The Dos and Don’ts of Quest Planning

As soon as we decided we were going to take a world trip of our own, we immediately started planning. Luckily, we are both planners and researchers. In fact, we often suffer from “analysis paralysis.” I won’t even change deodorant brands without thoroughly researching reviews.

Here is a brief list of the dos and don’ts that we applied to our Quest planning process.

Do: Plan your work, work your plan

One of the first things we did to start fleshing this thing out was to build a shared spreadsheet in Google. We knew this was a big undertaking. We needed a way to stay organized and keep track of the flurry of questions that came up. We knew the success or failure of this trip was up to us. We had to make sure we could stay on track and not get overwhelmed.

Here are some of the most important parts of our travel planning that we tracked:

  • Destinations and how long we planned to be there
  • Peak travel seasons and shoulder seasons (read: cheap times to visit)
  • Vaccine and visa requirements
  • Budget breakdown per person, per day, based on city/country/region
  • Things to consider (storm seasons, gear needs, other miscellaneous things)

Andy has a better attention span than I do, so he was really great about reading blogs and articles (all the way through!) to glean useful information and add it to our growing spreadsheet.

My strength is making lists. I kept track of all the questions or things to consider that would bounce into my head throughout the day. Then we would sit down and research them together.

Thankfully, there is an entire community of travelers who have done this very thing. And they have so generously shared their journey on the internet. There were very few questions that we couldn’t find answers to. It was all there at our disposal. What a time to be alive!

Three blogs that we referenced the most for budget and travel planning were:

Alittleadrift: A female solo traveler who backpacked for a year and has a super-helpful budget breakdown

Nomadicmatt: A very well-known travel resource for backpacking including location-specific travel guides.

Brokebackpacker: A travel website that focuses on educating people that travel doesn’t have to be expensive. The founder gives great advice for traveling for as little as $10 per day!

These blogs helped us wrap our heads around all things we needed to consider in our planning. They made the process so much easier. They also helped us grow our destinations list by introducing us to more budget-friendly places that we had never considered.

Do: Build your Quest Fund

Although budgeting isn’t as fun as dreaming of travel, it has to happen or those dreams will always be for someday. One page of our Quest Planning spreadsheet was dedicated to tracking our savings. We committed to saving half of each of our paychecks, auto-depositing that money into our shared Quest Fund.

I want to mention here that we had been living together since 2013 and married since 2016. But we didn’t have a shared banking account before we started planning the Quest. For years we had been sharing financial expenses, finding a way to split our shared cost of living relative to our income. We had a system and it worked ok.

Andy and I are very similar when it comes to saving and spending money. We never really had to worry about the others’ money habits. But we didn’t ever have a focused financial plan, either. I loved to track my spending and saving but Andy cringed any time I wanted to talk about a budget.

All that changed when we started planning for the Quest. We had a shared dream, and it was totally up to us to make it happen. It became a ritual that every month, we would sit down in front of the computer, pull up our account info, and see our savings number growing. We searched for ways to cut our living expenses and earn extra money here and there. (Stay tuned for a future post dedicated to that.)

Even though it was a steady rate of growth that we could calculate, it was so exciting to see the number increase. Every payday, every auto-deposit was bringing us closer and closer to our dream.

Do: Set a date

Once we set a savings goal for a budget that would allow us the style of travel we wanted, we were able to calculate a rough target date for departure.

This is where it started to feel real.

One of the first things we wanted to experience on this trip was walking El Camino de Santiago, a religious pilgrimage across northern Spain. We planned for this to be one of the first things we did, so we planned for the time when the weather would be most ideal to start (April-May).

I knew that my mom would be crushed if we blasted off before her birthday at the end of April, so we decided to leave in early May.

One of the really wild things about our departure date was that Andy’s mom, the flight attendant, was getting us standby flights to Europe.

This means that we didn’t know exactly what day we would be flying out. We didn’t even know exactly which city we would be flying into.

We knew it was kind of a crazy way to go about things, but we loved it. It only added to the sense of adventure.

When we got married in a hot air balloon back in 2016, we didn’t know until the week of our wedding if the hot air balloon would actually be able to fly on that date. Oklahoma weather can be unpredictable.

The pilot was skeptical and had a few suggestions for a backup plan, including a mid-week sunrise flight. I held out hope that my original (and only) plan would work out.

The week of our wedding, the pilot messaged me:

“You must be living right. Saturday looks great. See you then.”

So why should this adventure be any different?

And so we worked our plan, adding dates and marking off tasks from our beloved Quest Google sheet.

Don’t: Wish away time

We were so excited for this adventure and busy with working, planning, and saving, but we decided very early on that we wanted to be mindful of our time. We wanted to spend as much quality time with our loved ones as we could before leaving.

We loved our home and our community and we didn’t want to wish away our time with family and friends. We knew time is a precious resource that once spent, is gone forever. We tried not to start counting down to our departure and never said things like “I can’t wait to leave!”

We even started commenting on some of the luxuries that we knew we would miss. We loved sleeping on our comfy mattress, watching movies on our projector screen in our living room, cooking familiar meals in our kitchen.

As exciting as it was to leap into a life of adventure, we didn’t take our comforts or time with loved ones for granted.

Don’t: Let your dream burn you out

This planning process overwhelmed us at times. As exciting as it was, we had to do a lot of work to make it happen. Working long hours and side hustles, sticking to a savings budget, research, and a growing list of questions can take it out of you.

So how did we cope?

We drank boxed wine and played on Google Earth.

If you have never done this, thank me later.

We had so much fun jumping around to different destinations on the globe. Our TV setup is actually a 100” projector screen connected to our computer, so it felt like we were getting a pretty great view of places.

It helped us learn about places we had never heard of and helped orient us in our itinerary planning. It also helped us chill out and remember why we were doing this crazy thing in the first place.

Planning long-term travel can definitely be stressful. Try to keep focused on the excitement that made you want to do it in the first place. Have a plan, take action every day, stay focused, and try to enjoy the journey. Employ wine and Google Earth as needed.

Before you know it, you’ll be sitting at the airport wondering “Am I really doing this?”.

In the next article, I will talk about my various side hustles and how we lowered our cost of living to increase our Quest fund.


  1. Kathy Villarreal aka Mom

    Love this! So much research and organization~~and by The Way (?), what box wine do you recommend?

    1. Bota Box Nighthawk Black was our favorite! ?

  2. ridersgrimm

    We actually did something similar in 2003- quit our jobs and traveled the continental United States on our motorcycles, so we can relate to the years of planning for the dream. Love your sharing your process this way!

    1. Yes! Now that we’ve spent so much time on motorbikes, we might do something like that when we’re back. We welcome tips and insights!

  3. So glad to hear that you found the budgeting resources useful! What a crazy addition the pandemic has added to your RTW—but love that you’ve been able to spend so much time deeply getting to know Vietnam. Safe and happy travels as you continue! 🙂

    1. Your spreadsheets were a huge help in demystifying the planning process! Thank you so much for making them available. Our change in pace was hard to adjust to but we really lucked out in landing where we did. It’s proof that you can do all the planning and research you want, but you still have to adapt at the end of the day. Here’s hoping we’ll all be traveling safely again soon!

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