Trusting Inner Knowing - On conviction, uncertainty, and the courage to move forward

There’s a quiet but persistent question that shows up again and again in leadership—and perhaps most acutely for first-time founders:

How do I know?
How do I know this is the right direction?
How do I know this decision won’t cost us something essential?
How do I know when to hold my ground—and when to let go?

We often talk about conviction as though it’s a trait some people simply possess, as though a state of full clarity arrives and then certainty precedes action. But for most people—especially those operating in complex, uncertain environments—certainty is rarely available. Waiting for it can become its own kind of paralysis.

Not trusting oneself doesn’t always look like hesitation. Sometimes it shows up as flip-flopping between decisions, which quietly erodes confidence with each reversal. Sometimes it looks like over-consulting—asking one more person, running one more analysis—often without a clear sense of what “enough” would look like. Sometimes it shows up as pushing forward aggressively, mistaking force for confidence. And sometimes it looks like staying still, or stuck, because the cost of being wrong feels too high to bear.

Fear of failure can certainly play a role, of course. But often what’s underneath is more layered.

There is the fear of disappointing or negatively affecting others.
The fear of being judged—by investors, by teams, by peers.
The fear of making a decision that cannot be undone.
The fear that if this goes wrong, it says something lasting about who I am.
And, although it can feel counterintuitive, sometimes what we fear most is getting it right—and the unknowns that would open up if we did.

So, how do we know? How do we trust? This is where self-trust is often misunderstood.

Trusting oneself does not come from having confidence that you will be right.
It comes from having confidence that you will recover when you are wrong.

When leaders equate self-trust with being right—when every decision is measured against a capital-R “RIGHT”—the stakes become existential. Conviction can harden into defensiveness, or dissolve into indecision.

But when self-trust is rooted in recovery—in the knowledge that you can repair, learn, and re-orient—movement becomes possible again. Action no longer requires “certainty”. It requires coherence: a felt alignment across values, perception, intention, and action. A sense that, even as conditions evolve, this is something you can stand behind. Often it arrives quietly—this feels directionally right—before language, justification, or proof have caught up.

This kind of knowing is contextual, not absolute. It is shaped by experience, values, attention, and the ability to tolerate discomfort without rushing to resolve it. It strengthens through practice—especially the practice of noticing how you respond when things don’t go as planned.

For founders, this becomes increasingly important as building their business and organization grows more complex.

Early on, decisions are often reversible. Feedback loops are short. As teams expand, stakes increase, and there’s more distance—geographical, organizational, psychological—decisions carry more weight and less certainty. There can be a temptation to slow everything down, to seek broader consensus, to demand more data. Sometimes that is appropriate. And sometimes it is a sign that leaders are trying to manage complexity by demanding a level of certainty the situation simply can’t offer.

Inner knowing develops, in part, through learning to distinguish what kind of decision you are facing. Some decisions benefit from careful analysis. Others require experimentation. Some can be revisited. Others cannot. Self-trust grows when leaders stop applying the same decision standard everywhere and instead match their approach to the nature of the situation at hand.

It also grows through remembering past recoveries.

Most leaders can point to moments they would never choose again—decisions that didn’t work, paths that closed, mistakes that carried real cost. What is often overlooked is not the misstep itself, but what followed: the adaptation, the repair and the resilience that emerged quietly over time.

This is not about romanticizing failure. It is about recognizing that leadership is not a performance of infallibility. It is a constant practice of discernment under conditions that are messy.

Inner knowing is supported when we create enough internal safety to pause. This doesn’t have to be long; it is a deliberate, conscious moment. When we allow ourselves to feel discomfort without immediately needing to act. When we can distinguish what is happening from our fear-driven interpretations layered onto it—and urgency from importance. When we widen the aperture enough to see the forest we are in, not just the bark of the tree directly in front of us.

Over time, self-trust becomes less about arriving at the “right” answer and more about staying in relationship with oneself as conditions change. About being able to say, honestly:

I don’t know for sure—but I know how I will meet what comes next.