Getting Going: How to Overcome your Overwhelming to-do List

Today is the first in our Take the First Step series. The first step in any big effort or in following a dream is often the scariest and most challenging. Through this ongoing series we’ll share stories of people who took the plunge and how they took the first step towards their dream.

Long before we became the perpetual travelers of EverywhereOnce.com, we were an average couple in our mid-thirties with a hazy vision of a shared dream. Shannon and I both longed for a life on the road and saved diligently for years toward that end, but frugal living and saving were never our primary problem.

Originally we thought that our adventure would take us overseas, vagabonding across all the world’s continents. We love Europe, have barely scratched the surface of Africa, and have never set foot in Asia, South America or Australia. We knew we had a lot of ground to cover if we wanted to see it all—and that we’d never achieve these ambitions as long as they were constrained by our allotted yearly vacation time. For what we had in mind, we’d need months, or more likely years, of continuous travel.

So we’d talk, frequently over dinner but other times as well, about what we’d do, where we’d go, and most importantly, how we’d make it happen. But the conversations always ended with the same question: “What will we do with our cats while we travel?”

Our cats were part of our family, and they were either coming with us or we weren’t going. After deciding our felines would fair poorly in carry on bags, the conversation always ended with us postponing our travels. How depressing?

The answer turned out to be incredibly simple. It arrived out of the blue the way epiphanies normally do. As often happens, we were blinded to it by our preconceived notions. We assumed travel meant backpacks and hotels. Never did we seriously consider taking our house along for the journey.

It wasn’t until Shannon mentioned re-prioritizing our travels that all the pieces fell into place. If we started domestically, we could travel in an RV and take our pets along with us. If our goal really was to “see everything,” we’d need to explore the vast expanses of North America eventually. Why not start there?

With that realization, our dream instantly transformed from a gauzy, loosely defined, far-off objective to something specific and real. The recognition that everything we had talked about for so long was finally within reach felt totally amazing.

Then it almost completely fell apart.

It took us only a couple of days to realize that walking away from your life is easier in the dreaming than in the doing.

In the fantasy, we simply loaded up an RV or a backpack and set off on untold merry adventures. Back in the real world, we had jobs, and friends, and possessions and responsibilities. But more terrifying than anything, we had absolutely no idea what we were doing.

We had never owned an RV before; never driven one; never even slept in one. We didn’t know the first thing about the lifestyle. We soon discovered that things we used to take for granted, like having health insurance or even a driver’s license, required a physical address and we planned on not having one.

We were in over our heads, and the swim to the opposing shore seemed impossibly long. As we looked at the learning curve that confronted us, we felt as if our dream was steadily dissolving back into the mist. All the specificity that was so exiting at first now raised fresh doubts in our minds: Could we actually do this? Is this what we truly wanted? Wouldn’t it be easier to just stay put?

The answer to all three questions was a resounding “Yes.”

We absolutely wanted to start a new life of perpetual travel and we knew, or soon found out, that we were more than up to the challenge of making it happen. Yet it really would have been much easier to stay on the sidelines living the life we had while dreaming of the one we wanted. But we’ve always believed that dreams are meant to be chased. We just didn’t know where to start.

After a short period of hyperventilating and self doubt we realized the specifics were killing us. There were simply too many things to research, and we were getting overwhelmed by the details. We needed a plan to keep our heads above water.

Here’s how we coped and, eventually, prevailed:

Divide and Conquer

Early in the process, Shannon and I worked independently, often covering the same ground and running into the same dead ends. Duplicating our efforts made each task seem twice as large and take twice as long.

We had a tendency to gravitate toward the same tasks; probably because some were easier or more interesting than others. Specifically delegating responsibilities became absolutely necessary. By deciding early how to split up the chores we not only avoided duplication but also confrontations over the distribution of work that threatened to distract us from our larger goal.

Work the Critical Path

In any complex process, there is a natural order to things. Some things have to be completed before other things can be started. That critical path isn’t always immediately obvious. Not identifying it early can mean wasted effort trying to solve problems that can’t yet be solved.

An example for us was obtaining health insurance. One of our biggest financial concerns as U.S. citizens is that one of us will develop a chronic and expensive medical condition. We knew we’d lose our existing plan once Brian left his job. Going “naked” was absolutely not an option. Having a good plan, with guaranteed renewal, was so important to us we’d rather abandon our trip than go without.

With such an important problem to solve, it was natural to want to tackle it first. After all, our entire dream hung in the balance. But in the U.S., health insurance is governed by state regulation with each state having different requirements, restrictions and costs. We couldn’t start researching health insurance plans until we knew our state of residency. We couldn’t know that until we figured out how to become a legal resident of a state without actually living there (more on our eventual solution here: How to Become a Global Citizen).

Compartmentalize

We could have stressed about not having our health insurance buttoned up. We could have spent countless, fruitless, hours researching all the various options in all 50 states. Instead, we decided to ignore it for the time being. Health insurance simply wasn’t a critical path item. If we couldn’t solve the problem until tomorrow, we should delay worrying about it until then too. And we did.

Employing the adage, “out of sight, out of mind,” we went so far as creating two separate to-do lists. Our “Master Project List” covered absolutely everything we needed to get done until the day we walked out our front door for the very last time. That list was so overwhelmingly long we tucked it in a drawer and only consulted it when absolutely necessary.

We created a second to-do list that only included the next 5 or 10 things on our critical path. Only when we completed the things on that daily chore list, did we revisit our Master Project list.

Keep it Simple Stupid

We even broke large questions down into smaller ones. Instead of listing imponderable tasks like “Find the perfect RV to live in,” our daily to-do list had more basic questions like “Figure out the differences between a Class C motor home, a 5th wheel and a cow.”

That first question is really hard while the second is quite easy. By working up through a series of easy questions, we eventually arrived at a point where the answer to that hard question became obvious.

With short to-do lists of generally basic tasks, we were always crossing stuff off. We found that tremendously rewarding and motivating. Even though each item may have represented baby steps in a long journey, it felt like we were making real progress every single day. That feeling of progress kept us going when things got tough.

Keep your eye on the prize

In their book Dream Save Do, Betsy and Warren call it “Dream Porn.” We called it keeping our eye on the prize. Daily reminders and discussions about the end goal (a lifetime of perpetual travel for us) helped get us past all the inevitable rough spots.

When you’re deep in the weeds of minutia, it is easy to lose sight of the big picture. Take occasional breaks from those details to admire the beautiful landscape you’re working to paint. Remember why you set out on this journey in the first place and imagine the feelings you’ll experience once you reach your goal.

There is no question that chasing a dream is hard work. It’s easy to get discouraged. It is easier still to let the drift of current events determine the course of your life. We found these simple tricks and techniques kept us on track and motivated toward the life we had dreamed of for so long. Mostly it all boils down to a variation on some very old wisdom: the longest journey begins with a single step.

You just have to get moving.

Full-time travelers since April 2010, Brian and Shannon are as passionate about helping others break free from convention as they are about seeing the world. Shannon is a freelance writer and co-author of Novel Destinations: Literary Landmarks from Jane Austen’s Bath to Ernest Hemingway’s Key West (National Geographic Books). Brian is chief chef, big rig handler, photographer, and creator of the travel blog EverywhereOnce.