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9 to 5ish with theSkimm

Trinny Woodall on the Financial Reality of Being Self-Employed

9 to 5ish with theSkimm

theSkimm

Business, Entrepreneurship, Careers

4.71.9K Ratings

🗓️ 13 August 2025

⏱️ 33 minutes

🧾️ Download transcript

Summary

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 Sacrifices she had to make for being self-employed 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Hey Jack, I'm seeing your business everywhere. Have you got a new marketing person or something?

0:04.8

You could say I've got a new secret weapon for print. Print? Oh, Vista print, right? That's not a secret.

0:10.8

How did you know? Come on. Custom posters, branded mugs, stylish flyers. Only one place prints all that. Vista print.

0:17.7

Yeah, I got business cards, stickers, t-shirts, booklets, signage, even photo books from my last holiday.

0:22.6

Print everything for your business with VistaPrint.

0:25.6

If you need it, we print it at vistoprint.co.

0:28.6

.

0:29.6

I was in America with my partner who was also pregnant, and we were doing the Oscars with Diana Soya on the red carpet.

0:39.4

I felt this trickle, and I went to the loo, and it was blood,

0:43.1

and I thought, fuck, I've lost a baby again.

0:47.2

I'm Carly Zakin, and I'm Danielle Weisberg.

0:50.3

Welcome to 9 to 5-ish with the skin.

0:53.0

We've run into so many questions over the years and had so many moments where we needed advice,

0:59.4

and we got it from women who'd been there.

1:02.8

And that's what we're bringing you at this show.

1:04.9

Each week, we're helping you get what you want out of your career by talking to the smartest leaders we know.

1:10.4

Because we know your

1:11.7

work life is a lot more than nine to five. All right, let's get into it.

1:19.8

Hi everyone. Today's guest is Trinney Woodall. She's the founder and CEO of Trini London, a beauty

1:27.4

brand she launched after building a career in fashion and TV.

1:31.4

Trini always gravitated towards fashion, but before committing to the industry, she tried following in the footsteps of her dad, testing the waters and finance.

1:40.6

She hated it and pivoted to fashion where she became a well-known London-based style columnist in the 90s.

...

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