No #193 | November 2, 2025

by Matthew Boyd

Good morning, welcome to the weekly Lead It Cool newsletter.

Hope you all enjoyed the extra hour of sleep. This is also my annual opportunity to post my absolute favourite meme😆. Great song too.

In this week's Lead It Cool newsletter:

• 💔Heartbreak
• 🔐Cybersecurity
• 😆Teenagers
• 😎Cool Links

💔Heartbreak

There’s a song by Wilco called I Am Trying to Break Your Heart.

I suspect when Jeff Tweedy wrote it, he wasn’t thinking about sports, but for whatever reason, that song has always reminded me of what it means to be a sports fan. To love a team so much that, inevitably, it will break your heart.

Last night, the Blue Jays lost Game 7 of the World Series to the Los Angeles Dodgers. The circumstances were heartbreaking because they were... oh... so... close.

As time moves on there will be the usual platitudes (“there’s always next year”) but most fans know opportunities like this don’t come around very often.

But the heartbreak is proof that you cared.

That for a few weeks in October, we all believed. And that belief, no matter how fragile, fleeting, and foolish as it sometimes feels, is what keeps us coming back for more.

🔐Cybersecurity

This is a good reminder of the importance of cybersecurity.

It took me a few moments to catch the scam in this image. Do you see it?

😆Teenagers

It's that time of year...😜

😎Cool Links

🤔Leadership Habits that Build Trust and Respect. Most leaders think they’re good listeners. Few actually are. Listening is focusing so completely on the other person that you forget your own agenda for a moment. When you listen like that, people notice. They feel heard. They start sharing real information—the kind that helps you make smarter decisions.

⚽Diary of a CEO - Jurgen Klopp (podcast). Fantastic podcast with lots of great insights (h/t to GH for the recommendation).

🤯PlayPhrase. Type in any phrase you want and this website will generate movie clips where that phrase is used.

😑The Word of the Year. Dictionary.com's word of the year... is... 67. Sigh...

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