Learning Center

We keep you up-to-date on the latest tax changes and news in the industry.

The Retirement Tax Surprise: What Boomers Need to Know Before It’s Too Late

You did it. 
You worked hard, saved consistently, and now you're either enjoying retirement—or it's just around the corner.

You’ve been told for years to put money into retirement accounts, defer taxes, and wait for the golden years. But wait… no one told you?

Retirement might be your highest-taxed phase yet.

Seriously.
Between Social Security income, Required Minimum Distributions (RMDs), capital gains, Medicare premium adjustments, and even state taxes… it can feel like a financial ambush.

Let’s break down why this happens—and what you can do now to soften the blow.

1. RMDs: The Tax Bomb That Starts at Age 73

If you’ve saved in a traditional IRA or 401(k), you’ve been enjoying tax deferral for years. But the IRS eventually wants their cut.

That’s where RMDs come in.
Once you hit age 73, you’re forced to take money out of your retirement accounts—and those withdrawals are taxed as ordinary income.

Why it matters:

  • Your RMD could bump you into a higher tax bracket.

  • It could trigger higher Medicare premiums (thanks, IRMAA).

  • It might even impact how much of your Social Security is taxed.

What to do now:
Consider Roth conversions in your 60s to reduce your future RMDs. Yes, you’ll pay tax now, but it could save you significantly down the road.

2. Social Security Isn’t Always Tax-Free

Up to 85% of your Social Security benefits could be taxable depending on your total income—including investment income, part-time work, and yes, those RMDs.

Here’s the trap:
You think you're getting $3,000/month from Social Security.
But add in just a few thousand from another source, and suddenly, a big chunk of that is taxable.

Solution:
Work with an advisor who can map out income sources before you trigger your benefits. Sometimes, waiting a year or two—or rebalancing your withdrawal strategy—can dramatically reduce taxes.

3. IRMAA: The Medicare Surcharge You Didn’t See Coming

This one stings.
You file your taxes, enjoy a good year, and then boom—two years later, your Medicare premiums go up.

That’s IRMAA (Income-Related Monthly Adjustment Amount).
If your income exceeds certain thresholds, you’ll pay more for Medicare Part B and D—even if the bump was from a one-time event like a Roth conversion or asset sale.

Proactive planning = lower premiums.
A well-timed income strategy can keep you just under IRMAA thresholds. And in some cases, you can file an appeal based on a “life-changing event” like retirement or loss of income.

4. Capital Gains & Selling Assets in Retirement

Selling your long-held investments? Downsizing your home?
These capital gains could push your income higher than expected—and cause a domino effect with taxes, Medicare, and Social Security.

Even if you’re “living off savings,” your tax return may tell a different story.

Pro tip:
There’s a 0% capital gains bracket for certain income ranges. With the right strategy, you can sell appreciated assets without triggering taxes—but timing is everything.

5. State Taxes Still Matter—Even in Retirement

Not all states treat retirees the same.
Some tax Social Security, some don’t. Some offer pension exemptions, others tax everything.

If you’re thinking about relocating in retirement, don’t just compare housing costs. Compare tax policies. And if you’re staying put? Learn how your current state impacts your bottom line.

6. Your Filing Status Can Change Your Tax Life

A tough but important truth: Losing a spouse in retirement often means going from “Married Filing Jointly” to “Single.”

Which means:

  • Lower standard deductions

  • Tighter income thresholds

  • Bigger tax bills on the same income

If you’re newly widowed or preparing for that reality, it’s worth building a multi-year tax strategy now—not later.

7. You Don’t Have to Navigate This Alone

The retirement tax landscape is not DIY-friendly.
Rules change. Thresholds shift. And one wrong move (or missed opportunity) can cost you thousands.

But with the right guide, you can:

  • Smooth out income across years

  • Reduce your lifetime tax bill

  • Maximize your Social Security and Medicare benefits

  • And keep more of the money you worked so hard to earn

Let’s Build a Tax-Smart Retirement Plan—Together

You planned for retirement.
Now it’s time to plan for retirement taxes.

We’re here to help you make smart, proactive decisions that reduce surprises, minimize your tax burden, and give you the peace of mind to enjoy the years ahead.

Contact our office today to schedule a retirement tax check-up.
You’ve done the saving—now let’s make sure you keep more of it.

Share this article...

Want our best tax and accounting tips and insights delivered to your inbox?

Sign up for our newsletter.

I confirm this is a service inquiry and not an advertising message or solicitation. By clicking “Submit”, I acknowledge and agree to the creation of an account and to the and .

Benefits of having a business advisor

Your CFO, Reimagined as a Financial Doctor

Diagnosing root causes, prescribing solutions, and guiding your property business toward long-term wealth.

Our CFO | Advisor

Raquel is a passionate business owner. Now, she is returning to her grassroots with a twist - guiding clients with her expertise as a CPA, she can advise your company as your trusted CFO and Advisor.

  • Raquel Deodanes, MS, CPA

    Co-Founder

    CPA with Real-World Experience – I help property managers stay profitable, tax-efficient, and cash flow positive.
    Tax Strategist – Former advisor at California’s revenue agency.
    Trusted by 4,000+ Businesses – Experience across CA, FL, TX, NV, and beyond.
    Real Estate Investor – I understand the financial realities of property management.
    Entrepreneur – I’ve built businesses and know the challenges you face.

Frequently Asked Questions

We diagnose financial inefficiencies, treat problems like poor cash flow or rising costs, and guide you to long-term financial health. That includes cleaning up your books, forecasting cash flow, optimizing operations, and helping you grow your portfolio with confidence — just like a doctor builds a custom care plan for a patient.

Bookkeepers record transactions. CPAs file your taxes. We connect the dots — helping you understand your numbers, strategically improve them, and make smarter decisions throughout the year. We work alongside your existing team to drive performance, not just compliance.

If you're unsure where your cash is going, struggling with rising costs, planning to scale, or just tired of reacting instead of planning — now is the right time. We help you get ahead of problems, not just clean up after them.

Clients typically see improved cash flow, cleaner books, higher NOI, better financial reporting, and a lot less stress at tax time. More importantly, you gain clarity, confidence, and control over your business — and a partner who helps you grow it.

Pricing

Painless, transparent pricing.

Let us take away your stress and give you back your time. Choose your perfect package today.

Base

$499 /mo
  • Dedicated finance expert

  • Bookkeeping with accrual basis

  • Includes P&L, balance sheet, and cash flow statements

Core

$999 /mo
  • Includes everything in Base, PLUS

  • Industry KPIs and financial ratios

  • Monthly virtual 1-hr meetings

  • Monthly rolling budget forecasts

Growth

$1999 /mo
  • Includes everything in Base, CORE

  • Budget vs. actuals variance analysis and review

  • Payroll and HR Platform