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Expected to die, today he’s inspiring others to truly live.

World-renowned inspirational speaker + national bestselling author John O’Leary wants to help you wake up from accidental living so you can do, be, achieve and impact more through your life.

Join John twice a week!

  • Every Monday, John shares a quick burst of inspiration to help start your week on fire.
  • Every Thursday, John interviews an amazing guest on their story, successes, failures, lessons, and life to help you uncover tips to apply in yours.

Find the Live Inspired Podcast here:

Jan 28, 2021

How can you boldly walk forward from unfathomablchallenging circumstances? Jonathan Pitts, pastor, author and father of four joins us to share how he did exactly this after he tragically lost his wife.

Jonathan vulnerably shares his journey of loving Wynter, how he coped with losing her, and how he continues to find peace, strength, and hope in keeping her legacy alive.

Our encouraging conversation will remind you that even in the most difficult times, the best of our days remain ahead.


  • Jonathan’s mom, a White German-American, met his dad, a Black man, at a music school in New Jersey.
  • Having an Identity: Growing up in a bi-racial family, Jonathan is thankful his parents raised him with faith as it provided him strength. 
  • As a member of the ROTC program at Drexel University, Jonathan expected to serve his country yet met + quickly fell in love with his wife, Wynter Evans.
  • Take delight in the Lordand he will give you the desires of your heart. Psalm 37:4
  • Raising four girls five years old and younger + seeking a greater purpose, Wynter started For Girls Like You, a magazine that evolved into devotionals, books and many other tools for girls and their parents. Learn more here.
  • July 24, 2018:
    • 3:45pm: Jonathan approved the manuscript of their book Emptied: Experiencing the Fullness of a Poured-Out Marriage, which he now gratefully calls a "time capsule of our marriage".
    • 7:44pm: Unexpectedly, Winter makes her quick + quiet entry into Heaven.
  • Opposites compliment: Jonathan shares the differences that caused struggles early in their marriage were the things they most loved, appreciated + admired later.
  • Whatever is true, whatever is noble, whatever is right, whatever is pure, whatever is lovely, whatever is admirable—if anything is excellent or praiseworthy—think about such things. (Philippians 4:8)
  • Why are dark moments holy moments? (C.S. Lewis) Jonathan shares the emotional, sacred and deeply personal moment surrounding Wynter's passing in hopes of showing that death isn't scary.
  • Have no fear of sudden disasteror of the ruin that overtakes the wicked, for the Lord will be at your side and will keep your foot from being snared. (Proverbs 3:25)
  • Solace in solitude: While grieving, Jonathan's learned to embrace stillness and credits it in healing his mind, heart and faith.
  • Get a copy of Wynter + Jonathan Pitt's book Emptied: Experiencing the Fullness of a Poured-Out Marriage here.
  • Get a copy of Jonathan Pitt's book My Wynter Season here.


1. What is the best book you’ve ever read? Strong Fathers, Strong Daughters by Dr. Meg Meeker and Mere Christianity by C.S. Lewis.

2. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today? More hopeful + optimistic.

3. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be? Photos speak so much to me so an album of my family over the years.

4. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be? Tiger Woods.

5. What is the best advice you’ve ever received? My dad would always say, “all you have is your name,” as a reminder to maintain a good reputation.

6. What advice would you give your 20-year-old self? Just relax. Everything is going to be okay.

7. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read? Act 13:36 - David served the purposes of God for his generation and then he fell asleep.


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