Today, we’re diving into a conversation that so many women in their 30s and 40s are quietly living through, but rarely saying out loud.

I’m joined again by Jenni, who you might remember from a previous episode, and this time we’re going deeper into what it really looks like to have a non-linear career, a late ADHD diagnosis, and, as Jenni discovered, autism traits on top of it all.

If you’ve ever looked at your CV and thought,

“Why can’t I just stick to one thing like everyone else?”

or woken up already telling yourself you’re behind before the day has even started…

this episode is for you.

We talk about:

• The shame spiral of changing jobs, careers, and directions
• How a late diagnosis of ADHD and autism can trigger both grief and massive relief
• Why so many women in chaotic, high-pressure jobs — like policing, construction, and close protection — only realise later that their brains were never “the problem”
• And how to start moving from self-criticism to self-acceptance, without trying to “fix” who you are

This is an honest, vulnerable, and, at times, very funny conversation between two women who absolutely do not fit the traditional career box — and have finally stopped apologising for it.

So, if you’ve ever felt “too much”, “all over the place”, or secretly broken…

take a breath, grab a cuppa, and let this be your reminder:

you are not broken, and you are definitely not alone.

Let’s dive in.

Hosted on Acast. See acast.com/privacy for more information.

n this episode of She Dares Wins, Michelle is joined by sisters Mary and Teddy – two women who’ve carved wildly different but equally daring paths from the same family roots.

Mary is a fibrous plasterer working in heritage buildings and a trailblazer in a centuries‑old, male‑dominated trade. Teddy is a dental therapist who walked away from a high‑flying corporate role to work in rural Nicaragua, where she eventually met her husband.

Together they talk about risk, resilience, sisterhood, and what it really looks like to choose the daring route when nothing is guaranteed.

[00:02:47] Daring stories: quitting jobs & choosing risk

• Teddy shares how she quit a prestigious international dental job and followed her heart to Nicaragua.
• Mary explains her mantra: “take the risk or lose the chance” and why she always chooses the dare over the safe option.

[00:03:28] Motorway breakdown & battery change – live ‘she dares, she wins’

• The chaotic journey to the studio: Teddy’s car breaking down on the motorway.
• Mary diagnosing the battery, buying tools, negotiating with highway maintenance and changing the battery at the roadside in minutes.

[00:08:02] 500 toothbrushes & an NGO in Nicaragua

• Teddy’s decision to travel with a suitcase of toothbrushes to support an NGO dental project.
• Staying six months instead of three weeks, travelling the country, and eventually deciding to quit her corporate role.
• How this led to meeting her husband and redefining success.

[00:14:06] Mary’s path in a family trade – from “embarrassed” to expert

• Growing up around the family fibrous plastering business and returning after having her daughter.
• Being a woman in a male‑dominated heritage trade when it “wasn’t fashionable.”
• Deciding not just to be a female plasterer, but to be the best and “better than the boys.”

[00:17:16] Resilience, single motherhood & mental strength

• Mary on being knocked down in work and personal life and still getting up every time.
• Balancing running the business, raising her daughter alone, doing admin late at night and still choosing this life for the freedom it brings.
• How challenges that would be “massive” to others now feel manageable.

[00:21:16] Representation, role models & social media

• How Mary’s Instagram makes her visible to young girls who now see a woman on the tools as normal.
• Her daughter questioning words like “firemen” and assuming women run building sites.
• The importance of seeing someone who looks like you doing the thing you dream of.

[00:31:12] What they’d tell their younger selves (and why they wouldn’t change the hard bits)

• Both reflecting on mistakes, especially around relationships and risk.
• Teddy’s intense experience with a brownie in Amsterdam, how it surfaced unresolved trauma, and why she says “go to therapy before you have a brownie (or just don’t do them).”
• The idea that the painful chapters were necessary to become who they are now.

[00:39:25] The craft: heritage ceilings, the Guild & teaching the next generation

• Mary explains decorative mouldings and working on stately homes and castles.
• Her role in the Guild (founded 1509), becoming the youngest and only female journeyman so far, and the rarity of female master plasterers.
• Running workshops, Airbnb experiences and college sessions – creating safe learning spaces where no question is stupid.

[00:49:24] Identity, calling & coming home to yourself

• Teddy’s current RAF clinic role and living on base in Lincolnshire.
• The identity crisis of moving to rural Nicaragua: language, culture, lifestyle all changing at once.
• Realising not every part of her “old self” has to die – some passions and projects are meant to be carried forward into the new life.

Join Dare Club

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If you’ve ever felt like you’re ticking all the right boxes but living the wrong life, this episode is your permission slip to stop being “the good girl” and start being who you really are.

In this mash‑up episode, you’ll hear from:

• Meg – life coach, on shedding good girl conditioning and surviving the fallout
• Zoe – mindset coach, on the pressure to “find your purpose”
• Lucy Spraggan – musician & author, on delusional confidence, manifestation, and radical authenticity

You’ll be guided from people‑pleasing and burnout to purpose without pressure, community support, and owning your raw, unapologetic self.

By the end of this episode, you’ll move through these stages:

1. Recognising the Good Girl Identity Isn’t Really You
2. Allowing Yourself to Outgrow the Life You Built
3. Finding Purpose Without Crushing Yourself With Pressure
4. Rewiring Your Mindset So You Stop Beating Yourself Up
5. Finding Your People So You Don’t Have to Do It Alone
6. Owning Delusional Confidence & Backing Your Big Dreams
7. Living as Your Most Authentic Self (Even When It’s Messy)

If this episode resonates with you come join us at the Dare club community

Hosted on Acast. See acast.com/privacy for more information.