Why the 2026–2028 Window May Be Your Last Chance to Act Before the IRS Takes Control..
Let’s begin with a simple but uncomfortable question:
What if the greatest risk to your retirement isn’t the market, but taxation? Not this year. Not next year. But 5 to 10 years from now, when your flexibility is limited and the decisions are being made for you by the IRS.
If you’re reading this, there’s a good chance you’re like many, conservative Americans who did things the right way:
- You saved consistently
- You built meaningful balances in 401(k)s and IRAs
- You avoided unnecessary risk
- You didn’t chase trends
- You didn’t cut corners
- You followed professional guidance
You were intentional. You did what most people won’t. You sacrificed today to build a better tomorrow, and by every traditional measure, you succeeded.
But that’s not where the story ends. Because once you retire, the game changes.
You shift into the distribution phase, where a small snowball of taxes begins to form. One that’s strategically designed by the IRS to turn into an avalanche in the years ahead.
Most advisors don’t see it coming. And in the process, unknowingly guide you deeper into it, increasing your long term exposure to the IRS.
For decades, you were told to defer taxes. Max out your 401(k). Fund your IRA. Funnel money into pre tax accounts every chance you could.
And most people did exactly that. Year after year. Contribution after contribution.
But here’s the question:
What if the system (THE IRS) didn’t just set the rules, but quietly guided you into a position where you’re now locked into a lifelong, compounding tax liability?
One that doesn’t end with you, but continues on to your children, and even your grandchildren.
A system, through no fault of your own, you’ve likely never seen fully play out, and one that was never clearly explained in a way that reveals how it’s working against you.
Most people are focused on this year’s taxes, because that’s what their CPA and advisor focus on.
But the IRS isn’t thinking about today. They’re looking ahead—at your future tax brackets, rising RMDs, and the compounding tax liability inside your pre-tax retirement accounts. While you’re focused on the present, they’re playing a much bigger calculated game.
And for many reading this, it gets dismissed as something to deal with later, as a future problem.
But for many AMAC members, that future isn’t as far away as it once was.
And that tax avalanche is already building.
Because tax deferred does not mean tax free. It means tax delayed.
And the IRS didn’t do this as a favor. They’re playing a long game, waiting for a much larger payday. Because when that money comes out, every dollar is taxable.
Year after year,
Under rules you don’t control.
Not just what you put in, but potentially many multiples of it over time. Which means the IRS isn’t on the sidelines. They’re your silent partners. Positioned to get paid on every distribution. And the larger your accounts grow, the larger their future claim becomes.
Fast forward to the end of retirement… And the largest bill you may have paid isn’t healthcare. It isn’t a lifestyle. It’s taxes. What once felt like a smart advantage can quietly become one of the largest financial burdens of your life. Exactly as designed. Because the system is counting on one thing: That you stay passive, Follow the default path, And never question it.
But here’s where this becomes important…
Right now, we are in a rare, time-sensitive window, shaped in large part by policies under President Trump, where tax rates are historically low and planning flexibility is unusually high.
This “Big Beautiful Bill” era has created one of the most favorable environments we’ve seen in decades to take back control of your retirement accounts.
But this window will not stay open forever:
- Tax rates can rise
- Rules can change
And when they do, the cost of fixing this problem increases.
Often significantly.
So let’s be clear: You are not required to follow the IRS’s default distribution path.
There are alternative strategies. And for those who act while this window is open, this can be one of the most impactful financial decisions you ever make.
The difference between:
- Transferring hundreds of thousands to the IRS
- Preserving that wealth within your family
When the IRS Takes Control
Through Required Minimum Distributions, RMDs, the IRS forces taxable income out of your retirement accounts at age 73 or 75 depending on your birth year:
- Whether you need it or not
- Whether it’s a good time or not
- Whether it pushes you into higher taxes or not
Most members have never had a true conversation with a distribution advisor—never had an expert sit down and show them what their personal RMDs look like 8, 9, 12 years into retirement, how it impacts their future taxes, what it means in real dollars and cents, and how different strategies can change the outcome.
If that’s you, you’re not alone.
You may be working with an accumulation advisor, a wealth manager who helped you grow your money, pick strong investments, and build your portfolio, but this type of forward-looking, distribution-focused planning conversation rarely happens. And at this stage, distribution expertise matters just as much.
For many, these RMDs don’t just increase…they double, and compound perpetually.
So the real question to ask yourself is:
Have you seen what this does to your financial picture over time, have you seen the numbers, understood the strategies to take control… or are you still operating on the IRS’s default plan?
More specifically, have you seen:
- What your RMDs do to your tax brackets
- How they impact your Medicare premiums
- Whether they trigger IRMAA
- What they do to your net income
- How much of your portfolio ultimately gets lost to taxes
Because when we model this out, the numbers are rarely small. It’s often high six figures in additional taxes people never planned for. And almost every time, we hear:
“I had no idea, no one ever showed us this, I thought we were going to be in a lower tax bracket in retirement.”
RMDs create a chain reaction:
- Higher taxable income
- Higher tax brackets
- More Social Security taxed
- Higher Medicare premiums
- Less control over your money
- Ongoing erosion of your portfolio due to compounding taxes
So the question becomes: Is there a way to reduce, or even eliminate, this future tax pressure before it’s locked in?
For many retirees, the answer is yes.
But it requires action, before the window closes.
Because once RMDs begin, your options narrow. Once tax rates rise, the cost goes up.
And once time passes, the opportunity shrinks.
Roth Conversions:
This is where the conversation changes. Because for many retirees, Roth conversions represent one of the few strategies that can directly address this problem, before it becomes permanent.
They are not for everyone.
They are not a silver bullet.
But when they fit, and are executed correctly, they can be a powerful strategy, dramatically impacting your income, your taxes, and the legacy you leave behind. We strongly believe most AMAC members should have a conversation with a distribution expert to evaluate whether Roth conversions make sense for their situation.
Because when it’s done properly, with real projections, real numbers, specific tax software, and a clear view of your future, the answer becomes obvious.
This isn’t about opinions. It’s about math. Because this isn’t just a tax strategy, It’s a control strategy.
The difference between:
- Paying taxes on your terms
- Paying taxes on the IRS’s terms
When structured correctly, Roth conversions can:
- Reduce or eliminate future RMD pressure
- Create tax free income in retirement
- Lower lifetime taxes
- Protect a surviving spouse
- Reduce taxes on your children
- Increase control over your financial future
Why This Window Is So Unique Right Now
We are currently in a tax environment shaped in part by policies under Donald Trump.
What matters:
- Historically low tax brackets
- Expanded deductions
- Greater flexibility in income planning
- A temporary window before potential changes
In simple terms: Taxes are on sale.
And that creates a rare opportunity to reposition retirement assets at a lower cost than we’ve seen in years, an opportunity previous generations never had, and one that likely won’t be around much longer.
The Mistake That Costs People the Most
The biggest mistake isn’t doing this wrong.
It’s never properly evaluating it, never working with an expert, never using a proven, math-based process to get it right.
Because doing nothing is not neutral. It’s a decision.
And in many cases, it’s a decision to stay on the IRS’s path.
Where Many Advisors Miss
Very few advisors are true experts in retirement tax planning. Most are trained to help you build wealth, pick investments, manage risk, and grow your portfolio. They’re not trying to set you up to fail… but when it comes to distribution, that’s often exactly what happens.
Because accumulation and distribution are two completely different skill sets, and far fewer advisors are trained to help you unwind it efficiently.
Those are two very different skill sets, once retirement begins, the questions change. It is no longer just about growth. It becomes about:
- Strategically converting assets over time
- Managing tax brackets across multiple years
- Coordinating income, taxes, and Medicare
- Planning for the surviving spouse (avoiding widows tax)
- Reducing long term tax exposure
That is not basic investment management.
That is specialized retirement distribution planning.
And for many retirees, it can have a far greater impact than picking the right mutual fund at this stage.
What We Do Differently
This is a core area of focus. We help members evaluate Roth conversions as part of a complete retirement distribution plan, not as a one time transaction or isolated tax idea.
That means we look at the full picture:
- Lifetime tax projections
- Future RMD exposure
- Income planning
- Volatility strategy
- Survivor planning
- Estate implications
Because the real question is not: “Can you do a Roth conversion?”
The real questions are:
- Should you
- How much should you convert
- When should you do it
- And evaluation of what happens if you do nothing
6 Roth Conversion FAQs,
1 Are there income limits?
No. Income limits apply to contributions, not conversions.
2 Can I do this while working?
Yes.
3 Can I do this if I’m Retired?
Yes.
4 Is there a limit on how much I can convert?
No, there is no limit under current tax law.
5 Can I convert if I’m taking RMDs?
Yes, but RMDs must be taken first.
6 When is the best time?
Typically, 3 to 5 years before or after retirement, but earlier gives you more control.
Why This Matters More Right Now Than Ever
That is where clarity comes from. That is where real planning begins.
You haven’t missed the opportunity. We are still in a rare tax window.
- Lower rates
- Favorable brackets
- Planning flexibility
This is not normal. And it will not last forever.
This is your window to:
- Reposition assets
- Take control
- Reduce future tax exposure
The Question That Shapes Everything
Do you believe tax rates will be higher or lower in the future? Today they are historically low…
Because if they rise, and your money is still in pre tax accounts, you may be walking into a tax environment you didn’t plan for.
A 5 Question Retirement Tax Stress Test
Answer Yes or No:
- Do you expect most income from IRAs or 401(k)s
- Is over 50 percent in pre tax accounts
- Have you modeled RMDs
- Do you expect taxes to rise
- Do you have tax free income strategies
What Your Answers May Indicate
- 0 to 1 Yes, Strong position
- 2 to 3 Yes, Opportunity exists
- 4 to 5 Yes, High exposure
You Haven’t Missed It, But You Don’t Want to Wait
If you answered yes to two or more,
There is likely an opportunity here.
You just haven’t been shown how to evaluate it yet.
Because this isn’t about guessing. It’s about strategy. It’s about clarity. It’s about control.
See Where You Stand
Most people read this and move on.
A few ask: “What does this mean for me?”
If that’s you, you have two simple options:
Click below to evaluate your current situation and speak with one of our licensed distribution experts one on one.
Or click below to watch a 40-minute educational webinar walking through these strategies step-by-step.
From there, if it makes sense, you can decide whether to speak with one of our distribution advisors.
No cost, No obligation, No assumptions. Just clarity.
Written by Sean Keefe
CEO of AMG, Proud Partner of AMAC
This material reflects the opinions of the author and is provided for informational and educational purposes only; it should not be construed as personalized financial, tax, or legal advice. Always consult with a qualified financial professional, tax advisor, or attorney before making any decisions regarding your specific situation.
The opinions expressed by columnists are their own and do not necessarily represent the views of AMAC or AMAC Action.