313: Jonathan Pitts – Dreaming on the Other Side of Grief

Jonathan Pitts- Dream on the other side of grief

313: Jonathan Pitts – Dreaming on the Other Side of Grief

We’re talking with Jonathan Pitts who’s a bestselling author, speaker and he’s an executive pastor at The Church of the City in Franklin, Tennessee.  He’s also the proud dad and a big dream advocate for his 4 amazing daughters. 

Jonathan has pursued a number of big dreams… and has encouraged his family to dream big too.  In fact, his oldest daughter had a major role in the movie “War Room” at the age of 10!

But Jonathan will be the first to tell you that life can bring major challenges and tough setbacks too.  In fact, Jonathan was married to his beautiful bride Wynter… who was a successful author and magazine publisher. 

And just as they were putting the finishing touches on their book on marriage… Wynter passed away unexpectedly… leaving him a widower and the father of four grieving daughters.  As you can imagine… this totally rocked his world and the future and the big dreams Jonathan and Wynter had planned together completely dissolved.

So he… along with his daughters had to decide how they were going to live life and move forward.  And it’s been a tough… beautiful… messy… and wonderfully inspiring journey since.  Now… Jonathan has written a new book that offers us a real… intimate… raw… and ultimately hope-filled look at grief… and how to live life to its fullest after the tragedy. 

It’s called, My Wynter Season: Seeing God’s Faithfulness in the Shadow of Grief. We’re going to talk about it… and what it takes to continue to dream… and encourage others to do the same on the other side of grief.  Let’s do this!

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Jonathan’s newest book: My Wynter Season: Seeing God’s Faithfulness in the Shadow of Grief.

Jonathan and his wife, Wynter, co-wrote Emptied: Experiencing the Fullness of a Poured-Out Marriage and She is Yours: Trusting God as You Raise the Girl He Gave You

Jonathan now serves as president of the ministry he and Wynter founded together, For Girls Like You––a nonprofit organization featuring a magazine and resources for girls that grew out of Wynter’s desire to empower and equip their own girls and to provide parents with the resources and support needed to raise strong women. 

Jonathan’s Instagram: www.instagram.com/pittsjr26

Dream Together App


That’s right! Our DREAM TOGETHER App is here!

The “Dream Together” app is designed to help you clarify your goals as well as connect with like-minded individuals so you can “dream together” to make those dreams (big or small) a reality!


STEP 1: Download the app.

  • Find “Dream Together” for your Apple Device: HERE
  • Find “Dream Together” for your Android Device: HERE

STEP 2: Sign up and enter the group code: dreamthinkdo

STEP 3: Be inspired by the dreams that are already there.  Then… follow and encourage a dream or two!

STEP 4: Post at least one of your own dreams… and then invite friends to join you so you can DREAM TOGETHER!

Let’s do this!


As you probably know… this year we’re going after launching 1 million dreams this year!  It’s been amazing to see your response and your support.  LOVE that so many of you are on board with this mission.

At the same time… we need to acknowledge that in the midst of a global pandemic where many people are hurting from the loss of family members, it’s important to speak to the “tough stuff” too.  That’s exactly why we’re talking with Jonathan Pitts… because his unique perspectives can bring comfort and encouragement based on his own first-hand experience with unfathomable loss. 

In his book, “My Wynter Season,” Jonathan takes his readers on the emotional journey from “love at first sight” to complete blindsided loss in the midst of a season of losing family members (in a period of two years the Pitts family lost 6 family members including Wynter), to finding the beauty in seeing Wynter’s continued impact on the world.  

During our conversation… we talk about the importance of finding hope amidst the hardest days and the deepest grief.  Plus, we dig into ways to dream and/or dream again… after experiencing loss. 

I think you’re going to love this conversation.  I sure did!


  • 0:02 What to expect today
  • 2:08 Download the Dream Together App
  • 3:12 Meet Jonathan
  • 5:59 When Jonathan pitts and his wife started dreaming
  • 8:45 The best thing about dreamers
  • 11:24 When Jonathan and his wife started building the company together
  • 15:35 When everything changed for Jonathan
  • 19:20 How Jonathan and his family started to move forward
  • 23:22 Jonathans advice for anyone learning how to dream again
  • 30:05 Who Jonathan’s new book is for
  • 31:36 Mitch’s final thoughts


Powerful stuff.  What did YOU think?  I want to hear from YOU!  

Leave a comment below and let me know what stuck out to you!  And hey… please share this episode with someone who might need it!  Thanks.

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