Necessary Endings and Boundaries with Dr. Henry Cloud
Stay True with Madison Prewett Troutt
Madison Prewett Troutt
4.8 • 3.4K Ratings
🗓️ 29 December 2025
⏱️ 67 minutes
🧾️ Download transcript
Summary
Welcome back to another episode of Stay True Podcast! This week, Madi sits down with Dr. Henry Cloud, psychologist, New York Times bestselling author, and trusted voice on emotional and spiritual health, for a powerful conversation on boundaries, growth, and the courage it takes to let go. Together, they unpack why some endings are not failures but necessary steps toward the life God is inviting you into. From relationships and seasons to habits and expectations, Dr. Cloud shares practical wisdom on discerning when it's time to hold on and when it's time to move forward in faith.
Always remember to stay you and stay true.
Questions/topics discussed and answered:
• What "necessary endings" really are and why they matter
• How boundaries protect growth, freedom, and purpose
• Knowing when a season, relationship, or habit needs to end
• The role of wisdom, faith, and emotional health in decision-making
• How to move forward without guilt, fear, or shame
• Practical tools for creating healthy, God-honoring boundaries
AND SO MUCH MORE!
Helpful Resources:
For More From Dr. Cloud: https://www.boundaries.me
Necessary Endings by Dr. Henry Cloud: https://a.co/d/00tGTon
How to Get a Date Worth Keeping by Dr. Henry Cloud: https://a.co/d/e9UpR0J
Dare To Be True by Madison Prewett Troutt: https://a.co/d/gdfpHX5
Stay True Website: https://www.staytruepodcast.com
Stay True Merch: https://www.staytruepodcast.com/merch
Glorify: Get full access all year for just $29.99 at glorify-app.com/STAYTRUE
Connect with Stay True!
💙 Instagram | @staytruepodcast
💙 TikTok | @staytrue_podcast
💙 Follow Madison | @madiprew
💙 Follow Dr. Henry Cloud | @drhenrycloudofficial
Transcript
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| 0:00.0 | What is it in your life today that doesn't align with the future that you want? |
| 0:05.0 | What were the reasons that so many are stuck and not dating? |
| 0:08.0 | You don't put boundaries on someone. |
| 0:10.0 | You put boundaries on yourself. |
| 0:11.0 | We have self-control, not other control. |
| 0:13.0 | How do you have the hard conversations and create boundaries with your own family members? |
| 0:19.0 | If you're going to be screaming at me, I'm not going to have this conversation. Simple formula. Empathize and hold the limit. How do you know if something needs to end? You've got to get to the moment of hopelessness. How many new guys or new women are you getting in front of or meeting or talking to on a regular basis? Back to the dating thing, there's a lot of not cleaving that's going on because nobody's |
| 0:40.6 | leaving. |
| 0:41.1 | So you're on your own, pal. |
| 0:42.4 | You can come back for a sandwich. |
| 0:44.2 | That's what my dad told me. |
| 0:52.5 | What's up, guys? |
| 0:53.4 | Welcome back to another episode of Stay True podcast. I'm your host, Madison |
| 0:57.0 | Pruitt Trout. And I have in the podcast studio with me today a very special guest that I'm so |
| 1:03.1 | excited for you guys to hear from because I recently just got to share a stage with him at a conference |
| 1:08.6 | that we both did this past weekend. And I was laughing. |
| 1:12.6 | I was inspired. And my entire team who attended this conference took more notes when he was |
| 1:17.6 | speaking than when I was speaking. So slightly offended, but also inspired and encouraged. So I was like, |
| 1:21.7 | I've got to have him on the podcast. And I'm so excited to welcome Dr. Henry Cloud. He is a bestselling author. He is a speaker. He is a clinical psychologist, leadership expert, really has so much expertise in a lot of areas. So we're going to be talking about a lot of fun things today. But welcome to the Stay True podcast. Good to be here. I'm so excited for this. And I did just find out that you live here near me. |
| 1:45.2 | I do. |
| 1:45.7 | I do. |
| 1:46.0 | I'm like, for some reason, I was thinking he was in Dallas, Texas, but this is fun. This is a lot of amazing people. I was in L.A. for ever. I went to school in Dallas, but then after that I went to L.A. for my training. Got stuck. Got stuck. Got stuck. And you've written how many books at this point in your life? |
... |
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