DiscoverThat Greenwich LifeEp 2, Season 2: Why The Things That Stretch and Scare Us Help Us Grow The Most
Ep 2, Season 2: Why The Things That Stretch and Scare Us Help Us Grow The Most

Ep 2, Season 2: Why The Things That Stretch and Scare Us Help Us Grow The Most

Update: 2025-12-01
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This episode pulls back the curtain on the night so many of you followed, supported, and helped bring to life: That Greenwich Life Live at the Hyatt Regency Greenwich.

If you’ve ever taken on something that stretched you, scared you, or demanded a fuller version of yourself — this episode will feel familiar in all the best ways.

It’s about the honest emotional journey so many of us face behind creating something new: the excitement, the fear, the vulnerability, the imposter syndrome, the gratitude, and the surprising lessons that surfaced along the way.

From raising a GRAND TOTAL of $15,600 for Pencils of Promise (YES!!!), to the sea of sequins and sparkle — this episode is a reflection on what happens when a group of like-hearted women gather with intention.

I’m also recapping all the exciting things that happened between the end of Season 1 last spring and now. 

It’s an episode you don’t want to miss! 


Thank You to Our Sponsors and Partners

Thank You Also to Our Travel Partners

The Wanderer - Kennebunk, Maine

The Hilton Tulum Riviera Maya - Tulum, Mexico

Pestana Blue Alvor Beach - The Algarve, Portugal

Excellence Punta Cana - Dominican Republic

The Grove Resort - Orlando, FL


Let’s Connect!

If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. Watch this full episode on my Youtube Channel. 

Until next week - don’t just live your life, LOVE it!


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Ep 2, Season 2: Why The Things That Stretch and Scare Us Help Us Grow The Most

Ep 2, Season 2: Why The Things That Stretch and Scare Us Help Us Grow The Most