Your Pre-Retirement Checklist After a Successful Career: The Financial Moves, the Tax Windows, and the One Blindside That Catches Almost Everyone Off Guard

You've spent the past 30 years becoming really, really good at something.

You built a business, performed extensive surgeries, led teams, sat on advisory boards, navigated recessions, and have generally proven yourself to be highly successful (even if your spouse complains you forget to set the trash out on Tuesdays). You are, by any objective measure, a high-functioning adult who figures things out.

Yet, there's roughly a 70% chance that right now, 24 months from retirement, you are winging it.

Not maliciously or lazily. You're probably meaning to get serious about this. You've got it on your mental list somewhere between "get that shoulder looked at" and "finding a contractor to quote the bathroom remodel.”

But the tax planning is fuzzy, the income strategy doesn't exist yet, and your financial advisor is a perfectly nice person who has never once proactively called you asking to review your tax return or mentioned anything about a Roth conversion strategy.

Here's what I need you to understand. The 24 months before you retire are the single most financially consequential planning window of your life. Full stop.

More than when you started your company. More than when you hit your first million. More than any market cycle, any investment decision, any fee you'll ever optimize.

The moves you make (or don't make) in this window will echo for 30 years.

So stop winging it.

The Thing Nobody Tells You About the Finish Line 

Everyone talks about retirement like it's a destination. Like you're going to cross a line and arrive somewhere.

It’s actually more of a detonation.

On the day you retire, your income stops. Your identity shifts. Your schedule (you know, the thing that has organized every single day of your adult life) evaporates. The people who needed you, the problems that required you, the title that introduced you at every dinner party for two decades? Gone — or at least fundamentally changed.

And now your financial life, which was already complicated, gets dramatically more complicated because you have to manufacture income from the pile of assets you've accumulated. Oh, by the way, it needs to be done in a way that's tax-efficient, inflation-resistant, and designed to last longer than you think you're going to live.

This is not a passive process. It does not manage itself. And you need to understand that the playbook that got you here (earn a lot, save a lot, invest in a diversified portfolio, ride it out) is not the playbook for what comes next.

What’s next requires a completely different kind of thinking.

Let's start with taxes, because that's where the real money is.

Part One: Tax Planning — Where the Actual Wealth Is Made or Lost

1. Generate a Multi-Year Tax Projection (You Probably Don't Have One)

This is likely to sting a little.

If your current advisor or CPA has never handed you a document showing your projected tax liability, year by year, from now through your first decade of retirement, they are not doing retirement planning.

Instead, they're doing tax compliance. Which is necessary, but it is not the same, at all, and the difference is worth a significant amount of money.

A real multi-year projection maps out:

• Your income for each of the next 2-3 working years
• The year you retire (often your most powerful planning year in which income drops, brackets open up)
• The "income gap" years between retirement and Social Security
• RMDs beginning at age 73 or 75 and what they do to your tax rate
• How IRMAA surcharges will hit your Medicare premiums based on income from two years prior (a trap that catches a stunning number of smart people completely off guard)
• How Social Security becomes partially taxable depending on your other income
• Capital gains exposure across your taxable accounts

You cannot make intelligent decisions without this map. Anyone giving you retirement advice without it is incompetent.

Get the projection. If your current people won't build it, find people who will. 

2. Roth Conversions: The Opportunity That Has an Expiration Date

You retire at 63. You delay Social Security until 67 or 70 because you've done the math and you understand that 8% guaranteed annual growth is an extraordinary deal. For those 4-7 years, your taxable income drops dramatically. You are, for perhaps the first time in your adult life, in a low tax bracket.

The IRS is going to get their share of your traditional IRA / 401(k) eventually. The only question is whether they get it at 10%, 12%, 24% or higher. A Roth conversion strategy during those gap years lets you choose the rate. You pay taxes now, at the lower bracket, and every dollar inside that Roth from that point forward grows tax-free and comes out tax-free for the rest of your life, and eventually to your heirs.

We have personally executed Roth conversion strategies that produce six figures (nearly seven!) of lifetime tax savings.

Sadly, I've also sat across from people who are 75, looking at RMDs they can't avoid, in a bracket they're stuck in, wishing someone had explained this to them a decade earlier.

The window is real. It closes. Start modeling it now.

3. Your Unrealized Capital Gains Are a Ticking Clock

Go look at your taxable brokerage account right now. Not your 401(k). The regular one.

See those positions you've been holding for 15 years? The ones that have tripled or quadrupled? They’re wonderful. They’ve been a huge success.

They're also a tax liability that is quietly growing every year, and retirement (when you start selling assets to fund your life) is when that liability potentially comes due.

Most people's approach to this is basically: don't think about it and hope for the best.

Here is a better approach:

Sell and Pay 0% Capital Gains Tax – Did you know there’s a legal way to sell stocks (or any long-term asset) and pay zero capital gains tax? There is, but it takes a forward-thinking strategy. In 2026, a married couple filing jointly can pay 0% capital gains tax if their taxable income is below $98,900. In your first few years of retirement, even though you may need a significant amount to fund your lifestyle, there are ways of keeping your taxable income very low (if you’ve planned well). This provides opportunities to sell portions of those stocks without paying capital gains tax.

Donor Advised Funds — If you're charitably inclined (and many of you are), this is one of the most elegant tools in the planning arsenal. You donate appreciated securities directly into a DAF. You skip the capital gain entirely. You get the charitable deduction in a year when your income is high enough to actually use it. Then you make grants from the fund to the charities you care about on your own timeline. The IRS essentially becomes an involuntary donor to your favorite causes.

Gifting appreciated securities to family members in lower brackets (potentially your kids) can shift the tax burden to someone who will pay less on it.

Tax-loss harvesting in the years leading up to retirement, done intentionally as part of a plan rather than reactively, can create offsets against gains you'll need to realize.

This isn’t about avoiding taxes entirely. Unmanaged capital gains are an enormous, largely preventable wealth leak, and almost nobody manages them with any intentionality until it's too late.

4. If You're Selling a Business, Please Read This Twice

The structure of a business sale transaction is one of the most complex and consequential financial decisions a person ever makes. The difference between a well-structured deal and a poorly structured one can be (and I mean this without exaggeration) seven figures in tax impact.

Asset sale versus stock sale. Installment sale versus lump sum. Earnout provisions. Qualified Small Business Stock treatment. Opportunity Zone investments. Charitable strategies at the time of sale. State tax residency at the time of closing.

Each of these variables matters. Every one of them has a tax consequence.

Sadly, most business owners, in the excitement and exhaustion of actually getting a deal done, spend 95% of their energy on the negotiation and about 5% on the tax structure.

If you are selling a business in the next 24 months, the tax planning conversation needs to happen well before the LOI is signed, not after. Certain elections and structures can only be put in place prospectively. Once the deal is structured, your options narrow dramatically.

Find a tax advisor who has done this before. Specifically find someone who specializes in business sale transactions at your scale and engage them early. This is not the time for your general-practice CPA who also does your neighbor's S-Corp return.   

5. Your Estate Plan Is Probably Outdated and I Can Prove It

When’s the last time you actually read your estate documents?

I'll wait...

Here's what I know. If you have a meaningful net worth and your estate plan is more than five years old, statistically there's a good chance that the trustee or executor named in your documents is no longer the right person. . . or possibly even dead. Furthermore, the trust structure may not even reflect current law.

Your beneficiary designations on retirement accounts and life insurance (which completely override your will by the way) may reflect decisions you made in a completely different life.

Get a full estate plan review. More than likely there are things you’ll want to change. 

Part Two: Income Planning — Building the Machine That Replaces Your Paycheck 

6. You Need an Income Architecture, Not an Investment Portfolio

And before going any further, I AM NOT TALKING ABOUT ANNUITIES! That’s a topic for a separate article, but I have impassioned opinions about whether high-net-worth retirees should have any type of annuity. Sadly, many times the person receiving the most financial benefit from an annuity is seemingly the commissioned salesperson selling it. Not the client. I digress.

Here is a distinction that sounds subtle but is actually enormous.

An investment portfolio is a collection of assets optimized for an investment objective, i.e. growth, income, preservation, or some combination of the three.

An income architecture is completely different. It's a system designed to deliver reliable, tax-efficient cash flow to fund your life (potentially 30+ years) while managing the risks that actually threaten retirees: inflation, sequence of returns, healthcare costs, and the actuarial reality that you’ll probably live longer than you think.

They are not the same thing. And confusing them is one of the most expensive mistakes a retiree can make.

"VOO and chill" works great in the accumulation phase, but it has absolutely nothing to do with the distribution phase.

An overwhelming number of people retire with a great investment portfolio and no income architecture. They find out the difference about six months in, usually when markets are doing something inconvenient.

So what does a real income architecture actually involve? Less about what you own, and more about how you structure what you own for maximum tax efficiency and reliability. Here's where the real work is:

Withdrawal order is not obvious and getting it wrong is expensive.

Most people default to spending their taxable accounts first, then tax-deferred accounts, then Roth. As a general rule of thumb, that's not wrong. But as an actual strategy applied to your specific situation, it's almost certainly leaving money on the table.

The right withdrawal sequence depends on your tax bracket each year, your Roth conversion strategy, your Social Security timing, and what your RMDs are going to look like at 73/75. In some years, it makes sense to pull more from your traditional IRA than you technically need, filling a lower bracket intentionally, reducing future RMDs, and keeping your overall lifetime tax bill lower. In other years, you lean on taxable accounts and let the tax-deferred money compound. There is no universal playbook here. There is only your numbers, modeled out, year by year.

The people who manage withdrawal order thoughtfully, coordinated across account types and adjusted annually based on income, will consistently come out ahead of the people who just spend what's most convenient. Sometimes significantly ahead.

Asset location is the other half of the equation.

Most people think about asset allocation, such as the percentage in stocks / bonds / alternatives / cash, etc. Fewer people think carefully about asset location. In other words, which specific assets should live in which type of account.

This matters because different account types have different tax treatment. Interest income, REITs, and other tax-inefficient assets likely belong in tax-deferred accounts where the annual tax drag doesn't compound against you. Growth-oriented equities (particularly those you intend to hold long-term) are often better suited to taxable accounts where they benefit from lower long-term capital gains rates and a potential step-up in basis at death. Roth accounts, where growth is permanently tax-free, are ideally home to your highest-expected-return assets, because the tax benefit is most powerful when the asset being sheltered grows the most.

Done well, asset location can add meaningful after-tax returns without taking on a single additional dollar of market risk. Done poorly (or worse not done at all) it's a quiet drag on wealth that compounds in the wrong direction for decades.

The tax character of your income stream matters more than the yield.

In retirement, a dollar of Roth income, a dollar of long-term capital gain, a dollar of ordinary IRA income, and a dollar of Social Security income are not the same dollar. They are taxed completely differently, and the mix of where your income comes from in any given year has real consequences. They affect your marginal rate, your Medicare premiums two years later, how much of your Social Security gets taxed, and even your estate.

Building an income stream that draws thoughtfully from multiple account types is the actual job of retirement income planning. It must be done in the right proportions, in the right sequence, and in the right years. It requires coordination between your financial advisor, your CPA, and it needs to look forward, not backward.

You have to build this architecture before you retire. Not in month three when you realize your income isn't showing up the way you expected. Not after your first RMD forces your hand.

Before.

Truthfully, the foundation of this architecture should be formatted a decade or more before retirement.

But the window to design this is right now, while you still have earned income, while your tax picture is predictable, and while you have time to position assets deliberately rather than reactively.

7. Social Security: The Decision Worth More Than Most People Realize

“But Nick, Social Security is going bankrupt. I’m going to take it as soon as possible before it goes away.”

If I had a dollar every time I’ve heard someone say this. We don’t have time to list all the reasons why, but Social Security is not going to simply vanish like your Blockbuster membership in 2010. There are 70 million retirees in this country who vote in every election. Cutting it entirely would be the single fastest way for a politician to end their career, and self-preservation is the one bipartisan value left in Washington.

Every year you delay claiming Social Security past your Full Retirement Age, your benefit grows by 8%. Guaranteed. Inflation-adjusted. For life.

I will occasionally hear smart people dismiss this because 8% sounds modest in a bull market. These people are wrong, and I say that with conviction. An 8% guaranteed, inflation-adjusted annual increase on a benefit you can't outlive, with a survivor component for your spouse, is an extraordinary deal in any rate environment.

For most high-earners with meaningful assets and average-or-better health, delaying to 70 is the right call. But this isn't a universal rule. It is a scenario that must be modeled for your specific situation, accounting for health, cash flow needs, survivor benefits, and the tax impact of Social Security income in different claiming scenarios.

Run the numbers with someone who will actually run the calculations. The lifetime benefit difference between a thoughtful claiming strategy and a reflexive "I'll take it at 62" decision can be six figures.

Taking it early because you don't trust the government to keep their promises is an emotional decision, not a financial one.  

8. What Do You Actually Spend? No, Really.

Let me be diplomatic about this, which at times is not my strongest instinct.

Most high-net-worth people approaching retirement have a feeling about what they spend. A ballpark. A rough sense.

But when we actually build out a real retirement spending projection (housing, taxes, travel, dining, charitable giving, kids and grandkids, healthcare, subscriptions, the cars, the home projects, the random stuff that shows up) the real number is almost always materially different from the felt number.

Usually higher. Not always, but usually.

This matters because every piece of your retirement plan is downstream of your spending assumption. Your withdrawal rate, your asset allocation, your Social Security timing, your Roth conversion strategy, your whether-you-can-actually-retire decision, it all must be built upon a foundation of actual data, not vibes. 

Part Three: The Advisor Problem

9. Your Advisor Might Be Great at the Wrong Thing. You May Need a New One.

This is where I risk making some people uncomfortable. But I'm going to do it anyway.

The financial advisory industry is structured primarily around accumulation. Grow the portfolio. Beat the benchmark. Manage the allocation. This is what most advisors are built for, trained for, and compensated for.

What high-net-worth retirees actually need is fundamentally different: tax-optimized income distribution across multiple account types, Roth conversion coordination, Social Security integration, sequence-of-returns risk management, estate plan coordination, healthcare cost planning, and the emotional architecture to not blow up a perfectly good plan when markets get scary.

This is harder. It requires more integration across disciplines. It requires proactivity, not just responsiveness. And it's genuinely not what a lot of otherwise good advisors do.

So ask your advisor. Ask him or her directly, not rhetorically, the following:

"Can you show me a multi-year tax projection for my situation?" "How do you coordinate with my CPA and estate attorney?" "What percentage of your clients are at or near retirement?" "Are you a fiduciary, one hundred percent of the time, on every piece of advice you give me?"

That last question has a very specific right answer... Yes.

It should not be followed by a lot of verbiage and cross talk. The answer should be . . yes.

I recommend someone who is fee-only, earns no commissions, and is legally obligated to act in your best interest always.

If the answers to these questions are vague, I'm not telling you to fire your advisor. I’m just saying that a second opinion costs you nothing more than a couple of hours of your time.

With what’s at stake, that's a very reasonable investment.

10. The Team You Need vs. The Team You Have

Retirement planning done right is not a solo act. It's not even a duet. You need at least three people who are actually communicating with one another:

A Fee-Only Fiduciary Wealth Manager: Coordinates the plan, runs the projections, integrates investment strategy with tax and estate strategy. The quarterback. Should hold a CFP® and have no financial incentive to recommend anything other than what's right for you.

A CPA who plays offense: There's a version of a CPA who waits for you to show up in March with your documents and then tells you what you owe. That person has a role in your life. The person you want for retirement planning does something different. They are thinking proactively about what your tax picture looks like across multiple years and calling you with ideas. Both archetypes exist. Make sure you have the second one.

An estate planning attorney who does this regularly: Not a general practice attorney who does a will here and a trust there. Someone who focuses on estate planning for people with your level of complexity.

In more than two decades of doing this, do you know how many times I’ve come across all three parties doing this without our intervention? Maybe one or two.

Usually, they're all doing good work in separate silos, and nobody is connecting the dots.

Connect the dots.

Part Four: The Question That's Actually the Hardest One

11. Who Are You When You're Not "The [Insert Your Title]"?

Okay, time to get real for a minute.

I've been doing this long enough to observe something that no financial plan can fix. People who spend all their effort mapping out the financial part of their retirement struggle when they haven’t put any real effort into what they're retiring toward. The ones who walk into retirement with a clear sense of purpose and identity? They thrive, regardless of their net worth.

You've spent 30-plus years with your identity largely organized around what you do. Your title. Your company. The team that depended on you. The problems that required you. The mission that got you out of bed.

These aren't shallow things. They're how you've made meaning. They're how you've answered the question "Who are you?" at every cocktail party for three decades.

Retirement doesn't eliminate that question. It just stops answering it for you.

The people who navigate this well aren't the ones who have the biggest portfolios. They're the ones who were intentional about designing the next chapter. They are the people who identified what actually gave them meaning during their working years and found new contexts for those same drives.

The executive who loved building and leading teams doesn't have to stop doing that in retirement. The entrepreneur who thrived on solving hard problems can find plenty of hard problems worth solving that have nothing to do with quarterly earnings.

But you must be deliberate about it. It doesn't just appear.

Some questions worth contemplating:

What will you do with your Tuesdays? I ask this literally. Imagine a specific Tuesday, six months into retirement. What does it look like? If you can't answer that with any specificity, that's important information.

What does "enough" mean to you? Do you actually believe it? Most high-achievers I know have a complicated relationship with “enough.” They're good at accumulating and less practiced at feeling satisfied. Retirement forces this question into the open. Do you struggle with contentment? Let’s flesh it out now instead of being ambushed by it at 11 p.m. on a Wednesday when the house is quiet.

What relationships have you been underfunding? Work is very good at consuming the bandwidth that relationships need. Who are the people you've been meaning to be closer to? What would it look like to meaningfully do that?

Have you talked to your spouse about this? I don't mean "we've discussed retirement generally." I mean a real conversation about what each of you wants this to look like, what you need from each other, and what you're each anxious about. All too often, retirement is a couple’s decision that frequently gets made by one person, the one who's retiring, while the other person suddenly has their home occupied 24/7 by someone who doesn't know what to do with themselves.

This conversation, if you haven't had it, is more important than your asset allocation. I promise. 

The Close

Here's the honest version of what I've been trying to say for the last 4,000 words:

You've been really, really good at a hard thing for a long time. You've earned this transition. And the worst thing that could happen is for the financial and personal decisions of this moment, when the stakes are as high as they'll ever be, to happen passively, by default, without the same intention and rigor you brought to everything else that matters in your life.

The tax moves in this window are worth serious money.

The income architecture, built now, will give you a stability you can't buy later.

The decisions on whether to stay with your current advisor, whether to upgrade, whether to build a real team, have compounding consequences in both directions.

And the purpose question, the one that doesn't fit on a spreadsheet, is the one that will actually determine whether the next chapter feels like a gift or a slow, comfortable, bewildering fade.

You've got 24 months. Don’t waste it.

We do complimentary second-opinion reviews for people in exactly this window. No agenda, no sales pitch, just a real look at your situation from a team that does this every day. If any part of this article causes you to wonder whether your current plan has gaps, it’s probably worth an hour of your time.

Come find us.

Nick Murphy, CFP® is the founder of Counterweight Private Wealth, a fee-only, fiduciary wealth management firm serving high-net-worth individuals navigating significant financial transitions. Counterweight provides comprehensive financial planning, tax strategy, tax preparation, and investment management.

This article is for informational purposes only and does not constitute personalized financial, tax, or legal advice. Please consult qualified professionals regarding your specific situation.