In-depth guides on Social Security, Roth conversions, retirement withdrawals, Medicare, and equity compensation — written for people doing serious retirement planning.
Why the employer match always wins, but Roth vs. traditional gets complicated once you leave the US
Why moving your former employer's pre-tax 401(k) into a Rollover IRA can retroactively tax a backdoor Roth conversion you already finished — and how the December 31 rule saves or sinks you.
How the $72,000 (2026) total 401(k) limit splits across three buckets, whether you can shift more into the after-tax bucket by deferring less pre-tax, and why that trade is usually a mistake.
Why a large existing traditional IRA balance makes backdoor Roth conversions mostly taxable — and how to fix it before you convert.
Converting cash to a Roth IRA means the full amount is ordinary income — even the part that was company stock. Here's why, and when the special NUA rules could change that.
When you have room in the 12% income bracket and the 0% capital gains bracket, which one should you fill first — a Roth conversion or realized gains?
The $24,500 deferral limit and the after-tax bucket are two separate things — here's how the full $45K can land in Roth.
How US citizens abroad can drain their pre-tax retirement accounts at little or no US tax cost — and the traps that can wreck the plan
The math behind converting a $300K traditional IRA when you're already in a high tax bracket — and when it makes sense to wait.
A framework for deciding how much to put in pre-tax vs. Roth when you're already maxing out your 401(k) — and why the answer changes as your career progresses.
You run a sole proprietorship and an LLC. Do you get two solo 401(k)s, or one shared limit? It depends on how your LLC is taxed.
Whether you overestimate or underestimate your MAGI for marketplace insurance, the subsidy reconciliation at tax time has different consequences in each direction.
A $120K gain offset by a $120K loss carryover nets to zero on Schedule D — and that zero is what flows into your MAGI for marketplace and Medicaid eligibility.
How the drastically different IRMAA thresholds for MFS filers can turn a small tax savings into a massive Medicare surcharge — and when amending to MFJ fixes it.
Two different income tests, two different answers — and why the difference matters when you claim early
The break-even math on claiming early vs. late — and why the standard 8% return argument doesn't capture the full picture for FIRE retirees.
The Social Security estimator assumes you'll keep earning until you claim. Here's how to calculate your real benefit when you stop working years before filing.
How claiming your own Social Security before FRA permanently reduces your spousal benefit — and when it still makes sense.
Why waiting to exercise foreign-startup options until the price jumps converts what could have been long-term capital gain into ordinary income — and how a Section 83(b) election changes the math.
Why AMT from an ISO exercise is a one-time hit, how the credit carries forward, and what to watch for when you eventually sell.
The 'still working' rule, why some plans say no, and smarter ways to shrink your required withdrawals
When you switch employers mid-year, the $24,500 deferral limit follows you but the match doesn't. Here's the math on front-loading, true-ups, and capturing every matching dollar across two jobs.
A retiree with a taxable brokerage account and a Roth IRA — both 100% stocks with the same mix — wants to know whether to drain the brokerage first. Usually yes, but the exceptions are where the real money is.
Why the 'basis' you see in a Schwab account isn't the basis that lowers your tax bill
How required withdrawals work when you have several traditional IRAs and one of them turns into a pension-like income stream.
The surprising math behind intentionally skipping Required Minimum Distributions when your marginal tax rate approaches 50% — and why it almost never works.
How withdrawal ordering works when your 401(k) holds both pre-tax and Roth money — and why the order you draw matters for taxes, IRMAA, and ACA subsidies.
Why inherited IRA money is taxed as ordinary income, what the 10-year rule forces you to do, and whether a lump sum beats spreading it out.