How to Actually Enjoy Holiday Small Talk (And Give Better Gifts for Less) SB1771

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Dec 8, 2025

Charles Duhigg, Pulitzer Prize-winning author of The Power of Habit, shares engaging strategies to transform painful holiday small talk into enjoyable conversations. He emphasizes the power of asking deeper questions and truly listening to foster genuine connections, especially for introverts. The discussion also dives into the benefits of secondhand gifting, highlighting how thoughtful thrifts can save money and be more meaningful. From mastering brief interactions to smart gifting tips, this conversation is a holiday survival guide for everyone.

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ADVICE

Prepare Three Backup Questions

Before a party, write down 3 ready-to-use questions to pull out when conversation stalls.
Use them as a confidence crutch, not a script, so you can relax and engage naturally.

ADVICE

Ask 'Why' To Trigger Real Stories

Swap surface questions for deep ones that ask about motives, values, or experiences.
Ask “Why did you decide…?” to invite stories instead of one-word answers.

ADVICE

Invite Next Steps When Time Is Short

Match your short interaction to the other person's needs by inviting, not demanding, deeper talk.
If time's tight, thank them and ask to follow up by email or lunch later.

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Holiday parties make you want to hide behind the cheese tray. Gift-giving season makes your budget cry. This episode is your survival guide for both.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Pulitzer Prize-winning author Charles Duhigg to turn holiday small talk from awkward endurance test into something you might actually enjoy. Whether you're facing the office party, a family gathering with that cousin who won't shut up about crypto, or the neighborhood potluck where you know exactly three people, Charles reveals how to walk into any room with confidence, even if you're an introvert who'd rather be home watching movies.

The secret? Super communicators aren't the loudest people in the room. They're the ones asking better questions, reading the conversation correctly, and making others feel heard. Charles breaks down the skills that turn painful small talk into genuine connection, and why introverts actually have hidden advantages at holiday gatherings (yes, really).

Then the crew tackles the other holiday stressor of gift-giving that doesn't demolish your December budget. Joe, OG, and Doug explore the rising trend of secondhand gifting. It's not just about saving money (though your wallet will thank you). It can be more meaningful, more creative, and kinder to both your finances and the planet. From thrifted treasures to thoughtful "found" gems, they share how to give smarter instead of just spending more.

Plus, Doug's toilet paper trivia arrives right on schedule (because what's a holiday episode without something unexpected?), along with stories about neighbors behaving badly and a brief tour through apps you forgot you're still paying for.

What You'll Walk Away With:

• Charles Duhigg's framework for turning small talk into actual connection without feeling fake

• Why introverts have secret advantages at holiday parties and how to use them

• Smart, budget-friendly gifting strategies that feel thoughtful rather than last-minute or cheap

• The case for secondhand gifts and how to do it in a way that feels special

• How to avoid blowing your holiday budget without looking (or feeling) stingy

• Creative ways to personalize gifts without overspending or resorting to gift cards

• Why communication skills affect both your happiness and your financial decisions

This Episode Is For You If:

• Holiday small talk feels like torture and you'd rather shovel snow

• You want to give meaningful gifts but refuse to wreck your January budget doing it

• You're an introvert dreading the season of forced social interaction

• You're tired of generic gift guides telling you to "just spend less" without actual ideas

• You believe better conversations and smarter spending are both learnable skills

Before You Hit Play, Ask Yourself:

What's the most meaningful non-new gift you've ever given or received? Think about why it mattered. That's the kind of gifting Charles and the crew are talking about. Drop your story in the comments because we're building the anti-Amazon holiday gift playbook together.

FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-actually-enjoy-holiday-small-talk-1771/

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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