The higher you climb, the less you develop.


Hey Reader,

When did you last do something specifically to get better at your job?

If you’re having trouble coming up with an answer, you’re not the only one.

Most of us leaders follow the same path without even realizing it. Early in our careers, our main focus is on developing our skills. Great organizations invest in our learning, training opportunities, and chances to grow. We’re paired with mentors who are genuinely in our corner, and we spend days or weeks each year centered on growth and development.

Then, as we become more senior, the nature of that support changes. The mentors who were once invested in your growth now look to you to do the same for others. You might be leading training days rather than attending them. You’ve had so much experience in solving problems that rarely do you need to come up with a new solution. No one says it out loud, but the message is that you’ve made it. You know what you’re doing, and now it’s time to pass the torch to the next generation.

We can absorb that message without questioning it. And why would we? The training sessions aren’t as plentiful, calendars are already packed, and there are fewer obvious moments that signal we need to do things differently.

On top of our own busy schedules, it’s important to think about the environment that we find ourselves in. If you’re in a big organization that’s been around for decades, you’ve probably heard the phrase “That’s just how we do things here” more times than you can count. There’s a certain pride in what makes a company distinctive, and that pride can make it harder to question the way things are done, even at an individual level. And the same instinct can apply to how we approach our own development.

With all this in mind, it’s easy to believe that there’s nothing left to improve. And when you’ve worked hard to get to where you are, the idea of seeking out extra learning or coaching can often feel like something’s off. That little voice in the back of our head saying, “I’ve made it this far, I shouldn’t be struggling with this.” Even though there’s no such thing as a leader who’s “made it” and has nothing else to learn.

I like to think about learning through the eyes of a professional athlete. Think about it, people are training for the Olympics right now who have absolutely no ego when it comes to their training program. If their coach tells them to change their form, they change their form. If the data says they need to work on a specific weakness, they work on that weakness. They focus on the method so that when it’s time to perform, they’re better than last time.

Corporate culture tends to work the other way. We’ll constantly perform at a high level and rarely stop to evaluate ourselves. We keep doing things the way we’ve always done them because it works. But if we truly want to make change and lead in a way that feels right for us, we have to be willing to stay curious. We need to make sure we embrace a growth mindset.

And that doesn’t mean we suddenly have to clear our schedule and lock ourselves into a classroom. Most of us, when we imagine training, picture workshops or days out of the office. It certainly can be that, but it doesn't have to be. Take a moment to think about the times when you really learned something pivotal to your career.

In my experience, the most valuable lessons I’ve had didn’t come from a training day or classroom. They came from what most people would think of as a normal work day. In a conversation that went somewhere unexpected. In a decision you delegated and then watched someone else approach differently than you would have. In a piece of feedback you sat with long enough to actually hear.

Learning doesn’t just happen on a dedicated day.

So the question worth sitting with this week is a simple one:

Is there something you’ve been meaning to try or explore in your leadership that you haven’t got around to yet?

If you want some extra accountability, you can reply and tell me your answer. I’d love to hear it.

From one human to another,

600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246
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A Normal Tuesday by Clif Mathews

You built everything you were supposed to build. And you're questioning everything. Quietly. It's not burnout. It's not weakness. It's the slow realization that somewhere along the way, you stopped living your life and started managing it. You're not alone in this. I spent 25 years chasing achievement before I saw it clearly. Every Tuesday, I write about what I found. The patterns. The permission to want something different. The occasional uncomfortable truth. No optimization hacks. No hustle. Just honest exploration from someone a few steps ahead on the same path.

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