How often do I look at someone and think, “how the heck did she get there?” This podcast answers my question! I love the focus on the nonlinear career path of inspiring professionals and experts, plus Hillary’s questions about mistakes and time machines and more. I found the show via Emily Nagoski and I’m glad to be here.

I’m not a fan of when hit podcasts try to piggyback their success with another show. Love love Second Life and have listened to literally every episode; I am not a fan of Who What Wear Podcast. This latest episode the clearly Gen Z host and guest made fun of millennial style, uh who do you think your founder is…and the target audience?? Apparently not women over 30. I’ll listen to all Second Life episodes (love Hillary as host) but skip the WWW episodes; I’ll get my clearly outdated fashion advice from somewhere else.

I seemed to vaguely know about you and this show before being sent the episode where you interview my CEO. But nothing prepared me for self-aggrandizing question after question, for a privileged woman who has built a career off internal and external aggrandizement. I was aghast, that even tho this is a podcast about her personal journey to the top, how little the show focused on culture, or the individual experiences 250+ employees with her at the helm. Class action lawsuits, wrongful termination, labor law violation after violation. Ageism, nepotism, favoritism. The whole place she runs is rotten from the core as evidenced by her zero, yes ZERO percent approval rating on Glassdoor. The entire episode I yearned for just ONE question about how the topic at hand, her life experiences, may have led to how she views leadership in regards to the health of teams she is leading. I implore you, with the influence on culture that you have via this podcast, to focus less on how wonderful their meteoric rises to the top have been, and devote at least some portion of the interview to what they’ve done with that power. And what they individually are doing to insure the wellbeing (at work) of those in their stead. Otherwise all this will be is a standing ovation that nepobabies had their rise, and power hoarded, with no regard for those left in their wake. Thank you from Los Angeles.

As someone who just took the leap and decided to trust myself and go all in on building my dream business, this podcast is a huge source of inspiration and motivation!

Thank you for interviewing Courtney Storer. I loved hearing about her fascination with restaurants.

I always look forward to every single episode that comes out, and that’s not always the case with some podcasts. People who complain about depth, why? This is a podcast on peoples careers, it’s a story they’re telling, not an episode on how to heal yourself. I personally love that it’s just a conversation between two career driven women that already know each other, makes it an easy listen. And they live in a world I don’t, which is a plus!

Would love to see diversity in the guests and to go deeper in the conversations. Very surface level. The constant laughing at odd times is uncomfortable.

10/10

Longtime JCrew fan, even through the low times. LOVED this episode soo much. Thank you 💚🤍💗

Today was one of my very favorite so entertaining educational and had wanting to purchase immediately which I did! Thank you as always for delivering such a great interview

I truly love this entire podcast so much ❤️

I’ve been listening since the beginning, and it just keeps getting better. I love hearing all of the inspiring stories as I contemplate what I may do in the future. It’s one of the few things I enjoy looking forward to for myself as I run around raising little humans. Thanks for the refuge, Hillary! 💗

Jimmy Fallon level fake laugh. Guests clearly find it cringe that she’s cackling at the smallest joke.

These women sound so much like the Mean Girls cast, not to mention occasionally ridiculous, “oh I know, SO inspiring!”. Really? These days with everything going on, WHO CARES? Also, any fashion references they make are said so fast how does anyone get them unless they’re all listed online somewhere? Podcast for the 1% and kids still on their parents insurance plan/phone bill

Excellent podcast!!!

I never miss an episode. Can you interview Claire Saffitz? She would be great in the fall with her new book coming out.

Interviews with a lot of softball questions, especially with people whose companies may not have a great reputation from their employees. If you’re going to talk about design and retail, talk about the problems in the industry, and what leadership is doing to retain and develop their teams instead of just fawning over the C-suite people. Ask some harder questions - it will lead to better conversations. Otherwise it’s just fluff.

Love the Second Life show but would be way better if you would create a separate podcast for the WhoWhatWear episodes. Some people are not going to be into the WWW episodes as much as the second life ones, and it makes checking the updates a bit disappointing.

Love love love your show. I think you should interview Pati Jinich, she’s lovely & so interesting. I think she has a new cookbook too. Keep doing what you are doing, it’s so inspiring. Thanks Hillary!

Thank you Hillary for sharing your talk with Jing. I had the pleasure of meeting Jing last month at a conference and I loved learning more of her story and what a true warrior she is. Sending all the good vibes to you and Jing for building others up and bringing a higher level of compassion for women entrepreneurs.

The interview with Diane Kruger was not good. Bad questions. Too much fawning.

I LOVE THIS PODCAST! It is thoughtful. It is informs. It is empowering to women. So grateful for women who lift other women.

I will make this review short & sweet but Hillary is the best podcast host I’ve ever listened to and I am an avid podcast follower/subscriber. She has genuine (!) enthusiasm, interest, curiosity, and thorough research for each of her guests that span a plethora of backgrounds, industries, credentials, ages, and life experience. She doesn’t pepper in ads that disrupt the conversation and as a skilled interviewer, as any good host would, she has a list of questions tee’d up but also goes with the flow of the conversation and it’s two-way listening that many other podcasts don’t have – a marvelous rarity. Similar to the heavyweights like Oprah and Diane Sawyer, she doesn’t machine gun question guests. She adds her perspective and probes further on behalf of her listeners’ intel and entertainment. This podcast is divine in every way and I regularly pop by its homepage to give it its deserving five stars.

When I have time, this podcast is such a special part of my day. The guests are so inspirational and yet somehow relatable and vulnerable, thanks in large part to Hillary’s interview skills. The stories shared are really special.

When a friend recommended this podcast because he said it reminded him of my evolution, I was curious to check it out. I was a bit skeptical when I saw that many of the guests seemed to be half my age, but I gave it a try and got sucked in. Each episode is full of inspiring stories from people who have started brands I’ve heard of but aren’t extremely well-known. I feel motivated to keep going on my own endeavor. I’m learning as I listen, but it feels like I’m eavesdropping on a conversation between my big sister and her best friend. So fun!

Love this. Going into my second life right now this is exactly what I need ❤️

I listen to a lot of podcasts, randomly, when I can etc etc. I ALWAYS listen to this podcast. I admire Hillary as a person, yes. But I also think she is an incredible host. She has a great voice both literally and figuratively. She gives space but also encourages these women. I’m confused by the other reviews that are annoyed by her praise…clearly missing the point of this podcast. From here, I have found more and more people I’m inspired by. I honestly didn’t realize I wanted to be an entrepreneur myself until I realized how much this podcast—and those that I’d been inspired by—meant to me. Second life is >>>>>>>

If I could have dinner with any three people alive or dead Hillary would be one. She is my favorite interviewer and always blows me away with her questions. I know she would be a fabulous addition to my dream dinner party.

It’s almost like she’s laughing at her guests. A serious and heartfelt response does not warrant laughter. Strange and distracting.

I feel like I’ve lived many lives and am in a transitional phase as I embrace growth. I’m in my late 40s and I can feel the shedding and the yearning for new. I am familiar with change and transition and am no longer afraid but excited to see how I evolve and what comes next. This podcast is truly right on time and is just what I need in this physical and emotional time. So grateful to have come across this! Thank you Hilary!

Love the pod. I wish Hillary would ask open ended questions though rather than multiple choice / fill in the blank questions. Otherwise it’s great

I’ve been listening for years and I’m continuously inspired by the guests, stories, and conversation! Hillary is an amazing interviewer, always asking all the questions I wish I could ask. Thank you for keeping this going!

My favorite podcast, often will relisten and find myself hearing new pieces of wisdom and knowledge from these amazing voices. Hillary has a gift for interviewing in a truly authentic and original voice. I love cooking and listening or a long drive to enjoy and think about these stories and how they can support my own growth as an entrepreneur. Thank you Second Life and Hillary!

Such a sycophantic host I cannot bear the fake laughs and fawning. Athena Calderone was it for me and not in a good way - how many times can she say she is clever and the host egging her on endlessly! Ugh! No more - there are better options undoubtedly.

This use to be my FAV podcast, and while I still listen, it’s starting to lose its luster. I use to love the stories of these entrepreneurial women and how they built THEIR businesses, now it seems like it’s just Hillary going over someone’s resume in their careers at random companies. It’s honestly getting boring and uninspiring.

This podcast is so interesting, every episode leaves me inspired! 🤩

I love the potential of this show and all of the amazing guests but I can’t get past the host’s voice. Sooo distracting and cringey.

Such inspiring and real stories, enhanced by thoughtful questions by Hillary - very helpful life / career lessons & wisdom, especially foe those of us at the beginning of an entrepreneurial journey. The podcast name says it all - a very key theme in the multifaceted life of women with many lives to live!

I’m in transition mode into my second life and when I heard about this podcast I binged it . Still binging it- so empowering to hear other women’s stories, you relate you learn and most of all feel that much more confident in your dream and business! Thank you so much for doing this podcast <3

Second life came at the exact right moment. During the pandemic, I decided to look into going back to school. With the quarantine, and the busyness of everyone’s life around me, it felt lonely. The show was recommended to me, and I instantly felt “at home”, surrounded by women who had taken the same steps I am. Hillary is a fantastic host, has the most calming voice and asks the right right questions. It feels like an honest, constructive conversation between girlfriends. It has helped on days where my confidence about my decision is lower, and lifted my spirits about this period of transition. I’m at so thankful for it!

Often the guests are folks I’ve never even heard of, but everyone has a compelling story. Although not the focus, Hiliary and the guests do a great job weaving in how racism and sexism have affect their journey. This one is a weekly mush listen for me.

The hosts voice is too distracting- just personal preference. The sugar-sweetness is cloying to me. Someone else may see this as an attribute. I prefer a less efforted voice.

I used to LOVE this podcast. But it seems like all of the recent guests are famous actors, athletes, wives of athletes, etc...who have now decided to try something else. I’m not saying they’re not admirable, or that they aren’t working hard... but it’s easier to start over when you already have a platform. I need inspiration from people, like me, who are leaving a career, maybe raised their kids, left a marriage and decided to launch something new. I’ll keep checking back to see if you interview those kinds of guests again. Thanks!

I used to love hearing about the challenges of being a woman at work and hearing how they’ve overcome them. This show is not that anymore. Now it’s basically free promo for brands. You’re better off listening to a show like armchair expert when there’s a female guest or the skimm from couch show about successful women.

I initially really loved this podcast because it seemed like all of the guests had proven track records of hard work and success in their field. As a young women I really wanted to hear how these guests achieved their success and started their new venture; what were some low points before they hit success, and what they learned through the good and the bad. However after the first season it seems like the podcast has morphed into a vehicle for any big name to promote their new business, regardless of their track records. All of the guests have a product/service to promote (very few of them are successful women starting out on a second career that isn't a new business), and it feels like many of the questions/whole episodes don't really touch on issues that impact women at work and deter our success. I see this as a huge shame because young women need more stories of how successful women made it through the struggles to become revered, and then have the guts to start a new venture. I'm not really sure hearing how a celebrity, with huge amount of influence and capital, started a business, really achieves a goal of empowering women who don't have huge amounts of influence and captital.

This episode was WEAK. Aurora is an amazing, inspiring and intelligent guest and Hilary’s lackluster responses to her were reallllly telling. It seems like she did not want to get into the nitty gritty of the racial discrimination in the fashion industry. This podcast has gotten way too comfortable with asking the same questions over and over. I would really appreciate if Hilary switched it up and asked different questions catered to each specific guest.

I’ve enjoyed listening to this podcast for quite sometime as inspiration for someone ready for their second life. As a young physician it’s never felt particularly relevant to my career path but still has offered important themes and triggers for reflection. The last recent episode focused on a physician which was a delightful surprise. It’s so enlightening to hear physicians talk about their careers outside of the narrow scope of academia. It was also fun and much more interesting to hear the thoughtful interview questions from a powerhouse professional woman outside of medicine.

I don’t know why I’ve waited so long to rate this considering I suggest this to anyone and everyone looking for a podcast to listen to. What a great podcast! Totally inspiring and makes the smallest or largest life transitions seem so doable. Listening to this makes you feel like you’d have a bunch of cheerleaders cheering you on to find what makes you your happiest self! Thank you for always providing that extra nudge I need to get to my Second Life.

Love this series, very motivating and informative.

I continue to listen week after week because everyones story is different. Hilary asks the same questions to always make a complete story or timeline. Don’t wait download NOW