How To: Organizing Your Escape

Kristin and Doug Walsh, April, 2013

How do you plan for a multi-year cycling trip? Everyone will approach this a little differently. Like many before us, we didn’t want to over-plan, but quickly realized that there is a ton to do before you even roll out the door, especially if you’re planning to part with a lifetime’s worth of possessions. With two years still to go before our estimated departure date, we realized that time was moving very quickly and before we knew it, April 1st of 2014 would be here. While we were already spending time “doing trip stuff” and getting things done, we weren’t sure if they were the right things at the right time, nor did we know what downsizing tasks we might be overlooking.

Getting Started: Creating and Categorizing Your List

One night we decided to start a formal plan. We started by creating a list of tasks and then sorted them into four broad categories that seemed to encompass everything. Below are the four major categories and a few example tasks.

  • Gear and Logistics
  • Digital and Communication
    • Design website and content.
    • Decide on cloud storage provider.
    • Digitize family photo albums.
    • Create Facebook, Twitter, and Skype accounts.
  • Legal and Money
  • House and Property
    • Determine upgrades needed to sell house.
    • Sell possessions via Craigslist, Ebay, and yard sales.
    • Sell vehicles.
    • Decide long-term storage needs (storage unit and safe deposit box).

Build a Wall Calendar

You can do this next step on the computer if you want, but we recommend making an oversized calendar to hang on your wall. Not only will this provide plenty of inspiration, but it also serves as a daily reminder of what you still have to do, and how fast time is slipping away — for better and for worse.

task calendar
Hanging at the end of our hallway, our calendar reminds us each morning what we’re working towards.

We hung two large tri-fold poster boards horizontally on the wall and divided it horizontally by category. We then made some rough divisions vertically for month and year, counting down from our planned departure date.

Next Steps: Who and When

Next, we decided who would be responsible for each task according to our respective strengths and interests. We wrote these tasks on large colored Post-It Notes (pink for Kristin, blue for Doug, and yellow for the tasks we would tackle together). We then had to decide when these tasks needed to be completed. This was a little more difficult. We started by placing those that had to wait until right before departure and filled forward to the present from there. Any task that could be done sooner was moved up so that we could cross them off and continue onto the next. Don’t worry about trying to get this right on the first try, as the Post-It Notes allow you to effortlessly shift things around the calendar. Below are the time-frames we sorted the tasks into and a few examples including explanations for our timing choice.

  • 12-24 Months Before Departure
    • Develop preliminary itinerary and visa plan.
      • Where do you want to go? It’s helpful to have a general idea where you want to go, the comparative costs of living, and the distances between destinations. Determine which countries require visas, how long they’re good for, and where you might get them along your route.
    • Create a savings plan and budget tracker.
      • The more time you have to save, the better off you’ll be. Track this closely and do some test trips to determine the average daily budget to maintain your comfort level.
    • Create health plan and determine travel insurance provider.
      • Research was time consuming and was unlikely to change much. Some vaccines are a series need to be started many months before leaving and scheduling consultations with medical providers can take a few weeks.
    • Develop website and content.
      • This required learning the website development program, WordPress in our case, as well as designing and developing content in time to go live T-3 months.
  • 3-12 months before departure
    • Decide on cloud storage provider.
      • This one moved forward to T-15 months as there was no reason to wait and we found it useful for sharing planning documents.
    • Determine upgrades needed to sell house.
      • We wanted to enjoy any improvements (roof, new kitchen, new carpeting) before selling while maintaining their newness.
    • Sell possessions via Craigslist, Ebay, and yard sales.
      • Allowing plenty of time for selling items provided flexibility in waiting for the right buyer to pay our asking price.
    • Decide long-term storage needs (storage unit / safe deposit box)
      • After we decided what we couldn’t part with, we were able to decide on the size of the storage unit and safe deposit box we would need. Insurance options on both are nonexistent or require significant creativity, so we needed time for researching various options.
  • 0-3 months before departure
    • Contact cruise ship and freighter travel agencies.
      • Cruise and cargo ships fill months in advance so we needed to figure out which ones we needed to reserve sooner rather than later. This would apply to flights as well.
    • Create a will and scan important papers.
      • We were going to do this earlier, but wanted to make sure it reflected the closing/opening of credit cards and accounts taking place right before the start of the trip.
    • Research debit and credit cards offering free international use.
      • We needed to have time to open necessary accounts, create links for bill paying and transferring money, and close unnecessary accounts before leaving but not too soon. We decided on a Schwab checking account (worldwide ATM fee refunds) and Capital One credit card (no international fees).
    • Obtain new passport with plenty of pages
      • We wanted to make sure there were plenty of pages and plenty of expiration time left. Most visas require at least 6 months remaining before expiration on a passport.
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About Us

We're Doug & Kristin Walsh, a couple of Washingtonians who love to travel, both abroad and in the wilds of the Pacific Northwest. We set off to travel the world in 2014, primarily by bicycle. We're back home now, but the travel bug continues to be fed every chance we get.

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