Planning Your Life Means Being (a little) Selfish

Jonathan SlainProductivityLeave a Comment

I find myself on a plane writing this article to help you create your first life plan.  Where I’m writing this article is relevant for a couple reasons.  First, if you didn’t read my article in C&R Magazine last month, “My Life Was a Disaster And Then I Got Organized,” you can find it online here, it’s relevant because I wrote that article on a plane too.  Second, I want you to understand that I intentionally do a lot of writing on planes because it’s part of my life plan to finish a book and plane time allows me the freedom to detach from my phone and work and kids and do my best thinking.  Keep reading and I’m going to explain how you can write a first draft of your own life plan.

The flight attendant just made the standard announcement that if the oxygen masks drop you should first put on yours and then assist your kids, family, and other passengers with theirs.  In other words, you need to be selfish and save yourself first because if you pass out attempting to get the oxygen mask on your kids, then both of you may end up out of luck.  It got me to thinking that most people are so busy working to provide “oxygen” to their families that they often turn blue from lack of spending time on themselves.  We invest countless hours in pursuit of our kids’ interests but it seems self-indulgent and selfish to spend time planning our lives.  It’s too bad more people aren’t selfish because I believe that the more selfish we are in planning our lives, the happier we are and the happier the people around us are! 


Five years ago, I was fortunate enough to meet Paul Belair, a friend, business mentor and coach who changed my life forever.  I am a member of the Entrepreneur’s Organization (“EO”) and one of the products offered is the opportunity to have a mentor.  Paul was randomly assigned to be my mentor in 2012 and I had no idea what an impact it would have on me. 

The mentorship program in EO consists of monthly meetings between mentor and mentee.  I was excited to get together with Paul because I had heard about his reputation.  He built a large HVAC company thru acquisition, then organically grew the company from about $50 million in revenue to approximately $150 million in revenue in 60 months and sold it for 83x his original investment! 

I couldn’t wait for our first meeting so he could tell me what I was doing wrong in business and how I could replicate his success.  I was going to get an all-access, backstage pass to understand how this incredible business mind read the market, exploited weakness in his competitors, and executed the right strategies and tactics to build his company and maximize shareholder value.

The day of our much anticipated meeting arrived, and my expectations were not met at all!  Paul spent the entire meeting asking questions and listening.  After two hours (we met for breakfast), Paul gave me my first assignment: write a life plan.  He said the only way for me to grow my business would be to spend some time figuring out what I wanted to be when I grew up and how I was going to get there.

Over the next year, Paul and I met for breakfast monthly and by the end of 2012, I had a first draft of my life plan completed.  We never once met at my office or his office.  And, we hardly talked about Paul’s business or my business, but I was right about one thing, Paul did give me an all-access, backstage pass to something better.


A life plan is simply a tool that you will use to reach your personal definition of happiness and success.  It is your North Star that you look to when life gets complicated or when you’re confronted with a tough decision.  Ideally, your plan should be written before you really need it, when life is calm and you’re in a rational state of mind, not when you are on the precipice of a major life decision. 

For example, when I get asked to join a new board, take on a new client, or commit to an opportunity that is going to take up a significant amount of my time, I always filter the decision thru my life plan.  It’s funny how some opportunities “click” with my plan and others are an obvious “pass.”  For example, I recently was asked to be on the regional board of the Entrepreneur’s Organization.  This position will involve a significant commitment of time and travel over the coming year, but it will allow me to further several of goals in my life plan so it was easy to accept.  I used to agonize over these decisions.

The life plan has also substantially improved my financial health.  Before the life plan, I was thinking incrementally about how to increase my annual income by 20% or 30%…  Paul challenged me to be courageous and write a plan to create a 10x increase in my income.  I’m definitely not there yet, but I have far surpassed the 30% goal that limited my original beliefs.  Because I spent the time with my wife and family determining that we want to spend our money on travel and once-in-a-lifetime experiences, it’s easy for us to decide to stay in our smaller house and use public schools.  I’m not advocating that everyone make these same choices, but rather that you intentionally make decisions with your family about what matters most to you.  If you value a big house and private school for your family that is great, but you need to figure out what you will sacrifice in order to make that a reality.  I am advocating that you decide for yourself instead of letting the universe do it for you! 


We all get about 78 years on this planet on average; I want to make the most of my time.  The way I see it, each of us is living our lives according to a plan, the real question is whether you are writing the plan for your life or if others are writing it for you.  As for me, I don’t mind when friends and family pick what movie or restaurant we are going to, but I certainly am not leaving it up to anybody else what I am going to do with my life.    

I was at an event listening to brilliant speaker and coach, Jack Daly, and he quoted Dennis Waitley, “Most people spend more time planning Christmas and holidays then they do planning their life.”  Those words have really stuck with me because they ring so true.    

Jack Daly epitomizes life planning (and freely admits that he might take it a bit too far) in fact he publishes his plan online for the entire world to see and to hold him accountable!  You can check out his plan here

And, if you’re thinking that writing a life plan takes all the spontaneity out of life, well to some extent you’re right.  But, you don’t have to take this concept to Jack Daly heights.  And, it’s alright for you to include flexibility in your plan in case you’re at a point in your life where you want to try some different options before settling on your career, your partner, or what adventures you want to seek next. 

While I am going to share pieces of my personal life plan and the plan that Katherine and I have created for our family later in this article, I encourage you all to figure out your own format that is meaningful for you. 


Below are the three simple steps that Paul gave me to write my first life plan (note that I chose the word “simple” intentionally and that “simple” does not by any stretch of the imagination mean “easy”):

  • Step 1 – Commit to spend 16 hours on the plan. 
    • More specifically, for one month, spend 4 hours per week working on your plan. 
    • These 4 four-hour work sessions should be held in a relaxing place without distractions (including no phone and no computer). 
  • Step 2 – Create a template for your life plan by drawing a table like the one below.  Start filling in the boxes with things that you want to accomplish.  (Hint: don’t try to fill in all the boxes, just a few really important ones each year.)

It should look something like this:

Year 2017 2018 2019 2020 2025 2030 ~2062
Age 35 36 37 38 43 48 ~ 80
Learn Something New
  • Step 3 – Identify three areas you’re passionate about in life or business.  Define how you see yourself pursuing your passion and determine what skills or relationships you can leverage to get yourself there.

Along the way, I didn’t follow Paul’s advice perfectly.  (Maybe it’s the entrepreneur in me, I’m always looking for ways to do things a little bit differently, more uniquely…)  In reality, it took me over three months to get my 16 hours of life planning done.  When I sent Paul a note to confirm our second breakfast (a month after our first meeting), he asked me to email him my life plan.  I wrote him back that I didn’t have it completed yet.  He immediately wrote back and cancelled our breakfast and told me to just let him know when I was ready but there was no reason to meet before I finished the assignment. 

So, I hunkered down and kept working on my plan.  I progressed by spending time at Starbucks on the weekends (more like 2 hour chunks of time than 4 hours) and I often used my computer to type notes, do research for my life plan online, or check social media…  I personally found it relaxing to have my phone and computer with me for support.  It’s up to you of course.  If I was being pure with Paul’s steps above, I would have spent four hours in a study carol at the library with just a blank legal pad and a pen, but alas, I am only a mere man and sometimes the promise of a grande cinnamon dolce latte was necessary incentive to get me back to the assignment.

(If you are interested in a business coach, I highly recommend checking out Paul’s website but please understand that he only takes on a limited number of clients and almost always has a full roster.)    


Given the dramatic effect that life planning has had for me, I then got together with my wife Katherine and we wrote our first family life plan together.  We vowed to update our plan at least 2x per year.  Katherine and I have been religious about this commitment (each year we plan two trips together and make time to work on our life plan).

We also use our family life plan each year to update our “Slain Family Quest Board” which is a 3’x4’ white board in our home office that has very specific goals we want to accomplish this year. 

Finally, as I conclude this article, I’m proud and excited that Katherine is sitting next to me on the flight (we’re coming home from Vegas where we went to update our plan) and she is starting a draft of her own personal and career life plan.  I can’t think of a more productive way for you to spend your next flight.

Send me an email at [email protected] with the subject line “Life Plan Template” and I’ll send you a power point template for your own life plan.

Jonathan Slain works with specialty contractors and their executive teams to get control of their lives and businesses. For a FREE 90 minute meeting to discuss your business, he can be reached at [email protected] or 216-870-4219.  And, if you want to send him a draft of your first life plan, he’ll keep it confidential and quickly get back to you with some candid feedback!