Strategic Retirement Planning

Strategic Retirement Planning is the term I used to frame my podcast (RJ 002) with Rodney Brooks, retirement columnist for the Washington Post. I define a Strategic Retirement Plan as an overarching virtual plan – a collection of plans -written and unwritten. Many unwritten plans answer a question such as when do you plan to start taking Social Security. Even though a plan may be unwritten, it still requires research, analysis and sometimes expert advice. The process of developing a Strategic Retirement Plan helps you to proactively address the most critical needs and issues facing retirees.

A Strategic Retirement Plan has two parts – financial-related and non-financial.


  • Retirement Plan – this is a financial plan that covers the expected duration of your retirement. It uses many financial variables such as income, spending, investments, Social Security, and taxes. A good Retirement Plan will generate a cash flow analysis for each year of retirement and show your beginning and ending net worth. It is a crucial, must have component of your overall Strategic Retirement Plan. A retirement calculator of some kind is usually used to create this plan.
  • Investment Strategy – this includes asset allocation, investment mix, rebalancing frequency and timing & tax optimization across taxable and non-taxable accounts.
  • Estate Plan – this may include all or some of the following: a will; a living will; a pour over will; trust; living trust; health care directive; successors; and power of attorney.
  • Annual Budget – a plan to manage and control spending & savings over a 12 month period, typically a calendar year.
  • Plan for retirement income generation

When to start collecting Social Security?

Will you work in retirement on some basis?

How will you generate income from your investments?

Do annuities make sense for you?

When should you start withdrawals from a deferred savings account such as a 401K?

Do you have a 6 month emergency fund?

  • Do you want to purchase Long Term Health Insurance?


  • Do you have an understanding of what to expect in retirement? For example, have you learned about the 6 Stages of Retirement?
  • How do you plan to spend your free time in retirement?
  • Do you plan to stay in your home or do you intend to relocate?
  • Have you looked into the requirements associated with aging in place vs. a retirement community?
  • Which Medicare options should you select?

You should have most of these plans in place no later than age 50. However, some are not needed until later.

  • Plan for Income Generation – minimum 1 year before retirement
  • Long Term Health Insurance question – no sooner than age 60
  • Medicare Options – age 64 ½
  • The 6 Stages of Retirement – minimum one year prior to retirement
  • How to spend your free time – minimum one year prior to retirement
  • Relocate – this plan can be made and changed as desired; however, an assumption may be needed as input into your Retirement Plan
  • Aging in Place vs. Retirement Community – around age 70

The development of each of these plans is complex, requires research and often professional assistance. The reward of planning your retirement strategically is that you give yourself more control to manage your retirement the way you want it to go and not have your retirement outcome be left to chance.

If you’re interested in seeing how you’re doing, you can do so by completing my Strategic Retirement Planning Scorecard which is available for download in Word or pdf formats.

As always I invite your comments on this subject is the comments section below.

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