Episodes
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Notebooks at the ready—this is a masterclass in taking ideas to thriving ventures from one of the UK’s most dynamic businesswomen. Debbie Wosskow OBE has built, scaled, and sold multimillion-pound businesses, including Love Home Swap, and now leads the charge for female founded businesses with the £250 million Invest in Women Taskforce and her new venture The Better Menopause.
In this candid conversation, Debbie shares the lessons learned from decades of experience: the sunlit uplands as well as the darkness. With a different business for every decade of her life, Debbie’s playbook is packed with insights to inspire your next move.
(00:00) - The Wobbly Middle S1 E7 Debbie Wosskow(02:11) - Debbie's Early Career and Success(05:07) - Personal Reinvention and Challenges(15:19) - Building and Leading Female-Focused Businesses(24:46) - Navigating Uncertainty and Personal Growth
Our final episode of Season 1 will be out on Wednesday 8 January 2025. For additional insights, read The Wobbly Middle on Substack. You can also find us on LinkedIn, Instagram and Facebook @thewobblymiddle.If you are in the wobbly middle of your career, please share your story with us via our socials or email us at [email protected]. We'd love to hear what’s on your mind - and if you're out the other side, please let us know how you got there!
About the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital having left her role as CEO of a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her.Patsy Day is a lawyer on a break. As an intellectual property specialist, she has worked on everything from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting, The Wobbly Middle.
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Born in the New Mexico deserts where running water was a luxury, Dr. Emily Connally was an unlikely contender for the ivory towers of Harvard and Oxford — but with grit, brilliance, and a touch of rebellion, she soared. Yet her greatest achievements may not be in the lab...
When the pandemic struck, Emily applied the same expertise she used to map the brain’s complex pathways to chart a thriving grassroots network. Starting with a schoolgate foodbank, she built Cherwell Collective which is transforming how local networks tackle food waste and sustainability.
From elite academia to community hero, listen to Emily’s warm, uplifting tale of courage, ingenuity, and the power of pivoting when it matters most.
(00:00) - (01:37) - Introducing Dr. Emily Connally(02:53) - Emily's Early Life and Education(05:33) - Challenges and Triumphs in Academia(11:37) - Activism and Union Leadership at Arizona(19:30) - The Birth of Cherwell Collective(24:34) - Cherwell Collective's Impact and Future Plans
New episodes of The Wobble Middle released fortnightly. For additional insights, read The Wobbly Middle on Substack. You can also find us on LinkedIn, Instagram and Facebook @thewobblymiddle.If you are in the wobbly middle of your career, please share your story with us via our socials or email us at [email protected]. We'd love to hear what’s on your mind - and if you're out the other side, please let us know how you got there!
To learn more about Cherwell Collective, visit https://www.cherwellcollective.com/
About the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital having left her role as CEO of a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her.
Patsy Day is a lawyer on a break. As an intellectual property specialist, she has worked on everything from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting, The Wobbly Middle.
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Sophie was 37 when she was diagnosed with a life-threatening illness. Recovered but with a heavy dose of heartache, she had a choice to make: return to the legal career she had spent years building or follow her passion into the fires of the kitchen.
With humour, grit, and inspiring zest, Sophie Archer reveals how her strength grew to fuel her culinary dreams - all the way to MasterChef: The Professionals. This is a story that will ignite your own ambitions and leave you hungry for possibility.
New episodes of The Wobble Middle, released fortnightly. For additional insights, read The Wobbly Middle on Substack. You can also find us on LinkedIn, Instagram and Facebook @thewobblymiddle.
If you are in the wobbly middle of your career, please share your story with us via our socials or email us at [email protected]. We'd love to hear what’s on your mind - and if you're out the other side, please let us know how you got there!
(00:00) - From Courtroom to Chef’s Kitchen: A Feast of Grit and Glory(02:17) - Introducing Sophie Archer(06:26) - The Shift from Law to the Culinary Arts(12:16) - Building a New Career(18:03) - The Kitchen of Dreams(27:43) - Reflections and Future Plans(28:52) - Sophie's MasterChef Experience(30:11) - How to Cook a Gremlin Podcast(31:34) - Conclusion and FarewellAbout the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital having left her role as CEO of a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her
Patsy Day is a lawyer on a break. As an intellectual property specialist, she has worked on everything from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting, The Wobbly Middle.
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Midwife Nina Van Schaick felt a deep calling to support mothers through the transformative experience of childbirth. But as she witnessed the trauma caused by failures in maternal care, she knew change was urgently needed. With less than 2% of pharmaceutical R&D dedicated to maternal health, Nina decided to take action herself.
(00:00) - Introduction to The Wobbly Middle(03:08) - Nina's Journey into Midwifery(05:39) - The Emotional Spectrum of Midwifery(08:04) - Challenges and Changes in Midwifery(12:11) - Innovating with PeriPear(20:00) - Empowering Women in Midlife
Join the warm, funny, and bold FemTech innovator as she shares how she moved from the delivery suite to the boardroom to create meaningful change for women’s health.New episodes of The Wobble Middle are released fortnightly. For additional insights, read The Wobbly Middle on Substack. You can also find us on LinkedIn, Instagram and Facebook @thewobblymiddle.
If you are in the wobbly middle of your career, please share your story with us via our socials or email us at [email protected]. We'd love to hear what’s on your mind - and if you're out the other side, please let us know how you got there!
About the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital having left her role as CEO of a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her.
Patsy Day is a lawyer on a break. As an intellectual property specialist, she has worked on everything from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting, The Wobbly Middle.
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What happens when one of the most influential woman in the City resigns at the top of her game? Dame Helena Morrissey stunned the financial world when she stepped down as CEO of Newton Asset Management at 50 — without a fully formed plan. In this compelling episode, Helena opens up about the unfinished business that drove her forward; and how she learned to embrace discomfort as she forged a new path.
As one of the most prominent advocates for equal pay and opportunity, Helena also sets out her powerful vision for getting more mid-career women into investment roles. Listen in to hear how she’s making an impact yet again, transforming the future of women in finance.New episodes of The Wobble Middle are released fortnightly. For additional insights, read The Wobbly Middle on Substack. You can also find us on LinkedIn, Instagram and Facebook @thewobblymiddle.
https://thewobblymiddle.substack.com
If you are in the wobbly middle of your career, please share your story with us via our socials or email us at [email protected]. We'd love to hear what’s inspiring you or if you have a question for us - and if you're out the other side, please let us know how you got there!
About the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital having left her role as CEO of a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children imminently. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her.
Patsy Day is a lawyer on a break. She has worked on all things IP from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting The Wobbly Middle.
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Helen was made redundant while pregnant. In the playground, she watched as skilled mums - lawyers, accountants, architects - pushed swings, frustrated by the lack of jobs that could accommodate family life. Grabbing her phone and laptop, she decided to take matters into her own hands. In this episode, Helen Wright of 9-2-3 tells us of life at the forefront of the movement that is reshaping our working lives.
You can find Helen at www.923jobs.com
New episodes of The Wobbly Middle drop every two weeks. For additional insights, read The Wobbly Middle on Substack. You can also find us on LinkedIn, Instagram and Facebook @thewobblymiddle.
https://thewobblymiddle.substack.com/
If you are in the wobbly middle of your career and would like to share your story with us, please drop us a line via our socials or email us at [email protected]. We'd love to hear what inspiring you or if you have a question for us - and if you're out the other side, please let us know how you got there!
About the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital having left her role as CEO of a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children imminently. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her.
Patsy Day is a lawyer on a break. She has worked on all things IP from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting The Wobbly Middle.
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When they couldn't find help for their often young, sub-fertile patients who were being slammed by the perimenopause, Drs Susanne Hooper and Melanie Hacking took a sharp right turn in their own careers...
Find Susanne and Melanie at the Oxford Hormone Clinic.
New episodes of The Wobble Middle drop every two weeks. You can also read our Wobbly Middle musings on Substack at The Wobbly Middle. You can also find us on Instagram, @thewobblymiddle
If you are in the wobbly middle of your career and would like to share your story with us, please drop us a line via Substack or email us at [email protected]. We'd love to hear what inspiring you or if you have a question for us - and if you're out the other side, please let us know how you got there!
About the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital. Having left her role as CEO as a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children imminently. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her.Patsy Day is a lawyer on a break. She has worked on all things IP from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting The Wobbly Middle, a podcast about women navigating the path to their next career.
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Patsy quit her job. Susannah quit the city. Now they’re on a quest to find the path through the wobbly middle of their careers. This podcast is for every woman who’s asking “What now?”.
Hosted by Susannah de Jager and Patsy Day, The Wobbly Middle features interviews with famed city superwomen, dazzling entrepreneurs and revolutionary midwives and doctors who reveal what they’ve learnt through their own wobbly middle experiences.
Follow us on Instagram: @thewobblymiddle
Find us on Substack: thewobblymiddle.substack.com
About the hosts:
Susannah de Jager is podcasting in Oxford, consulting to start-ups and occasionally advising on scale-up capital. Having left her role as CEO as a boutique asset manager and asked "what next?”. Oh, and she’s moving country with her husband and two young children imminently. To say that she’s in The Wobbly Middle would be an understatement. This podcast is for her and for all those like her.Patsy Day is a lawyer on a break. She has worked on all things IP from anti-counterfeiting to publishing and from London to Ho Chi Minh City and back again. Patsy lives in Oxford and is currently immersed in podcasts producing SafeHouse Amsterdam (out 2025) and co-hosting The Wobbly Middle, a podcast about women navigating the path to their next career.
