What was the one conversation you had over the past year that really stuck with you? Maybe it was about tech, or war, or parenting, or Elon Musk. Maybe it was with your best friend, or your mentor, or a fellow entrepreneur, or your dad. But whatever it was, you’ll be carrying it with you into 2023—and probably longer.

In a year of so much unpredictability and volatility, these human-to-human moments helped us feel like we weren’t alone—or stuck in an AI simulation. And so we asked some of the most interesting and connected people we know—among them Seven Seven Six founder Alexis Ohanian, Thrive CEO Arianna Huffington, Cloudflare CEO Matthew Prince, Yelp CEO Jeremy Stoppelman and 15 others—to recount their most memorable conversation from 2022.

Many of the discussions within tech this year hung heavy on people’s minds, a stark departure from the high-flying days of the recent past. But many of the leaders we spoke to expressed unextinguished optimism about what’s to come. Take Hilary Coles, founder of teletherapy startup Hims & Hers, who recounted a conversation with her OB-GYN following her daughter’s birth: “Parenting has made me a lot more comfortable in being imperfect,” she said. “Not every decision I make will be perfect, and I’m taking more joy in the journey.”

What follows is a collection of perfectly imperfect moments from the past year. All interviews were conducted by The Information reporters Abram Brown, Annie Goldsmith, Margaux MacColl and Arielle Pardes and have been condensed and edited for clarity.

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