Ten Questions Retirees Must Be Able to Answer

These are the ten questions.  Below that are questions expanded and, in some cases, answered as well.
The specific and complete answers depend on your particular situation, goals, plans, income and financial assets.  I didn't make these up out of thin air; these are the questions that are actually on the minds of retirees and the worries they reflect.  My mission with a financial plan is to reduce worry and increase confidence.

1. How much can I safely withdraw? 
   Probably more than you think and more than your current brokerage is telling you you can.  After all, if your balance is shrinking due to spending, their income is shrinking too.  There are a lot of moving parts to answering this question and lots of opinions in my profession about each of those parts:  inflation, taxes, regulatory risk, volatility, market corrections, health care expenses.  Because this is a relatively complicated question, I focus on a cash flow plan as the foundation of every retiree's plan.
2. How long will my money last?
   Unless one of your goals is to leave an inheritance, what if you knew that your money would last as long as you will?  We can't know for sure but we can manage longevity risk.
3. Can I guarantee I won't run out of money?
   Yes. You can.
4. Can I protect my assets from losses?
   Yes.  You can.
5. How much tax will I pay?
   We can only guess based on current and projected tax policy.  Will required minimum distributions (RMD) age be pushed out to age 75?  Or even eliminated?  The key is, this is an important question to ask!  I have yet to meet with a new client who even has an estimate of their lifetime cumulative tax bill.  Believe me, seeing that number really motivates people to do tax planning.  Because you can not only significantly reduce your lifetime tax bill, you can reduce or eliminate the risk of future higher taxes.
6. How much could I lose in the next crash?
   Everything we recommend to clients in my firm must be based on evidence, on data.  In some cases the best, and only, data we have is historical with just a hint of future expectations.  It is essential to know not only the maximum drawdown risk in your portfolio but also the annual volatility as well.  Either one can decimate your cash flow plan.
7. Can I reduce my fees?
   Maybe.  Maybe not.  The question implies that you already know the fees you're paying.  Very few do because total fees include more than just the AUM (assets under "management" [quotes mine]) fees on your statement.  The key is, are you getting commensurate benefits for those fees?
8. Is it OK to start spending?
   What is the ideal spend down order of my assets?  Should I spend taxable money first or taxed money first?  When?  Why?  The only rational way to answer this question is to test alternatives to see which has the best results.  For your situation.
9. What if one of us dies?
   It comes as a shock for the surviving spouse to realize they don't get to keep both Social Security benefits when the other spouse dies. Will there be sufficient savings to make up the difference?  Will the survivor's monthly income needs stay the same?
10. What's the best way to leave assets to my beneficiaries.
    An indirect answer to this is the worst way to leave assets to beneficiaries:  In a pre-tax retirement account.  Unless you are the surviving spouse, the beneficiary will probably have to liquidate the account within 10 years.  This regimen makes it difficult to do any tax planning, especially if your adult child is successful in their own right.  One of the best ways to leave money to your children is with a Roth IRA.  Real estate and brokerage accounts have advantages also with the step-up in basis but it's becoming clear that Congress intends to limit or eliminate that tax dodge.

So, if you don't know the answers to any of these questions or even are unable to answer one of them, think about how you would feel if you could.

Your Constructive Comments are Welcome!