In this episode of Shadow Work, WTF?, I’m joined by my friend, student, mentor, colleague—and occasional co-conspirator—Breanna May, for a no-holds-barred chat about the messy, chaotic, and weirdly beautiful parts of life and business. You know, the kind of conversation where you’re halfway through and suddenly hit that wall of, “Wait... what the hell is any of this even for?” Yeah, we’re going there.We’re talking about what happens after you’ve done all the shadow work, personal development, and hustling to build the life of your dreams, only to realize you’re now sitting in the middle of an existential crisis wondering, “Wait... this is it?” Breanna and I get real about the highs and lows of entrepreneurship, why success can feel like one big ‘meh,’ and how to find meaning when you’ve checked off all the boxes but still feel like something’s missing.Expect personal stories, navigating business slumps, motivation crashes, and plenty of tangents—because somehow we end up talking about everything from nihilism to Tantra. This episode is packed with laughs, deep insights, and some “WTF am I doing with my life” moments we can all relate to.

Key Points and Timestamps

00:00:00 - Welcome to the Sh*tshow

• Meet Breanna, and why podcasting solo is like screaming into the void.

  
  

00:03:35 - So, You’ve Got It All... Now What?

• That awkward moment when you realize success doesn’t fix everything.

  
  

00:07:49 - Hustling for What Exactly?

• Spoiler: Chasing money and success is exhausting, but we still do it.

  
  

00:12:16 - The Biggest Lie in Personal Growth

• Plot twist: You’re never going to ‘fix’ everything, no matter how many crystals you buy.

  
  

00:18:48 - When Life Feels Like One Big "WTF"

• What to do when your goals stop making sense and existential dread kicks in.

  
  

00:27:37 - Marketing Without Being a Jerk

• How to talk about struggles without making people feel like total failures.

  
  

00:36:53 - Embracing the Hot Mess Express

• Newsflash: You don’t have to be perfect to be successful (or sane).

  
  

00:41:29 - How to Not Lose Your Soul in Business

• Trying to run a business without becoming a robot? Same.

  
  

00:49:25 - Spicing Up the Bedroom (Yes, We Went There)

• Caitlin spills on how she keeps the heat alive—even when baby-making is involved.

  
  

00:56:40 - Adulting Is Hard, Let’s Play Anyway

• Forget clubbing (sometimes)—here’s how to actually have fun as a grown-up.

  
  

01:03:00 - Final Thoughts: Are We Even Doing This Right?

• A reflective (but still kinda chaotic) wrap-up on life, business, and surviving it all.

  
  

• Follow Breanna May on Instagram: @iambreannamay

  
  



• Become a Shadow Work Coach: @shadowalcheycoachingacademy

  
  

If this episode resonated with you, please share it with a friend who could use some real talk about success, shadow work, and the wild ride that is life. Don’t forget to tag me on Instagram with your biggest takeaway!

• Instagram: @complete_bycaitlin