Insights & ideas
Plain-English thinking on retirement and taxes
The tax code changes, markets move, and the rules for retirees shift with them. This is where we make sense of it: no jargon, no hot takes, just what matters for your plan.
From the archive
Evergreen reads on retirement & taxes
Social Security Claiming Ideas
A four-part framework for deciding when to file for Social Security based on your marital status and work history, plus how the Social Security Bridge can fund income while you wait to claim.
June 7, 2024 · 6 min read
Read articleTax PlanningDodging Tax Jail and the Tax Torpedo
Retirement income can trigger unwelcome tax traps like 'Tax Jail' and the 'Tax Torpedo.' Here's how they work, and ideas to help you dodge them.
April 8, 2022 · 4 min read
Read articleTax PlanningWhat Is Medicare IRMAA?
Part of our retirement tax-traps series: IRMAA is the income-related surcharge that can quietly raise your Medicare premiums. Here's how it gets triggered and how to plan around it.
March 31, 2022 · 4 min read
Read articleTax PlanningReceiving the Premium Tax Credit in Retirement
How will you get health insurance after leaving your employer, and what will it cost? The ACA Premium Tax Credit can make coverage far more affordable in early retirement.
March 10, 2022 · 5 min read
Read articleRetirement IncomeTop 5 Social Security Planning Ideas
Social Security is one of the largest, most valuable retirement assets, with inflation-adjusted income worth $40,000 to $50,000 a year. Five facts, ideas, and opinions on how to claim it well.
February 24, 2022 · 5 min read
Read articleRetirement IncomeWhat Is the Social Security Bridge?
If you retire but want to delay Social Security to a later age, a self-funded 'bridge' provides secure monthly income from the end of your career until your benefits begin.
May 31, 2021 · 4 min read
Read articleTax PlanningUpdating Your W-4 With the Tax Withholding Estimator
The IRS Tax Withholding Estimator makes it easy to update your W-4, and getting your withholding right can put more in each paycheck. Here's how to use it.
February 12, 2020 · 3 min read
Read articleTax PlanningBe Aware of the Deferred Comp Tax Hit
Deferred compensation payouts can cause real tax headaches. Estimating the hit with your advisor ahead of time keeps a large payout from derailing your plan.
January 30, 2020 · 3 min read
Read articleTax PlanningFixing Tax Problems for Bonuses, Stock Compensation, and Dual Income
Bonuses, stock compensation, and two-income households often lead to a surprise tax bill, and a penalty on top. A few tips to clear up the mystery and stay ahead of your estimated payments.
June 12, 2019 · 5 min read
Read articleTax PlanningYour Charitable Deduction May Be Going Away: Here's How to Save It
Can you maximize itemized deductions in one year and take the standard deduction in the others? 'Bunching' your charitable giving is one way to keep the tax benefit. Here's how.
November 28, 2018 · 4 min read
Read articleIn the news
John's recent commentary
- CNBCApril 2026
Bessent says to adjust your paycheck withholding — but mistakes could trigger a tax bill
Read the article - CNBCOctober 2025
How expiring ACA health insurance subsidies may affect Roth conversions
Read the article - MarketWatchOctober 2025
Should I take the tax hit and withdraw my whole inherited IRA to avoid RMDs?
Read the article - MarketWatchDecember 2025
There are a few weeks left to supersize your Roth conversion without raising your tax bill
Read the article
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