Do What You Want, Or Just Get Old with Whitney Boyd
Episode Details

Today I talk to Whitney Boyd as part of a special series where I talk to friends about things I’ve always been curious about.  And they get to do the same.  I bring two topics, they bring two topics and we surprise each other - no notice and no preparing answers in advance.  It takes courage and I give Whitney a lot of credit for going through with it. Truth be told, she wasn’t 100% sold on the whole idea.  But as you’ll hear, there is nothing Whitney can’t do.  She’s humble, thoughtful and hilarious.  


I can’t explain why, but something magical happens when you put the right people in front of a microphone and press record.  Although we didn’t plan it, there was a theme that emerged.  It’s about getting older and watching your kids go through things that it feels like yesterday we just went through.  How hard it is to let them make mistakes.  And how much we can learn about ourselves after all these years, as we relive our childhoods vicariously through them.


Please enjoy, Whitney Boyd.


Key Takeaways
  • Just because you’re good at something doesn’t mean you’re meant to do it — and knowing the difference matters more than we admit.
  • The idea that we should constantly push outside our comfort zone is worth questioning. Sometimes comfort isn’t the enemy.
  • Kids often tie their identity to the thing they do most — and when that’s taken away, it can leave a real gap.
  • Parenting is full of invisible emotional moments — like grieving the end of a chapter your kid might not even be thinking about.
  • The things that occupy our thoughts the most (work, appearance, logistics) aren’t always the things we wish did — and that gap is worth paying attention to.
  • Relationships evolve, but expressing things like “I love you” can feel strangely harder as we get older — even when it matters more.
  • Life stages sneak up on you — one minute you’re raising kids, the next you’re balancing that with caring for aging parents.
  • Big life decisions (like where to live) are often less about possibility and more about the stories we tell ourselves about what’s practical or allowed.


Connect with Bob Mathers

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


Links & Resources

Vienna Waits - https://vienna-waits.com/

Whitney on LinkedIn: https://www.linkedin.com/in/whitneyboyd/

Whitney on Instagram:https://www.instagram.com/vienna_waits_studio/


Episode cover art for Do What You Want, Or Just Get Old with Whitney Boyd
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