Your First Solo Trip as a 40+ Woman Should Be “Wrong” (Yes, Really) episode artwork

EPISODE · Jan 7, 2026 · 12 MIN

Your First Solo Trip as a 40+ Woman Should Be “Wrong” (Yes, Really)

from Freedom Looks Like This – solo travel back to yourself · host Coach Damianne

What do you expect from your first solo trip, especially as a woman over 40? A lot of us carry the idea that if we plan carefully enough, choose the right destination, and do everything “properly,” the trip should go smoothly. It should feel relaxing and signficant! And when things go wrong, even in small ways, it can feel surprisingly upsetting. In this episode, I talk about why that expectation shows up so strongly for women traveling alone later in life, and what actually happens when a solo trip doesn’t go as planned. I share personal stories from years of solo travel, including moments of embarrassment, self-blame, and the pressure I still feel to be capable and in control. Tune in to understand how confidence, self-trust, and emotional regulation  get built over time, especially when you’re navigating a new place on your own. If you’re thinking about solo travel, worried about making mistakes, or feeling anxious about doing it “wrong,” this episode will likely feel familiar. Topics include: solo travel for women over 40, first solo trip anxiety, traveling alone as a woman, fear of making mistakes, emotional safety while traveling, midlife independence, and choosing differently. Support the showJoin the next Solo Trip Decision Workshop live on June 20. It's for women who've decided they want to take a solo trip and want help deciding the trip they actually want: https://freedomlookslikethis.com/trainingEmail: [email protected] Skool: https://freedomlookslikethis.com/community

Episode metadata supplied by the publisher feed · Published Jan 7, 2026

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What do you expect from your first solo trip, especially as a woman over 40? A lot of us carry the idea that if we plan carefully enough, choose the right destination, and do everything “properly,” the trip should go smoothly. It should feel relaxing and signficant! And when things go wrong, even in small ways, it can feel surprisingly upsetting. In this episode, I talk about why that expectation shows up so strongly for women traveling alone later in life, and what actually happe...

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Your First Solo Trip as a 40+ Woman Should Be “Wrong” (Yes, Really)

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This episode was published on January 7, 2026.

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