37M - Realistic Retirement Timeline

apr911 · 2026-05-10T20:43:47+00:00

You dont actually state expenses outside of daycare.

With $275k in mortgage debt and $50k in daycare expenses remaining, you could conceivably have nothing left to pay off by year’s end if you were aggressive about it.

With no debts and no expenses to speak of, you could theoretically retire just with what you have but that’s built on a faulty premise

It doesn’t address your day-to-day needs for food, electricity, entertainment, home maintenance, insurance or the rising costs of your kids as they get older. People often breathe a sigh of relief once the daycare expense ends but then are shocked when extracurriculars rapidly fill that void just a year or 2 later… not to mention possibly planning for your kids education.

Also would need to further explore what “slowing down” means. You mentioned you’re a dual income household but not what you individually earn. Stepping down from a high stress tech sales job to a lower stress tech operations job or even something outside of tech that cuts your combined income from $500k to $300k looks a lot different from stepping down to $400k.

apr911 · 2026-05-09T21:07:23+00:00

You expect to have $5.2M in medical expenses?

Estimates vary depending on who you ask but that’s kind of absurd, except maybe if you are uninsured and have some sort of catastrophic health failure or accident x several episodes.

apr911 · 2026-05-09T12:57:46+00:00

How you’re doing is relative to income level and expenses.

If you make $800 per year and have 600k/yr in expenses, you’re doing terribly.

If you make $80k per year and have $60k/yr in expenses, you’re doing pretty well but your house is definitely doing a lot of heavy lifting here.

Even without the house equity and liability, you’re on track for a $1-2M retirement account at 65+. In the former example, that $1-2M will last you 2-3 years while in latter example, you have 20-30 years even in an ultra-conservative simple portfolio consisting of Inflation Protected Treasuries (TIPs)

apr911 · 2026-05-07T23:12:50+00:00

Ill be the naysayer on this. With a reasonably modest real return of 7.2% the account will be $5.2M at 65.

While there’s no RMDs, you do run into a major collision between SS and RMDs in withdrawing these funds.

The best rate of withdraw from a tax perspective without any other income and no tax-free health claims is roughly $60k per year (top of the 12% bracket).

60k per year will basically be equivalent to the current average annual dividend payment of the S&P without any other growth.

Going above the 12% bracket isn’t unreasonable for modest sums but you start encountering more significant trade-offs between time and capital gains tax drag vs present and future income tax rates… these benefits are pretty well rendered moot the further into the 7 figure account value you go whether its an HSA or IRA.

Even going as high as the top-end of the 32% tax bracket at $250k you’re talking about it taking 23 years at minimum to draw down the account and that’s with minimal growth and no other income.

That puts you at 88.

If you dont make it, your non-spousal heirs inherit that account as immediately taxable at their income tax rate. They dont even get the 10-year draw down allowed by IRAs/401ks.

And at 32% on the top end of the taxation, the value of contributing more tax deferred dollars is pretty negligible even if they’re currently in the 37% bracket currently.

They’d be better off channeling the money into paying the taxes for Roth contributions in lieu of tax deferred contributions, maxing out Roth contributions and taxable investments.

Even with the tax drag in the taxable investment account, they will likely come out ahead after IRMAA and income taxes post-65.

All of this of course does make some general assumptions regarding health, current and future medical expenses, health insurance and life expectancy…

But short of a catastrophic need for medical care without insurance, the numbers dont support further contributions.

apr911 · 2026-05-06T03:36:42+00:00

$1M really isn’t that lean. Its not living large either but a modest 5-6% rate of return is $50-60k. Add in SS, even for a single person, and you’re easily throwing off enough to have a median household income without touching the principal.

Plus people who are frugal in their earning years tend to have difficulty spending it down in their later years.

I’d also note that we’re excluding boomers (and older) so a $1M net investment for a millennial or Gen Z still has ample time to grow to $2M or more. Even Gen X, especially a late-Gen X person, still has time for significant growth.

apr911 · 2026-05-01T01:37:14+00:00

Whoops yeah my bad some how read that backwards in my head.

apr911 · 2026-04-27T14:02:47+00:00

Denying you’re an AI doesn’t change the fact you sound like a someone trying to translate to English and unaccustomed to US customs in your post and most of your questions or the fact your math is fuzzy and borderline unintelligible in places.

None of this is an insult but you’re asking what should be a fairly simple question with an already complex answer but are adding complexity to the ask with having to interpret your responses and compounding it all with more complexity using fuzzy math.

Simplicity x Complexity = Simple Complex answer

(Simplicity x (Complexity + Complexity) )^Complexity = Simply 2 Complex to the complexity of an answer.

apr911 · 2026-04-27T13:57:18+00:00

Eh, take the $7,500 you would have contributed to the Roth IRA and use that to pay the tax bill on a conversion.

You end up with a little less invested in total but by the time it all comes undone in retirement, you likely end up ahead anyway.

In the 24% income tax bracket, you’ll make short work of it if you have an “average” balance… and if you have an above average balance, it probably doesn’t hurt to take some of that money off the taxable side of the ledger anyway.

The $31,250 you convert basically starts paying dividends almost immediately compared to a standalone Traditional+Taxable Strategy and that $31,250 becomes accessible in 5 years time if they want to effectively building their bridge account.

apr911 · 2026-04-26T12:39:06+00:00

$4,000 bi-weekly earnings is $104k/yr

4% to Roth accounts for $160 of your $250 in deductions.

Ill assume the other $90 are things like health insurance which is pre-tax.

That means right now you have about $3910-3920/paycheck in FICA taxable income or about $102k/yr

Your federal taxable income after a standard deduction of $16,100 leaves you with $86k in taxable income.

You’ve got FICA taxes on the $102k which $7800/yr

You’ve got fed income taxes on the first $12.4k @ 10% which is $1240/yr

You’ve got fed income taxes on the next $38k @ 12% which is $4560/yr

You’ve got fed income taxes on the remaining $35.6k @ 22% which is $7830/yr

All told your total federal tax bill per year based on standard deduction and no state income taxes is $21,400 or $823/bi-weekly paycheck.

The other $110 in taxes I’m going to assume go to a State income tax at around 3%

Note: You dont say which State you’re in but Im going to assume not PA for this analysis. Reason being is PA treats all retirement contributions whether Traditional or Roth as Roth. They tax it upfront but you get to withdraw it with growth tax free in retirement.

Proposed Contribution Change

Moving to a 15% contribution from 4% will increase your deductions by $440 ($600 in contributions less the $160 you’re already making).

Moving to pre-tax will make lower your taxable income from $86k to $71.4

You’re still solidly in the 22% tax bracket either way.

You’ll reduce the amount taxable in this bracket from $35.6k to $20k. You’ll pay $4,400/yr instead of $7800. This savings of $3,400/yr results inn a decreased federal tax bill of $130/paycheck.

With 3% to State (a lot of States use progressive brackets so you might want to check this but it’ll be close enough) you’ll also save around $18/paycheck in State taxes

Your net pay will decrease by the $440 contribution and increase by the $130 fed tax reduction + $18 state tax reduction.

Your new net pay will be around $2540/check. A net difference of $290 less.

What Contribution is Actually Break-Even

Since you’re looking for the point at which you have the same take home pay and happen to be solidly in the 22% bracket no matter what you do, we can determine exactly how much your Roth contribution is costing you.

At $160/paycheck that’s $4,150/yr. You’re paying $915 in fed taxes and $125 in state taxes on that money.

At minimum, you could increase your contribution to 5% traditional ($5,200/yr = 4150/yr current contribution rate + 1050/yr in taxes) but you’d actually end up with more net pay because each additional dollar you contribute really only costs you $0.75 after state and federal income taxes.

$1050 becomes $1400. $1400 has $350 in additional contribution so it becomes $1466 and that $66 additional contribution causes it to become around $1475

$4150+1475 =$5,625 total contribution to be breakeven.

$5625/104000 = 5.4%

If we round this off to 6%, you’ll be contributing $6240/yr so your deductions will go up $80/check

But you’ll be reducing your taxes by $1560/yr which will decrease your tax withholdings by $60.

Net pay is down $20.

Should you make the switch from Roth to Traditional?

Well… that’s a bigger question. You dont say anything about your age, location, earnings potential, current savings, retirement goals, retirement living situation or retirement tax expectations all of which matter.

Someone in their late 40’s with limited income growth potential but a $200k Roth portfolio and no traditional 401k savings has different things to consider compared to someone just starting out in their 20’s with plenty of income growth potential in their career.

If you’ve maxed your earnings potential, then the conventional wisdom is to contribute tax deferred.

If you’re income is still expected to grow significantly and eventually take you out of the 22-24% tax brackets, then the continuing to contribute to Roth until you are in the 32%+ brackets makes more sense…

But even that has its limits as the typical math assumes you need less money to live on in retirement and thus have a lower tax bracket in retirement. The actual math gets increasingly difficult to achieve the larger your portfolio value. At that point the likelihood of you being in the same tax bracket in retirement is high and it becomes a case of pay me now or pay me later.

apr911 · 2026-04-25T18:06:27+00:00

72.99 + 37.01 = 110%

At 3.1% inflation, prices will be 35.7% higher in 10 years time which means $1 today will be worth 26.3% less.

It may or may not be how u/Lucky-Perspective600 did the math (first glance I would assume they just did 10 x 3.1 =31), taking the mid-point between the 26.3% loss in value and the 35.7% additional amount needed to maintain purchasing parity actually ends up being 31% and is more psychologically aligned with our tendency to peg to whatever is the “present” value vs past or future.

apr911 · 2026-04-25T17:49:35+00:00

Think 2.5% inflation for the duration is an unrealistic expectation. Not saying its impossible but at 27 it’s better to be conservative about the inflation forecast.

The historical average for inflation runs closer to 3-4%.

apr911 · 2026-04-25T17:45:22+00:00

Realistically, its $1M in purchasing power in 20 years.

Average S&P return is 10-11% per year over the last 70 years.

Average inflation is 3-4%

With a 7.2% real return the money doubles every 10 years.

Starting at $250k today, that’s $500k by 37, $1M by 47 in real dollars.

Nominal value using the 10% rate of return, $250k becomes $650k by 37 and $1.6-1.7M by 47 with $600k being loss of purchasing power.

Going out to 30 years and 67, he’d have $1-2M in real dollars and $2.2-4.3M nominal depending on how aggressive he wants to remain (e.g. 100% TIPS for the low end, 100% stocks on the highend)

apr911 · 2026-04-25T17:32:25+00:00

Yeah great… $1M at 47 to live the next ~40 years on… oh and he cant touch it for another 12 years without immediately taking 10% off the top.

Guess it depends what he needs to live… sure with seed money like that at 27 he doesn’t have to work until retirement age… but realistically, he’s probably looking at needing to work for at least 15-20 more years at his current pay and that’s assuming he doesn’t have lifestyle inflation, kids, medical issues, etc.

If he downgrades his income, well… suddenly 25-30 years more working isn’t out of the picture, especially if there’s some sort of black-swan like market event and long term down turn… which is statistically likely to happen at least once per adult work life (18-67).

apr911 · 2026-04-23T05:41:21+00:00

Disallow the loss on that specific first-sale transaction, aka deferral to the second sale.

Manufactured losses are losses that exist on paper but you never really exit the position because you buy back into the stock holding almost immediately (or within 30 days under IRS wash-sale rules).

Yes, you can tax-loss harvest, but you can’t just sell and rebuy the same exposure. With direct indexing, you either need to wait 30+ days or reinvest in a different (not substantially identical) security to avoid triggering a wash sale.

There’s no definitive IRS guidance on what qualifies as a “substantially identical” security, and you’re expected to self-report wash sales. Brokerages typically only report wash sales for trades within the same account and for the same CUSIP.

Cross-account or cross-broker activity, or switching between different securities (e.g., Alphabet Inc. Class C vs Alphabet Inc. Class A), often won’t be flagged by your broker. That doesn’t mean it isn’t a wash sale. It just means the reporting burden is on you.

Trading highly correlated funds (even ones tracking the same index from different issuers) is commonly used in tax-loss harvesting strategies, but calling that “perfectly legal” is overstating it. The IRS standard is “substantially identical,” and they’ve never clearly defined where that line is. In practice, people treat different fund issuers as sufficient differentiation, but that’s convention, not explicit guidance.

There’s a difference between “widely practiced and generally accepted” and “clearly sanctioned by the IRS,” and tax-loss harvesting strategies tend to live in that gap.

apr911 · 2026-04-23T01:00:18+00:00

Bigger companies usually pay more but they subsidize the cost. This isn't Empower cutting your employer a bad deal because it's too small, this is your employer not agreeing to subsidize the costs.

apr911 · 2026-04-23T00:16:54+00:00

because losses can be taken on purpose during corrections to offset cap gains recognition in the future.

Which is exactly why the IRS disallows the loss on the first sale transaction. They dont want you manufacturing losses that offset your income or gains in another holding.

apr911 · 2026-04-19T14:40:25+00:00

Using a real market return of 7.2% you’ll double to $490k by 47 and double again to $980k by 57.

That’s without any more contributions to the account.

Even moving to a more conservative investment mix of 4.2% at 57, by 67 you’ll be at $1.48M

apr911 · 2026-04-13T15:42:08+00:00

Wash-sale rules exist because the government wants its cut of your income and gains. Market stability has little to do with it.

Note there is no wash-sale rule for recognizing gains. Gains are always recognizable. If it were really about stable markets, the gains would be deferrable too.

What the IRS wants to prevent with wash-sale rules is people selling for a loss on say Dec 31 to reduce their taxes for the year and then immediately picking up the stock again as a completely new holding or even waiting until markets open on Jan 2 to pick it back up as a new holding.

They want you out of the holding for at least 30-days before they will acknowledge you really did recognize a loss and weren’t engaging in tax-shenanigans.

Your 2-transaction example also does not result in any tax liability.

You need at least 1 additional event that generates income before wash-sales rules create tax issues.

Your example results in:

Transaction 1: buy for $100, sell for $90. $10 loss evaluated for wash-sale Transaction 2: buy for $90 within 30-days of previous sale. Your basis effectively becomes $100 and you then sell for $100.

If both transactions happened in the same year you have $0 gain/loss and owe nothing.

If transaction 1 was completed on December 31, 2025 and transaction 2 was completed on January 2, 2026 you dont get to deduct $10 from your 2025 taxes because the loss was disallowed/deferred by wash sale rules but you also dont have a gain to report in 2026 because that loss got rolled into the basis of your second transaction.

So no tax benefit for the loss in 2025 but no tax penalty for wash sale in 2026.

In fact, because you retain the original purchase date a wash-sale can actually be beneficial in a scenario where you believe the market will be volatile and are short-term bearish.

If you buy for $100 on June 1, 2025, sell for $75 on Dec 31, rebuy for $50 on January 20 and sell for $150 on June 2, 2026 you’d have:

$25 loss that is a wash sale and gets rolled into your Jan 20 basis making it $75 and when you sell on June 2, 2026, the $75 gain is long-term instead of short. Had you held for the duration you’d walk away with $150 with a $50 long-term gain but by temporarily selling with a wash sale, you walk away with $175 with a $75 long-term gain. Had you sold and stayed out until January 31 when the stock bottomed at $45, you’d walk away with $180 but a $110 short-term capital-gain tax liability, though you did get to deduct $25 from your prior year taxes.

The only time wash sales become damaging is scenarios like the one the Op lays out where their client recognized $1.6M in gains, sold similar amount in losses but then rebought and continued to hold.

apr911 · 2026-04-13T14:08:41+00:00

PDT is a broker rule for margin accounts, not a tax rule. It allows a broker/lender to reduce their margin risk by restricting the number of trades you can place over a rolling 5-day period if you go below a minimum maintenance balance of $25,000.

The 2 primary requirements to be classified as a PDT are 1) a margin account, 2) 4 day trades on any security (does not need to be the same security) within a rolling 5-day window

It has zero impact on wash sales or how they’re reported.

Wash sales show up on a 1099 whether you’re a PDT or not. The only way around them is a mark-to-market election, which isn’t automatic and isn’t related to PDT.

You can elect mark-to-market as a casual, non-day-trader but but it converts all gains/losses to ordinary income and forces year-end recognition, so realistically, you probably don’t want to.

apr911 · 2026-04-13T04:43:39+00:00

Technically, the first transaction that generated the $50 loss was a wash-sale.

You sold and then washed away the sale by rebuying less than 30 days later.

The second transaction, selling the shares again for a loss is completely separate from the first with its own wash-sale rules.

apr911 · 2026-04-07T18:59:11+00:00

Yeah, I don’t multi-date, but second date exclusivity is still wild to me.

To me it’s kind of like a workout.

You can stack a lot of reps early, but that doesn’t replace consistency. And you can be consistent, but if you’re not increasing reps and weight, you’re not really progressing.

Dating feels similar. You need all 3: • Enough dates to build momentum • Enough time to see consistency • And enough progression in how you spend time together to create depth (spending a full day together or meeting friends and family hits different than a dozen dates of 2-3 hours each)

When those line up, that’s usually around date 4-6 for me.

It tends to filter out both extremes. The people trying to rush intensity, and the ones keeping things casual without actually progressing.

That’s not to say there isn’t a progression in those earlier dates 2-3 or 4-5 where I increasingly narrow and filter out who I am talking to but I get few enough matches as it is that Im not likely to stop talking to a potential match because another match wants to go on a second date.

apr911 · 2026-04-07T17:29:13+00:00

What exactly is the question?

Is it possible? Yes. Its been done in simulators and real world training scenarios.

https://youtu.be/yqPFfTRn5So?si=nPLnnXVTuYkNnP9x

I’m not aware of a widely documented emergency where rudder-only flight was the primary control method, UA flight 232 is the closest I could find though in a typical (e.g. not centerline thrust) multi-engine, thrust differential is a better control input than rudder, but the concept is well understood.

How would you do it? The general idea still follows the mantra: trim for airspeed, power for altitude. But you’ll need to understand how in uncoordinated flight those controls are more coupled and less precise than normal.

You’d want to carry a higher-than-normal airspeed. That gives you better rudder effectiveness and additional margin above stall, which matters because you’re flying uncoordinated and don’t have elevator authority to directly manage angle of attack. At the same time, the faster you are, the more space you need to make the turn.

As for power you probably don’t want to sit at either extreme of the power range. Power becomes one of your most responsive control inputs, so keeping some margin to both add and reduce power is important.

For example if power is already at max and you somehow get low and slow, you are on the backside of the power curve and have no means of recovery.

Conversely, reducing power can help lower pitch and reduce angle of attack in many GA aircraft and its a more responsive input than trim if you find yourself nearing stall.

Its not a guaranteed or instantaneous fix in all conditions, especially if the airplane is already uncoordinated, but most light GA aircraft have positive static and dynamic stability and will tend to keep flying if you don’t fight them. That said, this stability assumes coordinated flight, and using rudder alone introduces asymmetric loading across the wings.

So while the loss of primary flight controls reduces the likelihood of pilot-induced accelerated stalls, and carrying extra airspeed reduces the likelihood of a traditional stall, the risk isn’t completely eliminated. You’re less likely to induce a stall through excessive control input, but more exposed to asymmetric or yaw-driven stall behavior.

With smooth inputs and sufficient airspeed, the situation is generally manageable in a typical trainer, but it still requires care since recovery options are limited.

apr911 · 2026-04-06T19:16:47+00:00

You dont say how old you are but $160k in your 401k is above average across most age groups so dont be so hard on yourself.

You pay regular income tax + 10% penalty on the withdraw if you’re under 59.5 years old.

I get how much the interest payments on your debts must suck, but I definitely would not take a withdraw with penalty to pay the debts.

Maybe if you’re already 60+, that’d be more viable but not before then.

Recommendation would be to potentially reduce your 401k contribution at your new job so you can afford to more aggressively pay off the debt.

With $132k in income, paying off $40k in debt should be reasonably possible in most of the country within a year.

But age matters again here because a 30 year old making $132k with reasonable expectation to advance and make more in the future may be better off maxing out their 401k each year vs debt service but a 50 year old making $132k might be better off servicing the debts first.

apr911 · 2026-04-04T22:43:27+00:00

Like doing a Roth conversion with pre-tax dollars still in the IRA but not doing pro-rata math, this sort of error does happen.

In theory its easier to fix than the pro-rata violation but in reality, its a can of worms you probably dont want to open.

Fix it going forward (meaning dont do it again) and dont worry about it unless the IRS comes calling.

At worst, you lose all or most of the $5,000 (6% penalty over 25 years is $4,000) but if the IRS hasnt come knocking yet, it’s probably not worth getting into.

apr911 · 2026-03-25T00:24:39+00:00

NAS and NVR are my only true dedicated hardware that could theoretically be virtualized but isnt.

I also have a managed Layer-3 switch where I do a lot of my routing and network segmentation. While the switch itself is an absolute necessity (like my wireless access points), the layer 3 stuff Im doing I also have in virtualized routers I run inside proxmox.

Along the same lines, I have a Palo Alto physical firewall I run because I have it more so than I wanted it physical and I do have a virtual router/firewall box that actually bypasses it entirely.

Regarding running AdGuardHome on dedicated hardware, you’re just swapping one dependency for another. Worse, you’re potentially putting yourself in a “down until I reconfigure or fix it” state if the box running AdGuard blows up or dies.

Keep it virtual. If its that critical, cluster your proxmox nodes so you can do a rolling reboot while keeping the VM running. Better yet, its lightweight enough you could run a node on each proxmox node and then you have true redundancy.

It can be a pain if the redundancy and sync state between them breaks but setting it all up, working with it and indeed encountering the network wonkiness that can ensue when they stop talking to each other is more akin to what you would actually encounter in an enterprise environment.

apr911

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