Dear Nina: Conversations About Friendship #146 - Tolerate Uncertainty & Stop the Overthinking Spiral in Your Friendships with Dr. Jackie Henry
If you’ve ever reread a text 10 times, filled in every silence with worst-case scenarios, or found yourself leaving too many hangouts with friends regretting what you said, this conversation is for you. Psychologist Dr. Jackie Henry and I discuss tools to stop overthinking your every friendship move and learn to tolerate uncertainty in your relationships. We rarely know what someone else is thinking, and we need to stop assuming we do. Wouldn't it be refreshing to just be in your friendships and not feel like you're "performing" to always say and do the exact "right" thing? Dr. Jackie offers Dear Nina listeners practical tips for getting out of your head and back into your life so your friendships can thrive.
KEY TAKEAWAYS
- Silence usually means “busy,” not “they secretly hate me.”
- Budget your “energy bucks.” Rumination is a waste of energy; spend wisely.
- Constant overthinking can create distance between friends and lead to miscommunication, anxiety, and the fear of judgment.
- Work to tolerate the unknown: there's power in letting things unfold naturally in friendships.
- Lead with curiosity. A simple “Hey, when’s good to chat?” beats the story your telling yourself about why someone hasn't responded.
LINKS & RESOURCES
- Dr. Jackie Henry’s Substack: Less Thinking, More Living
- The Dear Nina monthly friendship challenges. (The April one was mentioned in this episode.)
- The TikTok account I mentioned about recounting awkward moments. @amymaurercreel
MEET DR. JACKIE
Dr. Jackie Henry is a psychologist, writer, and founder of Less Thinking, More Living—a platform dedicated to helping people stop overthinking and start fully embracing life. Based in the Twin Cities, she also works as a wellness consultant and has a private therapy practice. Dr. Jackie combines humor, heart, and relatable insights to help individuals navigate life with greater ease and presence. Outside of work, she's at the cabin, playing board games, or enjoying happy hour with her husband, four daughters, and their small but mighty dog. You can find her on Instagram @dr.jackiehenry or on Substack at Less Thinking, More Living.
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