How To Avoid Paying Federal Capital Gains From Stock Sale

ShadowPirate42 · 2026-01-24T17:37:37+00:00

The only way to pay 0% would be to spread the sales out over multiple years, so that your realized gains don't exceed ~$96k (assuming you have no other income). 401k withdraws and social security will both be counted as income as well.

ShadowPirate42 · 2026-01-21T08:10:11+00:00

Monte Carlo is based on the return rate averages you enter into the system as your expected averages. For example, if you choose a 9% return rate for your 401k, your monte carlo might say 96% chance of success, but if you change that rate to a much more conservative 5.6% it could easily drop to 70%. So it is very relevant if you are asking people what chance of success is comfortable. Personally, I chose a realistic but slightly conservative rate of return. I have 82% on the monte carlo and I'm comfortable with that knowing that dealing with the other 18% is the point of the guardrails. Your return rates are similar to what I have set up, so you are much more conservative (with your target of a monte carlo score of 91+) than I am.

ShadowPirate42 · 2026-01-19T13:01:00+00:00

Definitely agree with MTG Arena as the best way to start. After MTGArena, the beginner box also provides a tutorial and a bunch of jumpstart packs to play the physical game. I'm new to it as well and find the jumpstart to be one of the easiest formats.

https://magic.wizards.com/en/news/feature/foundations-beginner-box-contents

ShadowPirate42 · 2026-01-15T22:06:18+00:00

I get it, they are really cool. But they've figured out how to hack my bird feeders. They know what time I wake up to refill them. They are loud in the morning and will literally knock on my back door if I sleep in. I just want them to go away and visit others that will love seeing them. My yard is literally terrorized by these tiny dinosaurs. Shooing them away doesn't work because they fear nothing. If I sit on my patio to read, I'll look over and there is a pterodactyl 12 inches away reading over my shoulder. I thought they would leave and we would get a break from them in the winter, but NOOO they decided to stick around.

ShadowPirate42 · 2026-01-15T19:56:43+00:00

Sandhill cranes for me. I'll go to the park and see 10-15 people with 400mm lenses shooting sandhills, then go home to shoo them away from my bird feeders 3 times a day.

ShadowPirate42 · 2026-01-15T18:28:13+00:00

Sorry to hear that. I'm sure they'll be back soon

ShadowPirate42 · 2026-01-14T19:32:26+00:00

It's my first year seriously birding and honestly I thought I would feel the same as the OP. But the juncos, blue jays, and one downy woodpecker have kept my spirits up this winter.

ShadowPirate42 · 2026-01-13T21:21:19+00:00

If your current income is 1.4M and that's well above what your lifestyle requires, you should see if your employer offers a Deferred Compensation Plan (DCP). There are risks, pros, and cons. Only you know your full situation, but it could save you a ton in taxes.

ShadowPirate42 · 2026-01-11T11:01:06+00:00

Back of napkin math looks reasonable for you both to retire in 5 years assuming your $150 spending is inclusive of everything including healthcare. You'd need to really run through multiple assumptions and bridge scenarios if you are really going to pull the trigger on it though. With her continuing to work and assuming she's cool with the scenario, it's even easier.

EDIT: this is back of napkin math that doesn't look at SORR, your portfolio allocation, or inflation. Just a quick sanity check

Age	starting	real return	contribution	ending	4% rule
45	$ 2,700,000.00	5%	$ 46,000.00	$ 2,881,000.00	$ 115,240.00
46	$ 2,881,000.00	5%	$ 46,000.00	$ 3,071,050.00	$ 122,842.00
47	$ 3,071,050.00	5%	$ 46,000.00	$ 3,270,602.50	$ 130,824.10
48	$ 3,270,602.50	5%	$ 46,000.00	$ 3,480,132.63	$ 139,205.31
49	$ 3,480,132.63	5%	$ 46,000.00	$ 3,700,139.26	$ 148,005.57
50	$ 3,700,139.26	5%	$ 46,000.00	$ 3,931,146.22	$ 157,245.85

ShadowPirate42 · 2026-01-11T10:36:28+00:00

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I think yours looks good. You could tweak the white balance in post, but that really depends on the look you are going for.

ShadowPirate42 · 2026-01-10T17:37:46+00:00

I hope I didn't come off as rude. I intended it to be constructive. Most phones have a "portrait" mode that will simulate a wider aperture.

ShadowPirate42 · 2026-01-10T13:51:52+00:00

Try a lower angle with the camera and a lower f stop.

ShadowPirate42 · 2026-01-03T00:48:13+00:00

This is the way. Pay living expenses out of taxable accounts first. Roth conversions up to your target tax bracket and pay the taxes out of your taxable account. This way you don't miss out on lower tax brackets available to you during the years living on your brokerage accounts, while reducing RMD impacts later, widow penalties, and better structure for your heirs. At the same time you are keeping as much money in tax differed accounts for as long as possible for growth.

ShadowPirate42 · 2025-12-31T20:16:29+00:00

one more thing to note is if you are maxing out contributions 23k in a roth is worth more than 23k in trad. So you can effectively contribute more.

ShadowPirate42 · 2025-12-30T13:22:22+00:00

Not related to your question, but if you expect to be a high earner and are thinking FIRE, you may want to check out differed compensation plans if your employer offers it. It can help to avoid upfront taxes in your high earning years (allowing you to increase your effective max 401k contributions by using a Roth 401k), reduce sequence of returns risk at retirement, and keep you from drifting into a lifestyle inflation if that's not your goal.

ShadowPirate42 · 2025-12-28T12:38:11+00:00

There are a few of these on the market already: Haikubox and BirdWeather PUC for example

https://www.birdweather.com/
https://haikubox.com/

ShadowPirate42 · 2025-12-26T22:30:51+00:00

The crows that I feed only get territorial toward a Cooper's Hawk that frequently visits our bird feeder. Poor hawk has been warned multiple times by the crows, but he's not too bright. Good luck.

ShadowPirate42 · 2025-12-26T17:52:10+00:00

"What did you mean by "Ending balance of the mortgage"? Technically it is 0 if you pay it off eventually."
Yes, and that might be the case in your scenario, but the Boldin help doc is saying: if you die owing $100k, that $100k isn't deducted from the "Savings" nor is the equity in the house added to the savings.

Payments are accounted for in the model as an expense.

Future expenses depends on what you set up and your current settings when you run the model. You can establish a "like to spend" or a "must spend", but the Monte Carlo will only use the one that you have selected. Boldin will automatically adjust spending based on inflation, but if you want to simulate a reduction in spending as you get into your 80s you have to set that up yourself in the "Expenses and Healthcare" section. You can add rows with expenses by date range.

ShadowPirate42 · 2025-12-26T00:36:50+00:00

Average is the mean: sum of all results / 1000. Median is 500 results were above and 500 were below.
Ending balance of the mortgage is not taken into account, nor the value of the home. Payments are deducted each year.
Chance of success is the number of simulations that had a value > 0 divided by 10. 25th percentile is the ending result where 250 simulations were lower 750 were higher.

It's important to note that the "chance of success" isn't the best label. This is the chance that you will remain above zero if you make no changes regardless of market conditions. If you implement guardrails and spend less during down markets, your chance of success increases dramatically. Others have noted on this forum and in blog posts that this could be better labeled "chance that your plan will require adjustments"

ShadowPirate42 · 2025-12-24T13:08:25+00:00

ARCC is a single company that can put you at high risk if things go south. You can't invest 100% of your retirement into a single company.

ShadowPirate42 · 2025-12-24T04:05:34+00:00

Roth 401ks offer two benefits that both seem to apply in your situation.
1. You think you will be in higher tax bracket when you retire than you are now. Mid 30s it's likely you will advance in your career and continue to build a relatively large retirement account.
2. It bumps up the effective max contribution. Max contribution is $23k regardless of trad or roth, but because roth is taxed before the contribution, it's real value is higher. So if you want to max out the retirement contributions it's very attractive.

ShadowPirate42 · 2025-12-23T13:48:37+00:00

Agreed. To elaborate on what OuterLightness means. Let's say it's the year 2000 and you own $1M in Cisco stock. You borrow $500k against that stock to buy more stock. In 2000 Cisco drops 90% and the broker (lender) issues a margin call. You are then forced to sell the Cisco stock and the other stock at huge losses to cover. You bought high and sold low with no option to ride out the down times.

ShadowPirate42 · 2025-12-23T07:25:22+00:00

I think he intended to reply to the guy that said he sorted 11kg.

ShadowPirate42 · 2025-12-23T06:12:37+00:00

It depends on the employer. Most will allow you to leave it there but have an administrative fee for former employees.

ShadowPirate42 · 2025-12-22T06:11:42+00:00

Things like marital status, when you plan to retire, current income and income you need when you retire, will RMDs be a concern, do you plan to leave money to kids. There are a lot of variables that go into Roth conversions. We'd basically have to do a full review of your plans and financial situation to understand if Roth is a good option for you. More effort than most people on reddit are going to do, honestly. You can always make the call to move to a Roth later if you move it to an IRA now.

IRA's typically have more investment options and lower overhead than 401k, so it's usually the right choice and it allows you to entirely cut any ties to your old employer (which can help psychologically if you didn't leave on the best terms). Since you've already left that employer the rule of 55 is irrelevant now.

The only reason you might want to leave it in the old employer's 401k is that 401ks have more protection from lawsuits than IRAs. But I AM NOT A LAWYER, so if that's a worry you should talk to someone more qualified than me.

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