We Are Women Unapologetically

Executive coach and former HR powerhouse Lauren Leftkowitz shares how chasing a Roomba (yes, really) became the metaphor—and the moment—that changed her life. After breaking both shoulders in a freak accident, Lauren was forced to stop doing what she’d always done: over-function, over-give, and overachieve.

What followed was a journey of rehab, recovery, and radical honesty. In this candid conversation, Lauren opens up about what it really takes to shift from high-performing burnout to a life that doesn’t require recovery. If you've ever been the “fixer,” the “go-to,” or the woman holding it all together—this one’s for you.

Connect with Jessica on LinkedIn

Chapters and Time Stamps

00:00 Introduction and Guest Introduction

00:56 Lauren's Journey: From Burnout to Breakthrough

02:37 The Turning Point: Breaking Both Shoulders

05:25 Realizations and Changes: Embracing Coaching

09:23 Balancing Work and Personal Life

13:07 The Importance of Asking for Help

23:02 Defining What You Don't Want29:12 Understanding What You Truly Want

30:13 Exploring Career Transitions

33:28 The Importance of Transferable Skills

38:52 Navigating Workplace Boundaries

54:00 Building a Support System

56:44 Final Thoughts and Advice

📈 Key Takeaways:

• Burnout doesn’t always look like collapse—it often looks like high achievement.

• Boundaries aren’t selfish. They’re sacred.

• You don’t need a perfect plan—you need a clear “no.”

• Over-functioning is not leadership.

• You’re allowed to change without knowing every step first.

• Recovery starts when you stop pretending “fine” is good enough.

Download the full transcript here:

Lauren Leftkowitz is the founder of Fine is a Trap Coaching, a leadership development firm helping high-achieving women break cycles of burnout and build careers rooted in clarity and courage. After two decades in corporate HR, Lauren now empowers women to own their “no” and reclaim their leadership on their own terms.

🌐 Connect with Lauren

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In this powerful episode of We Are Women, Unapologetically, host Jessica Cumming sits down with Alison Young, aka The Blissful Hiker, to explore the raw truth behind forced reinvention, invisible loss, and the courage it takes to keep walking — literally and figuratively.A classically trained flutist who lost her ability to play due to a rare neurological disorder, Alison didn’t just survive cancer and job loss — she hiked 5,000 miles solo to reclaim her identity. From the New Zealand Te Araroa to the Pacific Crest Trail, Alison’s story is a testament to choosing curiosity over certainty, growth over comfort, and thriving over simply surviving.If you’re navigating transition, grief, or a loss of identity — this conversation will walk right beside you.

💡 Connect with Jessica→

Follow Jessica on LinkedIn

→ Book Your Complimentary Strategy Session 🔑

📅 Episode Chapters & Timestamps:

00:00 – Intro
Welcome to We Are Women, Unapologetically. Meet Alison Young, trained flutist turned long-distance solo hiker.

01:33 – Musical Roots & Unexpected Loss
Alison reflects on her early music career, playing with legends and touring the world—until a neurological condition halted everything.

03:34 – Career Pivot to Radio
She transitions into public radio, becoming a music storyteller on-air for 13 years.

04:45 – The Trail Beckons
Alison begins hiking as emotional healing, leading to a leave of absence to hike New Zealand's 3,000 km Te Araroa trail.

06:00 – Lessons from the Sandflies
Symbolism from New Zealand's infamous insects: keep moving, stay present, and embrace impermanence.

11:19 – Demotion & Identity Crisis
Upon return, Alison is demoted at her radio job. She opens up about grief, reinvention, and the power of support systems.

14:47 – Asking for Help & the Gift of Nourishment
Her breast cancer diagnosis and the life-saving simplicity of asking for help—starting with food.

16:21 – Being Pushed, Not Punished
Alison shares the emotional gut-punch of forced transitions and how she reframed it with support and strategy.

24:00 – The Doomsday Clock & Pacific Crest Trail
Her husband builds a spreadsheet. She plans her next 5-month solo hike across the U.S. west coast.

27:41 – Voiceover, Podcasting & Reinvention in Real Time
Post-hike, Alison launches a new creative life as a voice artist, podcaster, and speaker.

34:02 – Lessons from the Trail
From "embrace the suck" to "the trail will provide," Alison shares thru-hiker wisdom and spiritual truths.

38:08 – Final Message

📈 Key Takeaways:
"I choose to thrive." Why Alison prefers "thriver" over "survivor" and her call for others to step out, 52 weeks a year.

• You don’t need to see the end to take the first step. Reinvention starts with presence.

• Loss (career, identity, health) can be a portal to purpose.

• Community is survival gear. You don’t have to hike alone.

• Ask for help—especially when you think you should be fine.

• Thriving means choosing forward motion, even in uncertainty.

  Download the Official Transcript Here

  
  

  Going though your own career pivot- Download my free guide. You don't have to do it alone.

Episode Summary:

In this episode of We Are Women, Unapologetically, Jessica Cumming calls out the quiet epidemic plaguing high-achieving women: invisible burnout. With stats from McKinsey, Deloitte, and the American Psychological Association, she reveals how career pressure, emotional labor, and unspoken grief are silently draining women dry.

Jessica shares her own wake-up call and what it took to stop performing wellness and start reclaiming real energy, joy, and connection. She breaks down the neuroscience of numbness, explains why “pushing through” backfires, and offers practical, science-backed recovery strategies—starting with the Power Pivot Daily Journal.

If you’re exhausted, disconnected, or just feel like you’re going through the motions—this episode is your permission slip to stop pretending everything’s fine and start choosing you.

💡 Connect with Jessica:

→ Follow on LinkedIn

→ Book your Complimentary Strategy Session here🔑

🕐 Chapters + Timestamps:

00:00 – Introduction: Welcome to We Are Women, Unapologetically

00:18 – The Exhaustion Epidemic: Understanding Burnout 01:54 – The Silent Struggle: High Achieving Women and Burnout

07:29 – Personal Story: A Wake-Up Call

11:07 – Recognizing Burnout: Subtle Signs and Symptoms 14:30 – Recovery and Rest: Practical Strategies

21:39 – Conclusion: Embrace Change and Choose Yourself

Key Takeaways:

• You’re not lazy—you’re running on empty. Most high-achieving women are managing personal and professional crises simultaneously.

• Numbness is not weakness. It’s your nervous system’s survival response.

• Burnout is not just about stress. It’s about disconnection—from yourself, your joy, your purpose.

🔥 Episode Summary

In this powerhouse Part 2 episode, Jessica Cumming drops the truth about what it actually takes to build your next chapter without blowing up your current one.

If you’re a high-achieving woman navigating a pivot—career, identity, leadership—this one’s your permission slip to stop the burnout spiral and finally leverage the assets you already have. Because you’re not starting from scratch—you’re starting from experience.

Jessica walks you through her proven Pivot Stack™ framework, how to protect your emerging vision, and how to track meaningful progress (even when it feels slow AF). Plus: scripts, boundary language, and her signature Power Pivot Toolkit.

This episode is your reinvention masterclass—with receipts.

💡 Connect with Jessica:
→ Follow on LinkedIn
→ Book your Complimentary Strategy Session here🔑

Executive coach Jessica Cumming breaks down how to pivot with power—not burnout. Learn the 4 hidden assets every woman should leverage to reinvent her career with confidence and clarity.

Chapter Markers

• 00:00 — Introduction to We Are Women Unapologetically

• 00:54 — Leveraging Your Professional Network

• 01:50 — Identifying and Utilizing Transferable Skills

• 02:57 — Building Credibility and the Halo Effect

• 03:58 — The Power of a Unique Perspective

• 05:02 — Protecting Your Emerging Vision

• 06:49 — Communicating Your Pivot Plans

• 08:08 — Maintaining Momentum in Your Pivot

• 09:01 — Tracking Progress Points

• 11:21 — Introducing the Power Pivot Toolkit

• 12:41 — Final Thoughts and Fierce Encouragement

Key Takeaways

• The Pivot Stack™: The 4 most overlooked assets women already have (and how to leverage them)

• Why your dormant network might be your biggest pivot unlock

• The truth about transferable skills (and why most women don’t own theirs)

• How to protect your pivot from energy vampires, people-pleasing, and overcommitting

• The monthly progress points you must track to stay out of the burnout spiral

• Exactly how—and when—to talk to your manager about your pivot

• Scripts for saying no with clarity (and no apology)

• Why “identity shift” is the most underrated part of successful reinvention

  
  

Featured Tools & Resources (DM for Details)

• 🎁 Power Pivot Toolkit for just $27
  Includes:
  ✔️ 2-Hour Power Pivot Planner
  ✔️ Strategic Conversation Guide
  ✔️ Power Pivot Tracker
  ✔️ Boundary Scripts
  ✔️ Identity Bridge Workshop

  
  "The most powerful pivots rarely make headlines. But they always make impact." – Jessica Cumming

  
  

  Free Guide: The Power Pivot

  Want even more structure to build your pivot without the burnout?

  Download your free guide:
  👉 The Power Pivot: 5 Strategic Steps for Professional Women Ready to Show Up, Unapologetically, and Reinvent Their Career

  Related Resources

  Episode 10: Pivot While You Prosper (Part 1)
  

  
  Episode 8: Transferable Skills Masterclass: Unleashing Your Professional Superpowers
  

  
  

  
  

  
  

Discover how high-achieving women can pivot their careers without burning out. In this episode of We Are Women Unapologetically, Jessica Cumming shares how to make a slow, strategic shift that protects your peace, power, and paycheck.

💡 Connect with Jessica:
→ Follow on LinkedIn
→ Book your Complimentary Strategy Session here

🔑 Key Takeaways

• Career stagnation post-pandemic is real—here’s how to shift smartly

• Why burnout isn’t a badge of honor—it’s a red flag for misalignment

• The 3 pivot paths: Parallel Build, Strategic Stretch, and Skill Stack

• You only need 2 hours a week to build your next chapter

• The 4 roadblocks sabotaging women’s pivots—and how to beat them

⏱️ Episode Chapters + Timestamps

• 0:00 – Welcome to We Are Women Unapologetically

• 0:17 – Outgrowing Your Role Without an Exit Strategy

• 0:54 – Tension Between Where You Are and Where You’re Meant to Be

• 1:42 – The Case for a Slow Pivot

• 1:53 – The Hidden Cost of Standing Still

• 2:28 – Disengagement Is Misalignment, Not Laziness

• 3:00 – When Bills and Boundaries Make Pivoting Complex

• 3:42 – How Delay Impacts Burnout and Career Satisfaction

• 4:06 – Strategic Movements Over Dramatic Leaps

• 4:20 – Younger Generations Pivot Faster—What Can We Learn?

• 5:08 – Redefining the Pivot: Not a Leap, a Realignment

• 5:59 – Pivot Track 1: The Parallel Build (aka Side Clarity)

• 6:52 – Pivot Track 2: The Strategic Stretch (Grow Inside Your Role)

• 7:56 – Power Move: Advocate for Internal Development

• 8:39 – Personal Story: Sign Language and Stretch Initiatives

• 9:43 – Pivot Track 3: The Skill Stack

• 10:20 – 50% of Employees Will Need Reskilling by 2027

• 11:00 – Choose the Track That Resonates Most for You

• 11:18 – Your Pivot Budget = Time + Energy

• 12:00 – 36 Minutes a Day: The Real-Life Time Crunch

• 12:32 – Non-Negotiables Must Stay Sacred

• 13:30 – The Link Between Stress and Physical Health

• 14:24 – Find Your Peak Time for High-Focus Work

• 15:15 – All You Need Is Two Hours a Week

• 16:09 – The 3-Move Execution Plan

• 16:47 – Move 1: Have a Strategic Conversation

• 17:41 – Move 2: One Commitment With Skin in the Game

• 18:36 – Move 3: Make It Public—Visibility Fuels Confidence

• 19:33 – Personal Story: The Podcast Accountability Pivot

• 20:28 – Protect the Vision Without Burning Down the Old

• 21:06 – 73% of Successful Transitions Are Gradual

• 21:43 – Be Patient—Fast Isn’t Always Wise

• 22:02 – The 4 Roadblocks That Will Try to Stop You

• 22:15 – Roadblock 1: The All-or-Nothing Mindset

• 22:33 – Roadblock 2: Perfection Paralysis

• 23:00 – Roadblock 3: The Expert Expectation

• 23:27 – Roadblock 4: Identity Attachment

• 24:04 – Your Pivot Doesn’t Have to Be Loud to Be Powerful

✨ Download the FREE “ Powerful Pivot” Guide Here
Start building your next chapter without burnout. This powerful, free PDF gives you clarity, focus, and momentum.

“You don’t have to be reckless to be revolutionary. You do not owe anyone a dramatic exit.”
— Jessica Cumming

📥 Download the Full Transcript → Click Here
📣 Subscribe, share, and leave a review—it helps more women find the power in their pivot.

In this unapologetic episode, Jessica Cumming gets real about one of the hardest (and most misunderstood) parts of reinvention: when your personal growth makes people uncomfortable.

Whether you're shifting careers, stepping into your power, or finally choosing you—this episode will help you stay rooted in your truth, even when the people around you don't get it.

With signature boldness, clarity, and compassion, Jessica walks you through the scripts, strategies, and mindset needed to navigate the messy middle of becoming who you were meant to be.

If you’ve ever felt like you’re standing in the hallway between “what was” and “what’s next”... this one’s for you.

💡 Connect with Jessica:
→ Follow on LinkedIn
→ Book your Complimentary Strategy Session here🔑 Key Takeaways:

• Why your growth feels threatening to people—even if they love you

• The neuroscience of why resistance feels like rejection

• 3 powerful scripts for different relationship types (inner circle, mentors, outer circle)

• How to stop over-explaining and start owning your pivot

• A powerful mindset shift: You are not losing people. You are outgrowing versions of yourself that made them feel safe.

📥 Download the Full Transcript → Click Here
📣 Subscribe, share, and leave a review—it helps more women find the power in their pivot.

⏱ Episode Chapters & Timestamps:🎧 Spotify Chapters – When People In Your Life Don’t Get It

00:00 Welcome to We Are Women Unapologetically

00:20 Growth Will Challenge Your Relationships

01:01 The Hallway Between Who You Were and Who You’re Becoming

02:00 This Is Not a Career Shift — It’s a Power Reclamation

03:00 Why People Resist Your Evolution

04:15 The Science Behind the Resistance

05:45 Walking Through It Anyway

06:10 Jessica’s Personal Pivot Story

08:25 Stop Explaining Your Purpose

10:00 How to Navigate Relationships When People Don’t Get It

10:30 Inner Circle Scripts

11:10 How to Talk to Your Professional Network

11:50 How to Handle the Outer Circle

12:40 Dealing With Negative Opinions & Pessimism

14:15 Protecting Your Peace

15:10The Power of Finding New Community

16:30 Therapist vs. Coach vs. Mentor

18:30 5 Power Moves to Anchor Your Evolution

22:00 Final Word: You Don’t Need Everyone to Understand

In this episode of We Are Women Unapologetically, Jessica Cumming shares how to identify your transferable skills, reframe your resume, and speak your value with confidence. Includes a free downloadable CORE method guide.

You're Not Starting Over—You're Starting From Experience

Learn how to reframe your brilliance using transferable skills you already have. This episode walks you through the CORE method to own your impact and pivot with clarity.

📅 Download the Free The Transferable Skills

💡 Connect with Me: Follow me on⁠⁠ ⁠⁠LinkedIn⁠⁠

Book a Complementary Success Consultation to see how we can work together ⁠⁠⁠Here⁠⁠⁠

Episode Summary:

You’re not underqualified. You’re under-translated.
In this episode, Jessica unpacks how to reclaim your power in a career pivot without reinventing yourself. Whether you're returning to work, shifting industries, or simply ready to be seen for what you actually bring to the table — this one's for you.

You’ll walk away knowing:

• How to reframe “basic” job tasks into strategic value

• What hiring managers really want to hear in your resume

• Why 65% of your skills are already transferable (and how to prove it)

• How to use the CORE method (Communication, Organization, Resilience, Execution)

• The exact shift that makes you sound essential, not just experienced

🔥 Bonus: Includes a free downloadable worksheet to map your own transferable skills using the CORE framework.

​Chapters & Timestamps:

0:00 – Welcome & Why This Episode Matters
Intro to transferable skills and why you’re not starting from scratch.

1:30 – Jessica’s Own Pivot Story
From leading global teams to building a successful coaching business — proof that your past experience does translate.

2:30 – The Real Difference Between Hard & Soft Skills
Soft skills aren’t soft. They’re power skills. And they’re more in demand than ever.

3:50 – The Great Reshuffle & The AI Shift
Why transferable skills matter right now and how to future-proof your value.

5:00 – The CORE Method Overview
Communication. Organization. Resilience. Execution. Your new framework for identifying your transferable superpowers.

6:30 – CORE Deep Dive: Communication
Questions to uncover how you’ve driven impact through communication.

7:30 – CORE Deep Dive: Organization
How you brought order to chaos and why that’s a leadership trait.

8:30 – CORE Deep Dive: Resilience
What tough seasons taught you—and why your emotional endurance is marketable.

9:30 – CORE Deep Dive: Execution
The receipts. What you did, how you did it, and what changed because of you.

10:45 – Resume Reframes: Before & After
Real examples of how to turn basic job tasks into high-impact bullet points.

12:00 – Undervaluing Language to Avoid
Stop saying “I just helped…” and start owning your results.

13:30 – The Impostor Syndrome Trap
How self-doubt shows up in your language—and how to shift it.

14:30 – Corporate Translation Strategy
Turn job listing keywords into storytelling gold.

15:20 – The SOAR Method for Storytelling
Situation. Obstacle. Action. Result. Craft messages that land.

16:20 – Building Your Pivot Pitch
A step-by-step template to confidently explain your shift.

17:45 – Addressing Skill Gaps
You don’t need another degree—you need strategic upskilling.

20:30 – Your 3-Week Reinvention Plan
Week-by-week actions to gain clarity, confidence, and career momentum.

26:00 – Final Thoughts
Your experiences aren’t just history. They’re fuel for where you’re going.

​📥 Download the Transcript:

Prefer to read or revisit the highlights? Download the full episode transcript ⁠here⁠

Subscribe, share, and leave a review—it helps more women hear this message!

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Episode Summary:

In this powerhouse episode, Jessica Cumming tackles the one topic most women avoid during career transitions: MONEY. With her signature blend of truth-telling, real-world strategy, and zero fluff, Jessica unpacks exactly how high-achieving women can afford to pivot without losing their minds—or their financial footing.

Whether you’re navigating a layoff, plotting your exit, or just sick of playing small in a paycheck that drains your soul, this episode gives you the mindset reframe, tactical plan, and bold permission slip to make a move.

​💡 Connect with Me: Follow me on⁠ ⁠⁠LinkedIn⁠

Book a Complementary Success Consultation to see how we can work together ⁠⁠Here⁠⁠

🔑 Key Takeaways

• 
  

  • How to calculate your financial runway (and your emotional support number)

  • Three income gap strategies: consulting, bridge jobs, and passive income

  • How to restructure your expenses without living like a monk

  • The psychology of money—and how fear-based decisions sabotage us

  • The 3 pillars of long-term financial resilience

  
  

Episode Chapters & Timestamps (will be added later this week)

​📥 Download the Transcript:

Prefer to read or revisit the highlights? Download the full episode transcript ⁠here⁠

Subscribe, share, and leave a review—it helps more women hear this message!

_________________________________________________________

Other ways to enjoy this podcast:

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⁠Apple Podcasts⁠

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Episode Summary:

Let’s get real—ageism is still alive and well, especially for women navigating career transitions in their 40s and 50s.

In this unapologetically honest episode, Jessica Cumming breaks down why your years of experience aren’t the problem—it’s how you’re framing them. You’ll learn how to rewrite your career story, leverage your leadership, and completely shift how hiring managers and decision-makers perceive your value.

Whether you're job-hunting, consulting, or trying to stay relevant in a fast-evolving workplace—this episode is your roadmap to reclaim your power and redefine your professional presence.

​💡 Connect with Me: Follow me on ⁠⁠LinkedIn

Book a Complementary Success Consultation to see how we can work together ⁠Here⁠

🔑 Key Takeaways

• Recruiters judge resumes in 6 seconds—don’t lead with tenure, lead with value.

• 60% of workers over 45 experience ageism. It’s real—and it’s mostly perception.

• Your years of experience are not a liability. They are your leadership advantage.

• Reframe outdated phrases to project strategy, not stagnation.

• Digital presence is your first impression—optimize LinkedIn, your email, your photo.

• Reverse mentoring and cross-generational networking drive opportunity and relevance.

• Staying relevant doesn’t require learning to code—it requires smart, adjacent skill growth.

• Consistency in upskilling is more effective than one-time intensity.

• Rewrite your LinkedIn headline to reflect where you’re going—not where you’ve been.

• Action matters. Jessica gives five specific steps to implement this week.

Episode Chapters & Timestamps

00:00 – Intro
Welcome to "We Are Women Unapologetically." Why this episode matters: age bias in the hiring process.

00:17 – The 6-Second Resume Rule
Recruiters only spend an average of six seconds on a resume—and long tenure can work against you.

01:00 – Ageism: The Unspoken Career Obstacle
Stats, studies, and real-world bias facing professionals over 40.

03:00 – Debunking the Myths About Older Workers
Resistant to change? Not tech-savvy? Set in your ways? Jessica calls BS—with data to back it up.

04:38 – Reframing Your Experience
Own your years. Reframe your language. Shift your story.

06:01 – Showcase Strategic Adaptability
Stop saying “I’ve been using Excel since 1985.” Start showing how you’ve evolved.

07:00 – Modern Language for Modern Value
Say this, not that: how to update outdated career language to stay relevant.

08:11 – Align Your Resume and Online Presence
Speak to your results—not your tenure.

09:49 – Digital First Impressions Matter
What your LinkedIn photo, headline, and email address are actually saying about you.

11:02 – LinkedIn Headlines That Attract
What to say (and not say) to knock down bias and stand out in search.

12:17 – Keeping Your Profile Active
The power of commenting, sharing insights, and building visibility.

13:45 – The Bigger Digital Footprint
Guest blogging, updated websites, and what Google says about you.

15:50 – Cross-Generational Networking
How to connect across generations for more opportunity and visibility.

17:39 – Reverse Mentoring & Modern Engagement
Text over calls, direct feedback over sugarcoating: adapt your communication.

19:46 – Staying Technically Relevant Without Burnout
What to learn, how to learn it, and why consistency beats intensity.

22:25 – This Week’s Action Plan
Jessica’s 5 assignments to start reframing, connecting, and positioning with power.

25:01 – Closing Motivation
“You’re not too old. You’re just not leading with the experience that sets you apart.”

​📥 Download the Transcript:

Prefer to read or revisit the highlights? Download the full episode transcript here

Subscribe, share, and leave a review—it helps more women hear this message!

_________________________________________________________

Other ways to enjoy this podcast:

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Episode Summary:

Feeling lost in your career transition? In this episode, Jessica Cumming breaks down why so many professional women struggle with identity shifts and how to reclaim your true self beyond work. Discover actionable strategies, personal insights, and scripts that will help you redefine success on your own terms!

​💡 Connect with Me:Follow me on ⁠⁠LinkedIn

Book a Complementary Success Consultation to see how we can work together ⁠Here⁠

See the video version here

Chapters & Key Takeaways:

0:12 - 1:14 | The Identity Crisis in Career Transitions

• 68% of women report feeling a loss of identity during career shifts. Why does this happen?

1:40 - 3:26 | Jessica’s Personal Journey from Dell to Rediscovery

• After 20 years at Dell, Jessica faced the harsh reality of not knowing who she was beyond work.

5:04 - 6:49 | Why Women Fuse Their Identities with Their Jobs

• The Harvard Business Review reports that 76% of professional women tie their self-worth to their careers.

9:10 - 10:10 | 7 Signs Your Job Title Has Become Your Entire Identity

• If your self-esteem rises and falls with your work success, this section is a must-listen.

12:46 - 14:54 | Reconnecting with Your Childhood Passions

• What did you love before your job title defined you? A key exercise to reconnect with your true self.

18:23 - 20:38 | How to Introduce Yourself Without Using Your Job Title

• Learn the framework to confidently present yourself based on impact, not position.

22:19 - 23:54 | Strategic Scripts for Networking & Interviews

• Use these tested scripts to communicate your value beyond a job title.

25:30 - 27:22 | Daily Practices to Reinforce Your New Identity

• Three simple but powerful habits to separate self-worth from work.

​📥 Download the Transcript:

Prefer to read or revisit the highlights? Download the full episode transcript here

Subscribe, share, and leave a review—it helps more women hear this message!

_________________________________________________________

Other ways to enjoy this podcast:

________________________________________________________

⁠Youtube⁠

⁠Apple Podcasts⁠

⁠Amazon Podcasts⁠

⁠iHeart Podcasts