Taxes

Tax efficient retirement planning requires thinking ahead. You can strategize your income, investments, and spending to reduce your tax burden.

Make choices to save into the right savings vehicles. Opt for pre-tax savings (traditional, SEP & Simple IRAs, 401ks, 403bs, 457s, 529s, HSAs, etc…) where you don’t pay taxes on the money you invest until you withdraw the funds in the future or after-tax savings (Roth IRAs and 401ks) are when you save money that has already been taxed.

You also want to consider how you can manipulate both income and spending to optimize your tax bracket.

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paying taxes in retirement

How to Pay Taxes in Retirement and Avoid IRS Penalties

Paying taxes in retirement means managing income streams, quarterly deadlines, and the IRS safe harbor, without an employer doing it for you.

April 9, 2026
A hand reaching in to stop a row of falling colorful dominoes, symbolizing a strategic intervention to protect assets and mitigate the impact of a heavy capital gains tax on investment returns.

Capital Gains Tax Brackets: How Income Pushes Your Rate Higher

Think you qualify for the 0% capital gains tax rate? Your other income may have already eaten that space. Here’s why, plus the 2026 brackets.

April 1, 2026
Roth conversion down market

Roth Conversions in a Down Market: The Tax Window Many Miss

A market drop lowers what you’ll owe on a Roth conversion. Learn how to turn a portfolio pullback into a long-term tax win.

March 26, 2026
tax season checklist

Tax Season Checklist: 10 Essential Considerations to Review for Your 2025 Return

Are you “lucky” enough to have to worry about #3? Did you remember #5? Explore all 10 tips on this tax season checklist.

March 4, 2026
state taxes

Which Are the Most Tax Friendly States for Retirees 2026?

Are you in a tax friendly state for retirees? Explore the best states for taxes and review the income and sales tax rates in all 50 states.

March 3, 2026
Roth conversions and deductions

The Overlooked Role of Tax Deductions in Roth Conversion Planning

Learn how deductions affect Roth conversions and when income can be converted without triggering federal tax. Tips for smarter Roth planning.

January 30, 2026
Timing Roth Conversions

Timing Roth Conversions: Should You Convert at the Start of the Year? End? Or, Spread Them Out?

Learn the pros and cons of different Roth conversion timing strategies and how to choose the right approach for your retirement plan.

January 16, 2026
year end tax tips

Year End Tax Planning Strategies to Keep More Money and Prepare for Future Wealth

These 13 year-end tax tips for retirement will help you minimize your 2025 taxes and reduce future tax bills.

November 6, 2025
asset location

Asset Location: How Tax-Smart Investing Can Supercharge Your Portfolio

Asset location is an important concept if you are trying to save and build wealth. Explore ways to locate funds to minimize taxes.

October 2, 2025
government shutdown survey

Survey: The Looming Government Shutdown and the Future of ACA Subsidies, Boldin Subscribers Express Concerns

Boldin survey reveals most Americans worry a government shutdown and also the threat to ACA subsidies and retirement confidence.

September 26, 2025
Roth 5 Year Rule

Understanding the Two Roth 5-Year Rules: A Key to Smarter Early Retirement Planning

Want to retire in your 50s and withdraw from savings? You need to understand the Roth 5 year rules to avoid penalties.

August 7, 2025
OBBBA Tax Updates

Boldin’s Recent OBBBA Tax Updates: What’s Changed, How It Impacts You, and New Opportunities for Optimizing Your Plan 

We’ve made the OBBBA tax updates in the Planner. Learn more about what’s changed and discover opportunities to optimize your tax planning.

July 25, 2025
obbba and retirement

The One Big Beautiful Bill Act (OBBBA) and Your Retirement

Explore 7 key provisions in (or consequences of) the One Big Beautiful Bill Act (OBBBA) — and what they could mean for your retirement.

May 22, 2025
early retirement withdrawals

Early Retirement Withdrawals: 5 Ways to Take Penalty-Free Distributions from Your Retirement Accounts BEFORE You Turn 59.5

Retiring before 59.5? Discover how to make penalty free withdrawals from your retirement accounts to help fund your early retirement.

May 1, 2025
catch-up contributions

Catch-Up Contributions: The Powerful Retirement Saving Secret for People Over 50

Catch up contributions are the IRS’s way of making it easier for savers age 50 and up to tuck away enough retirement savings.

April 24, 2025
tax planning tips

Taxes in Retirement: 25 Terrific Tax Planning Tips for a Wealthier 2025 and Beyond

Planning for the future should involve strategizing to minimize taxes. Explore 25 tips to help you plan, do retirement tax filings, and save money.

March 27, 2025
Roth conversion strategies

Strong Engagement & High Confidence: What Boldin’s Survey of Users Reveals About Strategizing Roth Conversions

Roth conversions are a powerful tax planning strategy, but how do retirement savers actually use them? A recent survey of Boldin subscribers reveals that users are not only highly engaged in Roth conversion planning but also taking meaningful action based on Boldin’s tools and insights. The results show that 93% of respondents have used Boldin’s […]

March 18, 2025
roth conversion planning

Planning for Uncertainty: Why Roth Conversions Require Iteration, Not Perfection (It’s an Art, Not a Science)

Discover the opportunities and limits of modeling your Roth conversion opportunities and get 6 tips for doing better.

December 19, 2024
QCD

How Making a Qualified Charitable Distribution (QCD) Can Save You Tax Money

QCDs are a way to help great causes and those in need, but they are also a way to manage your tax exposure and avoid unpleasant surprises. 

September 12, 2024
2026 Tax Brackets TCJA expiration

TCJA: Why Your Taxes Are Likely to Increase in 2026 and What to Do About It

Due to the the TCJA expiration, your 2026 tax brackets and rates will rise. Find out why and how to prepare for the increase.

June 13, 2024
roth conversion mistakes

Roth IRA Mistakes: 15 Common Roth Conversion and Savings Mistakes People Make

There are a lot of potential Roth IRA mistakes to be made: 1) Not doing it, 2) Not knowing the rules, 3) Timing, 4) Poor planning, 5) Overlooking spouse… and more!

April 11, 2024
social security and taxes

What You Need to Know About Social Security and Taxes

Yes. You might pay taxes on Social Security. Learn what to expect (federal, state and work penalties) and explore ways to reduce the expense.

April 4, 2024
Tax talk

Tax Strategies and Lingo Made Simple: A Useful Guide

Gain valuable insights into common tax terms and some of the most popular strategies for reducing what you pay.

February 8, 2024

Estimates for Your 2023 Data Are Now Available in the Boldin Retirement Planner

The Boldin Retirement Planner now shows an estimate for your 2023 year-end numbers. The 2023 values are available on all charts.

November 30, 2023

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