November

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January: Rethink Social Security. New rules that went into effect in December restrict some strategies for collecting Social Security benefits. Paying back earlier benefits to reset your monthly check at a higher amount and suspending benefits retroactively both have been curtailed, so if this was part of your retirement strategy, check out the public comments at regulations.gov. Search for document SSA-2009-0073. There's still a chance for more revisions after the comment period. February: Consider COBRA. If you're too young for Medicare, you have 60 days after your private employer insurance runs out to elect to continue coverage, typically at your own expense, through COBRA coverage. March: Plan for taxes. Do you expect to start making estimated tax payments this year? If you dread the task, consider asking your IRA holder to withhold taxes on your withdrawals. Now that you're living on investment income and, possibly, Social Security benefits, don't forget that Social Security benefits get taxed at higher income levels. Check out ssa.gov/planners/taxes.htm. April: Create a paycheck. You may have run some calculations showing you have enough assets to retire, but have you put an actual plan together for how to tap the nest egg? Most haven't. In a recent survey by The Principal of near-retirees, just 14 percent had put together an income plan, said Drew Denning, vice president, retiree services division, at The Principal. Figure out how much you'll withdraw each month, in what order you'll tap your taxable and tax-deferred accounts and how much monthly income you want coming from sources such as Social Security and annuities. May: Assess your spending. Now that you're several months into retirement, revise that retirement budget you made before quitting. June: Sign up for Medicare. If you're collecting Social Security, you'll be automatically signed up for Medicare Parts A and B, effective the month you turn 65. If you aren't getting Social Security, you can apply for both at the same time. If you only want Medicare, be sure to sign up three months before you turn 65 at a Social Security office. See medicare.gov/basics/socialsecurity.asp. July: Perhaps launch a second career. Now six months into retirement, are you discovering what you really needed was just an extended vacation? Check out retiredbrains.com. August: Cover your long-term care exposure. The ages between 50 and 65 are considered by financial experts as the "sweet spot" for making these decisions, before the insurance gets too costly or is unavailable. September: Organize financial records. Use this month to organize your estate and financial files so a spouse or significant other could make sense of them. October: Unconvert? This month is the deadline to unconvert a Roth IRA conversion. November: Update your will. Revisit your estate plan. Often, people do this when their kids are young and then forget about it.