Free Optimization Tools from an OR Analyst

Convert a Traditional IRA to Roth Without Paying Taxes?

People email me a version of the same hopeful question: how do I convert my traditional IRA to a Roth without paying taxes? I get why they ask. A Roth conversion lands a tax bill in the same year, and nobody enjoys writing the IRS a check for moving their own money from one pocket to another. So let me give you the honest answer first, and then the part that actually helps — the move that gets you as close to “tax-free” as the law allows.

Continue reading “Convert a Traditional IRA to Roth Without Paying Taxes?”

When Does a Roth Conversion Make Sense? What the Math Says

I spent the last stretch building a tool that answers one question I get asked constantly in the FIRE world: how much of my traditional IRA should I convert to a Roth each year? Put another way: when does a Roth conversion make sense, and how much should you do? The tool runs a real optimization model, not a rule of thumb, and the interesting part is that once I started feeding it realistic numbers, the math kept repeating the same handful of lessons. Here they are, in plain English.

Quick disclaimer up front: I’m an operations-research guy, not your accountant. This is what the model showed me, not advice for your situation. Talk to a tax professional before you act on any of it.

Building a Roth Conversion Optimizer: Lessons Learned

This is the third model I’ve pulled out of a spreadsheet and rebuilt as a web app, after the staff scheduler and the vehicle router. Going in, I assumed the optimization would be the hard part. It wasn’t. The solver finished in under a second every single time. The hard part was trusting what it told me — and the lessons that came out of that are the ones I keep coming back to.

Here’s what building a Roth conversion optimizer actually taught me. Not about Roth conversions — that’s a separate post — but about the craft of turning a twenty-year-old model into something other people can trust.

Roth conversion optimizer web app interface

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.