The Heels in the Hierarchy Podcast

You know their names. You know their achievements. But do you know what happened in between?
SJ and Pegsy are back — and this week they're doing something a little different.
Rather than a highlights reel in the latest of our looks at Inspirational Women, this episode goes behind the polished, press-ready versions of four extraordinary women — Reese Witherspoon, Maya Jama, Brené Brown, and Michelle Obama — and into the messy, uncertain, often uncomfortable middle ground that actually shaped who they became.
Because leadership isn't built in the spotlight. It's built in the struggle before anyone was watching.
What connects these four women isn't fame. It's something far more interesting — the gap between how the world saw them and how they actually felt inside. The quiet, persistent friction of not quite fitting the version of themselves that existed in other people's minds. And the series of small, often unglamorous decisions to choose themselves anyway.
In this episode:
How Reese Witherspoon's industry frustration became Hello Sunshine — and what that shift from "how do I succeed in this system" to "what if I build something different" means for anyone feeling overlooked right now
Why Maya Jama's confidence isn't the starting point — and what it's actually survived
The thing Brené Brown's research changed before it changed anyone else — and why the gap between knowing something and living it is one of the most human experiences there is
Michelle Obama on being defined by someone else's achievements — and why Becoming resonated with so many women across so many different circumstances
The pattern all four share — and the question it raises about your own messy middle
And we close with the one question worth sitting with today:
Where in your life right now is there a gap between how the world sees you and who you actually are?
You don't have to answer it today. You just have to be honest enough to ask it.
Someone in your life needs to hear this one. Share it.
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Links mentioned in this episode:
Reese WitherspoonHello Sunshine — About Us: The mission behind the company Reese builtForbes — 5 Leadership Lessons from Hello SunshineBusiness Upturn — Reese Witherspoon on struggling to keep Hello Sunshine afloat in its early days
Maya JamaGrazia — Maya Jama on imposter syndrome, confidence, and showing up anyway
Brené BrownTED Blog — Being vulnerable about vulnerability: Q&A with Brené BrownOn Being — Brené Brown: The Courage to Be VulnerableOprah.com — The Wholehearted Life: Oprah talks to Brené Brown
Michelle ObamaMichelle Obama's official site and Becoming
#HeelsInTheHierarchy #MessyMiddle #WomenInLeadership #ReeseWitherspoon #BrenéBrown #MichelleObama #MayaJama #AuthenticLeadership #ImposterSyndrome #PodcastForWomen

SJ and Pegsy welcome you back to Heels in the Hierarchy - and this week SJ sits down with someone whose career story genuinely stopped us in our tracks.
She welcomes Debbie - a woman who built a successful, people-focused career in beauty and medical sales, and then made one of the most unexpected pivots you'll hear about on this podcast: into a technical, commercial, male-dominated manufacturing environment.
"I've built confidence in one world — and suddenly none of it seemed to apply anymore."
That's where this conversation begins. And it might be where you are right now too.  
Different language. Different culture. Different rules. And COVID hitting just as she was trying to find her feet, derailing the hands-on training she desperately needed.
What unfolds is one of the most honest conversations we've had about what identity and confidence actually feel like when you step into a space that wasn't built with you in mind — and what it takes not just to survive it, but to stay, grow, and discover strengths you didn't know you had.
In this episode:
That first moment of thinking "I don't belong here" — and what Debbie did with it
How COVID complicated an already steep learning curve in a hands-on industry
Imposter syndrome in its rawest form — and the internal work of navigating it
Why asking for help is harder than it sounds in a culture that doesn't always model it
The relational and people skills that technical environments quietly need — and rarely acknowledge
What Debbie wishes she'd known before making the leap — and what she'd tell anyone out of their depth right now
If you've ever walked into a room and wondered whether you belonged there — this one's for you.
And if you know someone standing at the edge of a big career change, send this to them today.
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Everyone talks about the glass ceiling. SJ and Pegsy ask a more interesting question: is it always someone else's doing?
In this episode SJ and Pegsy have an honest, nuanced conversation about career progression — the real structural barriers women face, and the ones we sometimes build for ourselves. Because quite often, it's both happening at the same time.
From crowded leadership tiers and the difference between a mentor and a sponsor, to the confidence gap, the broken promises of "great progression opportunities," and the invisible emotional weight women carry around ambition — this is the glass ceiling conversation that goes beyond the headlines.
And crucially: it ends with practical routes forward. Not just what's in the way, but how to find the elevator when the ceiling won't budge.
In this episode:
Why sometimes the barrier is structural — and sometimes it's a traffic jam, not a glass ceiling
The critical difference between a mentor and a sponsor — and why it matters for your career
The confidence gap: why women wait to feel ready when others just go for it
Being sold "potential" rather than a pathway — and the interview questions that expose the difference
How glass ceilings look different across sectors — and why that nuance matters
Practical steps: owning your ambition, seeking sponsors, and testing limits before assuming they're fixed
Have you hit a genuine glass ceiling — or looked back and realised you'd underestimated yourself? We'd love to hear from you.
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Some of the best management conversations don't happen in a meeting room. They happen on a walk.
In this episode SJ and Pegsy explore the real evidence behind walking meetings — why movement boosts creativity, reduces fatigue, and quietly shifts the power dynamic in ways that make difficult conversations easier and honest ones more likely.
Drawing on research-backed insights and their own expertise in wellbeing and HR, they get practical about when walking meetings genuinely work best — appraisals, onboarding new starters, early performance conversations — and when they don't. Crucially, they also tackle accessibility, because any wellbeing initiative that excludes people isn't really a wellbeing initiative at all.
In this episode:
Why walking boosts creative thinking and reduces cognitive fatigue
How side-by-side movement softens power dynamics in management conversations
The management moments where walking meetings work best
Accessibility considerations every manager needs to think about
How small, consistent actions model a genuine wellbeing culture
Try it once this week — with one person, one conversation. See what comes up that wouldn't have at a desk.
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She failed the exams that were meant to define her future. It turned out to be the best thing that ever happened to her career.
In this episode SJ speak with Emmy, a payments product manager, about a journey that didn't start where she expected — or wanted — it to. Failing anatomy exams meant letting go of a lifelong plan to become a doctor, and facing a version of failure that felt deeply personal. What followed was a rebuild: new direction, new identity, and ultimately, a career and sense of fulfilment she couldn't have planned for.
This is a story about what failure actually teaches us, if we let it — and how the lowest point can end up being the turning point.
In this episode:
Emmy's path from a failed medical ambition to a thriving FinTech career
Reframing failure as a turning point, not an ending
The role mentors played in helping her find a new direction
Transferable skills — and learning to recognise your own value
Redefining success on her own terms, beyond job titles
Ever turned a failure into your biggest win? This episode will resonate.
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#HeelsInTheHierarchy #FromFailureToSuccess #CareerPivot #Resilience #FinTech #WomenInLeadership #CareerChange #Mentorship #PodcastForWomen #TurningPoints

A career break isn't a gap. It's a chapter — and it's time the workplace started reading it that way.
In this episode SJ and Pegsy explore Carol Fishman Cohen's influential TED Talk on "relaunchers" — women returning to work after stepping away for caregiving, health, or simply a different season of life. Rather than treating that time as something to explain away, this episode reframes it as exactly what it is: an intentional restart, not an ending.
They dig into why confidence often takes the biggest hit during a break, how outdated recruitment practices quietly penalise relaunchers, and the transferable skills — resilience, perspective, problem-solving — that so often go unrecognised on a CV. And crucially, they offer practical, actionable steps for both employers and candidates to make re-entry genuinely successful, not just survivable.
In this episode:
Carol Fishman Cohen's "relauncher" framework and why language matters
Why confidence dips during a break — and how to rebuild it
How recruitment processes can unintentionally exclude returners
The transferable skills career breaks actually build
Practical steps employers can take to support successful re-entry
Know someone relaunching their career? This episode is for them — and for the manager hiring them.
☕ Support us on Buy Me a Coffee🎧 Listen & subscribe: https://heelsinthehierarchy.podbean.com/▶️ Watch on YouTube: https://www.youtube.com/@HeelsintheHierarchy
#HeelsInTheHierarchy #CareerBreak #Relauncher #ReturnToWork #CareerRestart #WomenInLeadership #RecruitmentBias #TransferableSkills #PodcastForWomen #WorkplaceCultureLinks mentioned in this episode:Carol Fishman Cohen — "How to Get Back to Work After a Career Break" (TED Talk)

This episode explores the growing, often-hidden impact of elder care on women in the workforce — from 600 people quitting daily in the UK to the 1.4 million ‘sandwich carers’ balancing children, careers and aging relatives.
Hosts SJ and Pegsy discuss the emotional toll, anticipatory grief, financial pressures, workplace stigma and practical resources, and offer compassionate advice for both carers and managers on how to navigate and support this major life transition.
https://www.ageuk.org.uk/information-advice/care/
https://www.carersuk.org/help-and-advice/
https://www.citizensadvice.org.uk/
https://www.nhs.uk/social-care-and-support/help-from-social-services-and-charities/getting-a-needs-assessment/
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The difference between an ordeal and an adventure is your attitude. This episode is pure adventure.
To celebrate one year of Heels in the Hierarchy, SJ and Pegsy are throwing open the outtakes reel — the bloopers, the behind-the-scenes moments, and the bits that didn't quite make the cut. But amid the laughter there's something genuinely valuable here too: honest conversation about vulnerability, neurodiversity, feedback, and the wonderfully messy human side of putting yourself out there.
If you've ever wondered what goes on when the recording light is on and everything goes slightly sideways — this one's for you.
Enjoyed the show? You can support us here: ☕ Buy Us a Coffee
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A year in. What have we learned? More than we expected.
SJ and Pegsy mark one year of Heels in the Hierarchy by revisiting the themes that have resonated most deeply with their listeners: women's health, late and missed diagnoses, neurodivergence, and the systemic barriers that too many women still face at work every single day.
With personal stories, listener responses, and a call for workplaces to move beyond policy and into genuine action, this is a milestone episode that's as forward-looking as it is reflective.
In this episode:
The themes that defined Year One — and why they matter for leadership
Personal stories and listener voices
Why curious, trust-based management changes everything
What it will actually take to make workplaces work for women
Share this one. These conversations only grow when more people join them.
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Having a job is supposed to be the answer. For millions of people in the UK, it isn't enough.
In this episode SJ and Pegsy tackle one of the most uncomfortable realities in modern working life — in-work poverty. Rising living costs, part-time contracts, and a persistent gender pay gap are leaving workers, and disproportionately women, financially vulnerable despite being in employment.
But this isn't just a policy conversation. It's a leadership one. SJ and Pegsy explore what employers and managers can actually do right now — from flexible working and trust-based policies to discreet support programmes and smarter job design — to make a genuine difference to the people in their teams.
In this episode:
Why employment is no longer a guarantee of financial security
How the gender pay gap and part-time work compound the problem
Practical steps employers can take — beyond the employee assistance programme
Why psychological safety is the foundation for any meaningful support
If you find this podcast valuable, please share it — and consider supporting us: ☕ Buy Us a Coffee
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