With Whit

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 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.

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 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 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.

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 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 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.

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 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.

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 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 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.