Designing Your Life – How to Plan
Don’t Go With the Flow

Image by Ed Karjala
The Problem
As a result of my recent post, My Master Plan, I’ve had people ask me how I created my plan and what planning techniques I find to be most useful. To be honest, I’ve been a planner for most of my life. I was writing goals when I was a teenager although they were often grandiose and unrelated to anything I was doing at the time. I expected that good things would just eventually happen to me someday and I would start living the life of my dreams. It was only years later that I realized that this wasn’t going to work and that I needed to re-evaluate my philosophy.
Connect the Dots
I started using the typical short-term, mid-term, and long-term goal strategy and although it got me thinking a little bit more about how to connect my goals, I still wasn’t turning them into a reality. It easy to write down something like: “buy a yacht,” but without a plan for achieving it the goal was useless.
It was during my time in the Army that I learned about backwards planning and the benefits of planning your life from the end state rather than the current state. Although the Army uses the strategy much differently, it dawned on me that the same process could be applied to my goals and dreams very similarly.
What I started doing was defining my perfect day in say 10-20 years down the line. Once I had the entire day mapped out, I started realizing what was important to me and what was not. I then started prioritizing the important things and identifying what I would need to accomplish having, getting, or being them. I set up three categories for the end state:
- Things I want to do (live in a castle, sail Caribbean, backpack Europe)
- Things I want to be (pro Triathlete, Good father and husband, author/musician)
- Things I want to have (money, boat/car/whatever, investments, businesses, etc)
Having 10 million dollars sounds good, but what sounds better is knowing what I wanted to do with the 10 million dollars. Once I identified the 3 categories and what would fill them up, I started planning backwards from the perfect day. I went over every phase of my life, from waking up to going to bed. I set up 5 phases as my planning strategy and started moving backwards phase by phase until I reached my current state. For example, my goal of becoming a professional triathlete was part of my 5 phase plan, but I also broke it down further with a 3 step plan to becoming a professional triathlete. I also broke down my business goals the same way. I took the end state of owning business structures worth a certain amount and went backwards. I created income goals, levels of involvement, and investment/business building strategies along the way. Eventually, I reached my current state of being employed in the Army as a part-time webrepreneur. When I finished, I realized the beauty of the plan and the method. My entire future was written on a tablet in front of me and my destiny never seemed clearer. Not only did I have a clearly defined goal, but I also had a clearly designed and focused plan for how to get there.
Design Your Life
In my opinion, the key to defining and achieving goals is to connect them to where you are in life currently. I call it a personal business plan and everyone should have one. Without your own personal business plan, you are simply letting the current take you where it may.
You have to identify the steps needed to get from A -> B -> C -> D. Without that key connective ingredient, your goals will look like nothing more than far off fantasies. If you find ways to connect them step by step and prove to yourself what you’ll need to get there, you’ll find that not only are you more motivated, but the goals are much more realistic and easier to accomplish.
I have seen this work firsthand and the truth is that I am beating myself up for not realizing this key sooner. People tell you to create goals and to dream big, but what they don’t tell you is that dreaming big is the easy part. The hard part, and the part that pays off, is actually designing your life step by step. So take your current state, compare it to the end state that you desire, and figure out how to connect the dots. It is much easier than it seems and I promise you’ll enjoy it.
I’ll see you at the top.
By the way, if you are looking for some more great business ideas or how to make money online, check out my friend Chris Guillebeau’s Unconventional Guide to Working for Yourself. It is a fantastic course with a great guarantee. I wouldn’t recommend it if I didn’t buy it myself and my opinion is that for the price, you will not find a better guide to making money.
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