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

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Norma Kamali started her career when women were expected to type memos in Mad Men-esque offices, not build their own empires. She came of age in 1960s New York City and since then, Norma's become one of the most influential names in fashion. Norma is responsible for iconic looks like Farrah Fawcett’s red swimsuit, the sleeping bag coat, and some of the earliest activewear, before “athleisure” was ever a thing. At 80-years-old, she’s showing no signs of stopping. 

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

How a $29 flight and a basement boutique kicked off her career

What it took to walk away from a toxic business – and marriage

Why she took her brand to Walmart, even when people told her not to

How learning to ask for help changed her life

Why AI gives her a bigger creative high than anything else

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Author, businesswoman, designer, and chef Joanna Gaines used to let guilt and anxiety consume her. As a mom of five children, and as one half of one of the most successful lifestyle brands in the country, Joanna is now battling her burnout by letting go of those feelings. This week, we spoke to Joanna about that shift to free herself from the pressure of expectations and what it’s unlocked for her, professionally and personally. 

In this episode, Joanna shares: 

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Nili Lotan’s career didn’t begin on the runway. It started in corporate fashion, where she spent over two decades working at major brands like Ralph Lauren and Liz Claiborne. Then, in her late 40s — newly divorced, with a 9-year-old at home and two kids heading to college — she launched her namesake brand from the ground up. No outside investors or business plan. Just instinct, confidence, and a commitment to designing for real women like herself.

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

How she went from Israeli Air Force to the NYC fashion scene

Why she thinks every woman needs a good pair of jeans

The importance of betting on yourself, even when it’s scary

Why it’s never too late to start something new

How her own mom influenced her decision to be a working mom 

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Thasunda Brown Duckett, the President and CEO of TIAA, had a “meteoric rise” in the world of finance. As the former head of Chase Consumer Banking, and now as one two Black women who currently leads a Fortune 500 company, she realized early on that “work life balance” was a myth. Instead, Thasunda lives her life like it’s a diversified portfolio, allocating time and shifting her investment in different areas. So over time, she always outperforms. Tune in to learn how. 

In this episode, Thasunda shares: 

How to live your life like “a diversified portfolio” 

Her secret to building relationships at work

What it means to “rent your title, own your character” at work

Why she almost turned down her dream role

What you need to know to prep for retirement

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Sali Christeson actively suppressed her idea for Argent for years. She was killing it at her job at Cisco – she didn’t have time to start her own company. But after spending over a decade in male-dominated companies, where business casual was a non-negotiable, Sali realized that most women’s workwear just…wasn’t working. Sali tells the story of how she went from wearing pocketless pants to building Argent, a brand that actually works for the lives women lead.

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

How she set boundaries as an employee at Cisco – and how she implements those learnings as a founder

Why getting good at networking landed her investors and opportunities 

How she teaches female founders to reclaim their power instead of give it away

Advice on how to advocate for yourself to be included in conversations 

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After every election she’s covered, Abby Phillip has the same thought: I can’t do this anymore. It’s her mind waving a red flag – and a sign of burnout after months of chaos. Over the years, Abby’s had to navigate a fast-moving digital media world at the same time as some of the most divisive political chapters in our lives. Now, she’s sharing how she’s learned to push through –  and the secret that helps her stay grounded in the madness.

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

How being a first-generation American influenced her career choice

Why she needed to fail at Harvard before considering journalism 

How she made the most of an uncertain path at the then emerging outlet, Politico

The way she reframed getting continuously rejected from outlets

How she *really* felt about consequential coverage after the 2020 debates 

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When Cathy Engelbert found out she was pregnant, she resigned from a decades-long climb to becoming a partner at Deloitte. In her mind, being a good mom and a good exec couldn’t coexist. But one male colleague saw her potential — and told her so. That changed everything. Cathy stayed, asked for the flexibility she needed, and learned to advocate for herself. She went on to become Deloitte’s first female CEO. Now? She’s leading one of the fastest-growing sports leagues as WNBA Commissioner.

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

How sports turned her from a shy kid to a bold leader

Why the environments of Deloitte and the WNBA actually aren’t that different

Her first 9-1-1 call as league commissioner – and the one trait that helped her get through it

Why implementing Deloitte’s paid family leave policy was the “most courageous thing” she’s ever done

One way she thinks the WNBA can be a model for the men’s leagues 

Follow Cathy on IG: @wnbacommish

Follow Carly and Danielle on IG: @carlyanddanielle

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Dawn Staley helped Team USA’s women’s basketball team win gold at the ‘96 Olympics. It was the highlight of her career. Yet she fell into a depression that was so bad, she didn’t even want to look at a basketball. Nothing prepared her to process reaching such a milestone. She was left asking herself: now what? With a resumé is full of career-highs (hi, 3x national champ), Dawn says the real reward isn’t the trophy – it’s all the work it took to get there. Dawn gets into it all in her new memoir, "Uncommon Favor."

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

How many shoes she has in her collection (sneakerheads beware)

Why she aspired to play in the NBA – instead of the WNBA – growing up 

How the taboo nature of mental health stopped her from asking for help post-Olympics

Why she was insulted when approached for a coaching job 

The one thing she wants to see change for women athletes this year

PS: Dawn’s memoir is out now.

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Melanie Masarin once pitched Glossier’s founder to do a pop-up at a former fried chicken shop. Her response? “I don’t get it, but I trust you.” It was a career-defining moment for her. Because getting approval from the founder meant she couldn’t afford to mess it up. Listen as Melanie shares why being given major responsibilities in her mid-twenties shaped her career. Plus, how it prepared her to start Ghia, the non-alcoholic apéritif that’s now a millennial bar-cart staple. 

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

Her food-centered core memories growing up in the French Riviera 

The money-shock she experienced attending Brown University 

The once-in-a-lifetime chance she had to design the Glossier flagship store

Her journey shifting from founder-to-CEO mode, and the difficulties that come with it

How pivoting Ghia’s launch strategy actually paid off 

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