If you’ve ever felt isolated in your grief or unsure how to move forward after a major loss, episode 350 is for you. Jen Newberg, widow and founder of It’s Lifey, shares how she transformed her pain into purpose by creating retreats and support spaces for others navigating life after loss. Learn how connection, storytelling, and even unexpected tools like writing can become powerful pathways to healing—and why community is essential when rebuilding your life.

In This Episode, You Will Learn:

(2:40) Why Jen founded It's Lifey and how a retreat in Costa Rica inspired her mission

(5:35) Building a grief retreat from scratch—and why she’s focused on in-person connection

(9:10) How grief support circles offer more than comfort: they create deep bonds

(11:40) The unexpected healing power of writing—even for people who don't see themselves as writers

(15:00) How grief creates a ripple effect—and how to show up as a “grief ally”

(18:45) The trauma of sudden loss abroad and navigating bureaucracy after her husband’s death

(21:40) Why storytelling helps shrink grief—and how your narrative evolves over time

(24:30) Finding purpose through pain: why Jen views her work as a tribute to her late husband

(28:50) What “grief growing smaller” really means, and why the firsts are the hardest

In today's episode,  I'm joined by Jen Newberg, a Boston-based entrepreneur and community-builder who turned the sudden loss of her husband into a mission to support others through grief. Drawing from her own healing journey and background in nonprofit leadership—including her role at Boys & Girls Clubs of America—Jen founded It’s Lifey, a retreat and support organization for people navigating major life transitions, especially young widows.

Throughout this episode, Jen shares how creating It’s Lifey helped her rediscover purpose and connection, and why in-person community is central to healing. She reflects on the unexpected power of writing and storytelling—even as someone who never considered herself a writer—and how simple support, like a weekly text, can mean everything. Her insights remind us that while loss is inevitable, it doesn’t have to be faced alone—and that even in deep grief, purpose and joy can be found.

Connect with Jen Newberg:

Website

Instagram

LinkedIn

Let's Connect:

Website

LinkedIn

Instagram

Twitter

Pinterest

The Grief and Happiness Alliance

Book: Loving and Living Your Way Through Grief

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