282: Jen Underwood — How to Say What You’re Feeling

28 Jan 2026 · 45 min
Episode

28 Jan 2026 · 45 min

0:00

This is a transcript of Scaling Up Business episode 282 (host Bill Gallagher) featuring Jen Underwood (branded as the "Emotional Dominatrix"). Jen, a former teacher and clinical counselor who worked in social work, coaches entrepreneurs and leaders in emotional mastery — helping them identify emotional triggers, set boundaries, hold difficult conversations, and use vulnerability productively. The episode mixes practical frameworks with client stories (e.g., resolving fear-of-success and pricing/imposter issues, a client who renegotiated client terms and in ~3 months increased monthly income ~2.5x while halving her workload). Sponsor ad segments (DoxaTalent, Align/Scoreboard) and production credits are included.

Questions this episode answers

Alameda, California.

2021-10-20.

The client more than doubled monthly income (≈2.5×) while cutting business hours roughly in half over about three months.

Chapters

More from Bill

5:31
Podcast

The Busy Is Broken Manifesto

1mo ago
11:14
Podcast

360 Days a Year: Michel Kripalani's Redesign

1mo ago
55:15
Podcast

Amplify or Erode: The Daily AI Choice with Johan Roos

1mo ago
14:27
Podcast

The Four Sins of the Overworked CEO

1mo ago
50:20
Podcast

The Most Collaborative Teams Aren't the Best, with Ron Friedman

1mo ago
13:11
Podcast

Twice Up the Mountain: Tony Hartl's Second Climb

2mo ago
1:00:56
Podcast

Your Most Important Number with Lee Benson

2mo ago
14:06
Podcast

Is AI Making You Busier — or More Effective?

2mo ago
49:00
Podcast

Happier Aging at Scale with Arif Abdulla

2mo ago
16:27
Podcast

The Italy Test: Could You Leave Your Business for a Month? (Book Solo #9)

3mo ago
48:49
Podcast

Win-Win Selling with Doug C. Brown

3mo ago
See all content