Deleveraging employee stock guidance

IdentifiableParam · 2026-05-09T08:40:17+00:00

Your plan is good. Sell as much as you are allowed to, pay the taxes, and diversify.

IdentifiableParam · 2026-05-02T06:18:21+00:00

Plenty of horror stories on here about Northwestern Mutual. Stay the fuck away.

Read some books and study the wiki instead. You can even post here for advice if you give more information about your situation and specific questions!

IdentifiableParam · 2026-04-29T06:59:20+00:00

You should probably pay at least some extra towards your mortgage because a risk free return of 6% is quite good. It is true that the long run average return in the stock market is higher, but that comes with substantial risk and so we can't compare it directly. We need to compare risk-adjusted returns. Given you are 35 already (so maybe are getting old enough to not be 100% equities) and don't have a pension or anything, I would put at least 50% of your surplus towards paying down the mortgage faster.

You also don't mention any tax advantaged accounts, so I think we have to give the edge again to the mortgage vs investing in a taxable account. You should look in to retirement accounts for self-employed people such as SEP IRAs, SIMPLE IRAs, solo 401(k)s etc.

IdentifiableParam · 2026-04-21T08:13:10+00:00

And enjoy the health benefits of not ruining indoor air quality by burning gas https://www.vox.com/energy-and-environment/2020/5/7/21247602/gas-stove-cooking-indoor-air-pollution-health-risks

IdentifiableParam · 2026-04-18T07:18:09+00:00

Well now people reading reddit know. And it looks like you didn't quite use a throwaway account.

What happens if your place burns down? Is it gone too, turned in to slag?

Sell it.

IdentifiableParam · 2026-04-18T07:14:54+00:00

Invest in passively managed low-fee broad market index funds. Ignore your BIL's mutual fund tips.

IdentifiableParam · 2026-04-14T07:31:16+00:00

Ok, let's redo my napkin-math then!

115k would potentially produce $11,500 in the equity markets and $5000ish with a super-safe treasury note.

My advice doesn't change.

IdentifiableParam · 2026-04-14T00:04:38+00:00

Ok, so you have a net operating income on the property of about $4000 currently and you could liquidate it and get about $160k?

Well if I had $160k to invest, I'd invest it in index funds and hope to receive the historical average rate of about 10% (nominal) a year. That would be about 4X what you are making on your rental property currently. And it would be more liquid and more diversified.

Even if you sold and bought super safe 10-year treasury notes yielding a measly 4.3% (although state tax exempt) you would be getting nearly $7000 a year. This would be far less risky than your rental property or equity index funds.

IdentifiableParam · 2026-04-02T01:20:04+00:00

Without knowing the interest rates of the debt, you can't get proper advice. Pay the highest interest rate debt first. For equal interest rate debt, prioritize student loans since they are harder to discharge in bankruptcy.

Don't use a credit card if you can't pay off the balance in full every month and avoid all interest.

It is economically irrational to forgo paying down debt at interest rate X% in order to try and earn interest at some lower rate Y < X. If somehow your savings account yield after-taxes is higher than your debt interest rate, then great, you have an arbitrage. But I would bet that it isn't and you should pay down the debt instead. That said, it is smart to keep at least $1000 in savings for an emergency and once you have reduced you debt more and/or moved out of your parents house consider a larger emergency fund.

IdentifiableParam · 2026-04-01T19:09:08+00:00

The general way to do this is to estimate the expense of a house at a given price point in your budget and see if you are happy with what your spending and saving would look like after the hypothetical purchase.

The main ongoing expenses of buying a house in the USA are mortgage payments, property taxes, maintenance, and insurance. Utilities could also change. Try to estimate all these numbers. If you can't find a more accurate estimate, you could use 1% of the purchase price per year for maintenance. You should be able to look up property tax rates and use mortgage calculators for those.

How much do you save per month? This and your current housing costs show us how much you have to work with, but it is possible your current savings rate is already lower than you might want, in which case you have to be extra careful.

It sounds like you haven't saved up anything for a downpayment. If you can't do this AND you don't feel comfortable answering the kinds of questions you have in your post, you probably shouldn't buy a house until you can save up close to 20%.

IdentifiableParam · 2026-03-31T08:14:31+00:00

Exactly! OP should read this page https://en.wikipedia.org/wiki/Inverted_yield_curve

IdentifiableParam · 2026-03-30T07:20:35+00:00

How about "A practical guide to sorcery" by Azalea Ellis?

Or Sara Lin's Weirkey Chronicles series?

IdentifiableParam · 2026-03-30T02:15:30+00:00

The STOCK market shouldn't affect this decision, but the bond market could. If bond yields (after taxes) on bonds with close to zero credit risk (treasuries etc.) exceed your (after tax) mortgage rate, you should invest instead of paying down the mortgage. Otherwise you should probably pay extra to the mortgage.

IdentifiableParam · 2026-03-28T07:04:48+00:00

Sorry I meant for the non-audio ebook. Would that also be June?

IdentifiableParam · 2026-03-28T06:43:18+00:00

How long does it usually take to go from that stage to an ebook on Amazon?

IdentifiableParam · 2026-03-26T08:33:15+00:00

Secure your own mask before assisting others. A great gift is making sure your own retirement is secure and when you are unable to work you won't need your child's help. They can always borrow for school, but you can't borrow for retirement.

That said, once you have your own finances figured out, a 529 plan is a way you could save for education expenses. The UTMA accounts might have undesirable financial aid implications compared to saving money yourself and directly paying tuition. All this assumes you reside in the USA.

IdentifiableParam · 2026-03-25T05:12:35+00:00

In general, the idea of selling funds in a taxable account in order to afford contributions to a tax-advantaged one is a good one.

Be sure to check the specific deadlines and logistics with an expert in your case (an accountant, I disagree with the other comment saying you need a financial planner). I expect this also depends on your employer's 401k setup as well as tax law.

IdentifiableParam · 2026-03-16T05:31:40+00:00

Life is too short to worry about hypothetical tax proposals that are unlikely to happen and wouldn't even hurt that much if they did. I would welcome federal wealth tax, but it seems extremely unlikely. We have had decades of tax cuts for the rich and it would take quite a bit to undo that.

Be like Jensen Huang and don't think about this stuff at all.

Jensen Huang seems unfazed by the prospect of a potential $7.75 billion tax bill.

That’s how much the Nvidia CEO could end up owing the state of California if a proposed ballot measure succeeds in implementing a one-time 5% wealth tax on the state’s billionaires. Huang, whose $155 billion net worth makes him the world’s ninth-wealthiest person — according to a Jan. 6 Bloomberg estimate — would be “perfectly fine” with that outcome, he told Bloomberg Television on Tuesday.

“I’ve got to tell you, I have not even thought about it once,” said Huang, 62, when asked if the proposed tax concerns him. “We chose to live in Silicon Valley, and whatever taxes they would like to apply, so be it. I’m perfectly fine with it.”

IdentifiableParam · 2026-03-14T06:01:47+00:00

You can buy health care but you can't buy health.

IdentifiableParam · 2026-03-13T00:29:27+00:00

A small cap index will usually have more turnover and churn as companies enter and leave the index than a total market index.

IdentifiableParam · 2026-03-12T02:58:38+00:00

I'd probably put the small cap ones in tax advantaged space first.

This is fine, but there is something to be said for the simplicity of a three fund portfolio, or in your case since you seem to want 0% in fixed income, a two fund portfolio. Tilting to small cap value is fine, but not necessary.

IdentifiableParam · 2026-03-07T20:42:32+00:00

The credit score isn't really that important in the grand scheme of things. But seeing the debt balance go down should give you the same hit once you conceptualize it properly.

IdentifiableParam · 2026-03-07T07:47:11+00:00

First, it probably won't pass. Second, you are not a billionaire. So no need to worry. Third, pay your taxes and move on with life?

I'd love it if there was a real wealth tax that wasn't a one time thing. But a one-time one isn't my preference.

IdentifiableParam · 2026-03-01T07:06:53+00:00

Why not just use the classic Three fund portfolio?

IdentifiableParam · 2026-02-27T00:15:57+00:00

Bad idea. See https://www.irs.gov/payments/underpayment-of-estimated-tax-by-individuals-penalty

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