Second Life

Hosted by Second Life

Business Careers Society Culture Personal Journals Arts

Website RSS feed Facebook

Episodes

731

Latest episode

Oct 2026

Language

About the show

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.

Listen to episodes

60 recent

October 14, 202645 min

The Who What Wear Podcast: WWW20 Presents: Mandy Moore, From Teen Pop Icon to Award-Winning Actress

This month marks Who What Wear's 20th anniversary! To celebrate, we're spending all of October with guests who have left an indelible mark on the fashion-and-beauty world and grown up alongside us over the past two decades. This week, Hillary sits down in studio with iconic actress and singer Mandy Moore. Moore has been in the spotlight for over 20 years, from releasing her hit 1999 song "Candy" to starring in A Walk to Remember and This Is Us. Today, she reflects on getting her start as a teen pop star, her outstanding acting career, and her most memorable fashion moments from the past 20 years. Plus, she shares everything you need to know about her highly anticipated new show: The Land.  Watch this episode on our new YouTube channel, and be sure to subscribe!

October 12, 202649 min

Danielle Pheloung: Cofounder of Phe Phe

Danielle Pheloung is a content creator and cofounder of the fashion brand Phe Phe. Before amassing a following on social media and starting her own clothing company, Pheloung worked in finance. She started her career as an analyst at Morgan Stanley and later transitioned to working for Goldman Sachs as a private wealth management associate. Meanwhile, her sister Brigette McHale, otherwise known as Acquired Style online, was experiencing immense success on social media. Encouraged by her sister's success, Pheloung decided to start posting on TikTok. She showcased her corporate style and daily life while working a demanding job. Eventually, Pheloung made the decision to pursue content creation full time, leaving her position at Goldman Sachs. She continued to grow on social media, and with her sister, she launched Phe Phe in 2025. Today, Pheloung continues to make content and run Phe Phe, which recently launched its workwear line, inspired in part by Pheloung's first life in the corporate world.

October 7, 202642 min

The Who What Wear Podcast: WWW20 Presents: Chriselle Lim, the Internet's Original It Girl

This month marks Who What Wear's 20th anniversary! To celebrate, we're spending all of October with guests who have left an indelible mark on the fashion-and-beauty world and grown up alongside us over the past two decades. To kick things off, Hillary sits down with Chriselle Lim, one of the original fashion content creators. Lim began her career as a fashion blogger and YouTuber in the late 2000s, and over time, she paved the way for creators like herself to become a respected part of the fashion industry. In this episode, she looks back on the last 20 years of her life and career, shares what it takes to have longevity as a creator, and explains how her dedication to storytelling in all forms has taken her from blogger to creator to founder and creative director of Phlur.  Watch this episode on our new YouTube channel, and be sure to subscribe!

October 5, 202657 min

Rickie De Sole: Editor of Air Mail's Dress Code

Rickie De Sole is the editor of Air Mail’s style-and-fashion publication, Dress Code. De Sole started her career as a fashion assistant at Vanity Fair. After that, she moved into public relations at Prada, where she worked from 2007 to 2010. De Sole then returned to the world of fashion media at Vogue as a market editor, working her way up to accessories director. After, De Sole went to W Magazine, eventually becoming the fashion director before transitioning back to Vogue. There, she eventually gained the title of executive fashion director of Vogue.com. De Sole later pivoted to retail at Nordstrom, ending her time there as the VP fashion director. Throughout her career, she has also served on the board of companies such as Rent the Runway and Vestiaire Collective. Today, she leads Air Mail’s style publication, Dress Code, and serves as a senior adviser at Sandbridge Capital.

September 30, 202629 min

The Who What Wear Podcast: Denim Consultant Benjamin Talley Smith Returns to Talk Fall Trends and the New Guest in Residence Denim Line

This week, Hillary sits down in studio with denim expert Benjamin Talley Smith. Talley Smith  is a denim designer and consultant who works with the designers at your favorite brands—such as Khaite, Reformation, and J.Crew—to develop their denim lines. Today, he's chatting all about the new denim line he worked on for Gigi Hadid's brand, Guest in Residence, and his top trend predictions to look out for this fall.  Watch this episode on our new YouTube channel⁠⁠⁠⁠, and be sure to subscribe!

September 28, 202650 min

Casey Lewis: Creator of After School

Casey Lewis is the creator of the Substack newsletter After School. However, before she was writing to an audience of tens of thousands, Lewis was writing about youth trends on her blog Teen Fashionista. Later on, she started at Teen Vogue as an intern, and over the course of her time there, she worked her way up to senior digital editor. She left Teen Vogue to create Clover Letter, a daily newsletter for teen girls, which gained traction quickly and eventually got acquired by AwesomenessTV. Lewis then transitioned to a senior editor role at New York magazine, but she missed writing. So in 2021, she put in her notice and started her youth-trend Substack publication, After School. Today, she continues to write her newsletter to dedicated readers, makes accompanying content on Instagram and TikTok, and uses her expertise in youth trends to consult businesses, from early-age startups to Fortune 500 companies. 

September 23, 202633 min

The Who What Wear Podcast: Designer Christian Cowan Unpacks His Buzzy NYFW S/S 27 Show

This week, Hillary chats with designer Christian Cowan about his buzzy spring/summer 2027 collection and showing at New York Fashion Week. They discuss his biggest inspirations, the brand's evolution over the past few seasons, and the countless celebrities who can't get enough of his designs. Plus, he shares whether or not bridal is on the horizon.  Watch this episode on our new YouTube channel⁠⁠⁠⁠, and be sure to subscribe!

September 21, 202652 min

Second Listen: Lili Reinhart: Actor, Producer, and Founder of Personal Day Skincare

This week, we are giving a second listen to our very special episode with Lili Reinhart. Reinhart is an actor, producer, and founder of the skincare brand Personal Day. She knew she wanted to be an actor from a young age and spent her tween and teenage years auditioning, self-taping, and begging her parents to let her finish schooling online so she could concentrate on her craft. At 19, she was cast as Betty Cooper on the hit CW show Riverdale and spent the next seven years in a nonstop filming and production cycle. During this busy period of life, she still found time to pursue outside projects, publishing a book of poetry in 2020 and founding a production company. When Riverdale ended in 2023, it allowed her a moment to pause and consider what she wanted to work on going forward. Since then, she’s been developing projects with her production company that ignore the mainstream in favor of tackling topics like mental health. She’s taken on a few acting projects, like the TV series Hal & Harper, which premiered at the Sundance Film Festival last month. She also spent two years developing her skincare line, Personal Day,and has been receiving great reviews for its nonirritating formulas and effective solutions for acne-prone skin. Since this episode’s original release, Reinhart’s career has continued to thrive, and her latest project, The Love Hypothesis, premieres on September 23.

September 16, 202627 min

The Who What Wear Podcast: New York Fashion Week S/S 27 Recap: Opulent Textiles, Unexpected Jewelry Styling, and Deconstructed Tailoring

This week, Who What Wear senior fashion editor Anna LaPlaca and Associate Director Kristen Nichols headed straight from their final shows to the studio to recap all things New York Fashion Week. They dive into it all, from their most anticipated shows to designers on the rise to the trends to look out for come spring. Plus, they reveal the best color to incorporate into your spring wardrobe.Watch this episode on our new YouTube channel⁠⁠⁠⁠, and be sure to subscribe!

September 14, 202655 min

Annie Meyers-Shyer: Author and Creator of "This Oak House"

Annie Meyers-Shyer is the creator of the social media phenomenon and book This Oak House. However, before embarking on a renovation project that would turn her into an "accidental influencer," Meyers-Shyer started her career in the fashion industry. She first worked for InStyle magazine and then Harper's Bazaar. For a period, she transitioned into the tech space as the fashion director of MySpace, but she soon returned to the traditional fashion space, working in PR at Chanel. After working at Chanel for six years, she left to focus on being a mom full-time. When her mother-in-law moved out of her Los Angeles home, Meyers-Shyer decided she wanted to take on the home and, thus, a renovation project. She documented her journey on Instagram for her friends to stay updated, and what began as a small, casual account blossomed into a community of over 200,000 followers. Today, she has taken her renovation journey and documented it in a book called This Oak House, which releases tomorrow.