Ep. 115: Bravery Isn’t Confidence — It’s a Skill (How to Break the Comfort Trap) | Jill Schulman
Fri Jan 23 2026
Episode 115: If you’ve been feeling stuck, afraid to start over, or trapped in a “comfortable” life that’s quietly costing you your purpose… this episode is your wake-up call.
Today I’m joined by Jill Schulman — U.S. Marine Corps veteran, leadership development expert, and “happiness scientist” with a Master’s in Applied Positive Psychology — to break down the real science of bravery and how to build it in everyday life.
Jill shares her iconic “pink pumps to combat boots” origin story — including the moment someone told her on day one, “You’ll never make it,” and how she learned that bravery isn’t about heroic moments… it’s about showing up scared every day.
In this conversation, Jill explains why so many of us get trapped in the comfort zone (and why it actually makes us more fragile), then gives a practical blueprint to build courage through:
Brave Mindset (your inner dialogue + belief that you can do hard things)
Brave Actions (taking a step before you feel ready)
Brave Relationships (curating a “brave tribe” that won’t let you tap out)
You’ll also hear Jill’s best tool for decision-making when you feel lost. If you’re in a career pivot, identity shift, breakup, burnout, or “what now?” season — this episode will help you choose courage over comfort.
CONNECT WITH JILL:Jill shares her free bravery assessment + bravery blueprint at jillschulman.com and her book The Bravery Effect is available everywhere books are sold. You can follow her on Instagram, YouTube, and LinkedIn.
CONNECT WITH AMANDA:
Don’t forget to share this show with a friend and subscribe for weekly conversations on identity, healing, purpose, and becoming your future self.
Want to submit a question for an upcoming Wanderer Wisdom episode? Email us at hello@podcastforthelost.com or send an anonymous message to ngl.link/akpowers__
Follow the journey:
Website | @podcast.for.the.lost | @amanda.k.powers
TikTok | YouTube | Substack
AFFILIATE LINKS:
Momentum Shake → Spend $75, Get a Free Variety Pack
MONDAY Swimwear → 20% Off
Twenty2 Nutrition → 5% Off
PTULA → $10 Off
Oner Active → $10 Off
Beis Travel Luggage → $20 Off
U BEAUTY → $25 Off
time__line → 20% Off (code POWERS)
CHAPTERS:
00:00 From Pink Pumps to Combat Boots
08:18 The Journey of Bravery
16:29 Bravery as a Trainable Skill
24:39 Choosing Your Hard
25:53 The Illusion of Success on Social Media
27:07 Breaking Free from the Comfort Trap
31:34 Steps to Build Bravery and Confidence
31:58 Personal Journey Out of the Comfort Zone
35:46 The Impact of Taking Brave Steps
39:34 The Bravery Effect: A Parable for Change
45:24 Blueprint for Overcoming Fear
47:31 Embracing Challenges for Growth
More
Episode 115: If you’ve been feeling stuck, afraid to start over, or trapped in a “comfortable” life that’s quietly costing you your purpose… this episode is your wake-up call. Today I’m joined by Jill Schulman — U.S. Marine Corps veteran, leadership development expert, and “happiness scientist” with a Master’s in Applied Positive Psychology — to break down the real science of bravery and how to build it in everyday life. Jill shares her iconic “pink pumps to combat boots” origin story — including the moment someone told her on day one, “You’ll never make it,” and how she learned that bravery isn’t about heroic moments… it’s about showing up scared every day. In this conversation, Jill explains why so many of us get trapped in the comfort zone (and why it actually makes us more fragile), then gives a practical blueprint to build courage through: Brave Mindset (your inner dialogue + belief that you can do hard things) Brave Actions (taking a step before you feel ready) Brave Relationships (curating a “brave tribe” that won’t let you tap out) You’ll also hear Jill’s best tool for decision-making when you feel lost. If you’re in a career pivot, identity shift, breakup, burnout, or “what now?” season — this episode will help you choose courage over comfort. CONNECT WITH JILL:Jill shares her free bravery assessment + bravery blueprint at jillschulman.com and her book The Bravery Effect is available everywhere books are sold. You can follow her on Instagram, YouTube, and LinkedIn. CONNECT WITH AMANDA: Don’t forget to share this show with a friend and subscribe for weekly conversations on identity, healing, purpose, and becoming your future self. Want to submit a question for an upcoming Wanderer Wisdom episode? Email us at hello@podcastforthelost.com or send an anonymous message to ngl.link/akpowers__ Follow the journey: Website | @podcast.for.the.lost | @amanda.k.powers TikTok | YouTube | Substack AFFILIATE LINKS: Momentum Shake → Spend $75, Get a Free Variety Pack MONDAY Swimwear → 20% Off Twenty2 Nutrition → 5% Off PTULA → $10 Off Oner Active → $10 Off Beis Travel Luggage → $20 Off U BEAUTY → $25 Off time__line → 20% Off (code POWERS) CHAPTERS: 00:00 From Pink Pumps to Combat Boots 08:18 The Journey of Bravery 16:29 Bravery as a Trainable Skill 24:39 Choosing Your Hard 25:53 The Illusion of Success on Social Media 27:07 Breaking Free from the Comfort Trap 31:34 Steps to Build Bravery and Confidence 31:58 Personal Journey Out of the Comfort Zone 35:46 The Impact of Taking Brave Steps 39:34 The Bravery Effect: A Parable for Change 45:24 Blueprint for Overcoming Fear 47:31 Embracing Challenges for Growth