Forrest Gump’s Mama said it best; “Life is like a box of chocolates, you never know what you’re going to get.” Uncertainty is reality in every aspect of life, from selecting chocolates to money matters.

The best time to reframe and rewire your financial decision-making process is before you fully retire. Planning for retirement is more than just getting your financial life in order; it’s dealing with the psychological and physical aspects as well.

Steven Spurrier, (the wine guy, not the football coach), described what he termed his “Rule of Life”; You need someone to love; something to do; and something to look forward to. That seems like a good start toward leading a long, purposeful life after you retire.


Many folks believe that retirement magically will eliminate uncertainty and lessen the need for ongoing course corrections. This couldn’t be further from the truth. In our experience, the gap between expectations and reality in retirement is wider than in any other stage of life.

Of course, the most obvious uncertainty is how long retirement will last, or more directly, how long you will live. Some people will live for 30 years or more past retirement. This was unheard of even a generation ago. Preparing for that possibility requires substantial reframing and rewiring.

One of the best ways to accomplish this is to have a realistic philosophy toward uncertainty both inside and outside of your financial life. From a practical level, this means recognizing the presence of uncertainty by establishing margins of error for your goals. Life won’t happen precisely as you have planned–count on that.


The overarching priority in retirement is to maintain your pre-retirement lifestyle; this requires that you offset living cost increases with your financial resources. In other words, you have to grow your investments or your overall financial condition will decline after inflation is taken into account.

The need to achieve above inflation investment returns highlights one of the major disconnects between retirement expectations and reality. Some retirees believe that the need to invest in risky assets ends once they cross the retirement threshold. This is false. Most retirees will have to accept some measure of investment risk for the balance of their lives to stay current with the cost of living increases.

The most fundamental purpose of personal financial planning is to manage and deal with change. Within the decade prior to retirement and the first decade post retirement, nearly everything changes. Be prepared for these changes and most of all, adopt an attitude centered around flexibility. Start there. Ready for a real conversation?