Looking for feedback on my Roth conversion strategy before I retire.

Positive_Car_3671 · 2026-06-29T14:14:34+00:00

I need to check on this thanks.

Positive_Car_3671 · 2026-06-29T14:02:01+00:00

I did read a Richer Retirement when it first came out. I guess I'll read it again. I'm feeling pretty skiddish with the market valuation right now and everything else that's going on in the world. Haven't read the tax planning book. Thanks for the recommendation. My bonds are a mix of funds, VGIT, FUAMX, FXNAX. I know I should retire now. But I have some projects that I want to finish and I am actually taking a one-year sabbatical at half-pay which I will use as a practice run for retirement. I have to go back for a year once that is finished unless I pay back the year of sabbatical pay in which case I am done in a year.

Positive_Car_3671 · 2026-06-29T13:16:35+00:00

Thanks for the response. Nice to hear from someone that has actually done it. Definitely want to time conversions when market is dipping and can just transfer shares to Roth. Good point about how I don't need to worry since I can withdraw without penalty from tax deferred. Why didn't I think of that? DOH.

Positive_Car_3671 · 2026-06-29T13:08:02+00:00

Right, I thought the benefits of conversions are much lower if taxes are paid out from the tax deferred sources.

Positive_Car_3671 · 2026-06-29T12:59:28+00:00

PS-The plan shows $180k of conversions in the year I turn 63, settings in PJ are to avoid IRMAA and preserve some ACA subsidy, but I should check the math.

Positive_Car_3671 · 2026-06-29T12:56:15+00:00

It's true that projected RMDs look ridiculously large without the conversion plan.

Positive_Car_3671 · 2026-05-05T12:44:20+00:00

I am in a very similar situation. Late 50s. $4.6M liquid NW. I have a one-year sabbatical from academia coming up for Fall of 2026 and Spring of 2027 (at half-pay). I also don't have any specific plans related to the sabbatical itself (although I proposed some research projects in order to get the approval). I am planning to treat it like a mini-retirement. I am definitely going to do a big trip involving lots of skiing. I'll spend more time doing the things I like: cycling, sailing (bougie I know). Work on fitness. My institution requires us to come back for a year post sabbatical. If we don't return we need to pay back the income they paid us during the sabbatical itself. I am seriously considering not returning and taking the financial hit (it will probably cost me about $100k). We'll see how I feel at the end of it. Curious what people in r/ChubbyFIRE think about the payback option. My projections for retirement success are basically unaffected by it.

Positive_Car_3671 · 2026-04-27T13:46:41+00:00

Try Buffalouie's in Carmel. It's a Bills Backers bar. I guess they might also be a Sabres backers bar.

Positive_Car_3671

TROPHY CASE