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Crossing the Tax Valley

March 15, 2026

Before I retired, I thought taxes were going to be simple. I assumed I'd have much more flexibility managing my investment portfolio because I'd be in a much lower income tax bracket, and I wouldn't have to worry about long-term capital gains tax. Boy, was I wrong.

The RMD Surprise

I had heard of RMDs but didn't really comprehend the impact. RMDs (Required Minimum Distributions) start at age 73 or 75 depending on your birth year. You must withdraw a minimum amount each year based on an IRS formula:

RMD = Prior year-end account balance ÷ IRS life expectancy factor

The life expectancy factor comes from the IRS Uniform Lifetime Table and decreases every year, meaning the percentage you're required to withdraw grows as you age:

Age IRS Factor Approx. % of Balance RMD on $1M IRA
73 26.5 ~3.8% $37,736
75 24.6 ~4.1% $40,650
78 22.0 ~4.5% $45,455
80 20.2 ~5.0% $49,505
85 16.0 ~6.3% $62,500
90 12.2 ~8.2% $81,967
95 8.9 ~11.2% $112,360
100 6.4 ~15.6% $156,250

And remember, those RMD amounts are on top of Social Security and any other income you have, all taxed as ordinary income.

My Situation

I was a good saver and always maxed my 401(k) contributions. I had read about Roth IRAs but never contributed, because my goal was always to minimize current taxes, thinking things would be simpler once I retired. I was also earning above the income limit for direct Roth IRA contributions, so it was never really on the table.

I also made some good investments in my taxable account and typically held on to them because I didn't want to pay the capital gains tax. I bought Bitcoin at $6,000 and Apple at $21. My portfolio has a lot of unrealized gains, and it would be nice to reduce my exposure to some of the riskier holdings and lock in those gains.

The Roth Lesson I Learned the Hard Way

Once I retired and started researching, I realized I was going to face a substantial tax burden once RMDs kicked in. Converting as much of my IRA to Roth as possible became the most important thing I could do to avoid future taxes, both for myself and my heirs.

The first January after retiring, I immediately deposited the $8,000 maximum into a newly created Roth IRA. Oops. I hadn't done my homework carefully enough: you can only contribute earned income into a Roth, and being retired, I had no earned income. I was able to withdraw the funds before the end of the year without penalty, but I did have to pay tax on the small amount of appreciation that had accumulated in the account.

Lesson learned: Roth conversions (moving money from a traditional IRA to a Roth) are different from Roth contributions (depositing new money). Conversions have no earned income requirement.

What Is the Tax Valley?

When you convert assets from a traditional IRA to a Roth, you must treat the converted amount as ordinary income and pay taxes at your marginal rate. This is why the Tax Valley is so important.

The Tax Valley is the window of years between when you stop working, your W-2 income disappears, and when Social Security starts and RMDs kick in. During this period, your taxable income may be at its lowest point for the rest of your life. This is the time when you have the flexibility to convert larger amounts of your IRA into Roth without being crushed by taxes and IRMAA.

(IRMAA is a story for another day, but think of it as an additional tax. It is actually a surcharge on top of your Medicare Part B and Part D premiums, triggered when your MAGI crosses certain income thresholds.)

After a lot of research and planning, I decided it was worth paying more tax upfront. My strategy was to maximize Roth conversions up to the point where my MAGI (Modified Adjusted Gross Income) came in just below the IRMAA Tier 2 threshold, which also happens to align with the 24% marginal tax bracket.

The Capital Gains Tradeoff

With a plan for Roth conversions in place, the next question was: how do I de-risk my taxable portfolio and lock in those gains?

The hard truth: you can't have your cake and eat it too.

Tax-free long-term capital gains are available for married filing jointly couples with taxable income below $98,900. But if I was already filling my income up to the IRMAA Tier 2 threshold with Roth conversions, there was no room left for tax-free capital gains harvesting.

Short-term, I could have kept my taxable income low and harvested capital gains in the Tax Valley. But this would have hurt both me and my heirs in the long run. If I let my IRA keep growing untouched, I'd face substantially higher taxes from large RMDs in the future, and my heirs would inherit the IRA subject to the SECURE Act's 10-year rule, which could create a major tax burden for them.

How to Prioritize Assets for Your Heirs

When thinking about what to leave to your heirs, the order of preference is:

  1. Taxable accounts — Assets transfer with a step-up in basis at death, meaning all unrealized gains disappear. Your heirs inherit at the current market value with no capital gains tax owed on prior appreciation.

  2. Roth accounts — No taxes on withdrawals. Under the SECURE Act, non-spouse heirs must drain the account within 10 years, but since all growth is tax-free, this is still a highly favorable inheritance.

  3. Traditional IRA accounts — The least favorable to inherit. Under the SECURE Act, non-spouse heirs must take distributions and drain the account within 10 years, potentially pushing them into a higher tax bracket each year during that period.

My Choice

I chose to forgo long-term capital gains harvesting and focus instead on reducing my future RMDs and the tax burden on myself and my heirs over my lifetime. Others may make the opposite choice. It all depends on your individual situation, tax bracket, and timeline.

I just hope Apple and Bitcoin don't tank.