Hey Reader,

A friend of mine reached out recently, someone I’ve known for years. They’ve spent decades building an impressive career and a life that they’re proud of. They’ve always been one of those people who was energized by their work. They had the right attitude, they were engaged with their role, and by every external measure, they had built the life they wanted.

What they told me in private was a different story entirely.

We were talking one evening about what we hoped the next few years would be like. The casual kind of conversation you’d have between friends. And at one point, they told me how they really felt.

“I’m just white-knuckling it until I can retire.”

I was floored. I would never have guessed that they felt that way. They appeared so happy, for so long, that I think they even convinced themselves at points in their life. What made it harder was that I knew they had a couple of years left before retirement came around. They were resigned to the idea of spending a few years in what they described as misery, just hoping that afterwards, their “real life” would start.

And the hardest part about all this is that this isn’t the first time I’ve had this conversation with someone. These talks don’t happen too often, but they’ve shown me one thing that’s worth mentioning:

Too many senior leaders are performing a version of happiness just because they’ve “made it.”

There are very few places where we can admit how we truly feel. We definitely can’t say this on LinkedIn. Or post about it on Facebook. We’d be lucky to say it to someone in person and not become the talk of the office by the end of the day. So instead, we keep it inside, plaster on a smile, and just white-knuckle it until we find a way out.

Part of that silence is self-preservation. There could be real consequences for saying the wrong thing to the wrong person. But part of this is also from an unsettling feeling underneath all the pressure: guilt. When you’ve built an impressive career, reputation, and a life that others would want, how could you feel anything but grateful? It feels like a problem you’re not allowed to have.

So you keep performing. And because many people around you are performing too, you assume you’re the only one who feels this way.

You’re not.

We’re all part of this play, even though none of us signed up for it.

And underneath this performance are five patterns you’re probably familiar with. It’s worth looking at them again with fresh eyes.

​The Speed Trap​

• The belief that slowing down means falling behind, that rest has to be earned and stillness isn’t safe.
• This shows up as your calendar always being full, discomfort with silence, or a sense that slowing down even for a moment means falling behind.

​The Identity Trap​

• When the line between who you are and what you do disappears entirely.
• It can look like vacation anxiety, difficulty imagining life outside the role, or a fear that without your role, there’s not much left.

​The Title Trap​

• The belief that stepping back from your title would be a loss.
• It can look like evaluating opportunities by how they’d appear externally or staying for the title even after the work stops fitting.

​The Alignment Trap​

• Excelling at something that no longer connects to what you care about.
• It can look like going through the motions, or finding that you’re drawn to almost anything but the work in front of you.

​The Metrics Trap​

• The need to measure and quantify everything.
• It can look like obsessively tracking your progress or struggling to feel good about achievements unless there’s a number attached.

Most people who sit with these honestly find that one or two fit better than the others. That’s a good starting point for understanding where you are right now.

There isn’t a single solution to figuring everything out. Some of what needs to change comes down to organizational structure. You need to set stronger boundaries between your work and your life. Or you might need to tweak your work so it’s more aligned with your values.

No matter what the next step for you is, you just need to know: You don’t need to white-knuckle through things until retirement. And you don’t need to throw away everything you’ve built. What I can say right now is that you have permission to be honest with yourself. You don’t have to tell anyone how you’re feeling yet, and you don’t need to have everything figured out. If one of those traps in particular made you think, “That sounds like me,” tap the title for a worksheet to help you through it.

Whatever you’re feeling right now, you’re not alone. And if you discover something you do want to share, hit reply. I read every response.

From one human to another,

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