As I approach my last day in the U.S. for the next six months, I’m proud to announce that my planning document has a grand total of 94 items checked off the list.
I often cope with stress by organizing my way out of it. And nothing like a huge, daunting project to kick the organizing brain into high gear!
When I made the final decision to leave my job and travel, I had about six months left to plan. All I had at that point was a one-way ticket to Greece that I had bought with expiring airline miles and a bunch of dreams about where I might go. The preparation process was daunting: I couldn’t imagine all the logistics I’d need to work out, the things I’d need to research and book, the life things I’d need to get in order. I decided to approach it like I would any big project: with a well-organized Google doc laying out everything I could possibly think of, complete with checkboxes and a monthly timeline for each item.
The Google doc constantly evolved, new things were added, categories were refined, and slowly I began to check things off. Around May and June things became quite stressful, especially with many medical appointments and the customer service hell in which I found myself. As I wrapped up work in July I realized the to-do list was also wrapping up, allowing me to finally start to lean into the big feelings of a big transition.
Here are just a few of the things it took to get me ready for my six-month work break and travels around the world:
Money. My cousin Joe is my pro-bono financial advisor and one of the best, most generous human beings on the planet. He has helped me find financial freedom and truly changed my life since I started working with him many years ago. I hope he reads this. So when the person who developed my retirement plan told me in January I could easily stop working for a while and spend a boatload of money on traveling without really damaging my future, I listened. It was a huge and lasting confidence booster.
On top of our conversation, I created a detailed budgeting spreadsheet, based on my existing monthly budget and anticipated spend. Averaging out the more expensive and the cheaper destinations, my guideline is $50 a night for accommodation (higher than what is possible as a backpacker but far from luxury), and $25 a day for food. I have a large “fun” budget, and categories for all my regular things like workout classes, shopping, and subscriptions (pared down).
I got a new travel credit card in February for the points bonus, and then put my points skills to good use and leveraged a lot of free flights and hotels, which substantially cut down the cost. I also opened a new bank account with Schwab that refunds all international ATM fees.
I know the final number will fluctuate, but the all-inclusive working number for six months is $32,000. It’s a lot, but isn’t actually too far off from my normal living expenses.
Insurance. I was very stressed about health insurance. My job was making some changes to our insurance options in late March and gave us very little time to choose a new plan. I had less than two weeks to do a ton of research about how American health insurance works abroad, whether I should pay to extend my plan, and while I was at it, comparing long-term travel insurance plans that also cover healthcare. I learned that my job’s health insurance only worked abroad, maybe, if I was hospitalized, so it wasn’t worth keeping.
I chose an insurance company a fellow traveler recommended called Faye. It was a bit pricey ($1250 for six months) but covered what I need – any new doctor visits or emergencies, plus insurance for things like canceled flights. It also has a service to connect virtually with a network of doctors from the U.S. It doesn’t cover dental or vision coverage or preventative care.
Doctors. With my insurance in order, I decided to take care of any and all medical things I could while I still had my American health insurance. I had a regular check up, got a mammogram, got new glasses and contact lenses, saw a dermatologist, and took care of a leg pain (which became my last big to-do item, a surprise $400 bill that I am still trying to fight).
The dentist became my worst nightmare come true in 2026. I had my wisdom teeth removed in March. I went for a cleaning in June, where I was shown that I had a crack in my canine that would need to have a crown put in, a procedure requiring two visits two weeks apart. Along the way I learned that my dental insurance only covered $1500 a year no matter what, and given that this was my second major dental procedure of the year, I was hit with a $1600 bill for my crown. I was so upset and even researched getting it done in Greece for a few hundred dollars, but didn’t want the stress of doing that while I was away.
Vaccines. One of my medical visits was to a travel medicine clinic a friend recommended as part of NY’s Mount Sinai hospital network. The doctor I saw was amazing. I left that day with a Hepatitis A vaccine (which children today get regularly), a tetanus booster, a prescription for a vaccine pill regimen for typhoid that you take over a week (expensive), a prescription for malaria pills and an email address to ask the doctor where to take them along my travels, and 2 prescriptions for possible stomach problems while abroad. I opted to skip the Japanese Encephalitis vaccine that is common in Asia but not covered by American insurance, but I got the names of some Indonesian clinics to get the shot abroad for maybe $50 instead of $700. I also got some good bug spray recommendations.
My Apartment. I am deeply attached to my rent stabilized one bedroom apartment in Astoria, Queens, where I’ve lived for over 7 years. I had to decide whether to leave the apartment behind and store all my belongings (an unimaginable choice), keep the apartment and eat the cost (a really tempting option since I technically have the money), or find a subletter. I fought the decision for a long time, but in early May got permission from my landlord, posted on Listings Project, and found a subletter for at least 5 of the 6 months I’ll be away. She is a recent college graduate who is from Greece and will be working next door to my old office, which all feels right. I made a deal with her to store some of my belongings in the apartment. The rest of my stuff has been slowly making its way to my parents’ garage in eastern Queens. I’ve been cleaning a lot.
Shopping and Packing. I got a new suitcase, easily deciding not to go for a backpack despite lots of advice from fellow travelers. I’m too old for back pain. I got a travel yoga mat that I ultimately decided was too heavy to bring. Most of my shopping was for regular items that I already had and needed replacement, like sneakers and a day bag.
I also made a packing list. I found early on in my trip I started regularly obsessing over which items to bring with me. This t-shirt or that one? How many pairs of shoes? Which toiletries must I stay brand loyal to and pack a 6-month supply? (Answers: 5 t-shirts and 7 tank tops; hiking boots, sneakers, sandals, shower flip flops, and water shoes; contact lens solution, hair gel, and period products.) I did a practice pack a few weeks out which helped make some final decisions. I am taking a medium-sized checked rolling suitcase, my day-hiking backpack, and a small purse that can fit inside the backpack, plus an extra folding duffel bag in case.
Destinations. This is the fun part! In between all the logistics and stress I’ve been watching YouTube videos and comparing hostels to find the right vibe. Figuring out what countries to visit has been a long dream and it’s so exciting to see it become a reality. The destinations are like a puzzle, put together by comparing factors like cost, visas, flight paths, and the intangible thing I like to say is when a place calls to me. I settled on the 9 countries on my list around April.
I’ve been getting lots of advice from fellow travelers about not planning things too far in advance and letting my intuition guide me. I love that concept, and yes, sure, but also… I like planning. I want to maximize my experiences in all these new places and sometimes that means a lot of research and pre-booking for things that sell out months in advance. (Like a 3-day nature experience in Laos that I got the last spot for in for November when I booked in May.) Overplanning can of course set you up for disappointment, and it is not possible to over-plan 6 months of your life. But I like to know where I’m staying and generally what draws me to a place in advance. Over my years traveling I believe I have struck a good balance between having the basics planned for a new place and leaving space for flexibility and wandering.
As of today, I have a decent outline of where I will be each day. The first month and a half have been fully planned with lodging and transportation booked since March, because it’s Europe in the summer and things book up early. Southeast Asia is more flexible, though most flights are booked along with many of my accommodations and multi-day tours. Northern Thailand is fully booked for late November, because it’s during a popular festival and hotels were booked up when I was looking in June. Laos is loosely planned but not booked yet for November; and my last two destinations of Malaysia and the Philippines are not planned yet, though I have been researching and have an idea.
Day-to-day itineraries come last, and that’s something I will figure out when I’m there or a few days in advance. I keep lists of ideas as I learn about them in my Google doc tabs, one for each country.
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There’s obviously more that’s not on this list. (Passport renewal! Mail! International Driver’s Permit! Absentee ballot! Haircut!) This project has been a behemoth of a challenge. Much like travel itself, it has tested and stretched my limits. As I swat away the creeping thoughts about what I might do after this, I’m bolstered by the confidence of getting through this logistical project—knowing I can set my own path and work through whatever challenges the future might hold. All it takes is a good Google doc.
travels.of.tara 