The Voice

on confidence, insecurity, and keeping both

I want to write about something that doesn’t come up much in leadership writing, probably because it’s uncomfortable to admit.

Sometimes “the voice” shows up.

You may know the voice. The internal commentary that questions whether you actually know what you’re doing. Whether you’re as good as people seem to think. Whether the next conversation, the next interview, the next decision is going to be the one that reveals the gap between how you come across and what you actually feel on the inside.

I’ve been a VP. I’ve led organizations of hundreds of people. I’ve written books, given keynotes, and built platforms that serve thousands of engineers. And the voice still shows up sometimes. It’s not loud or constant, but it’s there enough for me to notice it.

I’m writing this because I think a lot of leaders feel this way and nobody talks about it.

What the Trail Taught Me

Last year I hiked the Pacific Crest Trail. 2,655 miles from Mexico to Canada. Somewhere around mile 1800, I noticed that a low background hum I hadn’t even known was there had gone quiet. I wrote about it in a post called Zen-Spy: the gradual discovery that the ambient worry that had been with me for years had dissolved somewhere in the miles.

What surprised me most wasn’t that the hum disappeared. It was that I hadn’t known it was there.

I think the voice is like that for a lot of leaders. It’s not loud enough to name. It’s just there, running in the background, occasionally showing up at inconvenient moments. Maybe before a hard conversation. Or when something doesn’t go the way you expected. When you’re between things and the external validation that usually drowns it out goes quiet.

Being between jobs, as I am now, is one of those moments. The calendar is clear, and nobody needs me right now. The decisions that confirm my judgment aren’t flowing. And the voice, which had been easy to ignore when I was busy, gets a little more airtime.

What I’ve Learned to Do With It

The instinct is to silence it. To push through, project confidence, and hope nobody notices. That instinct is understandable and mostly wrong.

The voice isn’t always lying. Sometimes it’s pointing at something real: a gap in my knowledge, a relationship that needs attention, a decision I haven’t fully thought through. Leaders who suppress the voice entirely stop getting that signal. They become the kind of confident that tips over into arrogance, certain they’re right because they’ve stopped listening to the part of themselves that might disagree.

But the voice isn’t always right either. Often it’s just old, and sometimes it’s blatantly wrong. It’s carrying fear from a context that no longer applies, or running a threat assessment on a situation that doesn’t actually require one.

What Zen-Spy taught me is that the goal isn’t to eliminate the voice. It’s to get better at listening to it without being driven by it. To notice it, take what’s useful, and let the rest be noise.

That’s not a skill you develop once. It’s a practice - and some days it’s easier than others.

Why This Matters for the Teams You Lead

Leaders who have made peace with their own insecurity tend to create safer environments for the people around them. They can sit with uncertainty without projecting false confidence. They can say “I don’t know” without it feeling like a collapse of authority. They can hear hard feedback without becoming defensive, because they’ve already had the harder conversation with themselves.

The leaders who have never examined their own voice, or who have buried it so completely they’ve forgotten it’s there, are often the ones who make it expensive for their teams to be uncertain. Who read honest questions as challenges to their authority. Who mistake psychological safety for weakness because they’ve never allowed themselves to be uncertain in public.

Your insecurity, handled well, makes you a better leader. Not because suffering is virtuous, but because the practice of sitting with discomfort and continuing to show up anyway is exactly what you’re asking your teams to do every time things get hard.

Still Zen-Spy

I’m still Zen-Spy. The trail name stuck because it described something real: a more grounded, present, observant version of me. That version doesn’t disappear when the voice shows up. It just notices the voice, acknowledges it, and keeps walking.

It’s not confidence instead of insecurity, it’s confidence alongside insecurity.

The voice shows up, but we don’t have to let it drive.

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If this resonates, or anything else I’ve written has, I’d like to talk.

Start a conversation here.