The Pursuit of Happywell

Ep. 8 Behind the Scenes: The Raw Truth About Starting Over


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In this raw and candid behind-the-scenes episode, Kristen and Scott peel back the curtain on what it’s really like to start something new — together. Whether you’re an entrepreneur, changing careers, or simply stepping into a new life chapter, this conversation is for you.

They dive into the high hopes, uncertainties, and unexpected lessons that come when you're building from scratch — all while doing life alongside your spouse. With very little prep and a whole lot of heart, they share stories about startup challenges, unexpected arguments (like co-working chaos and company names!), imposter syndrome, hiring a team, and staying grounded when the doubts creep in.

This episode will inspire you to embrace uncertainty, trust the messy middle, and stay true to yourself even when reinvention feels scary.

In This Episode, You'll Hear:
  • Why uncertainty is a sign you're growing, not failing
  • The surprising emotional work behind launching a startup
  • How working with your spouse can be hilarious (and humbling)
  • What to do when imposter syndrome tries to sabotage your momentum
  • The power of redefining success and setting new "life metrics"
  • How they are intentionally building a mission-driven company without burning out

Key Takeaways:
  • Both excitement and doubt are normal when stepping into the unknown. Growth always brings resistance.
  • Building a company (or a new chapter) is more about intentionality and less about hustle.
  • You don't have to be an "expert" — sharing your experience with authenticity can be even more powerful.
  • Protect your energy by honoring your current season and capacity.
  • Moving from "me" to "we" thinking can transform how you experience change and leadership.

Episode Timestamps:
  • 00:00 — Intro: Taking Big Leaps and Asking, "What Did I Just Sign Up For?"
  • 01:30 — The Reality of Starting Over (With Your Spouse)
  • 04:00 — Startup Expectations vs. Reality
  • 06:50 — Our Funniest Fights While Building Together
  • 12:30 — The "Uh-Oh" Moment That Made It Real
  • 17:30 — How This New Venture Changed Us Personally
  • 24:00 — Lessons on Unlearning Hyper-Independence
  • 30:00 — Feeling Like Imposters — And What Helped Us Through It
  • 40:00 — Life Is Always Life-ing: How to Keep Building Anyway
  • 48:00 — Holding Both Excitement and Terror
  • 55:00 — How We Support Each Other When One of Us Spirals

If you're navigating a new beginning right now or looking to get inspired in your current season of life, Kristen and Scott would like to invite you to join their upcoming Breakthrough Live Summit. While the in-person event is sold out, virtual tickets are available for the May 16th intensive, where they'll guide participants through exercises designed to create breakthrough, clarity, and forward momentum. Find out more and grab your ticket here.

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The Pursuit of HappywellBy Kristen and Scott Boss

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