From the outside, you would think singer, songwriter, actress, and TV host Rita Ora has always felt fully in control of her career. But like a lot of us, Rita struggled with self doubt about her career direction – on top of facing industry challenges. Still, none of that stopped her from achieving the multidimensional career she wanted. This week, we spoke with Rita about how she remained intentional and purposeful in the face of setbacks, and how she grew her brand and her confidence.

In this episode, Rita shares: 

The wellness practice she swears by 

How she manages her anxiety 

Why - and how - she’s created a “360-degree” career for herself 

Her experience suing her former label, Roc Nation, for neglect

The mantra she repeats to herself when she faces adversity 

Rita Ora on Taking Control of Her Career

9 to 5ish will be back in your feed on December 6th!
Anna Wesche is the brains behind a new podcast from Flamingo, an award-winning body hair and care brand whose mission is to champion women, their bodies, and their choices. In this After 5ish conversation, Anna shares her experience making some major career pivots, creating the opportunities you want, and how Flamingo’s brand new podcast, “Unruly”, centers female stories.

In this episode, Anna shares: 

Why she struggled to find purpose early in her career – and how she’s found it now 

What it was like to work full-time and go back to school 

The episodes of "Unruly" you won’t want to miss

After 5ish: Anna Wesche on Creating the Opportunities You Want

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: 

How she and Chip built a loyal and diverse audience 

Why she still has a “small business” mindset, despite all her success

The realities of raising five children and running her business

How she’s dealt with the pressure of other people’s expectations – and her own 

Her favorite activities that spark creativity

Joanna Gaines on Learning to Let Go of Guilt and Anxiety

Annie Jean-Baptiste is Google’s first-ever Head of Product Inclusion. TLDR: she’s a tech executive responsible for making all of Google’s products inclusive for every user. Annie is also the author of the critically-acclaimed book, Building for Everyone, the first book about building inclusive products across the intersections of 12 dimensions of diversity. Annie's work has inspired a movement at other tech companies and in other industries to prioritize equity in design.

In this episode, Annie shares: 

Why Google created a position for her – and how that came to be 

How she’s used her introversion as a leadership tool 

What leaders need to understand about designing inclusive products 

Why she’s still working on "speaking up" as a leader

Annie Jean-Baptiste on Building Inclusive Teams and Products

Actress-turned-entrepreneur Cameron Diaz and consumer brand builder Katherine Power (WhoWhatWear, Merit Beauty, Versed) had been friends for years before they decided to launch Avaline, their transparently produced organic wine brand. After realizing the wines they loved were full of additives and hidden ingredients, they saw an opportunity to create a new kind of bottle – and transform the wine industry in the process. We spoke with them about how they've transformed their careers, and their lives, by launching this brand.

In this episode, they share: 

Why Cameron left acting behind – and what that’s unlocked for her

Katherine’s tips for time management and efficiency 

What we can’t Google about Cameron 

How they broke into the alcohol industry 

The surprising things you should look for when choosing wine

Cameron Diaz and Katherine Power on Evolving Their Careers and Finding Peace

When Jen Psaki became President Obama’s White House Communications Director, she was pregnant. Later, she became President Biden’s Press Secretary, and she had to navigate her role as a mom and as the White House’s chief spokesperson. And considering when you work for the president, you’re expected to be on call 24/7, that's a big challenge. Today, we spoke to Jen about what doing both actually looked like for her – from the hard realities to the help she got along the way. 

In this episode, Jen shares: 

What a job interview with the president is like 

Why she regrets not seeking feedback early in her career

Her non-traditional approach to mentoring 

What she learned from not getting the job she wanted the first time  

How she set boundaries, even when on call 24/7 

Jen Psaki on Raising Kids While Working at the White House

Jada Pinkett Smith’s memoir, Worthy, has made a big splash for its bombshell revelations … and it hasn’t even been out for a week. But the book from the award-winning actress and talk show host is not just tabloid fodder – it’s also a critical part of Jada’s “reclamation journey”. In this episode, Jada tells her career story – how she’s navigated Hollywood, having a world-famous spouse, death threats, and public judgment. And come out stronger for it. 

In this episode, Jada shares: 

Her dream Red Table Talk guest 

Why she had to learn to deal with her self-judgment  

How to have difficult conversations with friends and family

Her perspective on *that* Red Table conversation between her and Will  

Why her alopecia diagnosis has been a great “teacher”

Jada Pinkett Smith on Why She’s Reclaiming Her Story

Michelle Crossan-Matos, the CMO of Ulta Beauty, is one of the most prominent marketing executives in the country. And she told us she didn’t just get to her position by crunching the numbers and digging into data. She used her intuition and gut instinct to launch new campaigns, solve problems, and grow brands. Today, we spoke to Michelle about how your intuition can be your professional superpower … if you know how to listen. 

In this episode, Michelle shares: 

Why she wakes up at 4:30am every day 

Why everyone needs to develop a sense of personal leadership, even if you’re not in the c-suite

The interview question she always asks candidates 

The professional mistake she learned the most from

How she combats decision fatigue at work

Michelle Crossan-Matos on How Your Intuition Helps You Win at Work

Joey Wölffer didn’t ever think she’d take over her family’s business, the Wölffer Estate winery. But over a decade after surprising herself and becoming the co-owner and chief brand officer of the beloved vineyard, Joey has transformed the brand and the business. You’ve probably seen their famous Summer in a Bottle rose or their sparkling ciders on shelves near you. And Joey’s done all of that while building her own fashion business, Joey Wölffer. On today’s episode, Joey shares her secrets to creating a unique and relevant brand.

In this episode, shares: 

How losing her father unexpectedly changed her mindset about her career

Why she wasn’t a fit for corporate America

Her experience building two businesses at once

What it’s like to work with her brother and her husband 

How she calls out a lack of gender representation in the alcohol industry

Joey Wölffer on the Secret to Creating a Unique Brand

Colleen Cutcliffe, co-founder and CEO of the groundbreaking probiotics company Pendulum Therapeutics, started the company with a big goal in mind: changing the way people think about their gut health. And on her journey, she’s had to challenge traditional – and sometimes outdated – thinking from the medical community and investors. In this episode, Colleen told us how she’s been able to disrupt the industry, and gives her advice for making changes in any workplace. 
In this episode, Colleen shares: 

How she convinced the dean of her PhD program to let her stay – despite almost getting kicked out 

Why her daughter’s birth inspired her to start Pendulum 

How she dealt with being told “no” 

The ways she’s cultivated trust and transparency with her team

Why she’s got Halle Berry on speed dial 


PS: Skimm'rs get 20% off their first month of any Pendulum product(s) with code SKIMM9TO5.

Colleen Cutcliffe on Challenging Outdated Thinking in the Workplace

Alicia Menendez, MSNBC anchor, award-winning journalist, and host of the Latina to Latina podcast, was so concerned about being likable at work that she wrote a whole book about it. She even created a name for that pressure women feel to be amenable in the office – "the likability trap." And as an on-camera journalist, she’s fallen into that trap throughout her career. In this episode, we spoke with Alicia about her journey with likability, how that affected her professional and personal wellbeing, and her recommendations for carving out your own professional identity. 

In this episode, shares: 

Why she didn’t go into politics like her father 

How she’s dealt with the pressure of other people’s expectations

What she’s done to carve out her own leadership style and professional identity 

How she talks to her daughters about likability 

Her advice for avoiding getting caught up in the trap, and getting your coworkers and managers to do the same 

Alicia Menendez on Avoiding the "Likability Trap" at Work

For over a decade, Emily Tisch Sussman was one of the top political strategists in the country, advising Democratic candidates and campaigns. Then, after having three children in four years, and faced with no childcare during a global pandemic, Emily realized she couldn’t get back to the top of her game… or back in the game at all. So, she stepped away from politics and the professional identity she had known for 15 years. Now, after going through her own major pivot, she’s talking to other women about their career journeys on the 'She Pivots' podcast. 

In this episode, shares: 

The line she used that got her every job she’s had 

Why she wrote an article saying her children “killed” her career – and how she felt after writing it 

Why she wasn’t connecting to the traditional narratives around being a working mother

Her advice for women who’ve also had to shift their professional identities 

What it'll take for politicians to pass policies that better support families

Emily Tisch Sussman on What Happened After Her Kids “Killed” Her Career

When Hill House Home first started, founder and CEO Nell Diamond wasn’t focused on selling the now-famous “Nap Dress”, or cultivating her Instagram presence. Rather, the brand started as a bedding company, and Nell’s Instagram was a space for her creativity. Seven years later, the Nap Dress is a cult-favorite, selling out in minutes, Nell’s created the model for the influencer-entrepreneur, and Hill House is now valued at $150M.

In this episode, shares: 

Why she followed her instincts to go into fashion, despite people telling her it wasn’t a “serious” profession

What her first job at Abercrombie taught her 

Why you don’t need to be a natural risk-taker to be an entrepreneur

The thing she wishes more executives would understand 

The tools she’s leaned on as a manager and executive

Nell Diamond on Paving the Way as an Influencer and Entrepreneur

Elizabeth Chambers has been through… a lot in the past few years. But the founder and CEO of BIRD Bakery isn’t letting her ex-husband or the headlines define her. She’s focused on expanding her business (which now has four locations) and helping her family heal. This week, we spoke to Elizabeth about how she’s found professional and personal stability.

In this episode, shares: 

Why she started BIRD Bakery

How she’s set boundaries in her professional and personal life 

What’s helped her on her healing journey – and why there’s no one size fits all path

Her outlook on parenting 

How she’s learned to sort through advice

Elizabeth Chambers on Rebuilding and Healing

Ashley Merrill, founder and chairwoman of the restwear brand Lunya, started the company when she was pregnant. As she built her brand, she was also growing her family, and her big career moments and her big parenting moments always seemed to align. On this episode, we spoke with Ashley about the misconceptions that being a parent is just a part time job, why we need to speak up about childcare support, and how she’s shifted her career as her children have gotten older. 

In this episode, Ashley shares: 

Why we need to adjust our expectations about being a working parent

How she made the decision to hire a CEO for Lunya 

What it was like to run two businesses during COVID

Why the flexibility of entrepreneurship isn’t always a good thing 

Ashley Merrill on the Misconceptions About Being a Working Parent

For most of her career, Isa Watson felt like she was living somebody else’s life. She started out as a chemist working her way up the academic ranks, and then she became a world-traveling VP at JP Morgan. And a lot of people online started to take notice of her impressive career. Isa felt she was always chasing the validation of a ‘30 under 30’ or ‘40 under 40’ list, while neglecting her relationships and her own happiness. So, she stopped obsessing over that public praise. And founded Squad, the app that provides the easy and fun way to talk to your friends – away from social media. 

In this episode, Isa shares: 

How she’s dealt with the pressure of other people’s expectations

The life event that put everything into perspective for her 

How she rebuilt her relationship with herself 

Why she added 'professional skydiver' to her resume

Her advice for setting better boundaries with social media 

Isa Watson on How She Stopped Obsessing Over Achievements

Lauren Wesley Wilson worked for politicians and crisis comms firms for years before she decided to start her own organization, ColorComm. ColorComm started as a luncheon series over ten years ago, and now has grown to become the nation’s leading women’s platform addressing diversity & inclusion across the communications, marketing, advertising, and media industries. This week, Lauren told us how she sought out to make the notoriously competitive communications industry more inclusive. 

In this episode, Lauren shares: 

How she navigated a cutthroat industry when she was starting out 

Why she knew she needed to start ColorComm

What she gave up to found ColorComm

How she made the time and space for her personal life

The goals she created for her personal life

Lauren Wesley Wilson on Making Competitive Industries More Inclusive

You know Erin and Sara Foster as the sister-act behind the VH1 hit show “Barely Famous”, the co-founders of the fashion brand Favorite Daughter, and as the creative minds who’ve helped brands such as Bumble and the Mirror. After growing up in the entertainment world, the sisters not only decided to take on that industry, but also to take on fashion and investing. We spoke to the Fosters about the value of taking career risks – and why they’ve decided to redefine what success means to them.

In this episode, Erin and Sara share: 

The unexpected famous person they are related to 

What they think of the “nepo baby” label 

Why accolades can actually be depressing

How their relationship has changed now that they’re in business together 

Erin and Sara Foster on How to Take Career Risks

Nyakio Grieco has been paving the way for inclusive beauty and supporting Black entrepreneurs for her whole career. She launched her first beauty brand, Nyakio Beauty, in 2002. Then in 2020, she launched Thirteen Lune, the e-commerce platform dedicated to elevating Black and Brown beauty founders. While Nyakio is one of the most celebrated entrepreneurs in the industry, the road to the top was paved with hurdles. Including shuttering and relaunching her original brand, watching that brand take off after she sold it, and starting over as a founder at 47. 

In this episode, Nyakio shares: 

Her perspective on failure 

How her optimism has served her throughout her career

Why she’s focused on bringing her friends along on her journey

How she stopped being a “people-pleaser”


PS: Skimm listeners can get 20% off Thirteen Lune products using the code SKIMM20. Valid for 30 days from June 7, 2023.

Nyakio Grieco on What They Don’t Tell You About Entrepreneurship

To wrap up this season of 9 to 5ish, we’ve got a bonus episode with author Avery Carpenter Forrey. She was one of the first employees at theSkimm, who pivoted her career to become a writer. Her highly-anticipated debut novel, Social Engagement, drops on May 23rd, and explores millennial wedding culture, class, and relationships. This week, we spoke to Avery about how she pulled off the pivot, what tactical steps she took to get started, and how she maintained relationships with her former colleagues. Plus, she shares what it’s like to be a new mother while promoting her book. 

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