Hosted by Who What Wear co-founder Hillary Kerr, Second Life spotlights successful women who have made major career changes. Guests share lessons they've learned through fearlessly daring to pivot, and how they've used skills from their "first lives" to navigate their winding career journeys.
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Hillary Kerr Podcasts

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Journal Entries
Samantha Hawley | Inspired by Brene Brown, Glennon Doyle, Marie Forleo, Hillary Kerr, Mel Robbins
Journal Entries is a podcast for ambitious women who feel stuck in patterns they can't seem to break. Your host, Samantha Hawley, is a Clarity Coach who helps you see your blind spots so you can stop self-sabotaging and start trusting yourself again. Whether you're a working mom feeling overwhelmed, an executive people-pleasing your way to burnout, or an entrepreneur avoiding the decisions that would actually move your business forward - this podcast will help you identify what's really keep ...
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181. September Reset For Working Moms: 5 Min Journal Prompts To Stop Waiting For Perfect Timing
7:26
7:26
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7:26September energy hits different, doesn't it? While everyone's making January resolutions, you're over here actually ready to change things. New routines, boundaries you've been avoiding, that business idea collecting dust - all because you keep telling yourself "when things calm down." Plot twist: They never do. 😂 Perfect for working moms who are: …
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The Who What Wear Podcast: Jewelry Designer Pamela Love on the Art of Adornment and Creating Her Own Tarot Deck
28:57
28:57
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28:57Pamela Love is the jewelry designer behind Pamela Love Jewelry, a line of sustainable, celestial-inspired jewelry. Since founding her namesake brand in 2008, Love’s timeless pieces have been highly sought after by those who share her love for tarot, astrology, and the spiritual world. Who What Wear Editor in Chief Kat Collings sits down with Love t…
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180. How to Stop Micromanaging Your Business & Kids WITHOUT Everything Falling Apart
9:20
9:20
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9:20When you're used to being the person who gets things done, letting go of control feels impossible. Your kid refuses to put shoes on. Your employee questions your timeline. Your partner loads the dishwasher completely wrong. Sound familiar? What if everything actually falls apart? Two things you'll walk away with: 🎯 The Two-Part Framework that stops…
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Jennifer Anderson: Founder of Kids Eat in Color
57:54
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57:54Jennifer Anderson is the founder of Kids Eat in Color, a platform dedicated to providing families with the resources they need to feed their children nutritious foods and build healthy eating habits. Anderson’s passion for nutrition started during her time working in the nonprofit space, leading after-school snack programs. Her experience inspired …
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179. Why You Feel Guilty Every Time Someone Offers to Help | 5 Min Journal Prompts
9:16
9:16
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9:16You know that feeling when someone offers to help and instead of relief, you feel... guilty? Like you should be able to handle it all yourself? If you've been telling yourself "I should be grateful they offered but I just can't accept it," this journaling session is for you. In this 5-minute episode, we're diving into what's really behind that guil…
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The Who What Wear Podcast: New York Fashion Week S/S 26 Recap
19:32
19:32
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19:32In this episode, Who What Wear Shopping Director Bobby Schuessler sits down in the studio with senior editors Eliza Huber and Tara Gonzalez to debrief on everything they saw during NYFW. They dissect the trends they saw on and off the runways—from aprons to feathers to hoop skirts—and dig into the overarching shift toward wearability and practicali…
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178. Finding your Purpose When You're Overwhelmed: Learn to RECEIVE
23:35
23:35
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23:35Hot Take: What if your purpose right now isn't to do more, achieve more, or figure out your next big career move? What if your actual purpose is learning how to receive? My business coach asked me what I'd do on a random Tuesday if I could do anything. My answer floored me: drink matcha, watch reality TV at noon, cook a real recipe with multiple st…
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Sarah O’Leary is the CEO of Willow Innovations, the inventors of the first wearable breast pump. She began her career as a consultant for private equity clients, learning firsthand how businesses make big decisions and developing her problem-solving skills. She then made the switch from advising companies to helping run them when she went to work f…
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177. Journal With Me: Emotional Braindump for Back to School Mom Overwhelm
17:57
17:57
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17:57Moms with kids who went back to school recently...UNITE! This week hit me like a freight train. New school routines, drop-offs that take FOREVER, schedule changes that make you question everything - and it's only Tuesday. So instead of pretending I have it all together, I'm taking you into my real, messy braindump journaling session. No pretty prom…
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The Who What Wear Podcast: Wednesday Hair and Makeup Artists Nirvana Jalalvand, Francesco Pegoretti, and Lynn Johnston on Moody Colors, Gothic Foundation, and Dark Circles
18:51
18:51
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18:51Nirvana Jalalvand, Francesco Pegoretti, and Lynn Johnston are the hair-and-makeup masterminds behind Netflix’s hit show Wednesday. To celebrate the release of the show’s highly anticipated second season, Who What Wear beauty editor Kaitlyn McLintock sits down with the team to discuss how they drew inspiration from the original black-and-white run o…
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176. Why Being A Mom Is So Hard: Postpartum Anxiety & New Mom Overwhelm W/ Brittany Olson
33:01
33:01
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33:01Are you drowning in motherhood while everyone else seems to have it figured out? Brittany Olson from Becoming a Mother podcast breaks down why becoming a mom hits so differently than anyone warns you about. We dive into matrescence (the scientific term for becoming a mother) and why it's not just the sleepless nights that knock you sideways. Britta…
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Sarah Harrelson: Founder and Editor in Chief of Cultured Magazine
51:40
51:40
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51:40Sarah Harrelson is the founder and editor in chief of Cultured Magazine. She initially thought about going into politics, but things changed when she discovered her love for publishing as an intern at Elle. She moved to Miami to work her way up the masthead at a smaller publication, climbing to the role of editor in chief in less than a year. She c…
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175. Why You Keep Avoiding Playtime With Your Kids | 5 Min Journal Prompts
8:50
8:50
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8:50You love your kids, but somehow you keep finding reasons to avoid actually playing with them. The dishes need doing. Emails need answering. That toy bin needs organizing. Sound familiar? What if the real issue ISN'T that you're too busy or too responsible? What if you're actually using those tasks to avoid something much deeper? In this 5-minute st…
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The Who What Wear Podcast: Fall 2025 Shopping Guide: Faux Fur, Sculpted Silhouettes, and Polo Shirts
36:25
36:25
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36:25This week, Who What Wear Shopping Director Bobby Schuessler sits down with Associate Director of Special Projects Kristen Nichols and associate shopping editor Audry Hiaoui to talk all things fall shopping. They get into all the trends they saw on the fall/winter runways and which ones they think will dominate the market. Whether you’re leaning int…
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174. How to ENJOY Playtime w/ Your Kids Without WISHING You Were Crossing Something Off Your To-Do List Instead
16:29
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16:29Picture this: You're on the living room floor, making robot sound effects while your kid transforms Bumblebee for the 47th time today. But instead of being present, your brain is screaming about the dishes, that work email you forgot to send, and whether you remembered to put the chicken in the crockpot. If this hits a little too close to home, you…
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173. Why Being a 'Good Mom' Makes Your Kids Meltdown MORE | 5 Min Journal Prompts
11:40
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11:40If you've been thinking "I'm doing everything right, so why are my kids so "difficult?" Like the harder you try to be the perfect mom, the more your kids seem to fall apart? I see you! You're absolutely crushing it at work - managing teams, solving problems, keeping everyone happy. Then you come home with every intention of being present, patient, …
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The Who What Wear Podcast: WWW Weddings: Unpacking The Plus-Size Bridal Dilemma, the “Fat Tax,” and the Designers Getting it Right
34:06
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34:06How size-inclusive is the bridal industry? In this episode, Associate Features Editor Ana Escalante breaks down her recent piece about her search for the perfect wedding dress as a plus-size bride. She and Editorial Director Lauren Eggertsen unpack the unfair dilemma that plus-size brides often find themselves in: either shopping for a mass market …
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172. Stop Chasing Work-Life Balance: 4 Internal Shifts That End Mom Overwhelm
20:46
20:46
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20:46You know that thing where you're working past bedtime because you convinced yourself "if I just finish this one thing, tomorrow will be so much easier"? Then you wake up and somehow there's even more waiting for you? That cycle used to drive me absolutely nuts. And after working with hundreds of ambitious moms, I've realized we're all chasing the w…
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Katlin Smith: Founder and CEO of Simple Mills
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54:23Katlin Smith is the founder and CEO of Simple Mills, a food company that makes a wide array of delicious gluten-free, grain-free, paleo-friendly, and non-GMO foods. Before starting her own company from scratch, Smith was a strategy and operations consultant. After years of relying on processed foods because of her demanding job, she switched to a P…
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171. How to Stop Feeling Guilty For Resting | 5 Min Journal Prompts
10:24
10:24
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10:24Exhausted but still organizing drawers at 10pm? Staying up for "one more episode" when you should sleep? This isn't about discipline - it's about the hidden beliefs keeping you from resting. This 8-minute strategic journaling session reveals why you can't give yourself permission to rest, even when your body is begging for it. We'll uncover the hid…
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The Who What Wear Podcast: Celebrity Hairstylist Chris McMillan on Creating “The Rachel,” Going Viral Before Social Media, and Launching His Haircare Line
30:39
30:39
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30:39Chris McMillan is a celebrity hairstylist with more than 30 years of experience behind the chair. He’s worked with everyone from Michelle Williams to Cindy Crawford to Kim Kardashian. This week, McMillan joins Who What Wear Senior Beauty Editor Jamie Schneider to look back on his career—from styling Farrah Fawcett curls for his mom to creating the …
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170. How to Stop Yelling at Your Kids: Guide for Overwhelmed Moms w/ Talia Anderson
48:21
48:21
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48:21You know that moment when you've asked your kid to get off the couch for the fifth time, and suddenly you're yelling way louder than you meant to? Then you spend the rest of the day feeling like the worst mom in the world? Yeah, me too. And apparently, so does literally every mom I talk to. Here's what you'll learn in this episode: 🎯 The real reaso…
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Alyson Stoner: Author and Founder/CEO of Movement Genius
1:11:36
1:11:36
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1:11:36Alyson Stoner is the founder and CEO of Movement Genius, a mental health platform designed to support child performers. Stoner started their career as a child star, acting in hundreds of projects as an actor, singer, and dancer. They got their big break as a dancer in Missy Elliot’s “Work It” music video and went on to star in Disney Channel’s Camp…
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169. Journal with me: Goal setting without the overwhelm (5 Min prompts)
6:34
6:34
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6:34What if pursuing your goals felt free, aligned, and way easier than you've been making it? You start with all this motivation, then suddenly your dreams feel more like burdens than possibilities. I was talking with someone inside Emotionally Empowered recently who's working full-time AND starting her master's program. She described her brain as "a …
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The Who What Wear Podcast: Too Much Costume Designer Arielle Cooper-Lethem on Maximalism, the Power of a Pioneer Nightgown, and London vs. NYC Style
28:40
28:40
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28:40Arielle Cooper-Lethem is the costume designer for Lena Dunham’s hit new show, Too Much. The hilarious and heartfelt rom-com, led by Hacks star Megan Stalter as Jess and The White Lotus star Will Sharpe as Felix, debuted on Netflix in July. This week, Cooper-Lethem joins Who What Wear Editorial Director Lauren Eggertsen to tell us what it was like c…
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168. 4 Reasons Journaling About Your Goals Isn't Helping You Achieve Them (& What to Do Instead)
15:27
15:27
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15:27Have you been told to write down your goals? That doing so would help you stay focused or actually achieve them? There's a BIG difference between regular journaling & strategically journaling towards your goals. Maybe you've been there - writing down the same goals week after week, checking all the productivity boxes everyone talks about, but still…
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Jess Jacobs is the chief executive officer of Coterie—a premium, high-performing diaper essentials brand. Before Coterie, Jacobs spent years making a name for herself in creative advertising. She got her professional start as a copywriter for an ad agency, working on campaigns for noteworthy brands like Saks Fifth Avenue, LG, and Revlon. She contin…
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167. Journal with Me: 5 Min Prompts for When You're Carrying TOO Much
8:57
8:57
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8:57Save this episode for when you have 5-mins to strategically break free from holding it all together! (Prompts below) I made this episode for the woman who feels like you're the only one who sees how much you're actually handling. Like everyone around you just assumes you've got it all under control, while you're secretly drowning in the weight of k…
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The Who What Wear Podcast: Author Amy Odell on Chronicling the Life of Gwyneth Paltrow, From '90s Fashion Icon to Wellness Mogul, in Gwyneth: The Biography
37:22
37:22
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37:22Three years after authoring the incredible biography of Anna Wintour, fashion and culture journalist Amy Odell returns to the pod to discuss her newly released biography of actress and Goop founder Gwyneth Paltrow. Through hundreds of interviews and countless hours of archival research, Odell chronicles Paltrow's life of cultural influence—from '90…
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166. What Your “Trophy Wife” Dream Is Really Telling You About Burnout & Your Purpose
19:43
19:43
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19:43You know that daydream where someone else handles all the big decisions while you sip coffee and plan lunch dates? You're not the only high-achieving mom having this "trophy wife" fantasy. Two women on recent calls - a CFO and a CEO - both confessed they'd love to give up everything they've built just to have zero responsibilities. In this episode,…
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Samina Virk: U.S. CEO and Chief Marketing Officer of Vestiaire Collective
57:42
57:42
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57:42Samina Virk is the U.S. CEO and chief marketing officer of Vestiaire Collective, a global luxury resale platform. As a young girl, Samina loved fashion. She grew up making her clothes, thinking she might break into the industry on the creative side. Instead, she started her career in tech, working in e-commerce during the dot-com boom. She eventual…
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165. Journal with Me: Boundary Setting *Without* Guilt (3 Prompts)
9:43
9:43
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9:43Ready to stop feeling like a jerk every time you protect your time and energy? This one's for all the women who know they need boundaries but feel guilty just thinking about setting them. I keep hearing this at networking events — successful women who can negotiate million-dollar deals but can't tell their neighbor they're not available to babysit;…
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The Who What Wear Podcast: WWW Weddings 2025: The Definitive Guide to This Year’s Bridal Fashion and Wedding Planning Trends
26:47
26:47
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26:47This week, Associate Director of Special Projects Kristen Nichols and senior fashion editor Anna LaPlaca are giving you the definitive report on all things weddings. Kristen runs through the biggest trends from 2026 Bridal Fashion Week, where she saw chiffon capes and voluminous skirts in full force. And Anna has the scoop from experts in the weddi…
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164. Why Your To-Do List Is Making You MORE Overwhelmed (How To feel More Organized)
26:43
26:43
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26:43This is for you if you stare at your to-do list and feel your chest tighten! You wrote everything down to feel more in control, but somehow you're drowning in your own handwriting. That master list that was supposed to save you? It's actually making everything worse. Episode Highlights: 🎯 The Control Trap - Why your 47-item to-do list is creating f…
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Ali Mejia is the visionary and cofounder of elevated sleepwear brand Eberjey. Although she’d always had a soft spot for pajamas (getting ready for bed was a self-care ritual in her home growing up), Mejia began her career on Wall Street. After graduating from Princeton, she followed many of her peers to New York City and got a job as a financial an…
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163. Journal with Me: Get Out Of Your Comfort Zone & Closer to Your Goals
9:48
9:48
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9:48Ready to journal through WHY you're not taking action on your goals you SAY you want to achieve? This episode is a follow-up to Tuesday's conversation about networking for introverts (one of MY goals!). I'm sharing the breakthrough moment that changed everything for me—and three journal prompts to help you stop using "responsibility" as an excuse t…
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The Who What Wear Podcast: The Bear's Molly Gordon on the Importance of Female Friendships—and Delusion—While Making It in Hollywood
32:28
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32:28This week, Who What Wear Co-Founder Hillary Kerr is chatting with our June cover star, Molly Gordon! You likely know Gordon from playing Claire in FX's The Bear, or from past roles in Booksmart, Theater Camp, Shiva Baby, and many more. In addition to acting, Gordon has approached her career from the angle of multihyphenate since the beginning. In f…
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162. The Secret to Networking for Introvert Executives & Entrepreneurs (Without the Overwhelm) | Guest: Heather Nelson
36:06
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36:06I used to write my "elevator pitch" in my phone's notes app before networking events. Like, word-for-word what I'd say if someone asked what I do. Because the thought of blanking out and stumbling over my words while some extrovert waited for me to get to the point? Absolutely not. Here's what my guest, Heather Nelson, taught me: the most successfu…
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Amrit Tietz: DJ and Co-Founder of Spread the Jelly
52:01
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52:01Amrit Tietz is an international DJ and co-founder of the modern motherhood platform Spread the Jelly. Although she initially set out to study economics, Tietz dropped out of college, unbeknownst to her parents, to pursue a path she was more passionate about: music. She auditioned multiple times for the West Australian Academy of Performing Arts, a …
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161. Journal With Me: Stop Feeling Guilty For Loving Your Career (10 min prompts)
10:45
10:45
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10:45Do you love your career but feel guilty about it? Many working moms struggle with conflicting feelings about loving their work while wanting to be present for their kids. In today's journaling session, we're diving deep into why you feel guilty for loving what you do and how to break free from that pattern once and for all. What you'll discover: Wh…
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The Who What Wear Podcast: What to Shop at the Nordstrom Anniversary Sale, With Nordstrom’s Associate Fashion Director Linda Cui Zhang
21:03
21:03
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21:03The annual Nordstrom Anniversary Sale is live, and to celebrate, Who What Wear Shopping Director Bobby Schuessler is talking to one of the great curatorial minds behind the sale—Nordstrom Associate Fashion Director Linda Cui Zhang. In this episode, Zhang reveals the product selection process for the sale, the trends her team prioritized, and the ne…
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160. How to Stop Feeling STUCK (and trust your inner voice)
8:44
8:44
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8:44"What do you want, Sam?" I'll never forget staring at my therapist like a deer in headlights when she asked me that simple question. I had NO idea. After years of putting everyone else first, I'd completely lost touch with my own inner voice. Is that you, too? You're not the only one who feels stuck between what you "should" do and what you actuall…
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Sarah Davis: Founder and President of Fashionphile
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44:07Sarah Davis is the founder and president of the luxury resale company Fashionphile. Davis was a self-proclaimed “debate nerd” during her teens and had early aspirations of becoming a lawyer. After earning her undergrad, she quickly enrolled in law school at the University of Maryland. Growing up, Davis had become accustomed to taking odd jobs to pa…
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159. The REAL Reason You Keep Avoiding That One Thing: 5 Min Journal Prompts for Self-Sabotage
9:16
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9:16There's ONE thing you've been putting off for weeks... months... maybe even years, right? The important action that would move your life forward, but somehow you keep finding reasons not to do it? In today's 5-minute journaling session, I'm getting vulnerable about my own 3.5-year avoidance story and sharing the exact prompts that finally helped me…
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The Who What Wear Podcast: Go Sports! Athlete Stylists Brittany Hampton and Manny Jay on Dressing WNBA It Girls, and Why It's More Than Picking Out Clothes
36:10
36:10
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36:10In this episode, Senior Fashion Editor Eliza Huber—Who What Wear’s resident expert on the intersection of sports and fashion—is sitting down with two stylists behind some of the best tunnel fashion we’ve seen in recent months. Brittany Hampton is a seasoned athlete stylist whose client roster includes some of the buzziest women in basketball: Paige…
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158. How to Stop Worrying What Others Think When You're Not Perfect(w/ Dr. Gretchen)
30:44
30:44
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30:44Ever walked into a meeting feeling like you're barely holding it together, silently praying no one notices you're winging it? Or picked up your kids from daycare after a rough workday, worried the other parents can tell you're struggling? You're not alone. That constant worry about judgment is exhausting—and it's stealing your confidence at work an…
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Denise Woodard: Founder and CEO of Partake Foods
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56:24Denise Woodard is the founder and CEO of Partake, an allergy-friendly food company. Woodard started her career in pound-the-pavement sales roles at Philip Morris and FedEx, gaining robust experience in winning business by providing genuine solutions to her clients. She then spent the majority of her early career at the Coca-Cola Company, starting i…
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157. Journal With Me: 4 Ways You're Sabotaging Summer Joy (5-Min Prompts)
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10:17Is your summer not feeling how you imagined? You might be self-sabotaging without realizing it. Ready to break free? The Energized Summer Challenge starts Monday - but registration closes THIS Friday, July 4th, for podcast listeners. Get details + join here → www.samanthapenkoff.com/energized-summer In this 5-minute journaling session, I'll guide y…
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The Who What Wear Podcast: Rhode Cosmetic Chemist and BeautyStat Founder Ron Robinson on Crafting Cult Favorite Products and the Buzzy Ingredient That’s Not Worth the Hype
19:14
19:14
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19:14Ron Robinson is the founder of BeautyStat and the cosmetic chemist behind Hailey Bieber’s skincare line, Rhode. Robinson began his career at Clinique in the ’90s and, over the past two decades, has worked on products for industry giants like Revlon, Avon, L’Oréal, and Lancôme. He launched BeautyStat as an educational platform for beauty enthusiasts…
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156. Why You're Always Exhausted: How to Stop Managing Everyone Else's Emotions
23:11
23:11
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23:11Ever feel like you're drowning in responsibilities while everyone around you seems fine? You're not broken—you're just carrying emotional weight that was never yours to begin with. You'll Discover: 🎯 Why your "self-care Sunday" isn't fixing your exhaustion (hint: you're treating symptoms, not the cause) 🎯 The childhood survival pattern that's secre…
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