The October Shift: Anchored by Courage

The calendar flips from September to October, and suddenly, it's not just a date change, it’s a mental one. The easy flow of summer, full of listening to people outside my usual circles, narrows. My summer was a gift: engaging with different people in amazing settings, from world-class thinkers at conferences like the All-In Summit to quiet conversations with friends by the campfire. I have been struggling to consolidate those threads into a coherent narrative that could be of use to my community of friends like you.

As we head into this pre-winter sprint, the core message is that we are all in this together. Our job is to find the courage to step up and make the contribution we can make.

Holding Two Things in Our Head

I’ve been consolidating a critical idea over the past few weeks, and it’s about how we move forward without burning out. It takes the ability to hold two thoughts at once:

• You are enough. Right now. Your current state is worthy.
• You can and should raise your standard. Seek your next best level of competency.

This isn’t a paradox. It’s the recipe for forward motion powered by purpose, not by anxious energy. That anxious striving, the stuff that drains your precious fuel, comes from feeling like you’re not enough. True growth is fueled by that peaceful self-acceptance. Knowing you're enough gives you the space to look for where you can be more.
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The ability to do this allows you to move forward with purpose and not with anxious energy, which ends up draining you of precious fuel.

Does this resonate at all?

What’s In the Bottom of Your Boat?

In a recent conversation about leading yourself, my daughter Brooke and I revisited a foundational family image: the boat. Specifically, what do you put at the very bottom to create a deep, heavy, and steady keel? What steadies you when the water gets choppy?

We landed on faith, courage, and duty. Those are the essentials that create a strong sense of self and commitment when the world feels volatile.

This image emerged from what we called the Boat Talk with Ryan and Brooke. When they turned ten, I told them they were going to go on great adventures, and Sara and I were going to spend the next eight years building them their own imaginary boat. Most importantly, they were the captain when we were in their boat!

The real message was about agency: they would be in charge of their own lives and their dreams. We’d be in our own boat, and we were jointly part of a fleet. It worked. At the dinner, the night before he left for college, Ryan even mentioned in the prayer that he was ready to get in his boat and start his adventures. I cried.

This scaffolding, this feeling of being ready for adventure, is what allows them, and us, to set high standards while still knowing we’re enough. It helps us connect to a cause and find the immense bonding that comes from working through difficulties with others.

The Choppy Waters of Change

Many times, in 2025, the amount of change, its pace, and its manner have shaken people. I have witnessed great despair tied to gun violence, and how we are grappling with how we communicate anger as a society; it can make you sad and mad.

This is where courage matters. As writer Peggy Noonan has recently observed in her columns, those who are the responsible parties, which is to say, all of us who seek to contribute, must invest in our ability to have courage and not let despair dominate our thoughts. When you are shaken, you turn to that deep keel.

This challenge is showing up in business, too. My observation, validated by people like Chamath Palihapitiya on a recent Allin Podcast, is that many mature industries, especially those run by Private Equity firms, do not have the right incentives to use AI in a truly transformational way.

Which begs the question: How long is it going to take for some of these mature industries to really take advantage of the power of the new tools?

The bigger the organization, the more they talk about using the new tools, but the less likely they are to actually implement them. It feels like the roles people have at these companies are rigid, almost like a bus route that can't change on its own. New processes and paths are treated like a virus.

This tension is real: the need from the top to say you are using the new tools versus the challenge for the people delivering the solution every day. Can you trust the new tech? Is it commercially ready? The companies that have been formed in the last two years, however, do have significant advantages in being AI natives, and not having to get rid of legacy systems could be a big deal.

Our Best Contribution Could Be with Our Family

If our geography can be a type of fate, and if our culture serves as a form of destiny, then family can be the crucible where both are formed.

So, as we head into this pre-holiday season, let's leverage our strong sense of self, purpose, and commitment to listen to where others are coming from and seek a broader alignment. Let's use our gifts to help others and have the courage to take action in the face of change.

Thanks for your friendship and readership,
Drew

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