Where The Why In Financial Planning Comes From

Saving and investing are natural, but only to a point. Here in the real world, people require motivation to carry out an extended plan. One like retirement income planning could easily cover 50 years, from now to the second death of a couple.

How do you stay motivated to complete it?

The apparent answer, discipline, is not correct. Discipline is hard work and works only for short periods. No one can use discipline alone as motivation over 50 years.

The answer comes from a chess grandmaster, José Raúl Capablanca. He was the World Champion from 1921 to 1927

“To succeed, you must study the endgame before everything else.” 

Study the endgame

“Why” is the motivation for doing a complex and often challenging task like financial planning.

In chess, the endgame is the part of the game that people can actually think through with fewer errors. When there are only a few pieces on the board, the vast number of options apparent in the middle game disappear. You can see how the goal works out.

Retirement is not the same for everyone, but there is a remarkable similarity. Like in chess, the variables to consider in retirement are fewer than those in midlife. Once you know what is likely and what resources and methods will work to sustain your chosen lifestyle, you anticipate and plan for it.

The opening is highly structured.

The pieces are confined, and the options are minimal. There are just a few strategic ideas, and the concept of time is important. There is a time-limiting clock, and wasting time here is costly later. Efficiency matters. You will have an advantage if you can reach a sound middle game position in one or two fewer moves. In chess, the first eight or ten moves are pretty much by formula. The openings have been studied for centuries, and the idea is to avoid ones known to be flawed.

All mistakes here must be remedied later. That takes resources and time, just like in life.

Take simple, known actions. Avoid mistakes. Prepare for the complexity to come. Common sense.

The middle game is the hardest. 

If you have a sound beginning, you can develop in creative ways in the midgame. That development has two parts. Creating opportunities and defending your opponent’s activity. The biggest mistake is to assume your opponent, or in financial planning, the world will behave in a way to optimize what you do. Neither does. Chess opponents present situations you had not considered, and the world does not remain unchanged in life.

Constant vigilance and thought to find a better approach given the circumstances is required. That’s difficult and many drift.

Having a sense of purpose and knowing what you seek in an end game plan is motivating. It simplifies life because it also creates many chances to say No!. You know why not and that keeps you on a track that works. When you understand how the end game will work and how it benefits you, you look for opportunities to reach one of the board positions that work for you. That’s the “Why.”

Knowing what you want and being able to identify techniques and tools that match your flow improve your play in the middle game.

Knowing why you must work at it and how you will succeed by doing so becomes easier.

The bits to take away

If you don’t know where you are going, and in some detail, there will appear to be more paths than there really are.

Confusion or absence of purpose is deadly in extended plans.

The opening is about establishing good habits like avoiding debt and saving.

The middle game is about developing new skills so you can adapt to change. The end game is where you have an unassailable position designed to suit your life goals.

Financial planning over extended periods turns out to just be organized common sense.

Don’t make it more complicated than it needs to be. Complexity is never motivating.


I build strategic, fact-based estate and income plans. The plans identify alternate ways to achieve spending and estate distribution goals. In the past, I have been a planner with a large insurance, employee benefits, and investment agency, a partner in a large international public accounting firm, CEO of a software start-up, a partner in an energy management system importer, and briefly in the restaurant business. I have appeared on more than 100 television shows on financial planning. I have presented to organizations as varied as the Canadian Bar Association, The Ontario Institute of Chartered Accountants, The Ontario Ministry of Agriculture and Food, and Banks – from CIBC to the Business Development Bank.

Be in touch at 705-927-4770 or by email at don.shaughnessy@gmail.com.

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