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Questions To Think About When Getting Ready to Retire

Cash Flow and Retirement

Getting ready to retire

Retirement represents a monumental shift in life. As with other major changes, the better prepared you are, the greater likelihood you will achieve your goals. Whether retirement is five, ten, or even twenty years down the road, make sure to consider the following.

Life style

  • When will you retire, and where will you live? 
  • Will you travel extensively?
  • What hobbies will you pursue?
  • Will you continue to work on a limited basis?
  • How long can you reasonably expect to live (based on parents’ longevity, current health, etc.)? 

Financial readiness

  • Have you (or will you have) saved enough to retire when you are ready?
  • How have you minimized your tax liability?
  • What are your current financial responsibilities, and will they continue into retirement?


  • What are your estimated monthly expenses, and how will they change in different stages of retirement (e.g., active vs. less active years)?
  • Will others (parents, children, grandchildren, charities) rely upon your financial support during your retirement years?
  • Do you have adequate health care coverage?
  • How will your long-term health care needs be addressed, and should you consider additional insurance?


  • How much risk is in your portfolio, and how will that change pre and post-retirement? 
  • Will investments have to throw off income in order to maintain your desired lifestyle?
  • How should you take your pension?
  • When do you have to take money out of your IRA?
  • Should you convert your traditional pre-tax qualified accounts into a tax-free Roth IRA?
  • What should you do with the money in your company savings plan?
  • Do you have a preferred mix of stocks and/or bonds? 
  • Do you have a targeted performance rate?

Income Strategies

  • What is your normal retirement age (NRA) for Social Security purposes?
  • What is the estimate of your Social Security payments at NRA?
  • Do you have a plan as to which assets to draw down first to ensure that you are maximizing the tax benefits of the overall assets? 

While the future holds many unknowns, one thing you can count on is this– Lenox Advisors is here to help. We have the background, experience, and extensive network to guide you and your loved ones past potential pitfalls while identifying unique opportunities. No matter what strategies we recommend, they will be part of a larger financial plan — one that you lead based on your goals and your situation.