Why Great Leaders Stop Looking for the Right Answer

"Which way should I go?" Alice asked the Cheshire Cat.

"Well, that depends on where you're trying to get to."

"I don't know," Alice said.

"Then any road will do."

I’ve been on many coaching calls where a founder will ask me: "How do I know if I'm focused on the right priorities?"

I can usually hear it in their voice – that mix of doubt and urgency. The weight of a hundred decisions pressing down. The fear that maybe they are leading their company in the wrong direction.

It’s like Alice, standing at the crossroads. Desperate for the "right" path. Paralyzed by uncertainty.

But the real danger isn't choosing the wrong road. It's waiting at the crossroads, hoping certainty will show up.

Because you're not confused about priorities. You're trapped in a search for certainty that doesn't exist.

Especially when you haven't gotten clear on where you're actually trying to go.

The Question Itself Is the Problem

Most founders believe that good leadership means finding the right answer.

The right strategy. The right priorities. The right way forward.

So when you don't feel certain, you think something's wrong. You doubt your judgment. You second-guess every decision. You freeze.

But here's the hard truth: The certainty you're searching for is a myth.

There is no "right answer" waiting to be discovered. Life isn't a quiz where you get an A if you pick the correct option.

The irony? The more you search for certainty, the more doubt you create.

Trust Your Energy, Not Just Your Intellect

So what do great leaders do instead?

They've stopped asking their intellect to solve a problem it can't solve. They've stopped looking for external validation and started trusting internal alignment.

The world’s best founders don't have more certainty than you. They've just stopped making uncertainty a problem.

They've learned to trust something deeper than their analytical mind – their energy, their intuition, their whole body's wisdom.

Think of it like being a sailboat captain versus a motorboat captain.

The motorboat captain says "I'm going here" and forces it – loud engine, toxic fumes, eventually running out of gas.

The sailboat captain feels where the wind is blowing, senses the current, and harnesses those forces to move forward.

One burns out. The other flows.

When you trust your energy, not just your intellect, something shifts. You stop asking "What should I focus on?" and start asking "What lights me up? What feels aligned with where I'm trying to go?"

I know how counterintuitive this sounds. We're trained to believe the hard stuff is the valuable stuff.

Take Valve, the gaming company, for example. They discovered this same pattern when they let their employees "vote with their chairs" – literally roll over to whatever project excited them, whenever they wanted. Total freedom to follow their energy.

What happened? The projects people were most excited to work on became the most successful games.

Your system has wisdom your intellect hasn't caught up with yet. When you feel genuinely excited about something, you're often sensing its likelihood of success before you can articulate why.

What This Looks Like in Practice

So how do you actually lead when there's no "right answer" to guide you?

Get clear on a vision that excites you: Not the "right" vision for your market or what looks good on paper. The one that feels authentic and energizing to you. Because if you don't know where you're trying to get to, any road will do – and you'll keep second-guessing which road to take.

Notice what lights you up: Pay attention to which work makes you feel alive versus which feels like obligation. That distinction isn't random but is useful data. Your zone of genius is the intersection of what energizes you and what you're naturally great at. Design your role around spending 70% or more of your time there.

Delegate everything else: The work that matters for the business but drains you? That's not a sign you should push through it but an indication of who you need to hire. Some of the best hiring strategies come from asking: "What does the business need that I actually don't want to do?"

Act on what excites you even when you can't articulate why yet: When you feel genuinely excited about something, there's often wisdom there your intellect hasn't caught up with yet. Trust that energy and let clarity emerge from action, rather than waiting at the crossroads for certainty to arrive.

Just Because It’s Easy Doesn’t Mean It’s Wrong

One of my clients was stuck in this exact trap.

"Product development feels like the right thing to focus on because it's hard, so it must be valuable," he told me. "But I hate it. Customer conversations light me up, but they feel too easy – like I'm avoiding the real work."

"What if," I said, "following the thing that lights you up is exactly what the company needs?"

He looked at me like I'd suggested he drive the company off a cliff.

But he did it anyway. He redesigned his CEO role around what actually energized him – being outward-facing, talking to high-value clients, learning directly from the market. Then he hired an exceptional head of product to own what drained him.

Six months later, the company had clearer product direction than ever before all because he followed what energized him.

He stopped searching for the "right answer" and started trusting.

And the path forward revealed itself.

With love,

- Dave Kashen

P.S. If you're struggling to distinguish between authentic wants and ego-driven "shoulds," ask yourself: Am I trying to fill a void with this, or am I genuinely excited about it? The answer will tell you everything you need to know.