Unwineding

the relationship advice every high-achieving woman needs ft. Kaela Ason

June 23, 2026·45 min
Episode Description from the Publisher

Hi ladiesss! This week, I'm joined by therapist Kaela Ason for a conversation that felt like therapy for every high-achieving woman who's ever overthought a text, treated dating like a checklist, or wondered why relationships can feel so much harder than everything else she's accomplished. We talk about why so many successful women struggle in relationships, why we get attached to people we barely know, and how anxiety can make us focus on being chosen instead of doing the choosing ourselves. Kaela breaks down the difference between anxiety and intuition, discernment and self-sabotage, and why so many of us intellectualize our feelings instead of actually letting ourselves feel them. We also get into people-pleasing, perfectionism, self-trust, and why having your life together doesn't necessarily make relationships feel easier. We talk:• why high-achieving women tend to overthink relationships• getting attached to people we barely know• treating dating like a checklist instead of asking how we actually feel• anxiety vs. intuition (& how to tell the difference)• discernment vs. self-sabotage• why people-pleasing shows up so often in dating• learning to trust yourself, even when relationships don't work out• trying to be chosen instead of doing the choosing• why successful women can struggle with relationships and vulnerability• perfectionism, self-worth, and the pressure to always have it all together• confusing peace with boredom and chemistry with chaos• building self-trust and learning to feel safe in healthy relationships & so much more. As always, take whatever you need and leave the rest. LOVE YOU. Learn more about your ad choices. Visit megaphone.fm/adchoices

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