What if the “right time” to see the world never comes?
Courtney Brady stopped waiting for it. After a breakup and a corporate job that left her running on empty, she flew alone to Vietnam for a volunteer trip. A year later, she sold her house, packed up everything she owned, and moved to China to teach English. Fast forward to today: 40+ countries, two moves abroad (China and Singapore), a remote career, and a life built on her own terms.
Courtney joined me from Mexico City, and we got real about the parts of solo travel that don’t make the highlight reel. We talked about the week she hurt her leg abroad and had to find doctors on her own, why it’s okay to spend a whole day in your hotel room feeling sad, and how a hostel check-in in Myanmar turned two strangers into lifelong friends. She also shares the money-saving hack that lets her stay in people’s homes for free (hint: it involves a lot of cuddly animals).
If you’ve ever felt like your life went off script, or you’re waiting on a partner, a friend, or a braver version of yourself before you book the trip, this one’s for you.
In this episode:
How the end of a relationship became the start of her travel life
Stepping off the “college, marriage, kids” timeline and finding people living differently
What nervousness looks like after 40+ countries, and how she builds self-trust
Getting through a lonely, injured week in Mexico City
What living abroad teaches you that a two-week trip can’t (including being a bridesmaid in a Chinese wedding)
Using expat Facebook groups to beat loneliness, even on a short trip
How her travel style changed at 39: boutique hotels, airline points, and pet sitting for free stays
Creative ways to afford long-term travel without being rich
Her message to women waiting for a partner before they go
The hardest part of remote work nobody warns you about
Her dream list: South Africa, Japan, Montreal, and a month living like a New Yorker
Quotes worth stealing:
“Stop waiting. Please don’t wait. Don’t put your life on hold.”
“The more you spend time with yourself, it builds trust in yourself, and you realize how much you can do on your own.”
“You can be sad for a day. You’re not wasting your time, even if you end up sitting in a hotel room.”
“Traveling with the wrong person is not fun. It can actually ruin a trip.”
“I don’t want a partner just to have one.”
“Even though their everyday routines might be very different, a lot of their feelings are very similar. You realize how much you actually have in common.”
“You don’t have to have a big overseas trip to gain something from it.”
“Remote work is the ultimate life hack.” (Megan)
Chapters:
00:01 Courtney’s first leap: a solo flight to Vietnam
02:45 Stepping off the life timeline and moving to China
05:05 What nervousness looks like after 40+ countries
09:35 A lonely week in Mexico City (and the power of a spa day)
15:00 What living abroad teaches you
19:50 Expat holidays, a Chinese wedding, and finding community
23:10 The people who changed everything
26:30 Solo travel at 39 vs. your 20s, plus the pet-sitting hack
31:45 To the women waiting on a partner
37:15 The real side of remote work
43:30 Courtney’s dream destinations
Follow Courtney:
TikTok: @wanderwith.court
Instagram: @journeywith.court
Substack: @journeywithcourt
Website: nourishthefreelife.com
Follow Megan / Belong to Where You Are:
Solo Travel Sisterhood (free community)
Substack: belongtowhereyouare.com
TikTok: @belongtowhereyouare
Instagram: @belongtowhereyouare_
