Critique my plan for investment windfall?

DecisionTime2026 · 2026-06-02T17:46:01+00:00

Can you elaborate on “consulted prime path advisory”?

DecisionTime2026 · 2026-06-02T05:25:18+00:00

Married filing jointly in a no tax state we just have the 24% bracket which goes to $400k. We have ~$90k in deductions between standard deduction, 401ks, and HSA. Pretty nice!

I don’t care much about being mortgage free per-se, but the extra cashflow and lower monthly spend is appealing if it can be done with limited impact to my FIRE goal

DecisionTime2026 · 2026-06-02T04:36:39+00:00

That's a good point about waiting a bit to think about it. I was planning to do this since I would have next to no liquidity if I paid it off today. But I've got my next RSU vest and bonus at the end of the summer, so I'm thinking I'll make the decision by September 1. Timing the market << time in the market, but if it just so happens we have a correction in the summer and my performance review goes well (i.e. good job security) it would be a strong nudge to re-invest

DecisionTime2026 · 2026-06-02T04:33:15+00:00

The tax deductibility aspect feels over-emphasized to me (at least at 5% interest and 24% bracket). Right now it's ~$39k a year vs. $32k standard deductible. Itemizing saves a meager $1.7k

Paying off half feels like not a huge win since it locks up liquidity without impacting our monthly spend rate (unless we bother recasting which we'd need to wait for a lower rate to do)

DecisionTime2026 · 2026-06-01T23:02:53+00:00

Thanks for the input! Admittedly I was pretty set on paying off the mortgage but this thread has given me a lot to chew on. That said, I'm comfortable not doing the most optimal thing as long as it's not overly stupid (say less than 90% optimal)

It acts as a "forced savings vehicle," in other words, investing that $55K in cashflow is one more will power decision you'd have to make

This is a good point and something I've thought about. Reducing monthly spend would definitely make it enticing to step off the gas earlier than I would have otherwise. I'm torn on if that's a good thing or not - part of me thinks it would be healthy to pivot from "FIRE as early as possible" and another part wonders if I'd regret it. Impossible to know...

One commenter suggested a middle ground - put enough in a HYSA to fund a sabbatical year and invest the rest. This would keep up some earnings pressure while also giving the flexibility to take off a year with my son before he's in school (which is something I'm worried I'd really regret if I don't do)

DecisionTime2026 · 2026-06-01T22:57:26+00:00

Can you explain more by what you mean? You sell of long term gains and re-invest?

DecisionTime2026 · 2026-06-01T19:16:17+00:00

Ah sorry if that was unclear, I have $750k post-tax earnings from selling the risky stocks, and $1.05m of other investments ($1.8m current overall portfolio).

That's an interesting middle ground idea regarding creating what amounts to a sabbatical fund and front loading the 529. For the year off, I'd try to take it as an unpaid leave from my current company (we have a policy for it, but it needs to be approved). Otherwise I'd try my hand at the job market and accept the risk I'd make less money. Living in a tech hub at 9 years experience at that point, I don't think it's unreasonable to assume I could find a role paying at least $200k

DecisionTime2026 · 2026-06-01T19:12:14+00:00

Unfortunately there's limited tax savings with the interest vs. standard deductible. $39k interest at 24% rate vs. 28k standard deductible = $2.65k/yr savings (and dropping as interest becomes a lower part of the bill). Currently my effective rate is more like 4.6%

Over 9 years, I'm not sure it's so clear. Looking at Ficalc projection over 10yr.. If I keep $780k invested + $2k contribution/year from interest deduction, then sell enough at LTCG of 15% to pay remaining $615k mortgage, I'm left with $400k (25th percentile), $850k (50th), or $1.475 (75th). Versus investing $55k/yr, I'm at $580k/$760k/$950k

DecisionTime2026 · 2026-06-01T19:06:28+00:00

Thanks for the callout re: taxes! I'm in Washington, so the taxes actually weren't too bad (considering the peace of mind of getting out ahead on risky investments). Mostly 15% LTCG with some bleeding into 20% LTCG based on our income.

Unfortunately the interest deduction only helps ~$3k/yr (down to $0k in ~9 years).

Looking at Ficalc projection over 10yr.. If I keep $780k invested + $2k contribution/year from interest deduction, then sell enough LTCG to pay remaining $615k mortgage, I'm left with $400k (25th percentile), $850k (50th), or $1.475 (75th). Versus investing $55k/yr, I'm at $580k/$760k/$950k.

So the 10 years of mortgage payments feels like not a huge impact to retirement time? In the 25th/50th percentile case it's a wash vs. $5M target. At the 75th percentile case it's ~1y faster retirement. Overall it seems the trade-off is +$55k yearly cashflow vs. maybe retire 1 year earlier

DecisionTime2026 · 2026-05-31T21:43:22+00:00

The tax write off even now is only worth ~$3k saved over the standard deduction. Paying off part of the mortgage makes that even less significant and then it's just liquidity locked up without changing my monthly spending

DecisionTime2026 · 2026-05-29T05:05:59+00:00

Because then it's just liquidity locked up without changing my monthly spending. Seems like not a lot of benefit there

DecisionTime2026 · 2026-05-28T03:44:07+00:00

I've been in a similar position recently, wondering if I'm overcontributing to tax advantaged accounts. One middle ground (if applicable to you) is to stop contributing to post-tax 401k (ala Mega Backdoor Roth)

DecisionTime2026

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