The Gratitude We Rarely Talk About

Most generational CEOs don’t lack gratitude.
They’re just carrying the kind that doesn’t fit on a greeting card.

It’s the kind that comes with tension, irritation, and hard-earned insight.
And it often points to exactly what’s ready to evolve.

Here’s what discomfort can reveal if we’re willing to listen.

As we head into Thanksgiving, I’ve been thinking about the usual messages we all receive (and send) this time of year. They contain some message of gratitude for team members, customers, partners, and family. And it is all great and true.

But the generational leaders I work with are holding something more complicated: it is gratitude, but mixed with fatigue, responsibility, and the weight of what still isn’t quite right.

So this year, I’m thinking about a different kind of gratitude.

I’m grateful for the things that make us uncomfortable.

I’m grateful for the moments when something in the business really starts to irritate us.

• The salesperson you overhear selling something you no longer offer.
• The website that doesn’t at all reflect your current customers and focus.
• The long-time partner who refers your competitor because they didn’t think you were a fit.
• The next-gen voice who is pushing to see a clear roadmap for professional growth and succession when you don’t have one.

I’m sure you have your own examples to add to the list.

In the moment, these things can feel frustrating, inconvenient, or even threatening. They often force uncomfortable conversations, or accountability for situations we have created ourselves.

But in almost every generational business I’ve worked with, these are the exact catalysts that move a family company from maintenance mode into true stewardship.

“How am I complicit in creating the situation I say I don’t want?”

Jerry Colonna, author of Reboot, lists this as one of the essential questions that leaders should be continually asking themselves. It’s a deceptively simple question, but in generational businesses, it forces us to look at our own role in the patterns we say we want to break.

And I think it is one of the practical ways that we can approach these “irritations” with humbleness, curiosity, and yes, even gratitude.

If we don’t like how the market is talking about us, what are we doing to change the conversation? If we are frustrated that the next generation doesn’t have an ownership mentality, what are we doing to foster it?

When, as leaders, we have the courage to meet these frustrations with openness, something remarkable happens: the discomfort actually becomes directional. You start to tackle problems that before had just simmered, and have conversations that were years in the making.

And that is the energy I want to take with me into the end of the year, and what I want for you. That “cleaning before company comes” kind of energy, the impulse to finally deal with things we’ve been stepping over.

So if you’re heading into the holiday feeling grateful and a little worn down or fed up, you’re not alone. You’re in the exact place where some of the strongest generational brands have found their next level.