Stephanie on Grief, Guilt, and Turning Regret Into Resilience

Grief has a way of dragging us back into every decision, every conversation, and every painful “what if.” In this deeply personal episode, Stephanie Renner joins G-Rex and Dirty Skittles to talk about losing her son Jordan to suicide, the guilt and regret that followed, and how she learned to keep moving forward without letting the past define the rest of her life.

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Sh!t That Goes On In Our Heads is a 2024 People’s Choice Podcast Award Winner (Best Health), 2024 Women in Podcasting Award Winner (Best Mental Health Podcast), 2026 Podcast Tonight Award Winner (Best Mental Health Podcast), and 2026 NYC Podcast Award Audience Choice Winner (Best Hosts), with over 4.5 million downloads and listeners in more than 160 countries.

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Mental Health Quote

“Love is not measured by the outcome.” — Stephanie Renner

Trigger Notice + 988 Crisis Reminder

This episode includes candid conversations about suicide, suicidal ideation, self-harm, grief, and the loss of a child. Please take care of yourself while listening and step away if you need to.

If you or someone you know is struggling or in crisis in the United States, call or text 988 to connect with the Suicide & Crisis Lifeline. https://988lifeline.org/

For crisis support outside the United States: https://findahelpline.com/

Episode Description

After losing her father, her mother, and her oldest son within a six-year span, Stephanie Renner knows what it feels like to replay the past and wonder what could have been different.

In this raw and deeply human conversation, Stephanie opens up to G-Rex and Dirty Skittles about her son Jordan, who died by suicide shortly before his nineteenth birthday. She shares what it was like raising a deeply empathetic young man who struggled for years with suicidal ideation, mental health challenges, and the feeling that he did not quite fit into the world around him.

Stephanie also speaks honestly about the guilt that can follow devastating loss. The questions come fast and hard: What if I had found the right therapist? What if I had been home? What if I had made one different decision? She calls them the “if-onlys,” and she knows firsthand how easily they can become a prison.

Over time, Stephanie began to understand that loving someone deeply does not mean you can control their outcome. That realization became one of the most important lessons of her life: Love is not measured by the outcome.

She also shares the unexpected signs that have helped her feel connected to Jordan, the community that surrounded her when she could barely function, and the ways grief changed her perspective on fear, work, and what actually matters.

After nearly 25 years as an attorney, Stephanie stepped away from the life she built and moved toward something more meaningful. Today, through her Regret to Resilience Method, she helps people work through regret, guilt, and shame after trauma or loss.

She also founded Gilly’s Friends in Jordan’s memory, turning his kindness into a lasting reminder: You matter. You’re loved.

Keywords: Stephanie Renner, Regret to Resilience, grief, grief recovery, suicide loss, suicide prevention, parental grief, guilt after loss, regret, emotional healing, self-forgiveness, resilience, trauma recovery, mental health awareness, finding purpose after loss

Meet Our Guest — Stephanie Renner

Stephanie Renner is a keynote speaker, writer, attorney, nonprofit founder, and creator of The Regret to Resilience Method. Her work helps people release regret, guilt, and shame after trauma or loss so they can move forward with greater purpose, confidence, and self-compassion.

Her work is deeply personal. After losing her father, mother, and oldest son, Jordan, within six years, Stephanie turned her own experience with grief into a mission to help others stop allowing the past to control what comes next.

She is also the founder of Gilly’s Friends, a nonprofit created in Jordan “Gilly” Guilford’s memory that spreads intentional acts of kindness and reminds people that they matter and are loved.

• Website: https://www.stephanierennerspeaks.com
• Gilly’s Friends: https://gillysfriends.com
• Instagram: https://www.instagram.com/srrnd/
• Facebook: https://www.facebook.com/stephanie.renner2
• LinkedIn: https://www.linkedin.com/in/stephanierenner/

Key Takeaways

• Love is not measured by the outcome. You can love someone completely and still not control what happens.
• Regret often lives in the “if-onlys,” where we convince ourselves that one different choice would have changed everything.
• Grief does not mean forgetting someone or moving on from them. It can mean learning to carry love and loss at the same time.
• Support matters. Sometimes the people who simply show up, sit with you, feed you, and stay close make survival possible.
• Belonging matters, especially for young people who feel like they do not fit anywhere.
• Purpose can grow alongside grief. Stephanie transformed Jordan’s legacy of kindness into work that continues to help other people feel seen and valued.

Actionable Items

• Challenge one “if-only.” Write down a regret you keep replaying and ask yourself whether you truly know that changing that one moment would have changed the outcome.
• Know who your people are. Identify two or three people you can call when life gets heavy, and consider whether someone in your life may need you to be that person for them.
• Do one intentional act of kindness. Send the text. Make the call. Buy the coffee. Check in. Small moments can carry more weight than we realize.

Important Chapters

• 00:00 – Meet Stephanie Renner
• 02:30 – Signs From Jordan and Staying Connected After Loss
• 08:15 – Jordan’s Mental Health Journey
• 12:00 – Surviving the Loss of a Child
• 13:35 – The “If-Onlys” of Grief and Regret
• 18:50 – One of Stephanie and Jordan’s Final Conversations
• 21:45 – Mental Health, Shame, and Creating a Kinder World
• 23:30 – The Community That Carried Stephanie
• 26:15 – Losing Fear After Losing So Much
• 26:55 – Grieving a Son While Losing a Mother to Alzheimer’s
• 29:30 – From Attorney to Regret to Resilience
• 31:00 – Letting Go of Mother’s Day Guilt
• 33:30 – Care Bears, Raccoons, and Signs From Beyond
• 41:25 – What Stephanie Would Tell a Younger Jordan
• 44:25 – Love Is Not Measured by the Outcome
• 45:40 – Favorite Word, Least Favorite Word
• 46:10 – Regret to Resilience
• 47:05 – Gilly’s Friends and Jordan’s Legacy of Kindness

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#MentalHealthPodcast #MentalHealthAwareness #Grex #DirtySkittles #Podmatch #GriefSupport #SuicideLoss #SuicidePrevention #GriefJourney #RegretToResilience #HealingAfterLoss #ParentalGrief #BereavedParents #EmotionalHealing #SelfForgiveness #TraumaRecovery #Resilience #FindingPurpose #GriefAndLoss #YouMatter

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If You Need Support, Reach Out

If you or someone you know is facing mental health challenges, please don’t hesitate to reach out to a crisis hotline in your area. Remember, it’s OK not to be OK—talking to someone can make all the difference.

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