Military Retirement Planning: Your Five Year Vision

Airport test image


  • Three reasons why you need a 5 year vision.
  • Using the Airport test to help you create your 5 year vision.
  • Lessons learned from doing the exercise.
  • Disclosure: Please note that some of the links above are affiliate links, and at no additional cost to you, I will earn a commission if you decide to make a purchase after clicking through the link. Additional information can be found on my disclaimers page.

This is not a normal way to start a blog, I mean, if there is an ideal way. Currently, I am deployed in a third world country. Our deployment was supposed to end and we should be on our way home in the next couple weeks, but with the COVID-19 pandemic has the world paralyzed. Our orders are to remain in place. That includes our relief. For just a moment I would like to step away from the chaos and think about military retirement planning for few. Mostly because with some luck, I won’t find myself in my current situation again. I read, listen to audio books and podcasts a lot, recently I came across a pretty cool way to create a 5-year vision and it just so happens to include an Airport. So while I do this exercise with hopes of taking an airplane home sooner than later I invite you to do the same.

There are many reasons to create goals or have a 5-year plan. Remembering the guidance from Stephen Covey’s 7 Habits of Highly Effective People, we want to one, “be proactive,” two, “start with the end in mind,” and three, “do first things first.”  Once we know where we want to end up, we gain the clarity required to create goals, habits and systems that will lead to that vision. That vision becomes our North Star, to guide our decisions towards our desired future. Questions or obstacles we encounter on the journey can now be weighed against this vision for an answer. Want to get a new job? Do you want to start a business?  Should we buy a new house? Any other important questions can be weighed against these ideals and whether they may lead to your desired future. The intent is to have clarity in your destination so that you can change the directions but still end up at your goal.  

1 Be Proactive

2 Start with the end in mind

3 Do first things first

The 7 Habits of Highly Effective People
-Stephen Covey-

Another reason it is helpful to have a 5-year plan is that you can then take the time to test your assumptions. Maybe your ideal future includes you selling all your possessions to become a minimalist, buying a sail boat and sailing around the world. This has been your dream since your eighth grade when you lived in Kansas. The only problem is that you never left Kansas or seen the ocean much less a sail boat. In five years, you can do mini tests to see if that is what you really want to do. Maybe start with a vacation to take sailing lessons. Then once you feel comfortable sailing, take a vacation where you actually live on a boat for a week or so. All the while slowly pairing down your possessions. Maybe this is exactly what you dreamed it would be and your path is set.  Maybe you find out that you get super seasick, or you absolutely hate the smell of the harbor at low tide or you have no desire to be stuck on a 20-30 foot boat with another person. The beauty is that you can reevaluate anywhere during that process and change your course.

While this vision is flexible and can be updated or adapted, we should try to do so sparingly. In Think and Grow Rich, Napoleon Hill notes, “successful people make decisions quickly, as soon as all the facts are available, and change them very slowly (if ever.) Unsuccessful people make decisions very slowly, and change them often and quickly.”  While we want the freedom to update or change our vision we want to be prudent to not change quickly. Take the time to build certainty into your vision by including a purpose. What is your “why?” If this is truly important to you, your “why” will allow you to endure and navigate the obstacles that will come. Your “why” will also keep you from changing you mind frequently. If a plane keeps changing its course, it may never make it to its final destination.

Now the exercise we are going to do was introduced to me by Pat Flynn, the Entrepreneur, Arthur and creator of the “Smart Passive Income” podcast. He is also a best-selling Arthur of three books, Let GoLet it Fly, and Superfans. I have read Let it Fly multiple times and I think Pat does a great job using personal exercises to facilitate the discovery of your calling or passions. In chapter 2 of Let it Fly, Pat guides you through what he calls the Airport test. 

Let’s say you’ve jumped into a Delorean time machine and zapped yourself five years into the future. You find yourself at the airport. As you sit in the terminal, waiting for your next flight, you feel someone tap your shoulder. You turn around and your face immediately breaks into a smile as you recognize an old friend from school. Your friend exclaims, “I thought that was you! It’s been to long since we’ve connected!”

       “Yes,“ you agree whole-heartedly. “I’ve missed you!”

With some time to kill before each of your flights, you both decide to catch up over a. Cup of coffee. As you settle into a table, your friend asks you, “So how’s everything going? How is life treating you these days?”

You respond with “AMAZING! Life couldn’t get any better.” And you really mean it.

Now here comes the key questions:

What is happening in your life five years from now that makes you respond like this?

Will It Fly: How to Test Your Next Business Idea so You Don’t Waste Your Time and Money.
-Pat Flynn

The exercise continues with folding a piece of paper into quarters. To do this fold a piece of paper once in half and then on the fold, fold it in half again. When you unfold it you will have four quarters. 

At the top of each section label it with the four main categories of your life. Some examples may include. Personal, Professional, Health, Family, Travel, Financial, or any other important aspect of your life. I am labeling with Family, Professional, Finances, and Health. Again, if you want to use another topic please do, this is your personal vision.   

As you think about the story above, under each individual heading write down what your perfect life looks like in 5 years, in this exercise i犀利士 t is perfectly okay to dream big!  It takes me forever to write these posts, knowing that, I would still like to write a book one day so I listed it below. Take 5-10 minutes per section or as necessary to fill out each section completely. Below is what I have listed for my professional quarter.   


-I am retiring from the military.

-I have multiple side hustles that match my current income and grant me the freedom to choose a job I really want to do instead of any job that is available.

-I have become successful and known in a new area and my skills are in high demand.

-I have written a best-selling book that provides value to millions of people. 

-My jobs allows me to help people improve their lives and I rewarded both personally and financially. 

-I have the flexibility to take any day off and spend time with friends and family as I choose.

-I make sound and ethical choices in my business dealing and strive to create win-win situations. 

Notice that these statements are not S.M.A.R.T. goals, they are brush strokes or ideas and outcomes that I currently desire for my future self. In future posts we will deconstruct and define some specific goals to achieve these ideals. For now, focus on that vision of your future, as it will play a key role as we define what is and is not important in future exercises. 

What are some of the key points you have taken away from this exercise? How different is your future self than who you are at the moment? Please share your comments below. Remember it is fine to be in a completely different realm at this point. It is also okay to already be exactly where you want to go. This exercise is designed to assist you in gaining some clarity on what you want in the future. We can bridge the chasm in future exercises that focus on how we will get there. As your life situations change your vision may change. That is perfectly normal. This is just an ideal starting point to build from.

If your folding skills are crap, or you are so OCD any symmetrical error will bother you to no end you can download a templated version this exercise enter your name and email below for a PDF copy. (Coming Soon) 



  • Disclosure: Please note that some of the links above are affiliate links, and at no additional cost to you, I will earn a commission if you decide to make a purchase after clicking through the link. Please understand that I have experienced all of these companies, and I recommend them because they are helpful and useful, not because of the small commissions I make if you decide to buy something through my links. Please do not spend any money on these products unless you feel you need them or that they will help you achieve your goals.

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