Attending conferences can be overwhelming — even for the most excited extroverts among us—let alone the introverts who challenge their comfort zone in the registration process alone.

Today, my friend Alisa and I do an in-person debrief of our recent week-long adventure at the TED global conference in Vancouver (my second time attending, her fifth). We cover conversation openers, the power of a genuine compliment, trying (and sometimes failing) to approach people we admire as a peer, handling the inevitable FOMO and big feelings that arise, when to call it quits (what I call “falling off the cliff”), and so much more.

Be sure to also keep an eye out on the Free Time podcast (even better, subscribe!) for Friday’s episode #196, where I share a mini daily audio diary that I kept on each day of the conference, with some additional reflections at the end.

More About Alisa: Alisa Cohn has been coaching startup founders to grow into world-class CEOs for nearly 20 years. She is the author of From Start-Up to Grown-Up, and hosts a podcast of the same name. A onetime startup CFO, strategy consultant, and current angel investor and advisor, she has worked with startup companies such as Venmo, Etsy, and more.

🌟 10 Key Takeaways

Have a repertoire of different openers to approach people with.
Wear a “talk piece” clothing item that invites people to comment on.
Approach as a peer vs. fangirling (which might occur anyway!)
Sit in a central public place to catch conference passers-by.
Message people right after you meet them about something you spoke about.
Text a “wish you were here!” selfie to mutual friends as a way to keep in loose touch.
Prepare for the emotional ups and downs you’re going to feel when you’re in large groups.
Embrace JOMO when you need a break, knowing when you’re at your best.
Don’t be afraid to call it early in the evening if/when you’re feeling New Friend Fatigue.
Follow up with connections after you return home by scheduling a dinner reunion.

✅ Try This Next: Alisa: Go and meet one new person—strike up a conversation with someone you wouldn’t normally speak to and see what happens. Jenny: Put yourself in the path of people. Is there an event, a book reading, even a bench in the park where you can encounter people you normally wouldn’t?

🔗 Resources Mentioned

📚 Books Mentioned

From Start-Up to Grown-Up by Alisa Cohn
The Long Game by Dorie Clark
The Happiness Project by Gretchen Rubin
Presence by Amy Cuddy
The Courage to be Disliked by Ichiro Kishimi and Fumitake Koga
Free Time: Lose the Busywork, Love Your Business
Pivot: The Only Move That Matters Is Your Next One
Life After College

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