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Planning with the End in Mind: A Planning Exercise

As a planning firm, Blackwood Family Enterprise Services strives to deliver innovative and meaningful results for our clients. That means we are always searching for and working to develop tools that improve the planning process and make it more authentic and user friendly. The “Planning with the End in Mind” Planning Exercise came out of a personal planning experience with my husband Patrick.

A couple of years ago, Pat and I were driving to the lake, having a conversation around the future of our recreational property. This inevitably brought in questions around retirement, what to do with our business, and the future. In other words, we found ourselves in an impromptu planning conversation. To prepare for some brainstorming, and because I have to write to think, I had divided a page in my notebook into 10 year increments. Looking at those 4 lines on the page shocked me. My heart actually started racing. And I was intrigued by my alarm. “Why,” I asked myself, “am I so alarmed by the idea that our time is limited, by the fact that we are actually going to die sometime?” I wondered, “Is this why I feel a little stuck in visualizing how those 4 decades are going to go?” If so, maybe we were going about this discussion all wrong. We should be starting at the end, the scariest part, and working our way back.

I asked Pat, “When do you think we are going to die?” He thought that was a little morbid and rephrased the question, “How long can we reasonably hope to live and be looking after ourselves?” After some discussion around our own health, our family histories and so on, we came up with an age. I wrote that number on the top of the page. “Ok,” I said, “Where are we? Where do you picture us living? At the cottage? In a house? What are we doing?” As we started working backwards, we realized 10 year increments were far too long; there seemed a big difference between who we would be at 80 and at 70. I divided my decades into 5 year increments and had the literal feeling of having created more time. All of a sudden the questions and the ideas were flowing.

We worked our way back to our present age with surprising speed and accord. Interestingly, the exercise of working backward from the distant future made it very clear what needed to happen 10-15 years from now. Previously, we had experienced frustration with the discussion because we could not agree on what that middle future looked like, I think, in part, because we did not want to give up on some of our youthful possibilities. Working backward narrowed our possibilities but in a good way. In fact, it turned our discussion away from what was possible to what we actually wanted. As we cycled back through the process several times, key milestones and “bucket list” items emerged, while others were revealed as no longer relevant or important.

Of course there are unknowns, and some wishes and hopes in our plan, but starting from the end helped us develop clarity around key destinations in the path. Now, every few months when we check in with our vision, I feel not alarmed but energized. I want to hit those milestones we have identified, and work on checking things off the bucket list. I am more confident in the unknown future: after all, I can’t adapt a goal to fit changing circumstances, if I do not have the goal to begin with.

At Blackwood Family Enterprise Services, we work to make planning meaningful for our clients. The “Planning with the End in Mind” Planning Process that Blackwood has developed, is an excellent planning exercise for anyone struggling to visualize his or her life but especially valuable for people in the middle of their lives who want to live the last half with vision and clarity.

Step 1: A discussion around the end game. Until when do you think you will live? Have a good, honest discussion around health, lifestyle, family history etc. Be realistic. If you are doing the exercise with a partner, ideally you want consensus around this.

Step 2: In the year of your death, where would you ideally be living? In a house? Condo? The same city as you are today or somewhere completely different? What other properties do you see owning at this time? In other words, visualize yourself in your life at this age. What are you doing? How are you spending your time? What people, places, things, and activities do you hope are in your life?

Step 3: Begin going backwards in 5 year increments. E.g. If death is 85, go back to age 80, 75, 70, 65, 60, 55, etc.

Work through discussion questions which will help you to see where you are living, your lifestyle, and how you spend your time. Really visualize yourself in your life. Think, “I am 75. Where am I? What am I doing?” Visualize.

This is essentially a brainstorming process. There is no right or wrong. The first time through, do not get bogged down by confusion or conflicting ideas and desires. Write them down and continue on. The process of cycling through the years a few times will hopefully provide clarity and consensus. Or it may identify areas where further discussion is required for consensus or areas that will require compromise. Remember, this exercise is not a “one and done” but something that you will want to keep coming back to over the years.

Milestones in each 5 year period will emerge. You will be able to identify key plans/goals you want to accomplish by a certain age. Then, you can start to think of the action steps you need to take in order to achieve those goals. The closer the milestone, the more detailed your actions steps probably need to be.

E.g. If you do not want to be working in your business at all by age 65, then you need to think about when to develop a succession plan.

E.g. If by age 60, you want to have a family recreational property complete, then you need to be designing at 55, arranging for a builder at 57, and so on.

Discussion Questions For the “Planning with the End in Mind” Planning Exercise:

(This is not an exhaustive list. Add questions that are relevant to your situation. The more questions you ask, the more clarity you have.)

  • Where are you living? What city (cities)? Home vs condo vs apartment…boat?

  • What does your home/condo/cottage look like?

  • Do you (still) own recreational property (properties)? How are you using them?

  • What is your lifestyle like?

  • What are you doing on a daily/weekly/monthly/yearly basis?

  • Are you travelling? What are key places to see?

  • What is your activity level? Fitness choices?

  • What are you doing for fun?

  • With whom are you socializing?

  • How do your children/grandchildren/family fit into your life?

  • Are you active in business/work? How active?

  • When are you selling your business or part of it? How is that happening?

  • What are your community/philanthropic activities?

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