The Pre-Retiree's Financial Planning Checklist

Blackbridge Financial | Feb 7, 2025

You Spent Decades Saving. Now You Have to Decide How to Spend It.

Most of the financial decisions you've made up to this point have had a lot of room for error. Save more this year, less the next. Pick one fund over another. Miss a contribution, make it up later. A bad year in the market isn't a hiccup, it might even be an opportunity. The math is forgiving when you have decades left to work with it.

That changes the moment you stop working.

The decisions that matter now aren't the ones you spent your career getting good at. When to claim Social Security. What order to draw down your accounts. How much of your portfolio should still be growth-oriented versus built to provide income or protect your gains. How much tax you're creating for yourself by not thinking about the sequence of any of this.

None of these are one-time decisions you can course-correct casually. Claim Social Security wrong and you can't take it back. Draw down accounts in the wrong order and you'll pay more tax than you needed to, for years. Keep your portfolio allocation like it's still 2010 and a bad first year of retirement can do damage you don't have time to recover from.

This checklist walks through six areas where pre-retirees typically have gaps - not because they weren't paying attention, but because nobody laid out the questions in one place. Go through it, see where you land, and use the linked articles to dive into whichever section matters most for you right now.

#1: Retirement Income Readiness

Most people can tell you how much they've saved. Fewer can tell you what that number actually needs to produce.

Ask yourself:

Do I know how much monthly income my savings need to (and can) generate, not just the lump sum?
Have I separated my needs (housing, food, healthcare) from my wants (travel, gifting, hobbies) in a retirement budget, or am I still working off a rough guess?
Do I know what percentage of my employment years' income I'll actually need to replace - and is it actually 80%, or is that just the number I've heard everyone repeat?
Have I accounted for the fact that retirement spending isn't flat? Most retirees spend more in the early "go-go" years and less later. Plans built on a flat number might be wrong in both directions.

The honest answer for most pre-retirees is that they have a spending number but not an income number. That's a meaningful gap, because the savings number tells you what you have. The income number tells you whether it's enough.

There are rules of thumb out there - the 4% rule, the "25 times your expenses" rule, and many others - and they're useful as a starting point, not a plan. Your actual safe withdrawal rate depends on your time horizon, your other income sources, market conditions at the start of your retirement, and how flexible you can be if things don't go as expected. Rules of thumb don't know any of that about you.

#2: Social Security and Claiming Strategy

This is probably the single question you've thought about the most and gotten the least clear answer on, because the honest answer is "it depends," and most sources online don't want to say that. It doesn't help that everyone has a different opinion on the best way to take your benefit.

Ask yourself:

Do I know my full retirement age, and what claiming early versus delaying actually costs or gains me in dollar terms?
If I'm married, have my spouse and I coordinated our claiming strategy - or are we each treating it as a separate decision?
If I'm divorced, how should I be considering my ex's benefit in my decisions?
Am I thinking about Social Security as part of my tax picture, not just my income picture? Up to 85% of your benefit can be taxable depending on your other income.
If I'm still working while claiming early, do I understand how the earnings test could temporarily reduce my benefit?

Claiming strategy is one of the few areas in retirement planning where the "right" answer is genuinely different person to person. Someone in poor health with no other income sources might reasonably claim early. Someone with a large tax-deferred balance and a spouse who claimed on a much lower earnings record might benefit significantly from delaying. There's no single answer that applies broadly, which is exactly why it's worth running your specific numbers instead of following a rule you read somewhere.

For more on this, see Can You Work While Collecting Social Security Before Full Retirement Age?

#3: Tax Planning Before You Retire

Here's the thing about tax planning versus tax filing: filing is what your CPA does every April, looking backward at a year that's already happened. Planning is what determines what that filing looks like, and it has to happen before the year is over, sometimes years before.

Ask yourself:

Do i know what tax bracket I'll actually be in the year I retire, and is it higher or lower than I expect?
Have I considered Roth conversions during any lower-income years before Social Security and RMDs begin? That window — often between retirement and age 73 — is frequently the lowest-tax stretch of someone's entire retirement.
Is my savings spread across taxable, tax-deferred, and Roth accounts, or is it concentrated almost entirely in one bucket? Concentration limits your flexibility later — you want options about which account to pull from and when.
Do I understand how required minimum distributions, starting at age 73, will affect my tax picture even in years I don't need the income?

This is the section where most of the "coordination" value in a real financial plan shows up. The tax decisions you make in the years right before and right after retirement can meaningfully change your total lifetime tax bill — and they're also some of the easiest to get wrong by accident, simply by not looking at the full picture.

#4: Investment Strategy for the Transition

Accumulation and distribution are two different disciplines. A portfolio built to grow for 30 years is not automatically the right portfolio to draw income from for the next 30.

Ask yourself:

Has my portfolio actually changed to reflect that I'm now 5–10 years from needing to draw on it — or is it still allocated the way it was when I was 40?
Do I understand sequence-of-returns risk — why a market downturn in the first few years of retirement does far more damage than the same downturn 15 years in?
Do I have a plan for which accounts I'll draw from first, and in what order, once income starts — or will I figure that out as I go?
Have I stress-tested the plan against a down market hitting in year one of retirement, not just against average historical returns?

The math here is counterintuitive to a lot of people: two retirees can have the identical average rate of return over 20 years and end up with wildly different outcomes, purely based on when the bad years happened. That's not something a generic "get more conservative as you age" rule accounts for; it requires actually looking at the order of withdrawals and the shape of the portfolio going into retirement, not just the overall risk level.

#5: Protection and Insurance Check

Your insurance needs haven't disappeared as you approach retirement; they've shifted. The mistake most people make is either ignoring this section entirely or assuming the coverage they bought at 35 is still the right coverage now.

Ask yourself:

Is my life insurance still sized for an income-replacement need from my working years, or has that need changed now that the mortgage is paid down and the kids are grown?
Do I have a plan for long-term care — self-insure, LTC insurance, or a hybrid policy — or is this something I've thought about but never actually addressed?
If I'm retiring before 65, do I have a bridge plan for health coverage until Medicare starts?
If my spouse's coverage currently depends on my employer plan, have I accounted for that gap in the transition?

None of these are urgent in the way a market downturn feels urgent, which is exactly why they tend to get pushed off indefinitely. But a long-term care event with no plan in place, or a multi-year health insurance gap before Medicare, can do more damage to a retirement plan than a bad market year ever could.

#6: Estate and Legacy Readiness

Estate planning has a branding problem. Most people associate it with either the very wealthy or the very old. In practice, it's a pre-retirement task, and it's one of the most commonly delayed.

Ask yourself:

Do I have a will and/or trust that reflects my current family and financial situation — not one drafted 15 years ago, before circumstances changed?
Have I reviewed the beneficiary designations on my retirement accounts and life insurance recently? These override what your will says, and outdated ones are one of the most common estate planning mistakes.
Do I have any structure around charitable giving, or is it something I've thought about but never actually set up?
Does my family know where the relevant documents are, and who to call if something happens to me?

This section tends to feel less urgent than the others, right up until it isn't. The good news is that most of it is a one-time setup with periodic review — not an ongoing burden — which makes it one of the highest-leverage areas to get in order early.

For more on this, see In Case of Emergency: Your Guide to Personal and Financial Preparedness

#7: The Coordination Problem

Here's what none of the six sections above tell you on their own: they don't operate independently.

Your Social Security claiming decision affects your tax picture. Your tax picture affects which accounts you should draw from first. Your withdrawal order affects how your portfolio needs to be allocated. Your portfolio allocation affects how much risk you're carrying into the exact years sequence-of-returns risk matters most.

Change one input and the rest of the plan shifts with it — which is exactly the problem with siloed advice. A CPA who only sees your tax return doesn't see your investment allocation. An advisor who only manages your portfolio doesn't necessarily know your Social Security claiming strategy. Nobody, in a lot of cases, is looking at all of it together.

A real pre-retirement review should look at all six of these areas at once, and specifically at how they interact — not as six separate checkboxes, but as one connected decision. That's the difference between a plan that happens to work and one that was actually built to.

Where To Go From Here

If you went through this and most of it felt familiar, that's a good sign — it means the pieces are there, they just may not be connected yet. If a few sections raised questions you don't have clear answers to, that's useful information too.

Either way, this is exactly the kind of conversation worth having before the decisions above get made instead of planned. If you'd like to talk through where you stand, Get Started and we'll look at the full picture together.

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. Rebalancing a portfolio may cause investors to incur tax liabilities and/or transaction costs and does not assure a profit or protect against a loss. Traditional IRA account owners have considerations to make before performing a Roth IRA conversion. These primarily include income tax consequences on the converted amount in the year of conversion, withdrawal limitations from a Roth IRA, and income limitations for future contributions to a Roth IRA. In addition, if you are required to take a required minimum distribution (RMD) in the year your convert, you must do so before converting to a Roth IRA.

The Pre-Retiree's Financial Planning Checklist