We made it to the end of the year Reader!

I was always planning to take a look at When Harry Met Sally for my New Year’s email, since it’s my all-time favorite movie and the New Year's scene still makes me cry every time. The recent loss of Rob Reiner hit me harder than I expected, and I realized it’s because he’s connected to so many stories that shaped me. It only feels fitting to end the year breaking down one of his films.

I’ve always loved a good rom-com, and When Harry Met Sally is iconic in the genre. There are movies you rewatch because they’re comforting, and movies you rewatch because they still feel true. When Harry Met Sally is brilliantly both.

The one thing that has always intrigued me about this particular story is the central question it poses: “Can men and women really ever be just friends without sex getting in the way?”

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But it’s not just a curious question—it’s the spine of the film. Every phase of Harry and Sally’s relationship exists to support, challenge, or complicate Harry's belief that the answer is no. As their story unfolds over a dozen years, we come back to asking the question, and trying to validate (or invalidate) his thesis.

When Harry Met Sally works not because it’s romantic. It’s because it presents an argument—and gives itself permission to be wrong along the way.

When it comes to public speaking, a lot of the clients I work with come to me with ideas of talks that are built around a topic:

• leadership
• resilience
• confidence
• heck, even storytelling

Topics are safe. Topics are expandable. Topics are comfortably universal.

But an argument is riskier.

An argument forces you to take a stand. It creates tension. It invites disagreement. It demands structure. And it gives your audience something to test as they listen.

Harry isn’t just talking about friendship. He is arguing for his worldview. Sally is too. The audience stays engaged because we’re watching their beliefs collide, soften, fracture, and evolve.

Without that argument, the story would just be two likable people orbiting each other for twelve years. Fine. Pleasant. Forgettable.

Thought leadership isn’t about having a perspective, it’s about interrogating one.

The magic happens when your stories function as evidence or push against the belief you’re exploring.

As you look at building your argument, try this:

1. Finish this sentence:
   “This talk is ultimately asking …”
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2. List 3–5 stories or examples you currently use. For each one, label it:
   • supports the argument
   • challenges the argument
   • complicates the argument
3. If a story doesn’t do any of those things, it’s either decorative, or it needs sharper framing.

The talks people remember are the ones built around a clear argument—the ones that challenge our worldview and invite us to think differently. How are your stories supporting or challenging an argument?

Thank you for sticking with me on this project the past four months. It's been so much fun and I really appreciate all of the lovely responses I get each week.

To loosely paraphrase a favorite quote from Finding Audrey, "May the coming year find you moving more or less upwards in your journey."

Cheers,