No #190 | October 12, 2025

by Matthew Boyd

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

We were at Costco the other evening and they're selling Christmas advent calendars that are the size of a door👀.

We bought 4 of them😂.

In this week's Lead It Cool newsletter:

• 🦃Thanksgiving
• 🤔Coaching
• ❓That's a Great Question!
• 😂Giving Thanks
• 😎Cool Links

🦃Thanksgiving

This Monday is Thanksgiving (in Canada!).

In my opinion, Thanksgiving is the best holiday. It doesn't have the gift pressures of Christmas, the high expectations of New Year's Eve, the sunburns from Canada Day or the sugar rush/crash of Easter. It's a day where the only expectation is to be with your friends/family and eat, drink and be merry.

Thanksgiving is also a day for gratitude, as it was traditionally a day to celebrate the harvest and the blessings from the year.

And did you know that expressing gratitude is good for your brain?

According to Harvard Health Publishing, "gratitude is strongly and consistently associated with greater happiness. Gratitude helps people feel more positive emotions, relish good experiences, improve their health, deal with adversity, and build strong relationships."

And if you're looking for pop culture inspiration on giving gratitude, look no further than Leonardo DiCaprio.

In the final scene of the movie Don't Look Up, as the meteor is moments away from ending all life on planet earth, DiCaprio's character, Dr. Randall Mindy, sits with the people that he loves for one final meal.

In a moment of existential clarity and inevitability, he says this:

It's a hauntingly beautiful quote that exposes the fallacy of constantly seeking more, when everything you need is often right in front of you.

Have a very happy Thanksgiving.🦃🍷

🤔Coaching

Earlier this week, a baseball pitcher for the Philadelphia Phillies (Orion Kerkering) made a terrible mistake that cost his team the game and the series. Here is the play.

My heart always breaks when a game is decided by one player's error.

As the dejected pitcher walked back to the dugout, his coach pulled him aside and gave him words of encouragement.

Someone on Twitter acknowledged this moment and shared a quote that a previous coach had taught him:

"There's a time to coach, and a time to have compassion."

Great quote for anyone out there who coaches youth sports.

❓That's a Great Question!

Have you ever noticed how often people respond to being asked something with "...that's a great question."?

Well there's a fun Freakonomics podcast that delves into why people do this.

​Here's the link.​

Spoiler: I think people say that because they think it accomplishes two things simultaneously: it allows them to stall for time, and it flatters the interviewer.

😂Giving Thanks

Dad jokes 😂

😎Cool Links

🔒The Great Lock In of 2025. Like many of us, a few content creators on TikTok entered 2025 with great expectations for all they might achieve, only to end the summer feeling somewhat adrift. But rather than admitting defeat, they decided it was time to get going. With typical Gen Z hustle, they declared that the Great Lock In of 2025 would start on September 1 and continue until the end of the year. Unlike New Year’s resolutions, The Great Lock In has an end date. And unlike many online challenges, the Great Lock In isn’t restricted to fitness goals. Everyone’s free to identify their own list of what they’d like to achieve. The goal is to take back control of your life in an otherwise uncertain world.

🙂The Girl Dad Movie Canon. One Battle After Another has a lot going on, but at its core, it’s a movie made by a dad of teenage daughters, about a dad of a teenage daughter struggling to accept that the reward of raising a child well is seeing her surpass you in every conceivable way. And remembering that when that time comes, you have to turn on your listening ears, hurry your ass into that car, and charge your damn phone. This is a rich tradition, with countless touchstones. In his desperation to get Willa back—and also let her go—Bob instantly became one part Taken dad and one part Father of the Bride dad, with a hint of Les Misérables amidst-a-revolution found father, packaged inside the schlubby pre-makeover complacency of Crazy, Stupid Love dad.

💡Wake up! Do Not Lie There Thinking! We will not “think our way” out of that chatter in our heads. We will not overcome it by reasoning with it or listening to it as if it were talking sense.

🤯Videos like this is why I still love the internet.

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Thank you!

Let’s connect! 💬 You can find me on LinkedIn and Twitter