How To Make Friends After 30 with Alyx and Bob | Chasing Curiosity and Sharing Boundless Insights from Ideas that Matter

Today we invite back Alyx Parks, a great friend, conviction coach, writer, fly fishing guide, and one of my favourite people to have unhinged conversations with.

This episode is a bit of an experiment. We both brought 2 topics to discuss, but didn’t tell each other ahead of time. No research, no prepared answers, no performance.

What came out was a wide-ranging, honest, funny, and surprisingly deep discussion about making friends after 30, tattoos and identity, fear of judgment, and why we’re all so afraid to just pick up the phone and call someone we miss.

Please enjoy, Alyx Parks - unhinged.

Key Takeaways

• Birthdays can bring a quiet kind of grief—not just about age, but about who we were, who we thought we’d be, and who we’re becoming.
• We’ve been conditioned to fear phone calls and doorbells, but random, agenda-free connection can be one of the greatest gifts we give and receive.
• Tattoos aren’t really about ink—they’re about identity, intention, permanence, and who we’re doing things for.
• Making friends after 30 is hard, vulnerable, and necessary—and sometimes it starts with simply saying hello or asking someone for coffee.
• Fear of failure is often really fear of judgment, and most of that judgment lives only in our own heads.
• Letting “future you” handle the hard moments can be a powerful way to move through fear and self-doubt.
• Growth often looks messy in real time—and cringing at your past self might actually be proof that you’re evolving.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

https://www.wilderpath.co

https://www.linkedin.com/in/alyxparks

https://www.instagram.com/ontarioflygirl

https://www.ontarioflygirl.com/