How to Handle a Relationship Crisis

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

1. Have a repertoire of different openers to approach people with.
2. Wear a “talk piece” clothing item that invites people to comment on.
3. Approach as a peer vs. fangirling (which might occur anyway!)
4. Sit in a central public place to catch conference passers-by.
5. Message people right after you meet them about something you spoke about.
6. Text a “wish you were here!” selfie to mutual friends as a way to keep in loose touch.
7. Prepare for the emotional ups and downs you’re going to feel when you’re in large groups.
8. Embrace JOMO when you need a break, knowing when you’re at your best.
9. Don’t be afraid to call it early in the evening if/when you’re feeling New Friend Fatigue.
10. 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

• Alisa on the web, Twitter: @AlisaCohn, LinkedIn: @AlisaCohn
• Articles: Andrew Wilkinson on Medium (founder of Tiny capital)
• Video: Lizzo thanking Beyoncé at the Grammy’s

📚 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

🎧 Related Episodes

• Other Shows: The Tim Ferriss Show — Alisa Cohn on Prenups for Startup Founders, How to Reinvent Your Career, the Importance of “Pre-Mortems,” and the Three Selves (#539)
• Pivot: 298: Networking in a New Niche and Becoming Broadway Investors with Dorie Clark and Alisa Cohn, 285: Cultivating Influence with Jon Levy, 293: 🍝 Are you a Spaghetti-Twirler or a Spaghetti-Thrower?
• Free Time:192: 📲 5 Creative Ways to Better Organize Your Phone Contacts, 196: What do Donuts, Coffee, Conversation, and Energy Cliffs Have in Common? (Coming soon!), 043: From Start-Up to Grown-Up (and Coach to Author) with Alisa Cohn, 035: The Long Game with Dorie Clark

Learn more about your ad choices. Visit megaphone.fm/adchoices