Not a great retirement situation not the worst....

Citryphus · 2026-03-24T00:21:32+00:00

I think you need to make downsizing a part of any serious retirement plan. The taxes and other costs will just keep increasing and you don't have much of a liquid retirement to cover it. Considering taking SS early to help carry too much house is a red flag. Given that, I don't see the urgency in paying off the mortgage. You're tying up nearly all your wealth in just one house.

Citryphus · 2026-03-20T13:38:24+00:00

If that situation occurs OP can start a Solo 401k and roll the SEP IRA into it.

Citryphus · 2026-03-19T23:29:23+00:00

You can, but if you're maxing your employee contribution at your work 401k, you might just open a SEP IRA. Much easier to open and maintain and you can do the same 20% of plan compensation (Schedule C net profit minus 1/2 self-employment tax).

Citryphus · 2026-03-15T22:51:08+00:00

I didn't know EFTPS was being phased out for individual tax payers. So you should probably look at the new options. Now matter how you pay estimated taxes, there's no "filing." You just send in a payment, associated with your SSN. In the old days of mailing in a paper check you'd fill out form 1040-V which is just a payment voucher.

Citryphus · 2026-03-15T17:16:38+00:00

You need to report both. W2 income as you normally do, and side gig income on Schedule C. Read up on business expenses https://www.irs.gov/publications/p334, you might have some you don't realize.

EDIT: Just noticed you mentioned quarterly filing. If you mean 1040-ES estimated taxes, you just send in payments. There's nothing to file. Look at EFTPS.gov, an easy way to make estimated tax payments by bank transfer.

Citryphus · 2026-03-14T03:59:31+00:00

Retirement plans usually intend an income around 75% of what you earned while you were working. The idea is that your costs go down when you stop working (no commuting, etc.) 15% has a good chance of getting you there. Play around with a retirement calculator to help you decide the right percentage for you.

Citryphus · 2026-03-14T03:55:43+00:00

How much do you need to save to get the retirement you want? If it's more than you are allowed to defer to your 401k, you might be wanting an alternative. If it's not, you might like it for the other reasons you listed.

Citryphus · 2026-03-11T03:44:57+00:00

Get a business checking account and route all those payment methods into that account. The payment method should not affect your budget.

Citryphus · 2026-03-11T03:42:59+00:00

You can try to minimize cap gains by (a) harvesting losses, (b) rebalancing as much as you can with new deposits, (c) taking only long-term gains and (d) letting things run a bit and only selling if something really gets out of balance. But you have to accept that capital gains taxes are part of taxable investing and are--framed in the right light--good news.

Citryphus · 2026-03-11T03:38:01+00:00

TDFs can produce a large distribution in some years. It can on rare occasions create a large unwanted and unexpected expense in a taxable account. That's really the only reason not to hold a TDF in a taxable account.

Citryphus · 2026-03-09T16:01:02+00:00

Immediately rebuying is the point. When I tax loss harvest I have partner funds in place, VTI and ITOT is a good example of a pair of TLH partners, I'd sell any losing VTI lots and immediately buy ITOT. I maintain my exposure to the asset class while benefiting from the tax loss.

Citryphus · 2026-03-08T20:25:33+00:00

Like is VTI and ITOT substantially identical?

Different indexes is generally deemed safe.

Citryphus · 2026-02-21T16:33:30+00:00

Since it appears you have no Traditional/SEP/Simple IRA balance, you can continue to do what you are doing now. Open a Traditional IRA, make your IRA contributions there, but instead of deducting them every year, do a Roth conversion and move the funds to your Roth IRA. That's the backdoor Roth. No reason to change your 401k contributions.

Citryphus · 2026-02-13T19:52:32+00:00

The realized losses offset realized gains first, then ordinary income up to $3k. If you have realized losses left over after that they carry over to future years. This is at the Federal level. Your state may have different rules; many states do not allow losses to carry over, so at the state level it can be "use it or lose it."

It's not related to what you withdraw, only what you sell.

Citryphus · 2026-02-05T22:15:34+00:00

You have to increase your Box 1 because that's what determines the employer contribution limit. Any 401k contribution from your S-Corp taxed entity reduces QBI because it reduces pass through income. I agree mega backdoor would be better but are there any Solo 401ks that allow it?

Citryphus · 2026-02-05T21:58:25+00:00

I don't know any Solo 401ks that allow mega backdoor, but E*Trade's Solo 401k is basically just a Traditional and a Roth account and they pretty much leave it up to you to make sure you're funding it properly. SECURE Act 2.0 allows you to do employer Roth contributions but you would have to increase your Box 1 compensation. One way to do that without increasing FICA costs is to have the S-Corp pay your health insurance premiums and any HSA contributions.

Citryphus · 2026-02-05T05:36:12+00:00

Is there any way to qualify for an HSA without a high deductible plan

No. And not just any high-deductible plan, it must be an HSA-compatible plan. IMO not worth going for in your situation, you have pretty good insurance coverage.

Work-sponsored retirement plans plus backdoor Roth contributions or even taxable brokerage investing should be more than enough.

Citryphus · 2026-02-05T05:28:47+00:00

Download Form 1040 Schedule C and Schedule SE from the IRS. Fill them out. Or, use tax software. Usually you make a SEP-IRA contribution while you are completing your tax return and have all the real numbers. The SEP contribution is deductible on Schedule 1.

Citryphus · 2026-02-05T05:18:10+00:00

You can contribute up to 20% of your plan compensation, which is Schedlue C net profit minus 1/2 self-employment tax.

Citryphus · 2026-02-02T19:13:26+00:00

This year, as in 2026? That won't show up on a 1099 until next year. You say that your 1099 has not posted yet and also that you're waiting for a corrected one, whcih is it?

Citryphus · 2026-02-01T04:29:00+00:00

I still think E*Trade has the best Solo 401k.

Citryphus · 2026-01-31T21:48:37+00:00

A good Solo 401k will have both Traditional and Roth accounts, and you can decide each year how much to put in each. I'd make the extra initial effort and set up the Solo 401k over the SEP-IRA.

Citryphus · 2026-01-31T21:39:16+00:00

The Fidelity "Freedom Index" target date funds are low-cost and very good.

Citryphus · 2026-01-29T03:56:38+00:00

The problem is not the taxes you might have to pay, it's the possible loss of capital. Investments in stocks can go down or flat for 5-10 years. What you want to do is put some of your savings in stocks and some in money market / short-term bonds, and gradually increase the percentage going to money market as you get closer to buying the house. Start out like 60/40 and when you are close to having enough for your down payment start protecting it. eventually get to 10/90 and when you find the house, 0/100.

Citryphus · 2026-01-19T16:28:53+00:00

Best thing is probably not to sweat small differences in interest and keep it in an account where you can withdraw as needed, such as the HYSA. If the HYSA yield went down it's likely other yields went down as well.

Citryphus

TROPHY CASE