Podcast

With Whit

From Dear Media Leisure, Society & Culture

I'm Whitney Port, and a lot has happened since you last saw me on The Hills. For starters, I'm a mom, I got married to the love of my life, Timmy, I run a business outside of fashion - it's time we finally catch up. There are so many facets that make up my life: relationships, parenthood, entrepreneurship, beauty, fashion, health, wellness and much more. Join me each week as we meet and discuss all these topics and more with trusted experts and favorite people on earth. Hopefully, we can embark on this new journey together with openness, honesty and a little bit of Whit.

Episodes
406
Releases
Weekly
Typical length
44 min
On air since
2019
Latest episode
19 hours ago

Episodes

406 episodes, newest first

  1. You Are Not Your Anxiety: Healing, Self-Worth & Attachment with Gabby Bernstein

    Episode 405

    Show notes

    This week, we're revisiting one of my favorite conversations with bestselling author, spiritual teacher, and self-help expert Gabby Bernstein. Gabby has spent years helping people navigate anxiety, heal from trauma, and build a deeper connection with themselves. We talk about everything from managing anxiety and breaking unhealthy thought patterns to understanding how our childhood experiences shape the way we show up as adults. Gabby opens up about her own journey through addiction, sobriety, and healing, and shares why real transformation often requires us to get curious about the parts of ourselves we'd rather avoid. We also get into attachment styles, self-worth, setting boundaries, and learning to prioritize our own well-being without guilt. One of my biggest takeaways from this conversation is that we don't have to fight or shame the parts of ourselves that struggle. Sometimes the most powerful thing we can do is learn to understand them.

    This episode is brought to you by Reef, Over The Moon, and Cotton: The Fabric of Our Lives.

    • To get 15% off your first order, go to http://REEF.com/WITHWHITor use code WITHWHIT at checkout.
    • Over The Moon is the modern bridal lifestyle brand for creating a life well lived. Visit http://overthemoon.com/ and use code WITHWHIT15 for 15% off your order.
    • Next time you find something you love, check the tag for cotton. Cotton is The Fabric of Our Lives. Learn more at http://thefabricofourlives.com/

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    48 min
  2. Sister Podcast from Mexico: Family Lore, Our Favorite Things, and a Few Tears

    Episode 404

    Show notes

    Coming to you from Cabo with two of my favorite people: my younger sisters, Paige and Jade! We’re on vacation with our husbands and sitting down to answer your questions about growing up together, who was the favorite child, what annoys us about each other, and whether we’ve always approved of each other’s partners. We also get emotional talking about our mom’s Alzheimer’s, missing our dad, and how we’ve become the people we turn to for things we once would’ve called our parents about. Plus, navigating motherhood, Jade’s skincare recommendations, and an unexpected discovery about my feet on the internet. A little crying, a lot of laughing, and a few husband interruptions. I love you guys, and so happy to share my wonderful sisters with you!

    This episode is brought to you by Over The Moon, REEF, Target, and The RealReal.

    • Over The Moon is the modern bridal lifestyle brand for creating a life well lived. Visit http://overthemoon.com/ and use code WITHWHIT15 for 15% off your order.
    • Find your new pair of clogs at http://reef.com/. To get 15% off your first order, go to: http://reef.com/WITHWHIT or use code WITHWHIT at checkout
    • Discover your next favorite find at Target. All that’s new and uniquely you. It’s in the bag.
    • The RealReal is the most trusted name in authenticated luxury resale. And now, get $25 OFF your first purchase when you go to http://TheRealReal.com/WITHWHIT

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1 hr 16 min
  3. Answering Your Questions, A Surprise Timmy Visit & My Night At The Victoria’s Secret Fashion Show

    Episode 403

    Show notes

    Hello my friends! How are we this Tuesday? Today, I'm catching you up on life lately and answering your questions. But first, a recap of my experience at the Victoria's Secret Fashion Show, including the vintage dress that got me excited to go and why showing up alone still gets me in my head. Next, an update on my embryo transfer plans and why even the most loving check-ins from people can stir up complicated feelings. Timmy pops in for an unplanned chat about money, work, and figuring out our next chapter. Plus, my current Housewives favorites, getting on the same page with your partner in parenting, which beauty treatments are worth the money and the ones I would skip, and of course, the contradiction I keep coming back to: wanting a quieter life, but worrying I'm not doing enough when I slow down.

    Thanks for being here and I love you.

    This episode is brought to you by Monarch, Reef, Target, Over The Moon, and Cotton: The Fabric of Our Lives.

    • Write your own money story with Monarch. Use code WITHWHIT at http://monarch.com/ to get your first year of Monarch Core half off at just $50.
    • Find your new pair of clogs at http://reef.com/. To get 15% off your first order, go to: http://reef.com/WITHWHIT or use code WITHWHIT at checkout
    • Discover your next favorite find at Target. All that’s new and uniquely you. It’s in the bag.
    • Cotton is The Fabric of Our Lives. Learn more at http://thefabricofourlives.com/
    • Over The Moon is the modern bridal lifestyle brand for creating a life well lived. Visit http://overthemoon.com/ and use code WITHWHIT15 for 15% off your order.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    47 min
  4. What’s Actually in Our Water? With Loonen Founder Clara Sieg

    Episode 402

    Show notes

    Today I’m sitting down with Clara Sieg, co-founder and CEO of Loonen, to talk about how her fertility journey and becoming a mom led her to question something most of us barely think about: our water. Clara shares how she found a sense of control during IVF through small changes at home, from buying organic food to swapping plastic for glass. But water felt harder to figure out, and preparing formula bottles for her daughter sparked the idea for Loonen. We get into microplastics, why she chose glass for Loonen, and what it was like to go from investor to founder. I still have so much to learn about microplastics, toxins, and what living a little “cleaner” can look like, but this conversation made it all feel more doable and less overwhelming. Start small and build from there. Thank you so much Clara, I love Loonen!

    This episode is brought to you by Stakt, Osea, Reef, Yoto, The RealReal, and Target.

    • Kickstart your routine with Stakt. Visit http://shopstakt.com/WITHWHIT and use code WITHWHIT at checkout for 20% off your purchase.
    • Give your skin a fresh start with clean, clinically tested skincare from OSEA. Go to http://oseamalibu.com/ and get 10% off your first order with code WITHWHIT.
    • Find your new pair of clogs at http://reef.com/. To get 15% off your first order, go to: http://reef.com/WITHWHIT or use code WITHWHIT at checkout
    • Add a little less screen time to your family’s day with Yoto. Head to http://yotoplay.com/ and use code WITHWHIT to save 10% off all eligible items
    • The RealReal is resale you can trust. get $25 off your first purchase when you go to http://therealreal.com/withwhit
    • Discover your next favorite find at Target. All that’s new and uniquely you. It’s in the bag.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    55 min
  5. I'm Gonna Get Dressed Up To Cook You Dinner, Bitch: Date Night!

    Episode 401

    Show notes

    We're back for a classic Date Night! I’ve been trying to slow down and take care of myself, but I’m also feeling that familiar pull to do more and figure out next projects. We talk about what actually feels restorative, how to know when you're ready to get back out there, and our dream of buying a lake house and documenting the renovation. There are, of course, many detours: whether audiobooks count as reading, why I'd never join Real Housewives, a costly flight-booking brain fart, and airing of grievances. Plus, we get into the difference between getting “the ick” and just “a little icky” and we realize it’s probably time to plan a date night that doesn’t involve microphones.

    This episode is brought to you by Target, Monarch, and Sam Edelman.

    • Discover your next favorite find at Target. All that’s new and uniquely you. It’s in the bag.
    • Visit http://samedelman.com/ to explore everything you need for fall and get 15% off with code WITHWHIT15.
    • Write your own money story with Monarch. Use code WITHWHIT at http://monarch.com/ to get your first year of Monarch Core half off at just $50.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    40 min
  6. What's Been Hard & What's Been Good: A Little Life Update

    Episode 400

    Show notes

    I thought having hernia surgery would mean a little forced rest.It’s been a lot more painful and limiting than I imagined, but I'm taking it day by day and figuring out how to slow down and let myself heal. This week, I'm catching you up on the last few weeks: why I’m giving my body more time before our next embryo transfer, my week with Sonny when Timmy was away, NY Fashion Week, some of the sweet and complicated parts of watching Sonny grow up, and how I’m really doing through all of it. It’s a casual check-in from home, where I’m feeling a little down, a little hopeful, and very ready to get moving again.

    This episode is brought to you by Sam Edelman

    • Sam Edelman has everyone covered this fall. Visit http://samedelman.com/ to explore everything you need for fall and get 15% off with code WITHWHIT15

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    29 min
  7. Sensual Noises, In-Law Drama & Lasting Love: Hotline Date Night!

    Episode 399

    Show notes

    Hotline Date Night is BACK. I am recovering from hernia surgery, Timmy just celebrated his 45th birthday, and we are here by our new fancy bookcase to cuddle up, listen to all your problems, and try to give our best advice. The questions were so good! We get into finding love after starting over, how much your tone matters in a relationship, setting boundaries while living with your in-laws, navigating a child-free family wedding, becoming more vocal in the bedroom, and making space for a partner who has trouble expressing what they need. We may not be qualified, but we certainly have opinions. LOVE YOU.

    This episode is brought to you by Sam Edelman.

    • Sam Edelman has everyone covered this fall. Visit http://samedelman.com/ to explore everything you need for fall and get 15% off with code WITHWHIT15

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    44 min
  8. How To Stay Connected To Your Child In A Distracted World with Dr. Shefali

    Episode 398

    Show notes

    Our kids are growing up in a world that feels faster, louder, and more overwhelming than ever. As Sonny gets older, I find myself thinking more and more about how this world is shaping him and reflecting on the choices I make as a parent. Today, I’m joined by Dr. Shefali for a conversation that made me take an honest look at what it means to raise a conscious child right now. We discuss how technology, social media, comparison culture, and constant overstimulation affect our children’s confidence, connection, and sense of self. She explains why boys and girls may experience these pressures differently and what their behavior can reveal about how they’re really feeling. I also ask Dr. Shefali about some of the things I wrestle with: screen-time boundaries, sharing Sonny online, protecting his privacy, and staying truly present when life feels so busy. We get into why kids need more stillness, play, nature, and face-to-face connection, and all the small actions we can take to help them feel safer, more grounded, and more connected to who they are. Dr. Shefali’s new books, Raising Conscious Sons and Raising Conscious Daughters, offer practical tools for understanding the distinct challenges children face today and a blueprint for helping them grow into connected, resilient, and authentic adults. Thank you so much Dr. Shefali!

    This episode is brought to you by Monarch, Sam Edelman, and OSEA.

    • Write your own money story with Monarch. Use code WITHWHIT at http://Monarch.com to get your first year of Monarch Core half-off at just $50.
    • Visit http://SamEdelman.com to explore everything you need for Fall and get 15% off with code WITHWHIT15.
    • Give your skin a fresh start with clean, clinically tested skincare from OSEA. Go to http://OseaMalibu.com and get 10% off your first order with code WITHWHIT.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    55 min
  9. Food Allergies Don't Have to Define Your Life (Here's How to Navigate Them)

    Episode 397

    Show notes

    Sponsored by Genentech, a member of the Roche Group, and Novartis Pharmaceuticals Corporation. Intended for US Audiences. This information is for general purposes only and is not a substitute for consulting your healthcare provider about food allergy treatment. Brooke and Dr. Ari Zelig have been financially compensated by Genentech and Novartis for their participation in this episode.

    What does it actually look like to build a full, independent life while managing severe food allergies? In this episode, Whitney is joined by Brooke, a 28-year-old medical student living with food allergies, alongside board-certified allergist and immunologist Dr. Ari Zelig, for an honest conversation about navigating everything from childhood birthday parties to dating, travel, restaurants, and everyday situations involving food. Brooke shares how being diagnosed with multiple food allergies forced her to become her own advocate at a young age, and how they ultimately shaped her confidence, relationships, and the physician she hopes to become.

    Dr. Zelig also discusses the importance of individualized food allergy management and shares information about a treatment option, XOLAIR (omalizumab), an FDA-approved prescription medication for subcutaneous use that can help reduce allergic reactions to multiple foods that may occur after accidental exposure in people with IgE-mediated food allergies one year of age and up. While taking XOLAIR you should continue to avoid all foods to which you are allergic.

    Together, Dr. Zelig and Brooke explore how patients can work with their allergists to create a plan that helps them navigate life while prioritizing safety. Whether you're living with food allergies yourself, supporting someone who is, or simply want to better understand the daily realities, this episode offers practical insights, encouragement, and a reminder that food allergies don't have to define your life.

    If you or a loved one has been diagnosed with food allergies, talk to your allergist and ask about XOLAIR. You can also find more information at XOLAIR.com. XOLAIR is one of several available treatment options for IgE-mediated food allergy and it may not be appropriate for all patients.

    What is XOLAIR?

    XOLAIR® (omalizumab) for subcutaneous use is an injectable prescription medicine used to treat food allergy in people 1 year of age and older to reduce allergic reactions that may occur after accidentally eating one or more foods to which you are allergic. While taking XOLAIR you should continue to avoid all foods to which you are allergic. It is not known if XOLAIR is safe and effective in people with food allergy under 1 year of age.

    XOLAIR should not be used for the emergency treatment of any allergic reactions, including anaphylaxis.

    What is the most important information I should know about XOLAIR?

    Severe allergic reaction. A severe allergic reaction called anaphylaxis can happen when you receive XOLAIR. The reaction can occur after the first dose, or after many doses. It may also occur right after a XOLAIR injection or days later. Anaphylaxis is a life-threatening condition and can lead to death. Go to the nearest emergency room right away if you have any of these symptoms of an allergic reaction:

    • wheezing, shortness of breath, cough, chest tightness, or trouble breathing

    • low blood pressure, dizziness, fainting, rapid or weak heartbeat, anxiety, or feeling of “impending doom”

    • flushing, itching, hives, or feeling warm

    • swelling of the throat or tongue, throat tightness, hoarse voice, or trouble swallowing

    Your healthcare provider will monitor you closely for symptoms of an allergic reaction while you are receiving XOLAIR and for a period of time after treatment is initiated. Your healthcare provider should talk to you about getting medical treatment if you have symptoms of an allergic reaction.

    Please listen to the Important Safety Information throughout and stay tuned for additional safety information at the end of the podcast. See full Prescribing Information, including Medication Guide, at bit.ly/XOLPI.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media.

    M-US-00032950(v1.0) 9/26

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    29 min
  10. Revisiting How to Find Your Personal Style with Allison Bornstein

    Episode 396

    Show notes

    Hey everybody, welcome back! We are currently out in New York for our niece’s Bat Mitzvah, so today we’re re-airing an episode with one of the BEST, Allison Bornstein. Allison is an incredible stylist who is all about helping people to find their unique personal style inside their own closets. Her style is so cool and effortless. She gives so many tips on how to find a little more joy in getting dressed in the morning and gives all kinds of outfit ideas for different scenarios. AND we also discovered that we were both interns at Teen Vogue. I know you'll love her if you don't already!

    This episode is brought to you by Monarch Money:

    Use code WITHWHIT at http://Monarch.com to get your first year of Monarch Core half off at just $50.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1 hr 11 min
  11. Summer's Over, Babe: Date Night!

    Episode 395

    Show notes

    It's Date Night! We're back in our home and Sonny is back to school tomorrow!! We’re talking back-to-school August chaos, upcoming travel, our latest house projects, my hernia surgery, ideas for Timmy’s 45th birthday, and Timmy being the new assistant football coach. Plus all the Date Night usuals, airing of grievances, and a little lesson in trusting yourself. Love you guys!

    Produced by Dear Media.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    28 min
  12. Can You Rush My Hernia Surgery So I Can Do My Embryo Transfer? A Solo!

    Episode 393

    Show notes

    Hello darling people I adore! How are we? I have a chill evening solo for you with a lot of thoughts. I've made some big decisions for myself. I'm making my world smaller and my dreams bigger and it feels good. I feel ready. I dive deeper into my decision to try to carry our baby myself, why I finally feel ready to move forward with our two remaining embryos, and how I'm trying to prepare myself without letting fear or pressure take over. I also get into where I'm at with social media and my career, and why creating content just for the sake of creating content doesn't feel fulfilling to me anymore. I'm trying to figure out what I actually want to wake up and do, not what I think I'm supposed to be doing. And I think I finally have an answer: I want to open a store!!! I share where this dream comes from, how connected it feels to my mom and my childhood, and why creating a space for fashion, connection, and community feels so exciting to me right now.

    Lots of life updates, some tears, some rambling, and a lot of figuring things out in real time. Love you all!

    This epIsode is brought to you by Monarch.

    • Write your own money story with Monarch. Use code WITHWHIT at http://monarch.com/ to get your first year of Monarch Core half off at just $50.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    32 min
  13. Caregiving, Community, & The Sandwich Generation with Care.com

    Episode 392

    Show notes

    What does it really mean to be part of The Sandwich Generation? This is a really personal one for me and I'm honored to welcome back Jill McNamara, LICSW, Vice President of Senior Care at Care.com and a senior care and aging expert, to talk about the emotional realities of caring for aging parents while raising a family. Following the release of Care.com's first-ever Sandwich Generation Report, Jill shares insights from a survey of 1,000 caregivers, revealing just how common and often invisible this experience has become. Together, we get into why so many caregivers don't recognize themselves as caregivers until they're already overwhelmed, the emotional weight of decision fatigue and anticipatory grief, why asking for help can feel so difficult, and the surprising personal growth that can emerge through caregiving. I open up about what's currently going on as my siblings and I continue to navigate our mom's Alzheimer's diagnosis and all the difficult decisions that comes with it as we figure out the best way forward.

    Whether you're currently caring for aging parents or simply want to be better prepared for the future, this conversation offers practical guidance, reassurance, and a powerful reminder that you don't have to navigate caregiving alone.

    To learn more, explore Care.com's 2026 Sandwich Generation Report and caregiver resources at http://care.com/sandwich, and follow @WeAreTheSandwichGen for ongoing support and practical tips. And if you're looking for care for your own family, whether that's childcare, senior care, or anything in between, you can use code WHITNEY35 for 35% off a Care.com membership.

    This episode is brought to you by Starbucks:

    • At Starbucks, full- and part-time baristas can build meaningful careers, while getting industry-leading benefits. Learn more at http://starbucks.com/partners

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    44 min
  14. A Month Together & We Didn't Fight Once: Date Night!

    Episode 391

    Show notes

    Hello hello it's Date Night with Whit with Tim! We are catching up after our Summer in Vermont and might need a little time to process the whole month, but we are sharing some of our biggest takeaways. We get into what it was like living in close quarters with family, how we didn't have a single fight, parenting through the moments when you're about to lose your sh*t, and what we're learning about patience, self-improvement, and letting go of the need to have everything figured out. Plus, Sonny's 9th birthday, our Vermont food faves, Love Island thoughts, and why the journey really is the destination. How wise are we? Happy dating to you and you.

    This episode is brought to you by Monarch & Starbucks.

    • Write your own money story with Monarch. Use code WITHWHIT at http://Monarch.com to get your first year of Monarch Core half off at just $50
    • At Starbucks, full- and part-time baristas can build meaningful careers, while getting industry-leading benefits. Learn more at http://starbucks.com/partners

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media.

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    31 min
  15. How to Make Your Own Luck: Lessons From a $500 Million Entrepreneur

    Episode 390

    Show notes

    What does it actually take to build a wildly successful business? And is following your passion really the best advice?

    I am so excited to share this conversation with you! I sat down with entrepreneur David Royce to unpack the mindset, habits, and lessons that shaped his journey. From growing up with financial instability and nearly going bankrupt in his first year as a business owner to becoming one of the top salespeople in his entire industry, David shares the biggest lessons he's learned about spotting opportunity, building scalable businesses, hiring great people, and creating systems that last. We dive into why some of the least glamorous industries can be the most profitable, what makes someone truly persuasive, how to stop confusing busyness with progress, and why "luck" might have a lot less to do with success than we think. David is a true wealth of knowledge and this episode is full of practical advice and mindset shifts that you can apply right away.

    Connect with David Royce on LinkedIn https://www.linkedin.com/in/david-royce-22539425/

    This episode is sponsored in part by the YAP Media Network, the #1 self improvement podcast network. Visit: https://yapmedia.com/

    This episode is sponsored by Staples. Back To School Season is almost here. To shop the most wonderful deals for school, check out http://staples.com/WithWhit

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    57 min
  16. Solo: I Have Something Embarassing To Admit...

    Episode 389

    Show notes

    Hi everybody, I'm coming to you from Vermont, where life feels slower on the outside, but my mind has been Busy. In this solo episode, I'm sharing an honest catch-up on everything that's been rattling around my head lately: why I've been feeling so exhausted, the anxiety of always thinking about what's next instead of where I am, the guilt and heartbreak of navigating my mom's illness, and a major shift in how I'm thinking about our fertility journey. If you feel similarly pulled between gratitude and grief, struggle to stay present during good moments, or wonder why one difficult thing can suddenly consume your whole mind, I hope my swirling thoughts help you feel a little less alone. Xx Whit

    This episode is brought to you by Monarch and Staples.

    • Write your own money story with Monarch. Use code WITHWHIT at http://monarch.com/ to get your first year of Monarch Core half off at just $50.
    • Back To School Season is almost here. To shop the most wonderful deals for school, check out http://staples.com/WithWhit

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    36 min
  17. Date Night From Vermont: The Hotline Is Open!

    Episode 388

    Show notes

    Helloo from beautiful Vermont! We are obsessed with being here and are having such a wonderful time, but also...Why does everyone here seem so mad at us?? We kick things off by venting about some less than friendly encounters before talking about everything we love about being here. Then, we dive into listening to your voicemails! We get into friendship fallouts, taking big leaps in your 20s, wedding budget stress, and the importance of keeping things fun in your relationship. We love you, keep the voicemails coming!

    Leave us a message here: https://www.speakpipe.com/WithWhitHotline

    This episode is brought to you by Staples.

    • If there’s ever a time parents deserve an Easy Button, it’s back to school season. To shop the most wonderful deals for school, check out http://staples.com/WITHWHIT

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    43 min
  18. Current Obsessions & Summer Thoughts: A Slightly Jet-Lagged Solo From Vermont!

    Episode 387

    Show notes

    Hey hey! It's the first pod from Vermont Summer 2026 and I'm coming to you slightly jet lagged from a beautiful porch. First, a little life update now that we have landed in Vermont and have the next 3 weeks here. Then, Rapid Fire Questions. I decided to turn this into a rapid fire episode and I get into all my little obsessions, current thoughts, ideas, and alllll the things I've been loving.

    Hope everyone had an amazing 4th of July weekend!

    This episode is brought to you by Staples.

    • If there’s ever a time parents deserve an Easy Button, it’s back to school season. To shop the most wonderful deals for school, check out http://staples.com/WITHWHIT

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    28 min
  19. Date Night: The State Of Everything + Love Island Hot Takes

    Episode 386

    Show notes

    Oh hey! We recorded a little Sunday morning Date Night sode and got into everything from preparing to leave for Vermont to Love Island hot takes, bad grocery store fruit, cuticle struggles, our growing list of grievances, and all of the random conversations in between. We are off to Vermont for a month! Please don't rob our house.

    If you’re starting a business, or running one that deserves better tools, Square helps you sell, manage, and grow without slowing down. Right now, you can get up to $200 off Square hardware at http://square.com/go/withwhit

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    33 min
  20. The Beauty & Weight Of Ordinary Things: A Solo

    Episode 385

    Show notes

    Hello Hellooo, time for a solo catch up! Sharing a bit of everything this week: the joy of watching the Knicks' playoff run, mom stuff and the uncertainty that comes with caregiving, the pressures of staying culturally relevant and do I even care about that??? Plus all the sweet things I'm looking forward to, namely Summer in Vermont that is coming up so soon and all the reasons I absolutely can't wait for it! This is a classic mixed bag With Whit solo for your ears, hope you are having a wonderful summer so far!

    This episode is brought to you by Square and Monarch.

    • If you’re starting a business, or running one that deserves better tools, Square helps you sell, manage, and grow without slowing down. Right now, you can get up to $200 off Square hardware at http://square.com/go/withwhit
    • Monarch helps you plan ahead, set goals, and make sure you're actually on track before it's too late to adjust. Use code WITHWHIT at http://monarch.com/ to get your first year of Monarch Core half off at just $50.

    This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

    Produced by Dear Media

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    45 min