The Key Retirement Planning Questions

Amar Pandit , CFA , CFP

The moment we think about Retirement Planning, the first thing that comes to our mind is Money (Means). However, Retirement is not just about Money but it is also about the Purpose (Meaning). Our HappyRich Sketch perfectly encapsulates this philosophy.

Thus, there are 2 sets of questions that are critical for a successful modern retirement (We call it the HappyRich Retirement). The question list is by no means exhaustive, but these are great starting points in your retirement planning journey. 


  1. How much is Enough?
  2. When can I Retire?
  3. Am I on Track?
  4. What do I need to do to be on Track?
  5. If I stop now, how many years do I have before I have to get back to work?


  1. Why do I really want to retire?
  2. How will I Invest my Life? What will a typical Retirement Day look like?
  3. Am I retiring from something or Am I retiring to something?
  4. What do I love doing that I can do for the rest of my life?
  5. Are there any regrets that I intend to address during this portion of my life?

Do take some time to reflect on these questions.

Mitch Anthony, Author of “The New Retirementality” writes a powerful line that sums up the above, “The greatest decision a retiree makes is not how they invest their assets but how they invest their life.