defend the decision because we made it, and being wrong feels like it will cost us authority.

But here’s the uncomfortable truth. A leader who cannot change their mind is not strong. They are brittle.

Real strength is the confidence to be wrong and try again.

That is not a moral statement. It is a practical one. It is especially practical in small business, where you do not have the budget or the time to stick with a losing strategy just to protect your pride. Big organizations can afford to be slow learners. They can carry expensive mistakes for a long time, sometimes without anyone outside the building noticing. Most smaller firms cannot. If you keep walking in the wrong direction, the numbers will tell on you quickly.

That is why curiosity matters. Curiosity is how you notice the early signs that the story in your head is drifting away from reality. A customer keeps asking the same question, which means your message is not landing. A deal keeps stalling at the same stage, which means something in your process is creating doubt. A key employee stops disagreeing and starts going quiet, which usually means they have decided it is not safe or useful to be honest. Those are not random annoyances. They are information.

The ability to change your mind is what you do with that information.

To be clear, changing your mind does not mean changing direction every week. It means having enough self control to separate your identity from your opinion. It means being able to say, given what we knew then, this made sense, and given what we know now, it doesn’t.

The leaders who do this well have a particular kind of confidence. They can make a call without theatrics, and they can revise a call without drama. They do not treat the update as an admission of incompetence. They treat it as a normal part of staying aligned with what the world is actually doing.

This is where curiosity becomes cultural.

If your team thinks you need to feel right, they will protect you from reality. They will soften updates. They will delay bad news. They will quietly build workarounds instead of bringing you the underlying issue, because workarounds are safer than telling the boss their plan is not working. If your team believes you would rather be right eventually than feel right right now, they tell you the truth sooner. They bring you what they are seeing, not what they think you want to hear. That is not just nicer. It is faster. It saves money. It prevents small problems from becoming expensive ones.

So when something goes sideways, and something always does, the question is not just what happened. The question is how you responded. Did you get curious, or did you start building a case? Did you look for the simplest explanation, or the most flattering one? Did you invite critique, or did you seek confirmation?

Brilliant but wrong does not help anyone. It does not help your team, it does not help your customers, and it definitely does not help your bottom line.

When you are wondering what went wrong, look around, listen, and ask yourself one question.

Am I arguing like a lawyer or a scientist?

Be a David in the time of Goliaths

When I wrote about taking advantage of volatility two weeks ago, I did not imagine just how quickly the roller coaster would take off. It feels like 2026 might be a year unlike any we have lived through. It is usually a fool’s errand to predict what your business will look like five years down the road, but right now it is hard to imagine what the landscape will look like even a month out.

Uncertainty does something strange to otherwise rational people. Customers hesitate. Vendors tighten terms. Good employees start scanning the horizon. Leaders who are usually decisive begin to second guess themselves because every decision feels like it carries twice the usual risk. Everything has an asterisk attached to it.

America’s small businesses are not built to withstand extended uncertainty. Most of us operate on thin margins and limited slack. We are built for motion, not for whiplash. That is exactly why leaders need to do something that will feel counterintuitive.

Now is the time to go all in on lean, flexible, easy to pivot strategies. Lean does not mean cheap. It means less waste and faster feedback. It means fewer bets that require you to be right six months from now, and more bets that let you learn what is true in the next few weeks. Flexibility does not mean indecision. It means building your work so it can bend without breaking.

If you have projects that you have allocated six months to, break them into smaller pieces that still produce something usable. Not “progress,” something real. A process that reduces errors. A trimmed offering that is easier for customers to say yes to right now. If a project cannot produce a tangible improvement in thirty days, it is probably too big for this moment, or too vague, or both.

This is also the moment to check on the relationships that usually sit quietly in the background. The vendor who always delivers. The referral partner you have not talked to in months. The long term customer who never complains but might be quietly rethinking spending. Do not wait until you need a favor to remember the relationship exists. A simple call that says, “How are you doing, what are you seeing, and how can we stay ahead of this together?” will do more for your resilience than another late night of spreadsheet work.

Most importantly, the communities you exist in need to be shored up and affirmed. When times get uncertain, it is tempting to narrow your focus until all you can see is your own ledger. I understand that instinct. But small business depends on trust, reputation, and customers believing you will still be there next month. In an environment like this, community is not a soft value. It is a hard asset.

The future will require leaders who lead with vision, but now more than ever, leaders also need compassion and a focus on the whole community, not just their own walls. Compassion is not charity. It is clarity about what people can actually carry right now. It is choosing fewer priorities instead of pretending you can do everything. It is taking care of the relationships that will outlast whatever this year brings.

As we all tighten our belts, it is tempting to circle the wagons. The problem is that circling the wagons also blocks your view. The only way through a season like this is together. We come out stronger if we lean on each other for ideas, help each other adapt, and create new pathways forward. Along with this will come new markets, new partnerships, and new visions for what life can look like.

There will be companies large enough to weather this storm with little change, but this newsletter is not for them. Their playbook is built on scale and buffers. Yours is built on speed, trust, and the ability to make decisions without asking ten people for permission. Make sure you are not looking at Goliath to learn how to be David.

If you are feeling the pressure right now, you are not alone. The goal is not to predict the future. The goal is to build a business that can respond to it. Shorten the distance between decision and feedback. Turn long projects into small wins. Strengthen the relationships that make you resilient. Invest in your community, because your community is what will carry you through.

- Dylan