Trinny Woodall on the Financial Reality of Being Self-Employed

Trinny Woodall went from recovering from addiction in her mid-20s to becoming one of the most beloved authorities in style and fashion. She landed a lucky break with a weekly style column in London, then parlayed her expertise into the TV show What Not to Wear. Life threw her some curveballs, from mourning loved ones to going through 16 rounds of IVF. Today, Trinny gets real about the sacrifices she had to make around those private battles because of her self-employment status. 

In this episode of 9 to 5ish, Trinny also shares: 

• Why she made herself try a stint in finance

• The financial reality of being self-employed that no one talks about

• Why she only took three weeks of paid family leave after having her daughter 

• What she learned from having her business fail during the dot com bubble

On Asking the “Dumb” Question

Trinny:  When people use acronyms of things – like EBITDA – I was like, I can either pretend I know in the room or I can just ask it in quite an authoritative way. So I'll say, remind me again what that stands for? When you don't have information, it's about how can you ask for the information but still with an authority that you're sort of saying, look: I'm not stupid, but it's something I haven't come across yet. Or I would have a notebook and if I was in a meeting where I thought, this is not the right place for me to admit, I don’t know something, I'll just write them down and I'll go and bloody learn about them. 

On How Failing in Business Early On Actually Helped Her 

Trinny:  I was 35 and I raised $7.5 million in six weeks from JH Whitney and Atlas Ventures…[my company] failed really quickly. Within two years, there was the dot com bust and I had to let go of 60 women… Also, we'd raise money quite quickly so we spent the money. From that experience, I literally wrote a book in my head of what not to do next time, so when I find myself at age 50 thinking I'm ready to do this business, I knew what I wanted the business to be.

On Why She Disliked Her Twenties the Most

Trinny: My twenties were the era I least enjoyed. Although I had the most fun, I also felt the most insecure, I felt the most unappealing. I really hadn’t had the best skin. Visually, I didn't feel good about myself. But when people met me, they got a very different impression from how I felt inside. 'Cause people thought I was super confident…and so there was a falseness I was carrying around. 

These quotes have been edited for clarity. 

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