The Retiree's Financial Planning Checklist

The discipline that got you here is the opposite of the discipline retirement requires.

For thirty-plus years, the rule was simple: save more, spend less, don't touch it. You got good at that. It's why you're retired.

But that instinct doesn't turn off just because the paycheck did. And the skill that built your portfolio isn't the skill that manages it now. Retirement asks you to do something you've spent your whole career avoiding — draw the money down, deliberately, without running out.

Most retirees we talk to have enough. What they don't have is confidence that they do — because nobody ever taught them how to turn a balance into a paycheck. That's not a knock on you. It's just not a skill anyone builds along the way.

This checklist covers the six areas that matter most once you're actually living in retirement, not just planning for it. Think of it less as a form to fill out once and more as a tune-up you come back to — because what was right at 65 may not be right at 72.

#1: Retirement Income Management

The biggest shift in retirement isn't emotional, it's mechanical: you go from adding money to accounts to pulling it out of them. And how you pull it out matters almost as much as how much.

Ask yourself:

• Do you have a specific, intentional withdrawal order across your taxable, tax-deferred, and tax-free accounts - or are you pulling from whatever account is easiest to get to?
• Do you know your current withdrawal rate, and whether it holds up over 20 or 30 years of retirement?
• Do you have a plan for down markets so you're not forced to sell depreciated assets for income in a bad year?
• Is your actual spending tracking what you budgeted for, or has it quietly drifted?

The order you draw from accounts changes your tax bill every single year. Pulling from a traditional IRA before a taxable brokerage account, for example, can push you into a higher bracket than necessary — while the reverse can leave tax-deferred growth on the table longer than it should be. There's no universal right answer here, but there is a wrong one: no plan at all, just habit.

#2: Social Security & Claiming Review

If you've already claimed, this section is a check-up: did the decision hold up, and is there anything left on the table. If you haven't claimed yet, this is still very much a live decision — and one of the more expensive ones to get wrong.

Ask yourself:

• If you haven't claimed, do you know what waiting another year actually does to your monthly benefit?
• If you're married, have you coordinated claiming between spouses — including what happens to the survivor benefit when one of you passes?
• Do you know how your benefit is taxed, and whether other income is pushing more of it into taxable territory?
• Is Social Security part of a coordinated income plan, or a separate check you don't think much about?

The claiming decision often gets treated like a single, one-time event. For a lot of couples, it's actually two decisions that need to work together — because the survivor benefit that outlasts the first spouse's passing is often the largest income source the surviving spouse has left. That's not something to figure out after the fact.

#3: Tax Planning in Retirement

Filing a tax return once a year is not the same as managing your tax bracket. In retirement, the second one is where the real money is.

Ask yourself:

• Do you know which of your withdrawals are taxable, tax-deferred, or tax-free — and are you sequencing them to manage your bracket?
• Are you tracking when your required minimum distributions start, and what they'll do to your income?
• Have you looked at Roth conversions in the lower-income years before RMDs begin?
• If you give to charity and you're subject to RMDs, are you using qualified charitable distributions?

RMDs are the clearest example of why this matters. The IRS doesn't ask whether you need the money — once you hit the age, the distribution is required, and it's taxed as ordinary income whether you spend it or reinvest it. Some retirees convert traditional balances to Roth in the years before RMDs kick in, deliberately paying tax now at a lower rate to avoid a bigger, involuntary tax hit later. It's not the right move for everyone. It's a move almost nobody considers without someone pointing it out.

#4: Investment Strategy for This Stage

Your portfolio's job has changed. It's no longer "grow as much as possible" — it's "produce income reliably, for as long as you need it to."

Ask yourself:

• Has your allocation actually changed since you retired, or is it still positioned the way it was when you were still working?
• Do you know how much of a market downturn your income plan can absorb before it affects your actual spending?
• Do you hold enough in stable, accessible assets to avoid being forced to sell growth investments at the wrong time?
• Have you revisited your risk tolerance now that you're spending from the portfolio instead of adding to it?

This is where sequence-of-returns risk shows up — the danger isn't a bad year in the market by itself, it's a bad year early in retirement, while you're also withdrawing. Two retirees can have the identical average return over 20 years and end up in completely different places, purely based on when the down years happened to fall. It's one of the more counterintuitive risks in retirement planning, and one of the most manageable, if you're looking for it.

#5: Protection and Insurance Check

Coverage you bought at 45 was built for a different set of risks than the ones you're carrying now. This section is about confirming what still makes sense — and being honest about the one risk retirees consistently underestimate.

Ask yourself:

• Do you still need the life insurance you have, or was it there for a purpose — income replacement, a mortgage — that no longer applies?
• Have you addressed long-term care risk, through insurance, self-funding, or a deliberate plan — or is it something you're hoping doesn't come up?
• If you're married, have you talked through what happens financially if one spouse needs care and the other doesn't?
• Is your beneficiary information current on every policy, not just named years ago but actually updated?

Long-term care is the one that catches people off guard, not because they haven't heard of it, but because they've heard of it in the abstract, as something that happens to "other people." At this stage, it stops being theoretical. The cost of care, whether it's covered, and who it falls on financially and personally are questions worth answering before you need the answer.

#6: Estate and Legacy Readiness

This is where this checklist should carry more weight than a lot of the planning you did earlier in life. Legacy questions stop being "someday" and start being current.

Ask yourself:

• Do you have a will and/or trust, and has it actually been reviewed in the last several years — not just signed once and filed away?
• Do your account beneficiary designations match your current intentions? These override your will, even when the will says something different.
• If giving to family or charity matters to you, have you considered giving while you're living, rather than only through your estate?
• Does your family actually know where your documents are and who to call — or would they be starting from zero?

That last question trips up more families than any of the technical ones. A will that's legally sound but sitting in a drawer nobody knows about creates almost as much friction as not having one. The paperwork matters, but so does the plan for someone actually finding it.

The Coordination Problem

Here's what all six of these sections have in common: none of them sit in isolation.

Your withdrawal order affects your tax bracket. Your tax bracket determines whether a Roth conversion makes sense this year. Your Social Security timing changes both of those. Your estate plan depends on account titling decisions that were made, or not made, back in Section 1.

This is usually where things fall apart — not because any single piece was handled badly, but because nobody was looking at how the pieces interact. A CPA sees the return. An insurance agent sees the policy. An estate attorney sees the documents. Nobody's necessarily looking at how a withdrawal decision made in March changes what makes sense for a Roth conversion in November, or how this year's tax bracket should shape next year's giving.

An annual review, done right, isn't a repeat of this checklist. It's a check on whether last year's plan still fits this year's numbers — because tax law changes, markets move, and your own situation shifts in ways that are easy to miss year to year when you're not looking for them.

If you've been managing these pieces separately, or you're not entirely sure how they fit together, that's exactly the conversation worth having. Get the conversation started here.

This content is for educational purposes only and does not constitute personalized financial, tax, or legal advice. Please consult a qualified professional regarding your specific situation.