Hey Reader,

A friend of mine reached out to me a while back. He's a senior leader who has spent decades building a career he was genuinely proud of. The kind that looks impressive on paper and earns respect in any room. He had the title, a strong team, and hit financial goals. But something had changed. He told me he needed a path that felt closer to his own idea of success. The next time we met in person, we talked through what his new path might be, and I asked him what his version of success looked like.

He laid it out without hesitating. An impressive title, a strong team, hitting bigger financial goals.

You're seeing the problem here, right?

Before he could go any further, I stopped him. I asked him why he needed that version of success. What was it about those goals that appealed to him?

He went quiet for a bit before he said,

“I've never really thought about it any other way.”

I've had versions of that conversation more than once. A lot of executives reach a point where they know something has to change. Then they go about planning what's next in exactly the same terms as what came before, without realizing it.

There's a Stoic idea I came back to lately. Seneca described two forms of poverty:

The first is not having enough to meet your basic needs.

The second is chasing more, even when you already have more than you need.

That second form of poverty is its own kind of trap, and it's dressed up as ambition. Most of us have been chasing goals in a certain way since we were young. It earned us praise, rewards, and celebrations from others around us. Over time, that becomes the only model for what success looks like. So even when we're looking for something different in our lives, we reach for the same playbook without even realizing it.

I've seen executives make seven figures and still feel like it isn't enough. There's this thought in the back of their heads saying, “Well, what if I try to go for $1.2 million? And maybe $1.4 million after that?” And still, if you ask them if they really need that much to feel settled, they wouldn't be able to clearly answer. They don't have a definition of enough. They just know that bigger is the right direction.

This is what I call the Metrics Trap. When we only value what we can measure (like money), the parts of life that can't be measured so easily start to disappear. Joy, meaning, real connection. And instead, we keep optimizing for what is easily visible, and wonder why the happiness we're chasing still hasn't arrived.

The harder part, and the part I don't think gets talked about enough, is what it actually feels like to accept that a smaller number might be enough. For leaders who have spent decades building their identity around achievement, accepting the idea that less is sufficient can sound like we've stopped trying to be our best.

Most of us have never actually defined what enough looks like. We set goals, hit them, celebrate, and move on to the next one. Sitting down and asking what would be enough for us is truly uncomfortable, especially for senior leaders. When we're used to being the high achiever, any answer that's less than “the best” feels like a failure, even when it's right for us.

The transition to a new form of achievement starts to feel like a loss before it feels right, and that's completely normal. At first, you will feel like you're going backwards, but being aware of that discomfort can make the process of finding what's right for you less disorienting.

A lot of what we’ve been exploring here is what I’ve built my keynote around. It’s a talk that helps organizations give their teams most leadership conversations don’t: the language to explain why they feel disconnected from their success, and permission to start exploring how to close that gap. If that’s a conversation you’d like to bring into your organization, you can reply to this email or find out more here.

When did you last pause to ask yourself what “enough” looked like?

Hit reply and tell me what comes up. I read every message.