S7, Ep1 – In conversation with Trinny Woodall
11 August 2025
Welcome to the debut episode of Life & Smile Season Seven, brought to you in our latest video format from our recording studio at Harley Street! Dr Reena kicks things off in style with a riveting conversation with British fashion icon, businesswoman, and renowned skin & beauty entrepreneur, Trinny Woodall.
From launching her incredibly successful Trinny London brand to confronting personal and professional reinvention, Trinny brings refreshingly candid insights into confidence, creativity, and resilience. Tune in to this conversation for life, style, and wisdom from one of the most iconic voices in the beauty industry.
Conversation Show Notes – The Recap
The show opens with an update of Trinny’s incredible career, rewinding back to the beginning. She describes how she went to boarding school very early and wanted to find a career that her banker dad would think, “OK, there she is.”
And so, Trinny went to work in the City during a financial crisis, feeling disconnected from who she was, with no clear career path. However, she always knew what made her happy: giving makeovers and beauty tips to her friends, something she’d been doing since her school days.
Coming out of rehab at age twenty-seven, Trinny saw it as an opportunity to start over—with the mindset to pursue what she actually enjoyed, rather than what she thought she should be doing.
From that point, Trinny became self-employed. She had a column in The Telegraph for seven years called What Not To Wear, which of course became a highly successful TV show. From there, she went on to do more shows across the world. For nearly twenty years, she worked independently, but each autumn brought the uncertainty of whether her contract would be renewed – highlighting the trepidation that can come with self-employment.
When offering advice to aspiring entrepreneurs, Trinny emphasises the importance of knowing whether you’re the kind of person who wants to leave work behind at 6pm or someone who thrives by being fully absorbed in their work – a mindset shift essential for entrepreneurs.
It wasn’t until she had travelled the world, speaking to and making over women of different ages, religions, skin tones, and attitudes, that she recognised a powerful similarity: women want to rethink their routines, but don’t know where to start. She realised the value in supporting women so they can shine their inner light and feel great about themselves.
Trinny London was created to give women the tools to feel like the best versions of themselves. It was founded when Trinny was forty-nine, and she reflects on how a much earlier experience of closing a business set her up for success. She shares the importance of preparing in advance and knowing what short-term sacrifices you’re willing to make for long-term gain. Creating a financial runway and giving yourself breathing space is key.
Trinny has worked on many impactful projects over the years, and Dr Reena guides the conversation toward the key moments that stood out. Trinny talks about feeling impact in many ways—whether it’s launching a cult product or igniting energy in women through her brand. She describes a recent ‘walk and talk’ event with hundreds of Trinny London followers to help address loneliness.
Today, Trinny London is a team of 300 people, with many new faces joining. This enables Trinny to be more hands-on with the brand’s core mission, ensuring that even someone who joined last week understands the brand as deeply as someone who’s been there for five years.
Her weekly schedule includes:
Monday: team-wide meetings
Tuesday: focused on marketing
Wednesday: dedicated to new product development
Thursday: a management day
Friday: a flexible mix of tasks
She also notes that social media makes up just 3–4% of her world, although it’s still a key part of her presence. Travel also plays a significant role in her work.
Energy is a core driver for Trinny. Her joy comes from bringing happiness to others, and she loves when people stop her on the street just to say hello. To maintain her energy levels, she relies on yoga, meditation, and staying grounded—always striving to bring the best version of herself each day.
As for her top essential products, Trinny lists:
- Her phone – to run her business globally and stay connected with her daughter
- SPF 50 – for everyday skin protection
Episode Key Takeaways – The Best ideas
Make your passion your career.
Ask yourself: What are you prepared to do for the bigger opportunities at the end?
Give yourself a financial runway when building a business to allow breathing space and reduce pressure.
Know your value and constantly check it.
Some people excel at working within a company, while others struggle with working for someone else.
On appearance: Sometimes you need to help the outside to let the inside come out.
We all need emotional connection.
When we’re stressed, we’re not always at our most efficient.
Perseverance, luck, and hard work combine to create opportunities.
Closing a business can teach you invaluable lessons.
Her Trinny London stack – her go-to for beauty on the go.
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