Sibling relationships, Senior Assassin & Airbnb

3 Things I'm Loving, Reading, Watching or Doing

1. Weekly Teen Email: Financial Sextortion
In my weekly email to my teens, I asked them to read this ESPN article. It’s sad and disturbing. Sometimes these emails are simply a link with little commentary followed by, “Let’s chat sometime this week about it.” It’s been a great way to open the door to challenging conversations.

2. Compatibility Test

An avocado story of marriage.

3. The AI Threat

Podcast - Ex-Google Exec: The Next 15 Years Will Be Hell Before We Get To Heaven! - Mo Gawdat

Would you prefer a future like The Matrix or Ready Player One? Gawdat suggests we might be heading toward a mix of the two. In his bleakest view, we’ll face 12–15 years of chaos before finding any kind of utopia, mostly because we humans can’t seem to prioritize the greater good in the age of AI. Interesting (and scary) discussion.

2 Quotes Worth Pondering

“Keep away from those who try to belittle your ambitions. Small people always do that, but the really great make you believe that you too can become great.” — Mark Twain

“Most people would succeed in small things if they were not troubled with great ambitions.” — Henry Wadsworth Longfellow

1 Big Dad Idea

The Blessing and Curse of Ambition

David Brooks recently wrote a fascinating piece about the blessing and the curse of ambition. He asks the million-dollar questions:

How do you marshal ambition’s energy without being consumed by its insatiable demands?

How do you live a driven life without becoming a jerk?

I think many parents can relate. We want to show up fully for our kids, but we also feel that tug to do big things ourselves. In my own life, it’s often a battle with the ego. Am I motivated by intrinsic good or by the extrinsic rewards of being recognized as good?

Brooks puts it perfectly:

The struggle is between excellence and superiority. Some people’s longings are noncomparative. If they are good at something, that satisfaction is its own reward. Others need to be better than. It’s not enough to be good—they need to come out on top of someone else.

Of course, we all like to think our longings are noble and noncomparative. But if we’re being honest, so much of our world is built on “better than.” Our schools, our careers, our social media feeds. They run on comparison and rankings.

I’ll admit I struggle with this at times. I enjoy the contest. Winning feels good and I’ve won a good bit in my life. But I’ve also had to wrestle with blurred lines and ask myself some hard questions about my deeper motivations. Did I care about being my best or just care about being better than someone else?

And as a parent, how do we offer up these tensions when we talk to our kids about ambition and hard work? For me, it usually means resisting the urge to deliver a mini-lecture. Instead, I like to put the actual question on the table and let them wrestle with it.

Now, the conversation gets even more interesting when you consider the ideas of the podcast I highlighted above. If AI radically reshapes work as we know it and purposeful work disappears, what happens to ambition? Can we find meaning if there’s no ladder to climb and no “better than” to chase?

That thought is both liberating and terrifying. It pushes me back to the question Brooks raises: what kind of ambition actually leads to a flourishing life? Maybe ambition isn’t about climbing higher, but about learning to climb with the right spirit.

I’m clearly left with more questions than answers. If you’ve unlocked a perspective I haven’t considered, I’d love to hear it.