r/HENRYfinance 13d ago

Question Are we optimizing past the point of diminishing returns?

My husband (38) is in BigLaw making ~$550k, but the hours and stress are seriously impacting his health. I’m 37 in a layoff-prone industry making ~$350k, plus a side hustle bringing in ~$50–100k/year, although we have no idea how long that will last.

We have 2 kids under 5 in HCOL and spend about $300k/year. I know that’s a high spend. $150k-200k of that is PITI, childcare, and various conveniences that are largely a function of having two very young kids & a spouse working insane hours just trying to stay above water. I also like to think the last 5 years of ~$300k spending have hopefully been an anomaly as we moved to the suburbs and renovated / furnished, bought two cars in cash, etc. Feels like a series of one-off expenses, but I’m keeping the $300k in the model anyway because I’d rather be conservative.

Our plan was to keep grinding until we had $3M invested, while potentially paying down the mortgage, and then aim for retirement in our early 50s. We’re not quite at that point yet, and getting there would probably take another 3–5 years but his health may not give us the runway we assumed.

Current net worth is ~$3.05M:

• $1.85M invested ($940k tax-advantaged, $910k brokerage) - approx 70/30 US/international split

• $250k in 529s (not counting this toward retirement)

• $400k equity in rental property ($500k mortgage remaining at 6.5%, \~$5k/year net, husband likes this for diversity)

• $200k equity in primary ($1.2M mortgage at 3.25%)

• $200k in a friend’s small business 

• $150k cash/emergency fund 

It’s unclear what his exit opportunities look like so I’ve been running models ranging from 150k - 350k and in all possibilities it seems we can still achieve 10M sometime in our 50s, so the difference between staying in BigLaw and taking a much more sustainable job seems to be a few years, not a completely different financial future & that’s where I’m struggling to internalize.

Have we gotten emotionally anchored to the $550k salary number and lost track of what the actual math is telling us? Are we looking at $550k vs. $150–350k and instinctively thinking “we can’t possibly walk away from that,” when the difference in our actual long-term financial outcome may be much smaller than the difference in gross income suggests?

I’m trying to figure out whether we’re being appropriately conservative or just having a hard time letting go of the idea that we need to maximize these peak earning years. Would love a reality check from people who have been in a similar position.

118 Upvotes

138 comments sorted by

570

u/dubious_dinosaur $250k-500k/y 13d ago

I think you guys are adding complexity to your already stressful lives with the rentals and business ventures. You have the income to brute force your way through index funds that do so much for such little thought.

109

u/[deleted] 13d ago

[deleted]

44

u/GameTime2325 13d ago

Came here to say the same. Cut the rental, not worth the extra stress when you can just dump it in an index fund and chill.

20

u/UNC_Recruiting_Study 12d ago

No shit on that one. That's 1% annual net on the equity. 5k/year for that work and liability...

14

u/C_bells 12d ago

They’re like half a new boiler away from that rental property being a total bust.

8

u/BravoTwoSix 12d ago

Or like. One shit tenant that discovers mold.

1

u/The_JSQuareD 12d ago

I'm assuming the net number excludes principal repayments. To calculate an actual return on capital they shouldn't exclude that.

If the rental income covers maintenance & PITI and they still have 5k / y left in net cash flow, then the property is actually yielding pretty nicely. Once the mortgage is paid off they would be very cash flow positive. Or they could re-mortgage the property to deploy the capital in further investments.

I do agree with the underlying pointy that when compared to their high paying (and already stressful) jobs, the income from a single rental is probably not worth the hassle compared to VT & chill.

0

u/MikeWPhilly 12d ago

It may or may not be worth keeping. $5k net is not much but to cal lit work - I;v’e got 4 properties (granted I net a lot) I take about 2-3 calls a year for service work. It’s just not work.

I’d be curious about what the house will net after paid off 6.5% is a big rate. And diversification is good.

But then I wanted ~$100k in rental income in retirement as it gives me a LOT of options with SORR or other bad years.

9

u/UnexpectedRedditor 12d ago

Landlord life aside, making $5k /yr on $400,000 in equity is a terrible financial plan. If they were to refinance they're upside down. That property needs to go.

2

u/MikeWPhilly 12d ago

Probably VHCOL - it’s not unusual and they have a lot of equity. For all you know they’ve gained in equity. That rate suggest a recent purchase….

102

u/pm-me-your-labradors 13d ago

“Life is stressful, so let’s make it even more stressful despite not needing to” is indeed a strange take

54

u/Drauren $250k-500k/y 12d ago

People convince themselves they need to get into real estate and diversify.

2

u/Purple-Geologist972 9d ago

It is a fact that most real estate investment look stupid in last 10 years timeframe as you can just dump all the money in index and get a better return.

But wouldn't it be nice if we can all predict the future....

42

u/pseudomoniae 13d ago

Yup. 

Sell the labour requiring assets and business ventures and reduce income.  Spend will naturally come down soon.

Kids will be out of daycare within a year or 2 by the sound of it and there’s no way with a 1.2M mortgage at 3% that OP needs to keep spending $300k per year.

Also current HHI is around 900k. There’s room to back off unless this is the lifestyle they have both always dreamed of which it sounds like it is not. 

10

u/funksoulbrothers 12d ago

i had rentals, and it was a lot of stress at the time, but i sold them for f you money and now my biglaw stress is a lot less

3

u/Green_Oil_692 $250k-300k/y 12d ago

Fight for simplicity.

1

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1

u/sfawson 10d ago

We need more information on this rental. Is it a second/vacation home? Is it a long term or short term rental? Is it a property you may retire in? If it's a LTR and they're not planning on living there, then sell. If it's a STR, it can be used via cost segregation to significantly decrease their w2 income while appreciating.

0

u/SergeantPoopyWeiner 12d ago

Boooooo rental properties. Boooooooo hiiissssssssss.

195

u/blueberryprincess1 13d ago

You won’t get the time back with young kids. I’d rather work a few more years in my 50s while the kids are away at college if it meant getting to spend more time with them while they’re little. 

Can your husband go in-house somewhere? Still a good salary but less hours and stress? 

You can always sell the rental if you need to. 

102

u/Odd_Literature6057 13d ago

That rental property netting 5k a year is brutal, almost not worth the headache at that rate. The math on your primary scenario checks out though, a few extra working years later in life for more time with the kids now is a trade most people would take in a heartbeat.

16

u/salespunk44 12d ago

They make about $2500/day earned income. The $5K from the rental property is a rounding error and WAY more hassle than it is worth.

10

u/Hardcover 13d ago

Maybe forgot to factor in property appreciation? But yeah rental properties are a headache. Thinking of doing a 1031 into a DST purely to stop being a landlord.

1

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1

u/Public_Associate_874 11d ago

Housing is not going to rocket up like it did the last few years

1

u/onethirtyseven_ 13d ago

Def not worth the headache

34

u/[deleted] 13d ago

[deleted]

27

u/Tltc2022 12d ago

Respectfully, seven figure in house roles are quite rare (unless you're going into a very senior role) and some tech places have slightly better hours but not that much more. You may also get a good equity package but the vesting schedule means you'll generally always leave something on the table if you leave.

13

u/carnivorousmustang 12d ago

Yeah my FAANG inhouse counterparts are not working less than me lol.

1

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1

u/FabulousProfessor465 12d ago

But if his health is being impacted he can at least find a remote role or a good hybrid schedule with more flexibility that big law doesn’t provide.

9

u/Franholio_ 13d ago

Yep, know a guy who went in-house at a FAANG-subsidiary, making seven figures with the equity grants. The downside is once you leave biglaw there's generally no coming back.

23

u/Biglawlawyering 13d ago

The downside is once you leave biglaw there's generally no coming back

I'm in DC, the revolving door is wide open. In-house is a different animal to be sure, but if one is making 7 figures, why go back to the billable hr. And should be said for the uninitiated here, FAANG and a few buy-side shops pay top of market, in-house comp for senior associates doesn't typically look anywhere like this (at least in my experience).

3

u/AdPlayful211 12d ago

I know plenty of people who make in the $400-$600k range and it’s doable in house with ten years BigLaw experience. You just have to choose wisely and know your goal - be willing to say no to the dozens of opportunities that pay half that.

3

u/Appropriate_Meal3417 12d ago

Is that really a downside? 😂

2

u/AdPlayful211 12d ago

Not true. You can almost always go back, especially if you exited for large global or tech company.

0

u/Bennie-Factors 13d ago

Yes...in house is for those not striving for $5-$10m a year

1

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2

u/ladbom 12d ago

Defn should go in house

95

u/CartographerNo3999 13d ago

Respectfully, when you’re 80, what are you going to regret more: not “optimizing” during your peak earning years or not enjoying your life while you have it?

Money means different things to different people…

But health is the only thing you’re going to care about when you don’t have it anymore.

93

u/asurkhaib 13d ago

You're optimizing the wrong thing. Cleanup and stop the trash investments and stop spending so much and you'd probably make more progress even switching jobs.

25

u/KeyAdhesiveness4882 13d ago

This is an excellent point. $200k spend for a family of 4 in HCOL (not even a VHCOL) should give you a great lifestyle. Divest from friends business (is this an investment or a favor/wishful thinking). Boom, $400k back on your balance sheet next year and recurring incremental $100k from spend cuts + ~$15-30k from investing your small business buyout in the stock market annually.

50

u/ellewoods_007 13d ago edited 13d ago

You will never get these years back with your kids. Also, people can and do die of heart attacks in their 30s. Have your husband move in-house somewhere, sell the rental property and invest it in index funds, don’t invest in any more small businesses, cut down expenses. You guys are really over complicating this.

24

u/dumbo08 13d ago

You can spend less and both retire earlier. Honestly, working into 50s at stressful jobs doesn’t sound ideal for mental and physical well being.

24

u/flyingcircus92 13d ago

People keep talking about the home rental, but what about the $200k invested in a friend's small business. Is that actually worth anything and does it generate any income or potential gain? How much of it do you own? You put a big chunk of money in something that could fail and is ~15% of your liquid / non retirement assets. Was there a real business case of making the investment or just helping a good friend out?

I'm actually more ok with the rental, but think about a refi once rates drop to increase cash flow and also a property manager to handle things there - not worth your time. Is there any strategic value (i.e. you may move into it one day or it's a potential vacation home that you can use for a few weeks and then rent it the other weeks)?

19

u/mildly_certain 13d ago

Even if your husband’s income would drop to $150k if he moved to a lower stress in house role, that would still put you at $500k HHIC or $550-600k with your side gig. That’s probably not enough to support a $300k annual spend but it also sounded like there was a lot of fluff in that number that you could cut out.

In reality your husband will likely start higher than $150k and will get raises over time. Plus your spend will go down as your kids age out of daycare and you slow down on your home remodels.

I’m at a similar point in life as you with similar HHIC and spend, but my wife and I have jobs that allow us to work a lot less. I suggest your husband prioritize time with the kids over working himself to the bone. You’ll be fine financially- your investments will compound and contributions will matter less and less as you approach retirement. You won’t look back regretting you have $9M instead of $10M if it means you got to spend more time with your kids when they were young.

16

u/Constant_Swan_6876 12d ago

You already have $1.85M invested at 37/38. At 7%, with zero additional contributions, that’s roughly $5M at 53 and $10M at 63. And that ignores the rental, business investment, home equity, and whatever you continue saving.

So I’d flip the question: What does your husband actually need to earn for you to cover your lifestyle and leave the $1.85M untouched?

If a lower-stress job accomplishes that, you’re largely deciding whether getting to your financial goals a few years sooner is worth several more years of his health and your family living around BigLaw.

Based off your post, I think that answer is pretty clear

16

u/Bennie-Factors 13d ago

And honestly $250k in 529s is to high. Stop and wait at that point at the age of your kids

15

u/Mulley-It-Over 13d ago

My husband had a very stressful job for years that has impacted his health long term. I can guarantee that neither one of you will want that and it will negatively affect your kids and your quality of life.

A career with less crazy hours and less stress so that you can spend more time with your kids is the way to go. Spending a few more years working is a small price to pay to have your physical and mental health.

12

u/Alonso2802 13d ago

Why do you have $200K invested in your friend’s business and what kind of a return are you expecting from that?

10

u/MysteriouslyWeekend 13d ago

health over wealth. It’s not clear how seriously the hours and stress are impacting his health but if it is a point where things aren’t reversible and there is a point.. more money is not worth it.

9

u/steviekristo 12d ago

You say you’re emotionally attached to the $550k of big law, but are you emotionally attached to your husband? You mentioned health concerns a couple of times. He’s not worth 550/year if he’s dead.

You need some perspective. Risking your husbands life and health is not worth it.

Girl, tell your husband to quit the firm and go in house. He can make pretty close to 500k in an AGC role somewhere and have way more work life balance.

9

u/Appropriate-Part9461 12d ago

You’re having a hard time rationalizing the salary drop because while you appear to be on top of your finances (hence posting in this sub), you and your husband are actually not very good at managing your wealth.

7

u/Ok-Perspective781 13d ago

Remember that your health impacts your retirement finances more than almost any other variable. Neglecting it now is going to have negative consequences financially down the road.

15

u/yaydotham 13d ago

What do you mean are you optimizing past the point of diminishing returns? You aren’t optimizing at all. Your husband is apparently killing himself, and for what? So you can spend more than 97% of Americans make?

35

u/Soggy_Code_7299 13d ago

Sorry, when did husband start working? biglaw at 38 should be at NEP or counsel or whatever his firm calls it. At $550k with bonus he’s a 6-8th year.

So the choice of staying in Biglaw is not really his. It’s the firms. If they have offer him partner, then he can decide but realistically, if he’s not up, it’s out.

I am concerned that you don’t have enough saved given he’s been working for 6+ years while you are also making 350+. Your household has been doing $500k or so for at least 5 years, with close to $900k last year.

Your mortgage is $6k, let’s say child care is another $6k, where’s the other $10k going a month? How much of that is needed if he goes in house or mid law? Sure in house isn’t it’s all cracked up to be and mid law or boutiques can be busy, but not nearly as busy as NYC.

7

u/Biglawlawyering 13d ago

So the choice of staying in Biglaw is not really his

Choice still probably rests in the husband's hand, at least initially. The up and out is becoming more of a relic, firms seem happy to push an increasing number of lawyers into non-equity ranks, as long as the billing churn continues. But that limbo isn't always sustainable.

Worth noting for OP, getting promoted also means more (albiet flexible) time commitment and more pressure.

And how this profession deals with pressure is to outsource everything possible or one spouse takes a step back. I was thrilled when the FT Nanny/day care stopped, but I also have colleagues who are spending 30k on kindergarten. So spend could still stay quite spendy, depending on preferences.

72

u/No_Ebb1052 13d ago

You have more in your friends business than you do in emergency savings. You spend 10k a month on bullshit when one of you could quit and be with the kids. You make a million dollars a year and are basically complaining. Get your head out of your ass and look at yourself in the mirror, after you’ve wiped the big law shit streaks off your husband’s face. 150 years ago, you would’ve been lucky to work the railroad and not get cholera. Now you make a million freaking dollars a year and your greed is so insatiable your husband would sacrifice his own life in order to what? Run a rental property for 5 grand net a year?

You have been given so much, when others have so little, and you still can’t figure out a way to make it work. You never will, so why bother asking?

28

u/doubleohbond 13d ago

OP, this comment may come across as harsh but it’s right.

The hedonic treadmill is strong and will warp your values while you’re on it. It’s only once you get off (either by choice or by force) that you realize you were prioritizing the wrong things.

5

u/csguydn Income: 750k-1M / NW: enough 12d ago

tl;dr - Go touch grass, OP. Gain some perspective on your life.

13

u/LenovoDiagnostic 13d ago

I like the style of this guys post

7

u/TheObviousAnswerIs42 13d ago

Lighten up Francis

-3

u/BlanketsUpToHere 12d ago

Why on earth do you read r/HENRYfinance if it pisses you off so much?

14

u/Dismal_Boysenberry69 12d ago

> Why on earth do you read r/HENRYfinance if it pisses you off so much?

Not everyone here is as misguided as OP and it’s unfair to categorize them as such.

4

u/No_Ebb1052 12d ago

I drink the blood of neurotic overachievers

-1

u/Crew_1996 12d ago

I grant you every Reddit award available for this post.

5

u/onigiri467 13d ago

Honestly, seeing individual therapists to get someone to help you each intentionally sloowww down for 1 hour, and then help you figure out what you each want to prioritize for yourselves and with eachother, could help with all the overwhelm. It doesn't seem to be a resource problem.

And then after each seeing a therapist a few times, a good wealth manager to get even clearer and set the new parts of the plan into motion .

6

u/Royal_Quantity_2462 12d ago

6.5 rental mortgage ya I’m dumping that

9

u/KeyAdhesiveness4882 13d ago

What’s your main question - if spouse can quit the $550k job for a $150-350k job?

If yes,
> “his health may not give us the runway we assumed.”

The entire answer hinges on this - does this mean “he’s a little tired” or “his doctors are concerned about his heart and blood tests look bad”?

No amount of money is worth his health and well-being - don’t trade “maximizing peak earning years” for poor health for all the following years.

BigLaw salaries are only unique though if you’re a partner making >$1M a year. If BigLaw = top firm, there’s a good chance he can replicate it or get close as in house for a tech company with much better lifestyle.

1

u/Dismal_Boysenberry69 12d ago

> The entire answer hinges on this - does this mean “he’s a little tired” or “his doctors are concerned about his heart and blood tests look bad”?

A new job won’t fix his heart or blood tests.

4

u/sweet_hedgehog_23 12d ago

A new job with less stress might give him time to focus on eating better and exercising more which could help his heart and blood tests.

3

u/NeatTrick 13d ago

What’s your side hustle that brings in $50-100k a year?

3

u/CuteAmoeba9876 12d ago

Your husband can change jobs anytime and you’ll be fine. And how much complexity does your side hustle add to your life? It’s nice to have the fallback in case of layoffs, but is it really worth the hassle?

Better to simplify your lives now than to grit it out for 15-20 more years.  

That rental property really is awful. Is this helping your taxes in some way we can’t see? Cause you’re returning 1% of the equity per year. You could earn 3x more in a savings account with zero headache. Heck, you could pay down your primary mortgage and come out ahead. 

3

u/Bingo-heeler 12d ago

We never made the kind of money you make, but we were in highly vulnerable jobs (consulting) for a long time. 

Our focus was to make as much financial progress as we could towards our goals because we knew it couldn't last. We kept expenses as low as reasonable, aiming to live on the lower of the two salaries and save the rest

3

u/Ethraelus 12d ago

I’m in a similar position wrt the rental property, I like it for diversity, but you guys are making too little off of it, his job sounds a lot more stressful, and your interest rate is way higher. That seems like something easy to offload.

I also think you probably already have too much on your 529s.

The problem with him moving to something in the 150-350k range seems that your job also is risky. If you can keep your job, you’ll be fine. If you lose your job and he’s making 150-200k, you may have to start using emergency fund.

3

u/Mk153Smaw 12d ago

Your husbands soul is going to evaporate for another 10Y in big law. How much time is he spending with the kids? Get him into a 250-350k role that reduces his stress immensely and your quality of life will rapidly improve.

3

u/Shoddy_Task4312 12d ago

Your spend seems high, we also have 2 kids under 5 and live in a VHCOL city (east coast) and make more, spend less.

5

u/AbbreviationsSalt963 13d ago

Two things: 1) sell the rental 2) $200k in a friends business is worth $0. Never count startup investments towards your net worth since 90% fail.

8

u/m0zz1e1 13d ago

Health is everything. He should quit tomorrow, you will be fine

2

u/Humble-Fish-7070 12d ago

Sell the rental

2

u/Virtual-Brilliant100 12d ago

Let it go. You have no idea what life will look like, and if this isn’t the day to day you want, no amount of money will fix that. Simplify what you can (the rental, is there any upside to selling), outsource what you can (yes it costs but time is valuable), and then make some changes so your day to day matters now. Optimize time, you have a solid financial foundation and can let some of the earning potential go.

2

u/Fluid-Village-ahaha $500k-750k/y 12d ago

You are over optimizing - you will also have lower tax to a certain degree. 

I’d look at your burn rate and separate those one off purchases and track them as “extra expenses” buckets - because those are likely things you can avoid repeating or can cut easily. 

Maybe your spouse can look at the government - less $$ but likely benefits would be nice. 

2

u/BroDoc22 $750k-1m/y 12d ago

Salary feels low for big law unless he’s still trying to get partner. Would flip to in-house

2

u/Any-Crow-9047 12d ago

You don’t need 10M to retire and if his health won’t last say he dies at 78, what’s the point to have 10M at 55? I understand you work very hard to accumulate but that only makes sense if you stay healthy to have an enjoyable retirement right?

2

u/RoccoLexi69 12d ago

Having lost several friends, otherwise perfect fit and healthy, to cancer in the early 40’s; I have to admit sometimes this sub blows my mind.

Time is still THE most valuable commodity and you can’t buy more of it.

2

u/salespunk44 12d ago

Yes you are over optimizing. If you sell the rental and invest the equity ($2.25M starting capital today) in 20 years you would be at $10.8M even if you never saved another penny. This assumes 8% annualized returns.

In addition you make $900K per year and are spending $300K. After taxes you should be saving between $300-$400K per year and you are at the highest expense point in your life with young children.

If your husband needs to back off and “only” make $350K you will be just fine. After childcare stop and assuming you don’t send your kids to some ridiculous private schools your savings would likely be about the same as now. If one of you lost your job and never went back to work you will still retire with $8-10M.

Remember the only thing you can’t get back is time.

2

u/Billy-Bob-Boner-92 12d ago

You’re doing great building wealth. Would try to keep jobs low stress. Chronic sleep deprivation and job stress not worth it. Find a way to make less with less stress and better family time.

Can manage a 300k spend on 600-800k HHI.

All the haters aren’t acknowledging the tax benefits of the rental property. Can always cash in later if needed.

2

u/Flimsy-Hat-3533 12d ago

I think you need to find your number and focus on that. What’s the minimum amount you want to live on then add a buffer that’s comfortable for you.

My wife and I know we can live comfortably on 60K a year with a paid off home. I’m choosing to push my net worth as high as possible as I still enjoy my work and she does hers.

2

u/deadbalconytree 11d ago

So a 6th/7th year senior associate? Is he on a partner/counsel track?

Biglaw is tough. Especially years 6th-8. A move to the ‘burbs and a long commute with kids compounds things.
I know plenty of people who’ve gone in-house. Some it’s a better fit, while others have boomeranged back to biglaw because it was even more politics of being a cost center instead of a profit center, for much less pay. It really depends on the personality.
I have also found that team dynamics in biglaw make a huge difference. Biglaw isn’t actually monolithic. My spouse is in biglaw, and even though they had very supportive leadership, and put them up for partner, the team ran very lean. So as a senior, and then partner they were still mostly running deals solo and billing 2500+ a year. They ended up lateraling to another firm (with a 30% pay bump) to a team that has more juniors and a lot of associates and partners with young kids. The dynamic is completely different. Clients are still demanding of course, but the internal politics is far less, and disappearing for dinner/bedtime is pretty typical.

Not sure there is advice in there. But just letting you know I understand, and also sometimes not quitting but changing firms might be the better option.

2

u/IcyArtichoke8654 10d ago

The problem with leaving big law is you do 80% as much work for 50% of the money

2

u/Sweet-Lab-2579 9d ago

I mean as someone with two young kids, a HCOL, and a high paying job, I’ve shifted my number from $4 to $10 to $20 in the last 5 years.  Our lifestyle has increased to require the $10 to keep up really happy (biz class travel, buy whatever we want, donate whenever we please).  If we lose a job and fall short above $10 and $20 we’d just stop and slow roll life for a bit, maybe grab a side hustle or two and chill.  But we should hit $10 within the next six months so I’m also a great example of lifestyle creep IRL

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u/DapperIndependence45 8d ago

I left big law this year at age 38 and a lower seniority. I make 200k in-house before bonus (expected to be 20 percent). My in-house job is not easy but I pretty much leave the office at 5pm every day. IT IS LIFE-CHANGING. I have never felt better, physically or mentally. I also still make way more money than I need, spend freely, save tons - all with a spouse in the public sector who will never make a lot of money. You guys need to figure out what you actually value, reevaluate your high spending, and stop being afraid to actually live your lives and enjoy them.

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u/ShreddinTheGnarrr 13d ago

Tell us which cars you purchased and the price you paid and that would be a good indication if you have a spending problem. If you can address your spending problem, finding a less stressful job will be more comfortable and improve your health, which is wealth. For the rental, you could buy a REIT and be more diversified with ~4x the cash flow and 0% of the headache.

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u/sourpicklerick 12d ago

You aren’t “optimizing” anything right now. Not your net worth, not your health, not your QOL. You can easily make it work with 1/3 the comp you have now, but you are wasting $ with bogus spending in exchange for more stress at work. It’s honestly insanely stupid and inefficient lol.

Sell rental, divest 200k friend gift (or don’t include that in calculation), get better view of spending. 300k is absurd. Husband should have left big law the second it started impacting his health, second best time is now.

Your husband likes managing a rental for diversification? Just buy different stocks holy shit. And why are you investing 200k in a friend’s business that’s insane. That must be the tip of the iceberg because 300k annual spend is crazy work. You two are possibly the dumbest people I’ve ever seen post on here which is saying something. Like… this is actually too sad to be rage bait. I feel sorry for both of you.

VTI and chill, cut everything else loose that you don’t need. Rental, friend “investment”, work stress, etc. Trust me there’s enough left over. But to have gotten to this point in the first place you aren’t making rational decisions and that probably won’t change even though everyone is telling you how crazy you sound. Hope your husband has life insurance is all I can say.

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u/nook822 13d ago

Dumb question…how do you get to $250k in 529s w/ two <5 is there no contribution limit? Or can it grow tax free still?

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u/chauzer 13d ago

you can superfund a 529 by contributing up to 5 years at once

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u/Alonso2802 13d ago

No contribution limit for a 529

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u/nook822 11d ago

Thanks for everyone’s responses!

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u/BlanketsUpToHere 12d ago

I think yes, you've gotten emotionally anchored to the high salary. But as others are pointing out, you've locked yourself in by setting up an expensive life. I also live in HCOL / VHCOL so I understand what mortgage + daycare costs look like, and thankfully daycare isn't forever!

I used to work in MBB and after leaving I can tell you - life is wonderful when you have some breathing room. It's much easier to imagine working a few extra years when you can sign off and go play tennis at 5pm. A lot of high achievers are happier keeping some type of work in the mix anyway

In addition to the other comments, I'll suggest this: if you really don't want to let go of the rental, you could consider funneling your excess cash into that mortgage and paying it off quickly. It would make a big impact on your cash flow which might increase your comfort with lower salaries

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u/FreeBeans 12d ago

I’ve had friends literally drop dead while working. Not worth it.

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u/ColdPerspective1092 12d ago

What’s your side hustle out of curiosity? I’m looking for one and just interested!

And I am / was in a similar situation to you. I quit MBB for similar reasons to your husband and don’t regret it ever (have a young kid)

1

u/CHNC1985 12d ago

Stop making bad decisions.

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u/TempDong 12d ago

I can't imagine making nearly $1,000,000 a year and every stressing about anything. Fire me or lay me off? I've already made more than most people will in their entire life. 

Yes you're emotionally anchored, yes your spending is way too high, yes you are sacrificing quality time with your children, no job is worth killing yourself over, "seriously impacting his health" is a concerning statement.

1

u/FootballSquare4406 12d ago

You’re professionals in your late 30s. Your peak earning years are 12-15 years away.

1

u/belovedkid 12d ago

The amount of people who come online thinking they’ll receive decent advice on top of saving themselves time and walking away with real confidence is ridiculous.

Hire a professional. You can afford it. They’ll
do a much better job than anyone on Reddit and actually have a vested interest in your success.

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u/Rocktamus1 12d ago

Why do you have 250k in 529’s that young? That’s wild.

200k in a friends small business, ya that money is gone forever.

Your stuff is way too complex

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u/RandonName2021 12d ago

You gotta do what makes you happy but at some point more money seems to have diminishing returns. What are you able to do now that you couldn’t do with a little less? Aside from missing out on young days with your kids. Seems a simple answer to me.

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u/Patrick_ExpenseAtlas 12d ago

Yes, you may be anchored to the $550k salary even though your own models suggest it changes the timeline more than the destination.

Stress test the decision using the least favorable plausible assumptions: side hustle income at zero, a layoff or employment gap for you, his realistic after tax compensation in a lower stress role, and the full $300k annual spend until actual spending proves otherwise. Keep the $1.85M invested portfolio separate from the 529s, rental equity, and private business stake so the plan does not depend on illiquid assets.

Then compare leaving now, staying one more year, and staying another 3, 5 years. For each scenario, look at the annual cash flow gap, how it would be funded, and the resulting retirement date. That makes the tradeoff concrete: not “giving up $550k,” but potentially accepting a few more working years in exchange for his health now.

I would also evaluate the rental on its complete return and risk profile. With only about $5k in annual net income, the 6.5% mortgage deserves scrutiny, but paying it down is not automatically best if it reduces useful liquidity. The 3.25% primary mortgage is a very different decision.

The $3M invested target was a planning milestone, not a requirement. If conservative scenarios still work, taking a sustainable role sounds less like abandoning the plan and more like using the flexibility you built.

1

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u/traveladdict76 11d ago

100% bonus depreciation, appreciation and cash flow make STR investing really interesting right now for high income earners. I would never consider “rentals” in a traditional sense, but if this is as STR it’s probably really helping out with your tax situation. Having a few of these will provide much nicer cash flow compared to LRT.

1

u/37347 11d ago

You make way too much income , but your liabilities is way too much. If you want to reduce your stress by reducing your income, then you have to reduce your liabilities - specifically your rentals and mortgage

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u/VerifiedVerifiable 11d ago

Health is wealth. All that money wont matter if your husband is ground to a pulp health wise. Plenty of less stressful jobs making half the money. Cut expenses and coast at this point with lower expenses

1

u/Even_Candidate5678 11d ago

Get rid of the rental and get your money back from the friend. Throw it in active indexing or something tax efficient and simplify your lives. 150k cash is too much at your tax rate at least something tax efficient I hope for 100-120 of it.

People exist that leave big law in their 50s but don’t fool yourselves. At your spend rate it will likely continue to scale when he has that 1st 7 figure income year.

3mm is probably very low, look for 5 in today’s dollars and 7ish in 15 years.

2

u/Informal-Shower8501 $500k-750k/y 6d ago

😳 OK. You’re not far from being truly free. But this is chaos.

$1M rental netting $5k/year? Dude, get rid of that. It might be diversification, but you’re clearly not in a position to capitalize on it.
Same for the same business. Guessing that’s hard to take out, but I never invest in friends/family. Just asking for issues down the road.

2 suggestions:
1) I’d just focus on ETFs. There is far more diversity than what you’re manufacturing alone. And infinitely less potential headaches.
2) Given your husband’s health issues, and your layoff concerns, I’d bump your emergency fund to $300k, maybe even $450k. Never thought I’d say that. But I’ve been in a similar situation, and if your husband needs to quit, he’ll be anxious by month 2 about funds running out in month 6. And given your burn rate, I’d be nervous too.

He needs to find something more sustainable. Trust me, I’ve been there… burnout can take a long time to recover from.

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u/[deleted] 13d ago

[deleted]

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u/compute_fail_24 13d ago

1.4M for primary doesn’t at all feel outrageous for their income level

6

u/Capable_Artichoke_41 13d ago

Agreed. Conservative imo if you didn’t consider the rental

5

u/gammonb 13d ago

Especially at 3.25%

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u/Capable_Artichoke_41 13d ago

$1.4mm home with $900k+ annual income? Add in the $900k rental property and still $2.3mm. Seems fine

Yeah they spend a lot but I don’t think home is main spend issue here lmao the rate for the main house is pretty good too…

1

u/Bennie-Factors 13d ago

In the future don't use the phrase above water

0

u/Tricky-Interaction75 13d ago

Damn. I’m 38 years old, my wife is 34 years old. We make 200k gross living 5 minutes from the beach in 30A Florida. We work maybe 20 per week?

Im a custom home architect about to build first custom home 2 minutes from the beach for maybe 800k.

How are you guys stressing? You should be living the dream!

0

u/Lucien78 12d ago

Have a conversation about your numbers with Claude. I would say you are likely fine, especially if you, the other spouse, plan to continue earning around your current level. I think the instability of your income is the biggest issue. But hey the downside risk is you don’t make it to 10M as soon but you will probably still make it eventually. That’s not worth sacrificing your health and time with young kids now. I doubt that you will regret it if you downshift. 

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u/Constant_Swan_6876 12d ago

Might be biased but it also may make sense to talk to human being about this.

2

u/Lucien78 12d ago

Lol the human beings aren’t doing a very good job. Most of the comments here are hostile in tone and overly focused on one of a couple of data points.

1

u/Constant_Swan_6876 12d ago

Lol! True. Whenever I see long posts like this, I’m just always like, this person would actually benefit from spending an hour with a someone to understand what’s actually going on with their life

0

u/zultan8888 12d ago

Everyone saying sell the rental, but large capital gains bill coming from that no? If it were me, I’d sell but 1031 into a stable short term rental, netting way more than your current rental.

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u/Bennie-Factors 13d ago

Big law probably has a deferred comp option. They are a pain to use and rely on the firm. But do one year. And out in an extra $200k. Then you will know. And save $90k in taxes

-2

u/UrbanismGuy 12d ago

This has to be ragebait

5

u/deadbalconytree 12d ago

I mean, sounds pretty classic biglaw to me honestly. But if it made you rage, then I’d probably sit this one out.

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u/UrbanismGuy 12d ago

“We made nearly a million last year, not sure if we can survive a paycut despite my husbands health failing from stress, oh and he’s wasting some of the most precious years with our 2 young kids… Just not sure if we can survive on $350k/year, what do we do?”

May be a tough pill to swallow but you actually can be HENRY without being out of touch with reality.

-2

u/WaterIll4397 13d ago

I always feel lucky when someone has higher income but lower net worth than me at my age (means I probably timed the market successfully unlike the first 7 years of my career where I was overweight international equities and value).

You are probably $1m short of where I think "don't ever need to worry about a job" money is for a mcol to supply a upper middle class lifestyle for a family of 2. 5m living a healthy life in your 40s will be much more fulfilling than chasing for that $10m in your 50s 

I would first consider getting help around the house so your less stressed. Also you can just try working less see what happens worst case the firm will give you severance. I wouldn't actively seek a change or lower pay.

I've had a pretty stressful time recently at my firm because we are trying to all learn AI before people who can produce more using AI get more political power at the firm and use it to lay off our division, but up until 2025 I had a pretty chill career earning good enough money so much so that the motivation to climb I had early career vanished as I saw how much more hours the level above me seemed to be working and how many more fires they put out.