Preview Mode Links will not work in preview mode

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:

Oct 15, 2020

After the sudden death of her 12-year-old son Jack, Anna Whiston-Donaldson felt lonely, heavy with guilt and uncertain if she could ever be happy again.

Anna began to courageously share her family’s tragedy + the puzzling, unclear territory of grief in hopes of helping others, first through her blog and then her New York Times bestselling book Rare Bird and children’s book A Hug From Heaven. Writing has helped Anna find comfort + strength.
Today, Anna shares how to find hope within impossible circumstances, positive ways to cope with grief and support others navigating darkness. If you’re grieving a loss, or love someone who is, this conversation is for you.


  • After Jack's death, Anna was unable to find resources for her grieving daughter Margaret. This inspired Anna to write children's book A Hug From Heaven. 
  • While home from college, Anna's mother unexpectedly died from a brain hemorrhage and although she was the "heart of the home", her family was unsure how to process the grief.
  • "When you have community around you, willing to acknowledge your loss, that helps strengthen you."
  • Anna leaned into her faith as a way to be close to her mom.
  • Isaiah 43: Do not fear, for I have redeemed you; I have summoned you by name; you are mine. When you pass through the waters, I will be with you; and when you pass through the rivers, they will not sweep over you. When you walk through the fire, you will not be burned; the flames will not set you ablaze.
  • "Life is full of "and". Sadness and joy."
  • Helping others who are grieving: The most important thing Anna + her family received after Jack's death was acknowledgment of their grief.
  • Fearing that Jack died alone, Anna met the paramedic that stayed with Jack until he was taken away from the scene, recalling the singing birds from the trees.
  • Luke 1:37: For nothing is impossible with God.
  • Against the odds, Anna unexpectedly finds out she's pregnant with a healthy boy named Andrew Luke.
  • Anna's advice to those who feel hopeless: I made a concerted effort to let myself feel, acknowledge + live with pain. While that was happening, gratitude found it's way in. Real joy + real hope are possible in every circumstance.
  • Get Anna Whiston-Donaldson's New York Times bestseller Rare Bird and her children's book A Hug From Heaven. 


1. What is the best book you’ve ever read? A Prayer for Owen Meany by John Irving.

2. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today? Open to possibilities.

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? Nothing.

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? My mom so I could acknowledge her as a wife + mom.

5. What is the best advice you’ve ever received? My mom told me, "Don't be afriad to leave anyone at the alter," because she's know's I'm a people-pleaser.

6. What advice would you give your 20-year-old self? Be more playful and don't take life so seriously. Relax.

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? She loved + she didn't give up.


About our sponsor: Keeley Companies wholeheartedly believes that if you get the people right -the results will follow. They set themselves apart with a forward-thinking culture that empowers their people and fosters loyal partnerships. Keeley Companies are a proud sponsor, partner, and super fan of the Live Inspired Podcast. Learn more about Keeley Companies. 


Pre-order your copy of IN AWE today to receive access to fun, interactive bonus features emailed to you in the lead-up to the book’s release! Visit 


Did you enjoy today's episode? Share it with your friends! Then subscribe, rate + review on Apple Podcasts.

Live Inspired with John daily on FacebookTwitterYouTubeLinkedInPinterest, Instagram + get his Monday Motivation email.