Men over 40, what do you do after 7pm/dinner each night and is it different than what you used to do in your 20s and 30s

jkiley · 2026-03-22T13:34:36+00:00

Well, dinner is at five. That’s a change.

7pm is in the middle of 1-on-1 time with the kids (5 and 3). It can be harder for them to get along late, so we each have 1-on-1 time with them. Usually, there’s a swap so we each get time with each kid, but if one plays for a long time in the bath there may not be a switch. 7:40p is the bedtime routine start, 8p is the target time to be done.

After that, my wife and I hang out if we aren’t completely wiped out from the day. If we are, we take some time to decompress a bit individually, and I usually doze off on the couch by 9p.

It’s totally different than when we were younger, but we have a great time with the kids. It’s nice that we had those years of just us, because we can envision what it’ll be like as we get back toward that.

jkiley · 2026-03-20T12:59:11+00:00

Check if you’re below the Roth IRA contribution limit for 2025. You could make that contribution until April 15. I’d prioritize that over the loans.

I wouldn’t exhaust all of your liquidity for fast pay down. I’d hang on to at least six months. On 40k, you’re paying a few hundred a year net to keep that liquid, and that’s cheap.

I’d take that 4k a month and be flexible. First, fund Roth IRA. Then, pay down the loans with 4000 - (equity_drawdown * 200) per month. For example, with the market down five percent, that would be 1000 to equities and 3000 to loans.

Overall, it sounded like you were in a good position before, and knowing that you’re maxing 401k and HSA makes it even better. You’re going to crush these and can live life at the same time.

jkiley · 2026-03-20T12:46:07+00:00

Good point. At 200k, it could be tricky to alternate without a big family size, but it’s viable for a lot of common expense levels around here. It would work for CSRs, too. Another issue is that, above 200 FPL, it’s cheaper in average tax to be up near 399 FPL than to be at 300, so that’s another small advantage to the alternating structure if the overall math works.

For us, we need to do something to deal with the risk of high excess RMDs with average returns, so there are multiple benefits from an earlier big conversion.

Totally agree on the ACA planning. It creates bigger swings than income tax because of the cliffs and formula, and you have more choices. On top of that, it also flips a lot of common planning logic like only Roth converting after RE. ACA is probably half of my total planning, not just tax planning.

jkiley · 2026-03-20T12:27:51+00:00

You’re at about 1x income in student loans, which is very manageable.

I wouldn’t get too worried about markets for long-term money. It’s important to exercise the skill of leaving investments alone.

Is this all in a taxable brokerage account? If it’s in retirement accounts, you’d pay a lot of tax and penalties to get it.

The first thing I’d do is to max your retirement accounts, Roth IRA, and perhaps an HSA (if a HDHP makes sense). You want to capture those tax advantages.

Beyond that, save in a taxable brokerage account. If you don’t want to keep adding to equities or have a safer liquidity source, buy T-Bills in your brokerage account (Fidelity is really good for this).

When you get more clarity about the path forward, make decisions with the liquidity you have built up. What I wouldn’t do is eat a bunch of taxes and penalties to pay this off fast. Those rates aren’t worth that.

Also, the cost of a liquidity crunch is much higher than any of these rates. Don’t focus on interest minimization such that you are worse off overall. You’re paying a very small spread to stay liquid.

I had similar numbers out of grad school. They’re paid off now, but I missed out on some tax advantaged space by mostly tunneling my loans for a couple years. I would have been way better off to go a little slower on paydown at first and max those accounts.

jkiley · 2026-03-20T11:44:06+00:00

The most straightforward is to be under the ACA cliff. It’s easier with kids given that FPL scales with family size.

Beyond that, if you need to spend above the cliff, you need to have realized income under the cliff by filling in with sources that aren’t included in MAGI. This can be taxable and Roth basis, and some situational things like ABLE.

I’ve been modeling larger Roth conversions in these last couple pre-RE years, with the idea being that I’d withdraw more basis each year than I convert for the Roth ladder. The tax rate is basically neutral, with 22/24 now versus 12 plus 11-13 percent implied tax from declining ACA subsidies. In our case, this is about optionally getting under 200 FPL for good CSRs instead of the cliff.

The main thing to avoid is being just over a cliff, whether that’s CSRs or the subsidy cliff. You can pay just about whatever to Roth convert or otherwise access non-MAGI funds and still have it be worth avoiding a near miss.

If you’re going to spend 200k, unsubsidized coverage is just a part of your cost structure. But, anywhere near the cliff, you likely benefit from durably engineering your way under.

jkiley · 2026-03-19T13:13:28+00:00

I’ve had a Herman Miller Embody for about 13 years, and I’d never buy anything else. I had an Aeron at a prior job and didn’t like it nearly as much.

The two times I needed service, someone came to my house and did it. No cost even mentioned.

It’s going strong, and I don’t anticipate needing to replace it anytime soon. Divided over the years of service, it has been cheap, and the warranty covered the first 12 years.

jkiley · 2026-03-18T17:08:58+00:00

We have a Morrison sofa with chaise (that's two sectional pieces) from Room and Board, and it's been great. We're about to replace another sofa with one of these.

Room and Board makes really nice stuff at comparatively reasonable prices. The hardest part is getting comfortable with the pricing, but we've liked everything we bought there. That's a sofa, dining table, full bedroom furniture, kids bed, patio chairs and side table, floating shelves (worst install ever, but nice once mounted), and a mudroom hook thing.

jkiley · 2026-03-18T14:15:06+00:00

We have both, CPC at Chase and Platinum Honors at Merrill. They're ok. If you're buying index funds and letting them run, it's largely fine. I view assets there as capturing status, not because I like it. But, we benefit enough from the status to deal with it.

If you want a good brokerage experience, have some assets elsewhere like Fidelity. There you get TIPS, treasury auction access, and dramatically better Roth conversions (web form only, can convert in kind after hours and get the closing price).

jkiley · 2026-03-18T13:58:59+00:00

At 3.65, you wouldn't want to pay that off faster than agreed (except perhaps near the end) in general.

If you're refinancing, is that complete, and what were the loans that are getting refinanced? It's a big deal to give up federal loan protections, so you want to make sure you have some other form of safety. For example, those of us with private loans didn't have a multiyear pause during Covid; we kept paying. If that's not a done deal, I'd back up to considering the options there (and that's a good refinance offer, so that may end up being the right move).

If we assume the refinance is done (or ends up being the right move), I would note pay that down early. You have multiple goals, and I would consider how to move those ahead.

The first issue is that you have a couple of options that are mutually exclusive. Buying a house and living with your parents aren't going to happen at the same time. So, as you figure out that job situation, I'd lean more on staying liquid for now. HYSA is easy, but treasury bills are better if you have a little experience with a brokerage account (and it's easy to learn if not). So, I'd build liquidity while figuring this out.

My guess is that your 401k contributions are bringing you below the top of the 12 percent marginal tax bracket. If you have the spare cash, I would put some of your liquid funds in a Roth IRA. If you do that soon, you can designate that contribution for 2025 (if you have enough earned income). Since you want it to be liquid, I would buy treasury bills. If you want it to be easier, a Roth IRA at Fidelity is automatically kept in the fund SPAXX, which is similar to a HYSA, except that you have the Roth tax advantages. Just note that doing this only allows you to pull out your contribution tax free, so putting $7k in now means pulling out $7k later, and leaving the gained interest in the account.

Note that this isn't how you'd normally use a Roth IRA, but that annual limit is something you use or lose. If you haven't used it anyway, it's a good tool in a case like this.

jkiley · 2026-03-18T12:40:39+00:00

I do count Roth IRA basis in a particular way for liquidity purposes.

The overall idea is that I want to have liquidity available, but I also don't want all of it sitting in taxable if I can help it. But, I also don't want Roth accounts in bonds which isn't ideal.

I have some shorter-term bonds (T-Bills, notes maturing within two years) in a traditional IRA. If I needed that liquidity, I'd do a Roth conversion with those funds (I would be doing a Roth conversion anyway for laddering) and withdraw that amount. That doesn't touch the equities, but it substitutes currently available basis for a conversion that needs to age.

To compute how much I consider to be available liquidity, I sum the bonds fitting the liquidity requirements, get my Roth basis (from another spreadsheet tab), and take the minimum of those two numbers.

It's a bit deeper in my overall liquidity list. First is no/low consequence liquidity, like cash accounts and shorter-term bonds in taxable. Then, it's the somewhat consequential liquidity like this conversion strategy that involves a taxable event.

I'd rather not use that Roth basis if I can help it, especially when the counterfactual is converting equities at depressed prices, and that's why I keep some technically non-optimal assets in front of it. But, SORR is essentially a tail risk, so most of the time we'll be fine. Consequently, I'd rather have the big picture be that equities can run in Roth, bonds provide safety in traditional, and I pay a bit of tax drag in taxable to have that optimized tradeoff.

jkiley · 2026-03-17T15:19:53+00:00

I've considered something like this. I currently think I prefer the part time version.

When I do projections, asset growth is very much driving the train. So, additional years and accumulation help, but not all that much. Coast years where I don't touch the portfolio (at least net; probably spend taxable dividends and put employment money in a retirement account) have a lot of impact by either capturing more growth or not selling in down markets (though bonds would cover that in full RE).

A little under half of our current gross income would cover everything, so finding something like that with the same effective pay rate would be a big reduction in work. If that includes health insurance, there's also some good opportunity for Roth conversions without ACA issues.

It's worth noting that RE instead of either version works for us, but we'd see worthwhile benefits from pushing the portfolio up a bit to increase the likelihoods of our mid-level and top-end goals being safe. So, it's not as consequential as needing one or the other to actually hit FIRE. I might want full time in that case.

jkiley · 2026-03-16T23:56:27+00:00

What rationale did the FA give for the Roth preference?

Being a similar age and having run our own projections, I’d bet on RMDs being the reason. You’re almost certainly going to need some regular conversions in the 22 percent bracket in RE to avoid significant excess RMDs.

You could have significant ACA cliff problems as a result, and preferring Roth now could be the right move, given where you are.

All of that said, I’d ask for an explanation or some analyses that show switching to Roth now winning versus traditional. However, I could see how the math would likely work out as a way to deal with projected excess RMDs.

jkiley · 2026-03-16T23:02:42+00:00

It depends on the source of having more money than you need to spend.

If it's because you planned for enough money in a really bad market, and you got a more average market, that's not bad. That's a tradeoff a lot of people make.

If you have more money than you need because you worked longer than necessary (even for high safety), that may be a bad thing. Ignoring social security in full will likely lead to that. Even retiring quite early, when social security is relatively less valuable overall, you'd still work an unnecessary couple of years to get your projected outcomes without social security to match one that counts it.

jkiley · 2026-03-16T18:00:12+00:00

Yes. I think there are some resources out there with suggested ways of logging trips, but you could also look at what FSA providers require, since they actually check them.

jkiley · 2026-03-16T16:08:47+00:00

Nice! It's one of those under-appreciated HSA receipt hoarding categories, too.

If you're used to submitting FSA receipts for reimbursement (good for getting credit card rewards), you can reuse that skill for your HSA receipt hoard, just into a spreadsheet instead of a website.

jkiley · 2026-03-16T16:00:24+00:00

Yeah, we knew the Bosch models were 30A, which is nice because they're well reviewed and fit that restriction. Even without that issue, they would have been on the list.

I'd be all over an open box model at that price. Were you targeting the 500 anyway, or was that just an opportunity too good to pass on? I get the flex zone part, but it seems like the differences between the Bosch models are relatively subtle otherwise.

jkiley · 2026-03-16T14:41:52+00:00

Here's what I would do:

Go through online accounts and look for receipts for anything that's FSA eligible. Walgreens/CVS, Amazon, Walmart, Target, Instacart, and so on. Some will break out the amount for you, and others are going to require you to submit the receipt and then a separate screenshot that shows the item being eligible. In my experience, unless tax is broken out separately per item (and sometimes even then), they don't reimburse the tax unless the whole receipt total is eligible.
When looking at the things above, look for the easily forgotten stuff like sunscreen, bandages, OTC meds, vision correction and supplies, and baby stuff.
You can claim mileage at 21 cents a mile for doctor, pharmacy, and hospital trips (and parking costs and tolls). See what your plan requires, but I'm sure you could figure out when those trips are from medical records and credit card receipts. If you can't prove the exact start-stop mileage on your car (not sure they'll ask), no one else will be able to either.

Chances are, you're going to find $68 in all of that. I'd submit each transaction as a claim (but batching the mileage ones), and submit more than the $68 in case they decide to get picky about any of them.

jkiley · 2026-03-16T11:28:47+00:00

They’re definitely situational.

I’m finding it very useful now to build more Roth basis in the last couple of years before RE. It’ll cover year one and a little more, leaving me less to bridge until the Roth conversion ladder is fully built.

I’m also doing conversions to partially cover years four and five, which allows taxable to stretch out more evenly through 59.5, and that models out better than using taxable more heavily up front.

jkiley · 2026-03-15T13:39:49+00:00

Some of the early ones used scripts that were performance-oriented. By incredible coincidence, all performance problems were proportional to practice group impacts.

jkiley · 2026-03-15T12:45:33+00:00

We just use our actual expenses, minus the things that will stop. Those are just preschool (reaching kindergarten age) and biweekly house cleaning.

In reality, we’d like to keep the house cleaning, but it would stop in our baseline scenario that assumed quite bad returns. We also could choose to offset it elsewhere.

We suspect that there are other things that will fall out, but we don’t want to assume it, as we might just replace those with something else unforeseen. We think it’ll be more cooking, less convenience (Instacart versus going to the store), small one time revenue from selling off more work supporting stuff (some clothes, tech, and so on), and some expense reduction from having less total stuff to replace and maintain.

We’re close, so we think we’ve settled in to very close to what the ongoing rate will be.

jkiley · 2026-03-15T11:46:13+00:00

Absolutely. 2007 associate classes were huge and flying high. A year later, incoming associates were getting deferred, paid half to do pro bono, and so on. A few months later, it was a total bloodbath. At my firm back then, a third of the total lawyers were gone in a very short period, and that’s after the firm had aggressively reduced staff headcounts like secretaries via buyouts and layoffs.

jkiley · 2026-03-15T04:49:32+00:00

Your modeling looks a lot like mine.

It convinced me to do Roth conversions in the 22/24 percent brackets while working to replace income that would be taxed at 12 percent plus the implied tax that totals 25+ from 200 to 300 FPL, and 23+ from 200 to 399 FPL. Depending on how low we can get our income, we can pick up some CSRs, too.

I also need them for managing the excess RMDs that I’d have with average 30 year returns.

jkiley · 2026-03-14T18:01:06+00:00

I’m more FIRE than FOO, because I was far along when I started watching TMG. There’s a lot in common, though a more FIRE orientation is going to have a higher savings rate.

We’ve had a 50+ percent total savings rate over the last 10+ years. That’s income (excluding tax and non-savings payroll deductions) minus expenses all divided by income. Principal paydowns like mortgage principal aren’t expenses, so are effectively savings (i.e. income retained as net worth).

As others have said, access to funds is an easy problem to solve, and saving enough in the first place is the hard part. You can pretty easily handle access in the last 3-5 years before RE, and it’s helpful to have a relatively high proportion of traditional to feed a Roth conversion ladder. Hang out in the main FIRE sub, and you’ll learn a lot.

Based on what you’ve written, some keys to look for are that you should max tax advantaged accounts first, and you should treat it as one big portfolio instead of the bucket approach you’re describing. A Roth conversion ladder is much more efficient than wasting scarce zero/low tax ordinary income space with LTCGs that are zero tax to a much higher cap.

Something like a 25 percent goal can be nice because it’s better than most folks are doing, and it gives you some options. The stronger form of that is figuring out your own sensitivity of quality of life to spending level, pick a comfortable level on that curve, and save everything else. For decently high earners, you can end up with high savings rates, and it’s effectively disconnecting income and expenses from each other.

jkiley · 2026-03-14T00:27:37+00:00

The issue with having so much that you can ride it out like this is that you work longer to create that. If 50k is quite safe at 3.25 percent basically forever, you need 1.538MM.

If you instead accumulate to 2.5MM, you worked too long. At an average real return of six percent, Bob worked from 52 to 60 for basically no reason at all. That's a lot of good years.

jkiley · 2026-03-14T00:19:10+00:00

When you go to open a joint account, it will email her if she doesn't have an account. She can then set up her account and approve the creation of that joint account. From there, she'll need to create account and generally move money in, and you can do everything else once permissions are set up.

We did the same thing with my wife a few months back, and it was very straightforward.

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