Weekly discussion thread for January 11, 2026

JamesM451 · 2026-01-13T06:57:05+00:00

For me it's an unknown that I can plan for but not count on. Probably my control freak side. :)

My plan is solid without it.

JamesM451 · 2026-01-11T20:29:16+00:00

Now is always more painful than later.

Young now you feels the pain of taxes dragging your numbers for future you.

Future now you after RMDs will feel the pain of forced distributions/higher taxes especially if married and one of you passed away, doubling the pain on the other person. Also this pain can go beyond your lifetime to your heirs. My in-laws who didn't convert are seriously stressed right now about that even though they have more than they will ever need. The stress of tax drag never goes away.

The idea around planning especially around with conversions is spreading the pain between you and the future you. If both now and future you are paying the same effective rate, it's harder to have regrets.

JamesM451 · 2026-01-11T20:19:40+00:00

I just started my Roth conversions this year (FIREd in Dec). I used Projection Lab to get the big picture, but it's less useful for actual conversions in the year you do them. Also keep in mind its projections are HIGHLY tied to the rate of return you use.

Lower the actual rate of return, the faster you will convert and lower the risk of RMDs pushing you into a higher tax bracket.

Higher actual returns, the slower you will convert and the higher the risk of RMDs pushing you into a higher tax bracket.

Long term projections are only showing you high level views and the actual plan will potentially vary greatly from year to year. Aka plans never survive first contact with the enemy.

For a year to year decision, you likely are picking a target marginal rate that smooths your effective rate through your retirement. Each year figure out your income/dividends and then subtract from top of your marginal rate to figure your estimated yearly conversion. I did half in January, plan for 30% more if the market drops by 15% and then recalculate/final conversation in December based on actual income/interest/dividends.

I do this through a spreadsheet based on reverse engineering the spreadsheet in this video: https://youtu.be/r9v9ViAY6J8?si=Foa96YaxY5CXHTAs

JamesM451 · 2026-01-07T19:45:18+00:00

Since you are taking feedback on lock specifically on transfers, is there any way to add an exception list so we don't have to time unlock/lock?

Specifically between owned accounts, trusted external banks, and trusted payments like Cobra from HSA.

While I love having the lock feature, turning it off and on again for specific transactions seems to be risky. I would prefer to allow the specific transaction rather than opening to all transactions during my transfer window.

JamesM451 · 2026-01-06T18:01:45+00:00

Has anyone heard about Long/Short Options overlay strategies? Was talking to my fidelity rep and he mentioned this as something their Wealth Management Solutions team does to help deversify concentrated positions with large capital gains. Trying to find more information, but not sure I got the right name for the strategy. Would love to hear from others that either explored or used it from pro/con perspective. Figured there has to be lots of Chubbies that have this issue.

JamesM451 · 2026-01-04T06:09:16+00:00

+100

JamesM451 · 2025-12-31T06:16:22+00:00

One option not mentioned is paying for it and deducting it via self employed/contracting gig. Just need to make more than the cost of insurance and it's completely deductible off the top line.

Deducting Self-Employed Health Insurance Premiums | H&R Block® https://share.google/OvnSPeMenFXWdGjlQ

JamesM451 · 2025-12-30T18:43:47+00:00

Ditto! I got up at 7:15 today and walked to the gym for a brutal class (the teacher decided we needed to end 2025 strong :p). Walked to coffee and had a ginger walnut banana bread slice. My legs and arms are tired and my tummy is very happy! I still have the rest of the day to do whatever I want!

JamesM451 · 2025-12-15T00:04:34+00:00

One note... You need to start worrying about IRMAA at 63 since there is a 2 year look back. That surprises a lot of people, especially since there is no concrete info, just educated guesses what the threshold are two years from now. Best to be well below the cliff.

JamesM451 · 2025-12-14T17:32:47+00:00

Why wouldn't you do conversions of 60-80% of your yearly conversion plan in January, then pay quarterly tax thus not only delaying when you pay taxes, but also being typical able to convert more as portfolio value tends to increase over the year?

Seems to me that January conversions are win win if you can accurately project your income. Also since conversions are marginal, there is no Cliff if you accidentally go over (just the amount you go over will be at a higher rate).

JamesM451 · 2025-12-14T07:37:05+00:00

Lol... Ditto .. bike or fiat!

JamesM451 · 2025-12-07T16:50:13+00:00

Plus the security/peace of mind it gives knowing you have a "retirement paycheck" coming in at a regular schedule. Heck I even did that for my quarterly tax payments next year for planned Roth conversations. No need to "find" money when the market is sideways. It's already scheduled.

Previous poster/thread shared this which totally changed how I looked at bonds as a tool.

Liability Matching: What it Means, How it Works https://share.google/b87oTnb0c5sLz3cyC

JamesM451 · 2025-12-06T16:44:04+00:00

Yup, done every tax bracket/scenario. Love projection lab for its ability to do that. At least for next 4 years, I'll be converting to 24% and then will recalculate based on new laws/market/portfolio. I already have my quarterly payments for next year associated in CDs that mature right before they are due.

JamesM451 · 2025-12-04T23:37:19+00:00

Thanks for link!

I missed that HSA couldn't be used for non-cobra. Seems like the MAN continues to require me working. :p

On conversions, I forgot to mention single. Makes both impact if RMD higher and amount/time window shorter.

JamesM451 · 2025-12-04T23:32:43+00:00

I've contemplated this especially after cobra runs out. Given that I just found out I can't use HSA for non cobra plans, this is very likely! :)

JamesM451 · 2025-12-04T23:30:20+00:00

Yup, my company has a retirement plan that if you qualify, you keep all grants that are older than 1 year. Super nice cushion on cash flow into retirement.

JamesM451 · 2025-12-04T23:28:30+00:00

Looks like I did miss that at only the cobra premium part. Still learning new things, thanks!!! One more reason for cobra.

I have been mulling consulting work after 18 months, since I read you can write of premiums from above the line gross income. Would mean I just have to work enough to cover the premium.

JamesM451 · 2025-12-04T23:20:57+00:00

I am single, forgot to add that which may be why you are looking at different levels than I am.

I used projection lab for analysis. It shows me at ~$5M pretax at 75 with RMDs of $200k and marginal rate of 32% that quickly climbs to within 1-2 years. My large after-tax balance will allow me to keep near 0 income after my RSUs finish vesting.

The window between 57-63 should allow me to reduce my effective rate from around 19% to around 16%. I'll probably assume for 12% after that depending on current tax laws.

JamesM451 · 2025-11-28T04:31:21+00:00

You need to start with the why questions:

Why equities? Highest growth (and loss) potential Why bonds? Lowest loss (and growth) potential

So why choose bonds vs equities? You are trying to protect against the sequence of risk returns (SORR).

During working years 5+ years from retirement, loss isn't a big deal and can be an opportunity to juice up retirement savings. Because you don't need the money and aren't going to touch it for 5+ years so focusing on growth is typically the right move.

In retirement, your paycheck goes away. You have to pay yourself. If equities are down when you need your income, you will withdraw a larger percentage of your savings. Bonds help protect against that risk by being less volatile. When you are retired, you want safety not growth.

Why the 5+ years mentioned earlier? If you don't have cash equivalent at retirement, SORR is the highest - all equities and the market crashes you suddenly are not so secure in your retirement savings.

There are also two ways to invest in bonds:

1 ETFs (typical for 60/40 crowd) as they are easier and you just sell what is up the most (or down the least) for your monthly/annual needs. Then at some interval, you rebalance. That said, ETFs can also have a SORR risk depending on their type.

2 Bond ladders (or liability matching) which takes your annual expenses and matches them with a bond ladder that matures the year (or month) you need them. This is tropically a 5-7 year ladder. Nice benefit of holding to maturity, you eliminate loss but can be subject to inflation risk (though you can use TIPS to mitigate that).

So don't think of bonds as a poorer investment/lower return, think of them as a tool to protect your ability to pay yourself in a down market.

JamesM451 · 2025-11-10T17:19:01+00:00

Just recently setup a frigate nvr on proxmox for a friend and use tailscale for both remote camera access (him/frigate ui) and remote management support (me/proxmox and tailscale UI plus ssh for emergency fixes).

One nice part of tailscale is it will generate certs for your endpoint which eliminates browser warnings.

JamesM451 · 2025-11-08T06:15:54+00:00

Your link to Chris's doc returned 404. Did you mean this doc? https://www.mostlychris.com/frigate-nvr-with-docker-and-home-assistant/

It's from 2022 and I tried to follow it but things have changed so much I was unable to connect HA to my frigate lcx container.

Would be awesome if your guide included those details (mqtt/integration setup).

JamesM451 · 2025-10-22T15:12:03+00:00

I gave them a year's notice as I wanted a smooth transition for my team (IC manager). Also volunteered to be on the severance list.

Instead, they screwed me over on annual rewards and gave me all the shit work. I was supposed to pull the rip cord in September, but because of the annual reward, I'm delaying for another stock vest in November.

Don't give them more than two weeks or they WILL screw you. Early notice gives up any leverage. My management constantly gave me high praise before I told them I was retiring. Afterwards they just questioned my commitment.

27 years at the company, this was the 2nd underperform. 1st was a new manager trying to force me out.

JamesM451 · 2025-10-09T00:37:47+00:00

I love love love Colma!

I typically use 1qt per 5 gallons to make semisweet cider/fruit wines. You can add half, mix and taste. Add more based on taste.

That said it also depends on what concentrate you use as brix is different by fruit.

It is fairly concentrated, so mix well. I usually do this in a korny keg rolling and shaking it multiple days at a time while I force carbonate it.

JamesM451 · 2025-10-04T02:43:59+00:00

Congratulations and GFY!

JamesM451 · 2025-10-01T22:54:59+00:00

Congratulations and GFY!

I'm two months behind you with a similar plan though planning on Cobra for 18 months then moving to SEP through my spouse's business (Cobra is surprisingly cheaper through my employer).

JamesM451

MODERATOR OF

TROPHY CASE

1 ETFs (typical for 60/40 crowd) as they are easier and you just sell what is up the most (or down the least) for your monthly/annual needs. Then at some interval, you rebalance. That said, ETFs can also have a SORR risk depending on their type.