Ep. 150 Everything I got wrong in my twenties
From how to twenty-something by Jess Diamond
April 27, 2026 · 20 min · Episode 150
About this episode
In this episode, Jess Diamond reflects on the lessons learned from her twenties, emphasizing that mistakes can lead to personal growth and better opportunities.
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ In this special 150th episode, I’m reflecting on everything I got wrong in my twenties — from my career path and health habits to dating, friendships, and self-worth. Looking back, those “wrong turns” were actually the experiences that led me exactly where I’m meant to be today. This episode is a reminder that you don’t know what you don’t know and that getting things wrong is often the very thing that helps everything work out. If you’re in your twenties and feel like you’re messing everything up, this conversation is for you. Sometimes the things that don’t work out are exactly what set your life up to work out better than you planned. Key Takeaways: The moments that feel like rejection or failure can actually lead you to better opportunities than you originally planned Don’t let your ego stop you from asking for help Whether it’s a college major, a job, or a relationship, choosing a different path is often a sign of growth Asking for help, setting boundaries, and choosing yourself takes strength The “wrong” job might be the thing that leads you to the right one. Pay attention to patterns, not promises…
People in this episode
Host: Jess Diamond
Topics covered
- adulting
- self-reflection
- career
- health habits
- relationships
- personal growth
Keywords
- twenties
- adulting
- self-worth
- career path
- friendships
- health habits
- failure
- opportunities
Mentioned in this episode
Organizations: Jess Diamond Coaching, Google Forms
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