Intentional Comfort and Joy in the Midst of Grief with Jenn Oglesbee

Jenn Oglesbee is a certified life coach and licensed clinical social worker, and the discussions that she and I had last summer on Instagram Live are what me to choose the “Intentional Comfort” for season seven on Jump Start Your Joy. We had a series called “What the Hell?,” and in it we discussed the events of the past couple of years, and how they impacted our lives. Jenn and I share a love of talking about joy, and have both woven it into our work. In this discussion, we are talking about finding intentional comfort and joy in the midst of grief.

It’s an honor to have Jenn come back a year later, and share more about her own journey. In December of 2021, Jenn lost her sister to a rare form of brain cancer. She has been open in sharing about how the grief has shown up in her life, and how losing someone as close as a sibling has felt. She and I had had an interview on the books at the end of last year, and she asked to reschedule our discussion until after she felt ready to talk about things. And, she offered to dive into how finding and making space for intentional comfort in the midst of grief has looked for her over the past few months.

As you’ll hear Jenn say in our discussion, she has been open with her grief and her story. I have found that inspiring, and I think many of us can relate to having the overwhelming feelings of grief during this time. Our grief may be different, as I have not lost a loved one, nor do I understand what it is like to lose a sister. But, Jenn shares a lot that I think many of us can relate to around the feelings of overwhelm, feeling out of control of our own situations, and what it looks like to sit with uncertainty.

I want to thank Jenn for being willing to share your story here and also to share it with those people that follow her on social media. I know , it means a lot to people to understand what grief can look like.

Here is part of what she shared in this episode about sitting with the feelings of loss and overwhelm:

“I had to just sit with this place of not just loss, but like I felt the floor come out from under me and all the things that brought me comfort, joy did not anymore. It was like it all went dormant and all went dark. And as someone who has hitched our wagon on joy (not only personally, but professionally) that was very disconcerting. And I couldn’t really do anything except just let it be.”

In this episode, Jenn Oglesbee and I talk about:

  • her joy as a child, doing dance parties, writing, and playing
  • the uncertainty involved around her sister’s illness and diagnosis, and navigating supporting her during the COVID pandemic
  • the difference between coaching and therapy
  • intentional comfort and joy in the midst of grief
  • looking for the little joys in life during hard times, even when joy feels like it is hard to grasp
  • the grief and uncertainty that many of us felt during the pandemic
  • surrendering to grief
  • giving yourself permission to take a break for emotions other than grief during mourning
  • how writing can help you process big emotions
  • sharing what feels right, to the right people, when you are ready
  • reconnecting with joy
  • how she jump starts her joy: with downtime, making time for creativity, giving yourself permission to look weird and feel foolish


Jenn Oglesbee’s website:

Our three Instagram lives from last summer: Part One Part Two Part Three

The mashup of the three Instagram Lives, as heard on Jump Start Your Joy