What Hard Seasons Actually Teach Us About Leadership

A theme in my last few episodes has been around the things carry into our leadership that we never planned to bring. The stuff that showed up because life handed it to us, not because we sought it out. So naturally, it’s been top of mind for me - not in a way that feels heavy, but in a way that feels clarifying.

I am not talking about a professional development course or a leadership book. I am talking about the seasons that changed you. The ones that required something of you that you did not know you had.

The Version of Yourself You Had to Leave Behind

I think most of us can point to a version of ourselves we outgrew. The leader we were before something cracked us open a little. Before we went through the thing that taught us patience we did not know we needed, or empathy we thought we already had.

The honest truth is that I used to think empathy was something you either had or you did not. Like a personality trait, fixed and finished. What I understand now is that empathy deepens. It grows with experience. Specifically, it grows when you have been through something hard enough that you stop assuming other people's lives look like yours from the outside.

That shift does not happen from reading about it. It happens from living it.

What Uncertainty Does to a Control Freak

There is a particular kind of difficulty that comes from going through something you cannot control, manage, or strategize your way out of. And if you are the kind of person who moves fast, sets high expectations, and runs toward challenges, that kind of uncertainty is its own education.


I have come to believe that the leaders who handle complexity and ambiguity best are not the ones who were born unshakeable. They are the ones who went through something that forced them to develop that muscle. Who had to learn, because there was no other option, how to keep functioning when the outcome was not guaranteed.

That is a different kind of resilience than the kind you get from a keynote.

Empathy Is Not a Soft Skill

I want to push back on the idea that empathy is something we bring to work despite professionalism. I think it is one of the most strategically undervalued things a leader can develop.

In partnership work, in team leadership, in any relationship where trust is the currency, the people who get the furthest are almost never the ones who played it most strategically. They are the ones people actually wanted to work with. The ones who showed up as real humans and made it safe for others to do the same.

There is a reason trust is hard to build and easy to lose. It requires consistency and a genuine interest in the person across from you. Not performing interest. Actually having it.

Building the Bigger Table

There is a difference between scarcity thinking and abundance thinking in leadership, and how much the hard seasons we go through can shift us from one to the other.

When you have been through something that stripped away the noise, you tend to get clearer on what actually matters. On who you want in your corner. On what kind of leader you want to be when things get hard.

And I think that clarity is what makes some people builders and others hoarders. The ones who go through difficulty and come out more generous, more connected, more committed to making room for other people at the table.

That is not an accident. That is the work.

What I Am Taking From This

I walked away from this conversation thinking about the moments in my own career where I had to unlearn something I thought I knew. The expectations I had to revise. The version of tough that I had to trade in for something more honest.

And I am reminded that the hardest seasons do not just happen to us. They happen for us, if we are willing to let them. Not in a toxic positivity way. In a real way.

The lessons you take from the muck are the ones that actually stick.

Check out the full episode: People First: Resilience, Authenticity, and the Art of the Frenemy ~ with Danielle McNamee on Apple Podcasts. 

Or watch it on YouTube.

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