Picture two people retiring on the exact same day.
Same amount saved.
Same investments.
Same effort, over the same number of years.
A few years later, one of them has a lot more money than the other.
Not because they picked better stocks.
Not because they got lucky timing the market.
They just happened to use a few tax strategies the other person never even knew existed.
Same savings. Same portfolio. Completely different outcome.
After 15 years of helping people plan for retirement, I can tell you most people have the basics down.
401(k) deferrals. Roth conversions. Maybe some tax-loss harvesting.
But there are at least five strategies most retirees never hear about — and they’re not loopholes.
They’re strategies your CPA already knows exist.
They just don’t come up unless you know to ask.
So let’s go through all five.
None of these require saving more or changing how you’re invested.
They just require coordination.
1. Stack a Roth Conversion With a Donor-Advised Fund
Everyone’s heard of a Roth conversion.
You move money from a traditional IRA into a Roth, and pay tax on it today instead of later.
By itself, that’s useful. But it’s incomplete.
The real power shows up when you can offset that conversion income with a big deduction.
Here’s a hypothetical to illustrate.
Let’s say you give $5,000 a year to charity, and plan to keep doing that for the next 30 years.
By retirement, your mortgage is paid off, and you’re no longer itemizing.
That means you’re getting zero tax benefit for a gift you were always going to make.
What if, instead, you funded a donor-advised fund with that same $150,000 today — all at once?
You’d still control the timing of when the money actually goes to charities.
But you’d get the full deduction this year.
That deduction can then offset the income created by a larger Roth conversion — the same year.
Take it one step further.
If you have an appreciated stock — say, one you bought years ago that’s grown significantly — gifting the stock itself (instead of selling it) avoids capital gains entirely, and the fund still gets full value.
There are limits on how much you can deduct, and the rules differ for cash versus securities.
So talk with your advisor and your CPA before implementing this.
But when it’s coordinated well, this single move can be worth tens of thousands of dollars over your retirement.
2. Map Your Lifetime Tax Liability, Not Just This Year’s
Most people plan taxes one year at a time.
You look at last year’s income. Maybe you squeeze in a last-minute IRA contribution or a small conversion.
That’s an incomplete way to think about it.
What matters isn’t this year’s tax bill.
It’s your lifetime tax liability.
Imagine a plan that maps your Social Security, dividends, capital gains, and IRA withdrawals over the next 20 to 30 years.
That gives you a projection of your taxable income over time — and you can overlay future tax brackets on top of it.
Now you can actually see where the opportunities are.
Is this a good year for a Roth conversion?
Or would a different year be better?
You can’t answer that without seeing the whole picture first.
Most people never get this view, simply because the tools they’re using — TurboTax, a CPA’s one-year snapshot — aren’t built for it.
The goal isn’t the smallest tax bill this year.
It’s the lowest tax bill over your lifetime.
3. Give to Charity While You’re Alive
I recently worked with a client planning to leave 20% of his estate to charity, with the rest split between his kids.
We modeled it out. That gift, in today’s dollars, came to more than $2 million.
Here’s the problem: leaving that gift at death gets zero tax benefit today.
So we asked a different question.
What if we pulled that gift forward — through a donor-advised fund or charitable trust — while he’s still living?
Working backwards, a gift of roughly $600,000 today could grow to that same $2 million by the end of his lifetime, assuming steady growth (this is a hypothetical example, not a projection or guarantee).
That $600,000 gift creates a deduction now.
A deduction big enough to offset a large Roth conversion, or gains from selling a rental property or concentrated stock position.
The estate plan doesn’t have to change who ultimately benefits.
It just changes the timing — so the tax benefit isn’t left on the table.
4. Use Net Unrealized Appreciation on Company Stock
If you hold company stock inside your 401(k), this one’s worth understanding.
Say you bought $50,000 of company stock inside your 401(k), and it’s now worth $200,000.
Roll the whole account into a traditional IRA, and every dollar you eventually withdraw gets taxed at ordinary income rates — the highest rates you’ll pay.
Net unrealized appreciation (NUA) works differently.
Move just the company stock into a separate brokerage account, and you only pay ordinary income tax on your original $50,000 basis.
The remaining $150,000 in gains gets capital gains treatment once you sell — and you control the timing.
There’s a bonus here, too.
If that stock has appreciated significantly, it can become the seed funding for the donor-advised fund strategy above — avoiding tax on the gain altogether.
NUA has specific execution rules, and missing a step can undo the benefit entirely.
This is one to run by your advisor and CPA before you touch anything.
5. Bank Your Losses — and Take It Further Than Most People Think
Here’s the simple version first.
You hold an S&P 500 index fund. It drops in value. You sell it, realize the loss, and buy a similar (not identical) fund to stay invested.
That loss can offset future gains on your tax return.
Now here’s the part most people miss.
The S&P 500 as a whole tends to rise more than it falls.
But the individual companies inside it don’t all move together.
In 2025, the index was up roughly 18%. But a meaningful share of the underlying companies posted a loss that same year (note for editor: verify and source this figure before publishing).
If you only own the index fund, you get the 18% — and no losses to harvest.
If you own the individual components, you can harvest losses on the ones that dropped, wait the required period, and buy them back — all while keeping similar overall exposure.
Do this consistently, and you build a bank of losses you can use later — when you sell a rental property, a business, or a stock that’s grown significantly.
Some people ask: doesn’t this just create more unrealized gains down the road?
It does. But most people don’t spend these accounts down in their lifetime.
When they pass to a spouse, child, or beneficiary, those assets get a step-up in basis — meaning the gains disappear for tax purposes.
You get the benefit of the losses now, and your heirs never pay tax on the built-in gains later.
None of This Happens by Accident
These five strategies don’t ask you to save more or take on new risk.
They ask you to coordinate.
Your tax strategy needs to work alongside your investment strategy — and both need to support your withdrawal strategy.
Get that coordination right, and it can be worth tens of thousands of dollars — or more — over the course of your retirement.
Get it wrong, and you’re simply leaving money on the table.
If you’re wondering whether your current plan is using any of these, let’s take a look together.
No pressure. Just clarity.
👉 Schedule a call and see what your retirement tax strategy could look like.