Step 2 — Plan

Introduction to planning

The second step to living the life of your dreams is to make a plan.

I get a lot of emails asking for advice. When I began planning my trip back in the early 90s, there were hardly any books about cycle touring and almost nothing online. So, I had to plan my trip from scratch. But now, there is an overwhelming amount of information and self-proclaimed experts popping up in every niche. You could spend months trying to sort it all out. But, rest assured, I can make this easy for you.

Planning is actually the easiest step of them all. In fact, it’s so easy that I recommend you plan no further than the next step of action you can take. As soon as you figure out that step of action, go ahead and do it, play, have fun exploring life. Soon, you’ll learn so much that the next step will become obvious.

It might sound contrary to being easy, but planning is impossible to do all at once. You are about to embark on a new adventure, which means you’ve never done it before and can’t know everything involved. So, don’t make the mistake of thinking you have to have a perfect plan before you can decide whether or not you are going to undertake your journey. Let your passion guide you. Give your passion the job to decide whether you’re going to do it or not. And what better way to discover if it was actually a good idea than just to do it. 

Of course, sometimes detailed planning is necessary. For that, I recommend the following process. Per the infographic above, you need three plans:

1. Plan for what you know.
2. Plan for what you don’t know.
3. Plan for what you don’t know that you don’t know.

Another way to think of this is the following: 

1. Known.
2. Unknown.
3. Unknowable.

Example

1. If you want to visit Italy, you need a list of places to visit, like the Colosseum in Rome.
2. You probably don’t know how to speak Italian. So, plan how you will communicate.
3. What happens if you get lost or lose your luggage? You’ll need a contingency plan or a backup plan. In other words, expect the unexpected. 

My favorite step here is #3 — the unknowable. That seems scary, but it is the place where we are discovering and creating a new reality. Whereas step 1 is saving money, making supply lists, sitting on trains and planes, et cetera, which can all be quite tedious. Step 3 is crucial — it is your backup plan. 

Your backup plan

It is presumed that you need a dream — a grand purpose — to begin living your life. Perhaps this is ideal; however, what if you feel lost? What if you are lost? Don’t worry. This is a natural starting point. It took me a long time to learn that I wasn’t supposed to have the answer — I get to create the answer. I’m very proud of this backup plan, and I hope you love the irony as much as I do. You’ll see that your backup plan is actually the reverse of the steps above. 

1. This is where my favorite step swoops in to save the day — Plan for what you don’t know that you don’t know. But how do you do that? Simple — find a map or mentor. That’s where my website and my decades of experience can help. I’ve already traveled this path. I’ve created the maps, and I can help guide you. In other words, I can teach you the process. The first essential map you need is The Map of Your Life.
2. Now that you have an idea of how life works, the second essential map you need teaches you How to Define Your Dream and Turn Your Dream into Reality.
3. The third step is where we get into the nitty-gritty of figuring out the who, what, where, when and how. There are endless solutions to these steps. I refer you to my Worksheets, and I have plenty of resources for How to plan a Traditional Travel Adventure.