#48 - When Grief Takes Over - The WHY Matters Podcast
Wed Feb 04 2026
Send us a text
In this episode of The WHY Matters Podcast, Jessica and Will share an honest, unfiltered conversation about grief in real time. After the loss of Jessica’s closest friend of 31 years, Doug, they explore what grief truly looks like — messy, isolating, and unpredictable. Jessica opens up about the anger, guilt, numbness, and exhaustion that come with loss, the pressure to keep showing up, and why sharing grief while you’re in it matters. This episode isn’t about fixing grief, but about honoring it and learning how to live alongside it, one day at a time.
@02:05 — Why We’re Talking About Grief
@07:45 — Losing a Best Friend
@12:40 — When Grief Takes Over
@19:30 — The Messy Parts of Grief
@31:55 — Hiding Pain From the World
@42:35 — Carrying Them With You
@1:06:56 — Living With Grief
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
PATREON
https://www.patreon.com/worldtowning
If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!
GROUP TRIPS
https://worldtowningvoyages.com/
Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.
COACHING
https://worldtowning.com/learn-2/
Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.
NEWSLETTER
https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa
10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.
MERCHANDISE
Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/
OUR SOCIALS
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@02:05 — Why We’re Talking About Grief
@07:45 — Losing a Best Friend
@12:40 — When Grief Takes Over
@19:30 — The Messy Parts of Grief
@31:55 — Hiding Pain From the World
@42:35 — Carrying Them With You
@1:06:56 — Living With Grief
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
PATREON
https://www.patreon.com/worldtowning
If you would like to support us in a greater capacity where you c
Support the show
More
Send us a text In this episode of The WHY Matters Podcast, Jessica and Will share an honest, unfiltered conversation about grief in real time. After the loss of Jessica’s closest friend of 31 years, Doug, they explore what grief truly looks like — messy, isolating, and unpredictable. Jessica opens up about the anger, guilt, numbness, and exhaustion that come with loss, the pressure to keep showing up, and why sharing grief while you’re in it matters. This episode isn’t about fixing grief, but about honoring it and learning how to live alongside it, one day at a time. @02:05 — Why We’re Talking About Grief @07:45 — Losing a Best Friend @12:40 — When Grief Takes Over @19:30 — The Messy Parts of Grief @31:55 — Hiding Pain From the World @42:35 — Carrying Them With You @1:06:56 — Living With Grief Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. PATREON https://www.patreon.com/worldtowning If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you! GROUP TRIPS https://worldtowningvoyages.com/ Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/ OUR SOCIALS Instagram: https://www.instagram.com/worldtowning/ YouTube: https://www.youtube.com/worldtowning Facebook: https://www.facebook.com/worldtowning Tik-Tok: https://www.tiktok.com/@worldtowning @02:05 — Why We’re Talking About Grief @07:45 — Losing a Best Friend @12:40 — When Grief Takes Over @19:30 — The Messy Parts of Grief @31:55 — Hiding Pain From the World @42:35 — Carrying Them With You @1:06:56 — Living With Grief Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. PATREON https://www.patreon.com/worldtowning If you would like to support us in a greater capacity where you c Support the show