HELLO, 2026
Waving Hello Mid-Leap: On Shedding, Becoming, and What Comes Next
Your friend's travel notes
Willo's 411
Curated travel guides from over a decade of wandering the world
Curated travel guides from over a decade of wandering the world
Everything on this site comes straight from my personal saved lists. Some are places I love and have gone to many times, and some I'd only heard of but it was marked as a solid resource from someone I trust. Either way, I hope these recommendations help you find something new wherever you're traveling to next!
~ xo, WilloGrowing up in America, we used to be able to dial 411 for information. Consider this site your personal travel tips hotline.
Left Steamboat Springs for Denver at 18. Dropped out of art school and started my first business. I learned a lot while burning bridges, maxing out credit cards, and going broker than broke.
Got a live-in nanny gig, saved up, bought a $1,000 Honda, and drove to LA with no apartment and one contact who wasn't even home. A few months later, I packed that same shitty car and moved to SF the weekend I turned 21. No job. No apartment. One friend. A hell of a lot of grit.
First time in Europe - two weeks in London and Spain. Something cracked open. 🇬🇧🇪🇸
Nine jobs and a Dot Com Bust layoff later, I launched my own design studio. I was finally making money - but I felt like I was selling my soul.
Put the client work down for a month and invested $5k of my savings to launch my own product line - my designs and illustrations on everything. It was like I could finally use all my skills to build something I actually wanted. Then the Great Recession hit.
Closed the product line. There was deep grief in coming to terms with it. Said yes to a co-founder opportunity anyway - shut everything down, signed the dotted line. It ended in lawyers, fallout, and flat broke. Licked my wounds and rebuilt - again - this time through coaching and creative consulting.
Another co-founder opportunity. We raised $1M seed round and I pitched at SXSW - won Best in Show. I finally had a seat at the table. It ended in more tough negotiations, but I knew something truer was calling.
Launched e-courses, got my coaching certification, co-produced a massive unconference that kept going for 5 years. Business grew 5x in months. Then, after 18 years in SF, I fell in love for the first time in a decade.
Sold everything. Moved halfway around the world to Hong Kong. Expat life - here we go. ✈️
Got sober. Changed my last name - officially divesting from damage I was still healing from. Ended a 4-year relationship. Moved to Thailand. Everything felt new.
Still in Thailand. Coaching, growing, figuring it out. The LightMap framework started taking shape out of private client sessions. Business grew 5x in a matter of months.
Burnt out from the tidal wave of change that 2017 brought, I moved to Bali - Ubud - to heal. Set everything down. Started writing the book for the first time.
Mexico for the summer. First time in South America - Buenos Aires in the dead of winter (regretted that part). Found love again at a women's retreat in Portland. A few months later, I packed up my apartment in Thailand and moved back to the US to give us a shot.
Pandemic. Portland. A relationship that turned co-dependent and toxic. I ended it. What followed was the darkest period of my life - grief so deep I didn't recognize myself. I maxed out a credit card and went to Mexico. I slowed down. I read. I journaled. I reached out to friends. And slowly, I nurtured myself back to the light.
Sold everything - again. Spent two glorious months traveling Europe. Landed back in Thailand and wrote the final version of my book in 6 weeks. Scored a 5-month housesit in paradise. More myself than I'd ever been.
Italy, Greece, Turkey, Dubai. Another Europe run. Still following joy wherever it leads.
Published the book. Made it to Australia - 5th continent! 🌏 Still going. Still rising. Over and over again.
The first half of this timeline only tracks the few international trips I took while living in the US. However, if you scroll over to when I moved abroad in 2014, you'll see I started traveling constantly! Even trips back to the US became adventures worth noting. That's when the passport stamps really started adding up! ✈️🌏
After 15+ years of booking flights all over the world, here are a few tried-and-true travel tips for you. Where are you traveling to next?
Price calendar, flexible date search, and fare tracking. My first stop for every trip.
Good price alert system and the Explore map is a fun way to see what's affordable from wherever you are right now.
Best when you don't know where you're going yet. Type "Everywhere" as your destination and it shows the cheapest flights from your city.
Formerly Scott's Cheap Flights. They email you when fares drop to places you want to go. The free tier is solid.
Finds hidden city fares where a connecting flight through your destination is cheaper than flying direct. Great for stopping to see a friend or getting a bonus few hours in another city.
Brilliant for building multi-stop itineraries and finding routes other sites miss. Huge for anyone doing long-term travel.
Book 6-8 weeks out for domestic flights, 2-4 months out for international - that's the sweet spot most of the time.
Tuesday and Wednesday departures are almost always cheaper than Friday or Sunday. Flying on the actual holiday is often the cheapest day of all.
Search in incognito mode. Some sites track your searches and nudge prices up if you keep coming back to the same route.
Once you find a good fare, always check the airline's website directly - sometimes it's a few bucks cheaper and you skip the middleman.
Love pets? Consider signing up for Trusted Housesitters - I traveled the world house- and pet-sitting for three years using this site, effectively spending more on flights than I did on rent! Great way to make traveling the world more affordable.
Want more resources and tips? Check the articles on the About page.
Curated travel guides from over a decade of wandering the world
Thanks for confirming. I'll send you a nudge when new cities or spots are added, only when there's actually something new.
View All Guides →Heads up: some places may have closed or changed since I was last there. Always double-check Google Maps for current hours & info before you go.
