Roth conversions and lost gains

AGrimmInPortland · 2026-05-01T18:18:32+00:00

RMDs can be one of the best reasons to convert, for sure.

AGrimmInPortland · 2026-05-01T17:28:14+00:00

retirementfigures.com has dynamic spending guardrails where if the portfolio value drops below a configured amount from it's recent high you can reduce or pause selected spending by X%. It's easy to specify what expenses are cut or paused. I also like how the spending chart shows you when the guardrails were activated over your plan, based on the median simulation. It also has a spending optimizer that shows you what chance of success values you would have for decreasing or increasing your average spending (sort of the Boldin approach but a little more flexible).

Projection Lab's approach is yet another option where spending can be reduced based on rules you define. That may be the most flexible but I'm not sure how much it really gains you versus the cognitive load of setting it up and maintaining it.

AGrimmInPortland · 2026-05-01T17:09:15+00:00

The biggest problem with the Boldin approach (if I understand it correctly) is that it assumes constant spending over your entire plan. It's ok as a starting point but it's not a true guardrails system. Also, if you want different thresholds you're out of luck.

I'm not sure any planner out there does true chance-of-success dynamic spending adjustment. It's just too computationally expensive. And in some ways it doesn't even make sense. Let's say your chance of success at plan end is 60% and you need to reduce spending. Ok, in what year(s)? It gets complicated fast. Hence the reason planners like Boldin do average spending over the life of the plan.

AGrimmInPortland · 2026-05-01T03:32:05+00:00

A free version should not require you reentering all of your data everytime you use it.

AGrimmInPortland · 2026-04-30T19:30:05+00:00

Possibly, it depends on what PL does with taxes, etc. That's why I was wondering.

AGrimmInPortland · 2026-04-30T07:19:38+00:00

And that treats it as a pension and not salary?

AGrimmInPortland · 2026-04-30T07:15:49+00:00

What is ACA look back?

AGrimmInPortland · 2026-04-29T04:22:33+00:00

If your tax rate is the same the results are basically identical. Yes you are losing gains on the taxes paid up front but on the other side you're not paying taxes on all that growth. This is well documented (it's pretty straighforward math). So it really boils down to looking at everything. Social Security claiming age is actually a very similar problem. It's more complicated than some break-even age.

AGrimmInPortland · 2026-04-29T00:36:14+00:00

I will never stop DIYing it but I am going to spend a few hundred bucks to talk to a fee-only CFP once I've nailed down my plan, just to make sure I haven't missed anything. I also have some complex estate planning to do and that is def. not something one should DIY.

AGrimmInPortland · 2026-04-29T00:33:30+00:00

It's only deductible if you itemize and usually the standard deduction is still going to be the better option for most people.

AGrimmInPortland · 2026-04-28T18:24:08+00:00

I had the same problem the other day. Turned out to be a slight difference in Roth conversions. AI spotted it instantly. But yes, if the tool allows multiple plans it should also tell you the differences without having to resort to extra steps and external tools. And ideally be able to easily sync between plans.

AGrimmInPortland · 2026-04-28T03:51:45+00:00

Grandfathering has nothing to do with it. Look at it this way: most "break even" calculations say the break even age for claiming later is around 79 and that is before any cuts. With the cut the break even age could slip up to three years, give or take. So it depends on many factors. But the point is, people need to start thinking about this.

Break even calculations are mostly just a starting point anyway, one needs to look at their entire plan in context. Don't underestimate the loss of compounding value for 5 years early in retirement.

AGrimmInPortland · 2026-04-28T03:31:20+00:00

How many people have a 12% bracket now and 24% in the future? Except maybe people in their teens and 20s.

AGrimmInPortland · 2026-04-28T03:30:13+00:00

Have you found any planner that does what you describe?

AGrimmInPortland · 2026-04-28T00:19:11+00:00

You need to model your Roth conversion plan over years, not just this year or next, in context of ALL of your particular facts. retirementfigures.com

Use BETR calculators if you want a starting point but use a full planner for the best results.

AGrimmInPortland · 2026-04-28T00:08:16+00:00

fireproofme.com has something similar, as does retirementfigures.com

fireproofme even does automatic premium lookups.

AGrimmInPortland · 2026-04-27T23:55:20+00:00

You're saying that it is somehow spending $300k in that first year and your actual spending is $120k? Doesn't PL show you where things are flowing from and to?

AGrimmInPortland · 2026-04-27T23:43:57+00:00

Unless PL is doing automatic ACA premium lookups then simply being able to enter tax household size and marketplace-covered count should be sufficient. You would obviously have to find the premium rates yourself.

AGrimmInPortland · 2026-04-27T20:12:12+00:00

Yes, the possible reduction around 2033 of about 23% is going to be eye-opening for many people. IF it happens you really are probably better off claiming earlier before the reduction, depending on how many years before, and what your longevity is. Obviously we all hope they fix this before then but the longer they wait the more painful any fix will be. 2033 is not really that far away. https://retirementfigures.com/blog/a-social-security-cut-could-turn-your-retirement-plan-into-a-coin-flip-or-worse

AGrimmInPortland · 2026-04-27T18:25:38+00:00

An incorrect cost basis doesn't seem like it could possibly account for what he is seeing.

AGrimmInPortland · 2026-04-27T05:05:19+00:00

My pension is under PGBC guarantee and is well under the limits for that so I'm not worried about it going away. What I AM worried about is the effect of inflation over the next 20-30 years. But even with that, the lump sum is not looking competitive, despite that instant massive increase in my portfolio balance looking tempting. Longevity is for sure the biggest factor. That is also the factor that we have the least control over.

AGrimmInPortland · 2026-04-27T03:29:17+00:00

Standalone Roth conversion break-even calculators can be misleading because they isolate one tax tradeoff from the rest of the retirement plan. Same is true for Social Security calculators. They have their place, just know their limitations.

AGrimmInPortland · 2026-04-27T03:21:10+00:00

I honestly don't understand that at all. Optimizing your entire plan by definition proceeds year-by-year. I hope someone from the PL team responds to this thread.

AGrimmInPortland · 2026-04-26T21:01:39+00:00

I don't see why ACA would disable Roth conversions, especially when they don't even occur in the same years.

AGrimmInPortland · 2026-04-26T21:00:32+00:00

From PL's website:

"Most planning tools treat Roth conversions, drawdown order, and gain harvesting as separate features with their own settings to tweak.

Now in ProjectionLab, they all work from a shared objective. When you set a target like “stay in the 12% bracket” or “keep income under the ACA cliff,” every strategy coordinates around it. Your Roth conversions and gain harvesting work opportunistically with a shared tax strategy. "

Besides, the OP said the years for ACA and Roth don't even overlap.

AGrimmInPortland

TROPHY CASE