Roth conversion Archives - Page 2 of 3

Free Roth Conversion Software (It’s Live)

A while back I wrote here that I was turning my Excel model into free Roth conversion software — and that post promised “coming soon.” It’s no longer coming; it’s live and free to use. No signup, no download, no spreadsheet skills required: enter your numbers in the browser, click optimize, and a real solver plans your conversion schedule year by year.

The Roth Conversion Math: A Linear Program

This is the “show your work” post in the series. If you came for the FIRE strategy you can happily skip it; if you want the Roth conversion optimization written out as an actual linear program — decision variables, constraints, objective — this is for you. It mirrors the Excel + OpenSolver model I described in part 2.

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.