66 weeks ago, we started The Huddle with one simple question:

What truth would have helped us sooner?

The idea was never to become another leadership newsletter.

It was to have the conversations we're living in real time as we build companies, lead teams, and try to become better leaders.

The conversations that somehow never make it into the job description.

Leadership has a funny way of making perfectly normal experiences feel deeply personal.

Like replaying a conversation all the way home, wondering if you were too hard... or not hard enough.

Putting off making a decision because you know the email you need to send will change someone's life.

Spending half of dinner half-listening because your mind is still in the meeting that ended hours ago.

Watching other leaders around you wondering why they seem so confident while you're constantly questioning whether you're getting it right.

Then someone finally puts words to what you've been experiencing.

And you remember…

You're not fucking crazy.

You're learning to lead people while you're still learning to lead yourself.

While trying to leave people better than you found them without abandoning yourself along the way.

And there aren't many things harder than that.

So whether you've been here since the beginning or just joined us recently, thank you for inviting us into your inbox.

We know attention is earned, not expected.

And if we're going to keep earning a place in your inbox, we want to make sure we're listening as much as we're writing.

So we'd love you to hit reply and tell us:

What's one part of leadership you wish you'd had more help navigating?

It doesn't have to be polished.

Just honest.

Your replies will shape where we take The Huddle next, whether that's the conversations we have, the resources we create, or the ways we can better support you along the way.

Thank you for spending part of your Mondays with us.

We don't take it for granted.

Appreciate you being here in the Huddle. For deeper dives into leadership and culture, join us at Out of Office: The Experience on YouTube and Podcast.

The Huddle

P.S. Know a leader who’d value this? Forward them this week’s Huddle.

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