Roth conversion Archives - Page 2 of 3

How Much Should I Convert to a Roth Each Year?

This post is about a question I keep circling back to as an early retiree: how much to convert to a Roth in any given year. Not whether to convert — I’m already sold on that — but the actual dollar amount, year by year. It turns out to be a surprisingly good little optimization problem, and this is how I think about it.

Hand-drawn sketch of the IRA to Roth conversion trade-off, tax versus time — This is how it started — the sketch in my notebook, long before any spreadsheet.

The Roth Conversion Ladder (and Its Blind Spot)

If you retire before 59½ with most of your money locked in a traditional IRA or 401(k), you run into an awkward problem: the money is there, but reaching it normally means a 10% early-withdrawal penalty on top of income tax. The Roth conversion ladder is the classic FIRE workaround, and it is the setup for everything else I want to write about in this series.

The Best Time to Convert a 401(k) to a Roth IRA

If you’re asking what the best time to convert a 401(k) to a Roth IRA is, here’s the short answer: it’s not a date on the calendar, it’s a low-income year. A conversion is taxed at your marginal rate the year you do it, so the entire game is converting when that rate is as low as it will ever be. Get the timing right and you move money to the tax-free side cheaply; get it wrong and you hand the IRS more than you needed to.

In-Plan Roth Conversion: Convert Inside Your 401(k)

An in-plan Roth conversion lets you move pre-tax money in your workplace retirement account into the Roth side of that same account, without rolling it out to an IRA. You’ll also see it called a “Roth in-plan conversion” or, in IRS language, an in-plan Roth rollover. Whatever the name, the idea is the same: take traditional 401(k), 403(b), governmental 457(b), or TSP dollars, pay the tax now, and let them grow tax-free from here.

How to Convert a 529 to a Roth IRA (2026 Rules)

For years, the big worry about 529 college-savings plans was “what if my kid doesn’t use all of it?” Pull the money out for anything but education and you’d owe tax plus a 10% penalty on the earnings. SECURE 2.0 changed that. Starting in 2024, you can convert a 529 to a Roth IRA for the same beneficiary — turning leftover college money into a tax-free head start on retirement. It’s a genuinely great feature, but the fine print is strict, so let’s walk through exactly how it works.