Take the Risk or Lose the Chance: Sisters Who Rewrote the Rules Teddy and Mary - Havana Little
She Who Dares, Wins.Show Notes
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.
Key Takeaways & Timestamps [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.
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