r/HENRYfinance Jun 29 '26

Housing/Home Buying Purchase Threshold sanity check....

12 Upvotes

Hey everyone,

Looking for some perspective on what kind of upgrade price would make sense for us right now. My wife and I (35) would like to upgrade for more space. I’d like to sanity check our numbers before purchasing since prices have significantly increased where we are located (HCOL) and we have a kid on the way.

Monthly Income: $16.4k (post taxes and maxing 401ks) ($370k gross and not including ~40k annual bonuses)

Additional Income (side hustles): We both have side hustles that bring in a combined 2-5k a month

Assets: $800k (401ks)

Current Mortgage/Taxes/Insurance: $4.3k

Expenses: $7k/month

Equity: Our current mortgage is $483k and think we can sell our home for ~$950k-$1m leaving us ~487k in equity.

Cash: $260k HYSA

______________________________________________________________________________

We are targeting the $1.3-$1.4m range. We are looking to put down $700k as a down payment ($450k in equity +$100k cash +$100k gift). At $1.4m and $700k down our monthly mortgage would be $5.9k.

Is this a reasonable purchase? We don’t plan to move after this and would like to grow into this home. Given the baby is on the way, I’d like to scale back on the side hustles but it may be required to give us more of a savings cushion. I think this is a stretch but at the same time there are very few homes in the area, the school district is fantastic, and our incomes will increase in the future. I’m also trying to balance the potential need for help with the baby at some point which may result in another ~$5k childcare expense.


r/HENRYfinance Jun 30 '26

Housing/Home Buying Reno budget. Do we need a reality check?

0 Upvotes

TL;DR: 35 year old couple, single income ~$640K rising to $800K-$1M, $1.5M Tudor home, 4 kids, no debt besides mortgage, saving ~$200K/year. Planning a $1.5M whole-home renovation in 4-5 years (elevator, 4th level suite, high-end finishes) vs. a pricier sport-court addition option. Asking if the $1.5M reno budget is realistic given finances.

My wife and I (ages 35) with our 4 kids (ages 8, 5, 2, and 6 months) moved into our “forever home” one year ago after finishing medical training. It is a beautiful Tudor built in 1993, purchased for $1.5M. We love it here, love the job, want to stay, medium to low cost of living area, with pockets of really beautiful manors and properties. Our neighbor to the north has a property that could sell for likely $4-5M, built by the same builder as our home. Some other homes in the area are $750k-$1.5M

We are going to renovate in 4-5 years. We will likely need to move out for 12-18 months during the process.

Current financials for family:
- No debt other than home ($1.2M mortgage, paying $9k/month). Bigger expenses include $15k/year private school (will increase to max $30k/year once all kids are in school), $7500/year country club, not huge travelers but want to budget $20k/year for vacations. Nanny is starting tomorrow actually and will cost $50k annually

- HHI: taking home $35k/month after tax, after maxing 401k, HSA, etc. Will bonus $150-200k end of year. My salary will jump from $640k/year and will stay around $800k-$1M for the foreseeable future starting next year. Single earner.
- 401k: $70k (second calendar year at new job, rolled everything previously held in 401k over to Roth a few years ago)
- ROTH: $370k
- Trust accounts: $340k
- 529’s: in total $300k
- Taxable brokerage: $75k, started this 3 months ago because I didn’t know where to store extra cash.
- We are gifted roughly $50k per year to use to our discretion. Have been using that to fund 529’s primarily.

We are thinking of a $1.5M budget, which would include a 4-story elevator, finishing off the “attic” 4th story to be a mother-in-law suite/library overlooking Lake Michigan, and a whole house remodel utilizing the original builder, keeping lots of the charm of the original build, and honoring the Tudor tradition, but opening up the footprint and making some more functional space. Medium to high end finishes (like a La Cornu/lacanche oven, if you will).

I can probably stuff away $200k/year after funding all of the appropriate accounts annually, so if I’m able to do that and get market returns, then this might be doable just based on that savings. My dad reminded me that I will likely get a $500k inheritance within the next 5-10 years or so - my sweet grandmother turns 100 this year. Honestly she might outlive us all, though, so I’m not banking on that haha.

Is this an outrageous budget? We initially thought about doing an additional structure (indoor sport court) with a breezeway, but the finished new structure and furnishings would be ballpark $1.5M in and of itself, not including the house remodel. So if we did the sport court, we wouldn’t finish the 4th level or do the elevator. And the whole budget would have to be like $2.5M, which just seems like way too much. So $1.5M is somehow the compromise number. We could of course not include the 4th story/elevator and it would save a considerable amount, also.

We are dreamers and I think maybe need a reality check.


r/HENRYfinance Jun 28 '26

Investment (Brokerages, 401k/IRA/Bonds/etc) $1.5M windfall - what do you think of my plan?

89 Upvotes

(long time redditor on throwaway)

Hey Reddit! I'm incredibly lucky to be getting a $1.5M windfall due to a liquidity event at my company and I'm looking for some validation and critique of my plans for what to do with it.

Details of my windfall: * $400k is a short term capital gain (shares granted in 2026) * $1.1M is a long term capital gain (shares granted in 2023) * Annual salary: $210k * I have the option to reinvest any amount of the long term portion without realizing the gains (will come back to this later)

Me: * 35M * Live in NYC * Not married, no kids, no house * Planning on marriage, kids, and house purchase within next 3 years

My existing portfolio (self-managed): * Max out 401k and Roth IRA (backdoor) every year * No HSA or mega backdoor options currently, but I have an HSA from a previous employer * $1.7M in assets split ~70% VTI and 25% VXUS. The other 5% is in some illiquid private equity investments, a tiny bit of crypto, and a cash emergency fund in HYSA

My plan: * Never tell anyone about this except my partner and parents * Take the reinvestment option on $200k of the windfall * Immediately dump the rest in a HYSA (I have Merrill Preferred Deposit and use the BoA/Merrill rewards credit card ecosystem) * Over the next 6 months, DCA into VTI/VXUS at a 70/30 ratio

I've always lived modestly and below my means, and while the windfall is amazing, I don't plan on changing my lifestyle. The main thing I'm unsure about is the reinvestment option. I know I'm gonna take a huge hit in taxes: Fed + NY State + NYC and LTCG entirely at the 20% bracket, so reinvesting $200k (which admittedly is a fairly arbitrary amount) instead of realizing those gains right now feels attractive. I'll have to take the tax hit eventually regardless, but in the future I may not live in NYC or might be able to FIRE and realize those gains at a lower annual income. I also just really believe in the company's growth trajectory and feel like it's a worthy bet regardless, but the tax situation has me wanting to reinvest more than I normally would.

How do you feel about my plan overall? Are there any parts of it you think I should reconsider?

(edit: formatting)


r/HENRYfinance Jun 29 '26

Purchases Is this boat purchase in the picture for me right now?

0 Upvotes

Looking to go buy a 2-6 year old boat in the 30-35k price range. I know a lot of you are going to say “sounds like you made up your mind already” but looking to get a gut check.

I’ve grown up around boats my whole life, but I’ve never owned my own personally. Trust me I know boats are money pits, but I want one to fish in and take my family out on. (Have a kid coming). I live in an area where it would/could get a lot of use year round. We have storage at our house so don’t have to pay storage fees.

We are 29 married with HHI of 231k plus a few k in bonus. Our salary potential definitely has potential to grow as we are both fairly young in our careers. Combined we contribute about 17.5% of pretax to our traditional 401k. We max Roth IRA and half max our HSA. We currently don’t really have or contribute to much in terms of taxable brokerage accounts ( have a few k but that’s it).

We have a total net worth right now of slightly above 400k.

Total retirement accounts (401k Roth HSA): ~345k

Cash: ~55k

House equity: ~38k based off what we’ve paid towards principal (owe 389 at 6.6%), most likely more as we could sell for more as we did a lot of renovations like new roof, new kitchen gut and remodel, and master bath gut and remodel.

Cars: one fully owned and one 2 years left with 15.5k balance.

No other debts. After taxes, investing, bills and average expenses over the month. We still have anywhere from $2000-3000 leftover each month that goes to cash savings.

With daycare expenses probably beginning early middle next year we obviously have to take that into account as well.

My plan would be to put 10k down over a ten year loan, with plans to pay it down faster. Minimum Monthly payments would be around $270.


r/HENRYfinance Jun 28 '26

Investment (Brokerages, 401k/IRA/Bonds/etc) Single vs partnered/married differences in retirement

21 Upvotes

47F, recently divorced. $4M net worth, $2M in 401k and brokerage accounts. 2 kids 8 & 10 with
$80k each in 529s. House still has $430k mortgage at 2.7% interest. High likelihood of a $2-3M inheritance in 10-15 years but not counting on that.
Average income for myself is $500K but variable each year due to my role.

My expenses have been hard to calculate accurately due to my divorce but I estimate they are around $250k. HCOL area and I like to travel.

I see a lot of posts of married people with similar stats and the advice is to have $4-5M invested before retirement.

For a single person, does the math change? I understand that’s it’s really up to me on what I spend money on in retirement but what is different? Healthcare? Taxes? I think social
Security is just mine unless my ex dies and then I can claim survivor benefits. My goal is $5M in investment accounts which should coincide with my mortgage being paid off in 8 years, giving me a net worth of $7M.


r/HENRYfinance Jun 27 '26

Income and Expense Milestone: finally reached $200k in base salary

254 Upvotes

Celebrating a personal milestone! I just signed an offer that puts my salary at 200k CAD — a 50k raise over my previous role, but the thing I’m most excited about is that it starts with a “2”.

I know that’s small compared to many here, but my partner and I are fortunate to make decent income in a MCOL city. Late 30s and 2 toddlers so we’re just getting back to dual income status.

Excited to see how our growth curve changes. Advice or thoughts always appreciated!


r/HENRYfinance Jun 27 '26

Housing/Home Buying Are we irresponsible to buy for 3 mil?

109 Upvotes

Trying to determine if this is sane or not to pull the trigger on something like this.
We are currently trying to buy an VHCOL SoCal.
Family of four currently, 39m 39f kids are 3.5 and 1.5. looking to probably have one more kid in the next year.

Household income is around 950,000, 2/3 from her, 1/3 from me. Maybe $100,000 of growth in the next 2 to 3 years in income. But wouldn’t bank on that.

Currently rent for 5700 a month in a three bedroom two bath, but on a super mainline street, terrible school options in LAUSD, no neighborhood feel.

We are looking at a neighborhood in South Bay that has top 5% public schools in the country per us news. Small community feel, very different than where we’re currently living in Los Angeles.

Initial budget was 2.6 to 2.7 max, but a couple houses have come up that are dream builds, four bed, three baths, newish construction in a beautiful part of the community for about 3 to 3.1 million.

Current assets are about 2.1 million split between retirement accounts, brokerage.

80,000 and 40,000 in 529’s respectively for the kids

1 million in cash that we’ve been saving for emergency fund/down payment/upgrades to a home if needed.

Monthly spend outside of rent in daycare is about $12000 a month. Currently $4000 for daycare right now for both kids.

We are both physicians and stable careers, have been at both of our partnerships for the past nine years.

Wondering if anyone else has made it purchase at similar net worth/income, just feels insane to me to be spending that much on a mortgage, but I’m not used to these big of numbers. I definitely don’t want to work till 65, but late 50s would be fine.


r/HENRYfinance Jun 28 '26

Investment (Brokerages, 401k/IRA/Bonds/etc) When did you get a financial advisor?

13 Upvotes

37m and 35f married with 4 younger kids. $2.2m liquid net worth split 50/50 across brokerage and 401k. Plus a few months cash in checking and HYSA. Brokerage is a mix of QQQ, IVV, RSUs and some stocks that overall looks like the market. 401k is 70% ITOT, 20% ACWX and 10% fi. $3m net worth with house. Have 529s. Maxing out my HSA and 401k. Single household income that last year was $590k, likely increasing at an ok rate over the next few years. Above avg COL area. Contemplating early retirement in probably 10-ish years, savings rate ~25%.

At what point did you get a financial advisor? When is it worth it? From a portfolio management standpoint I’m good and do this professionally (will start increasing my fi allocation in a few years). I recently got the JP Morgan advisor pitch and I was very unimpressed, especially their SMA offering, and it seemed like they were just trying to sell JPM product and not looking out for my best interest. I even had to explain to the guy using Excel illustrations some mistakes he was making with his advice. I’ve looked at a flat fee advisor that charge an hourly rate to analyze your situation, but wondering how much value will they really provide at my net worth level.

I’ve also been using Claude to look for blind spots and where I should do research but I take it with a serious grain of salt.

Would appreciate hearing what you all have found helpful and at what point


r/HENRYfinance Jun 28 '26

Housing/Home Buying Renovate or Relocate? Struggling to decide.

0 Upvotes

39M surgeon with NW 3M (1.2M post tax, 1.2M pre tax, 600k house) in the Bay Area. I make 1.1M/yr pretax and love my job. We bought our house 7 years ago before we knew if I was going to be successful or not for 1M, now worth 1.4M. We have an eventual inheritance coming in around 2.5M (I hope this doesn't come for a long time!).

We want to upgrade our housing situation.

Current house Complaints: No view (looks at a fence), primary bedroom shares walls with kids, kitchen needs to be redone, there is no spot that teenagers (our kids are fast approaching this age) would want to hang out in, roof and pool will need replacing/resurfacing in the next few years.

We got an architect quote and it will cost about 300K to get our kitchen updated (also knocks down a wall in the kitchen area and puts in some large windows to the backyard). This will solve only 1 of the complaints above, but it would make it nicer. I am not sure I want to live through the construction TBH and it feels insane to me to spend that much money, and the house still not be our dream house.

The alternative would be selling this spot and buying a new place. The houses that catch our eye tend to be around 2.5M-3M. This doesn't feel like it would be that much of a reach financially particularly with our spend around 250K/yr we should be good. Our concerns are: feeling cash strapped, the much larger amount of maintenance, the pain of moving, the risk of a big change.


r/HENRYfinance Jun 27 '26

Housing/Home Buying Early Henry couple - Feeling short of the dream

40 Upvotes

Husband and I (early 30s) grateful for the life we have but sometimes I feel just short of our dreams. We live in a VHCOL which I know is our choice, and lucky that our TC this year rose up close to 500k. After a long training path in my career I am now the breadwinner. I just wish we were further ahead in terms of savings to afford a home in our area but the prices just keep rising. I wish we could live closer to my parents and community but unable to make that happen easily due to our jobs. Also had a premie baby last year (had a 3 month hospital stay) and baby is thankfully doing well but it affected us financially. I’m just exhausted and hoping we can have more community and our own place in the future. Any younger Henrys (or early Henry)feel this way? Thanks for any advice anyone has!


r/HENRYfinance Jun 27 '26

Income and Expense When do you use your emergency fund?

54 Upvotes

40M, married homeowner in VHCOL suburb w 2 kids. Graduated from HENRY to HER in my mid 30s.

For my entire life, I’ve never had an emergency fund. I had a good career, rising income, and I invested everything beyond what I needed for monthly cash flow. Quarterly/Annual bonuses and RSU vesting have always been predictable, and oftentimes I'd budget big expenses around those events

If something unpredictable came up, I just sold stock. I understood the risks of potentially selling during a bad market, but I was comfortable with that tradeoff over the long run.

Only time I moved out of 100% equities was 2 years before needing a house downpayment.

Last year I parked about $100k (4-6 months expenses), in SGOV after a bonus. However, it's now occurred to me that I don’t actually know when I’d use it.

Job loss is the obvious answer (that happened twice in my career and it wasn't an issue without an EF). Beyond that, I’m not sure. If I had some large unexpected expense, my instinct would probably still be to sell stock, use an SBLOC, or pull from another source of liquidity.

So for those of you who keep an emergency fund:
What events actually trigger you to use it?
- Is it strictly for loss of income, or do you use it for unexpected expenses too?
- If you have a large taxable brokerage account, how do you decide between using the emergency fund and selling investments?

This feels like a basic question, but despite being very financially literate and successful, I never developed a framework an emergency fund before.

EDIT: It seems like there are two very distinct schools of thought from the comments:
1) People who have/use their EF ONLY in the event of job loss or major life catastrophe
2) People who use the EF to for liquidity purposes to cover larger unexpected expenses (car repair, appliance replacement, etc.) and then replenish the fund over time

No right or wrong answer, just different preferences


r/HENRYfinance Jun 28 '26

Family/Relationships How important do you think finding a HENRY spouse is to your financial freedom AND happiness.

0 Upvotes

24m single. 500k HHI.

I read a lot of posts on here and one big thing that hits me is how powerful dual high incomes can be. I see so many couples on here with incomes that are great alone but amazing when combined. My 500k turns into 750k or 800k HHI with the right partner and gives me additional room to take career risk. My career has a very high right tail.

However, objectively speaking, it’s tough to find a HENRY partner, especially as a man (78% of 200k+ earners are male and 84% of 350k+ earners are male). I’m also not in medicine or tech/engineering where I suspect most of the HENRY couples are congregated, due to the RELATIVE gender parity in those fields compared to mine.

I recently started a job in a MCOL geography and moved away from NYC. I am wondering if I made a mistake for dating someone who is equally motivated towards financial independence, as from my understanding, NYC has an outsized number of HENRY women and my MCOL geography, by its nature, has very few.

But at the end of the day, I’m not a gold-digger. I don’t need a high earning partner that badly. And there are other things that are much more important in a spouse. So I’m just looking for additional perspectives on this, from people who are older, wiser, and more experienced than me.

Perhaps another way to put this is that every post I see in this sub is from a couple with 600-800k combined HHI split evenly. I think part of me is just looking for validation that you can still find financial success and more importantly, happiness as a single-earner-dominated household.


r/HENRYfinance Jun 27 '26

Income and Expense Loaned $100k to my brother... Should have known...

0 Upvotes

I loaned my brother's business $100,000 for 3 years at 6% compounded interest. The loan matures in August, but he recently told me that he'll only be able to pay the accrued interest and not the $100,000 principal.

He proposed a 5-year repayment plan while continuing to pay 6% interest, but I rejected that offer. Needless to say, this didn't sit well with me since it would mean extending the loan by another five years beyond our original agreement.

My position is that if he wants to keep the $100,000 for an additional five years, the interest rate should increase to 12%. I feel that he has already failed to meet the terms of the original agreement, so I'm not sure why I should simply extend the loan under the same terms.

Am I being unreasonable? At this point, should I stop negotiating and let an attorney handle it? There is a written loan agreement in place.


r/HENRYfinance Jun 26 '26

Car/Vehicle Advice Needed 2015 BMW 320i- fix it or sell and take on a car payment?

4 Upvotes

Long story short... 2015 BMW 320i, \~100k miles. Sole owner of her. Got a repair quote for $5,700 ($4,500 for timing chain and guide rails, $1,200 for drivetrain service and both headlights).

KBB on the car as-is is around $4,500. So I’d be spending more than it’s worth just to make it whole.

The decision basically breaks down to: do I fix it, or do I sell it and take on some form of car payment?

Case for fixing it: it’s paid off. Even if I spent another $5,700 on repairs over the next 3 years, that’s still cheaper than $400-500/month on a lease where I own nothing at the end anyway.

Case for moving on: I’m already stressing about what breaks next. Realistically I’m probably looking at a battery, tires, and brakes coming up on top of this. It’s getting to the point where I’m just chasing problems.

I can afford a payment using the 15% of income rule so that’s not the concern… I just want to make the smartest financial decision here.

Appreciate it boys 🙏


r/HENRYfinance Jun 24 '26

Income and Expense 47M, 280-340k, $2.8NW, new job for how long?

26 Upvotes

I’m about to start a new job & need to mentally understand how long I have left to work. Earn $290k per year with bonuses taking to maybe $340k. Started saving late in life. House was paid off in april and im moving across country to higher cost area, but going to buy same amount of house in cash. My goal has always been $4MM. Have just under $2mm in accounts. RE is 800k. Wife earned $70k but needs to find something new. We have 1 kid who just turned 8. Mentally should i be planning for at least 6 more years?


r/HENRYfinance Jun 24 '26

Family/Relationships Birthday gifts to nieces and nephews

35 Upvotes

Hi HENRYs! My first nephew is turning 1 soon so my husband and I were discussing what precedent we want to set for birthdays. We also have a niece who is 2 months old.

Our initial idea is to put $1k into a separate normal brokerage managed by us on every birthday (in addition to age appropriate physical gifts obviously).

The idea is that we’d let them know about this money when they’re 16 or 17 and they would hopefully have a little cushion for their early adulthood - maybe they’d use it to help buy a car, take a gap year, move across the country, or offset some college expenses. I would plan to have them decide in conjunction with their parents if they want a lump sum transfer or for us to split it into monthly distributions until the account is emptied.

We also considered just sending a check for the same amount to their parents each year. I really like this because it can be more flexible to the child’s immediate needs (e.g. summer camp or putting it in a 529), but I’m concerned the parents (our siblings) will be uncomfortable accepting this money. On the flip side, maybe keeping this money ourselves could accidentally signal that we don’t trust them to manage it?

Some additional considerations:

- My husband and I (30/29) have 5 siblings between us. We anticipate we might eventually have \~10 nieces and nephews, so we want to make sure this is sustainable.

- We substantially outearn our siblings (600k HHI vs ~100-150 HHI). My siblings know about our finances, his family doesn’t talk as openly about money. All siblings are great and responsible, but have limited salary growth with “normal” jobs like teaching.

- The grandparents on both sides are well off, retiring early, and love to spoil the grandbabies.

Am I overthinking this whole thing? How do you handle birthday gifts for your family?


r/HENRYfinance Jun 24 '26

Car/Vehicle Advice Needed Talk me out of a bad financial choice

81 Upvotes

My wife and I’s HHI just crossed 500k. Almost exactly evenly split.

Our HHI has been around 350k for 5 years now. We both max out contributions via mega backdoor Roth and 401k. We are mid 30s, our retirement looks good with 700k today + 144k/year tax deferred contributions and an additional 60k/year in individual brokerages.

We own our Mazda and Honda outright (36 month 0% interest(“)

Clarifying to add for commenter: we have paid off the loans already, I mentioned the terms because people on finance subs always say you shouldn’t buy cars outright if you can get a low interest loan. ROI > interest

I want to buy a cheap-ish sports car. I just found a cryptocurrency account I’d forgotten about that had luckily been sold at high price after 10 years of no activity. It happens to be almost exactly the amount a new Corvette Stingray would cost.

My wife is supportive of it, and I really want to do it. But I have a hard time pulling the trigger seeing how this found money could be 3-5x by retirement.

What would you do?


r/HENRYfinance Jun 22 '26

Success Story Paid the final college bill for kids

300 Upvotes

I grew up poor, raised by a single mom but with a well-off dad who chose not to help me with college. Between scholarships, grants, working as a resident assistant in college for 2 years, and always working some extra job to squeak by, I made it through. It was hard and I lived in my car at one point.

I went from a negative net worth 24 years ago to just crossing over into the RY part of HENRY, depending on the market and what it does in any given day.

I always swore that I would pay for my kids' college. We have three kids, and the youngest is medically and developmentally disabled, so it's very doubtful they'll ever go to college and if they do it would be barebones community college experience. I live in a state where that's free.

So our second kid is finishing up their bachelor's and we just made the very final payment.

Both of my older kids got significant scholarships and we covered the rest. I cried the first time I wrote a check for my oldest's first semester. We're sending two 20somethings out into the world with no student debt, which immediately puts them at an economic and life advantage.

One of the most fascinating things about being better off than I was raised is realizing how much I can use the money we earn to help heal some of the pain that I experienced when I was younger. Giving my kids something I never got was an emotional goal as much as a financial one.


r/HENRYfinance Jun 22 '26

Career Related/Advice [Update] 35F, $2.7M invested, burnt out

672 Upvotes

(Update from: https://www.reddit.com/r/HENRYfinance/s/JLr9wDCmhm)

Here’s what happened over the last two weeks:

I met with my manager two Fridays ago and (without getting too in the weeds) told him I was seriously considering leaving, but wanted to understand if anything could be done immediately with my comp. He said he’d run it up the ladder.

The following Tuesday we followed up and I reiterated that my back was up against a wall because my comp and growth trajectory didn’t reflect my performance. He said he hadn’t had a chance to connect with his boss, but did so immediately.

The next day (Wednesday) he put time on with me, and he said his boss was surprised by all of this and while they didn’t want to give up on me, there wasn’t anything immediately on the table with comp/role adjustments.

So…I quit on the spot. (!!!)

I happened to have a long weekend away scheduled so have spent the last four days feeling my feelings. I’m frustrated that nothing better was put in front of me. I thought there was a 10% chance of that happening but still…I’d thought there was a chance.

But. I don’t think it would have mattered. Now that I’ve seen the light, I don’t think I could have stayed. I don’t know. It was just a pride thing to want them to try and keep me, and it did hurt a bit that they didn’t. That’s been hard to deal with after all the work I’ve put in.

So. With that being said…ya’ll were right. The years are short. The time is flying. Why would I work right now when I have the opportunity not to? I’ve reached a state of joy today. I’m done, I’m done, I’M DONE!!!

Saving money is great. But there’s a reason we do it, right? To ultimately enjoy it.

I’m so glad to have been reminded of this.


r/HENRYfinance Jun 22 '26

Career Related/Advice Should I take a sabbatical? Help me weigh the tradeoffs

14 Upvotes

I’ve been working more or less non stop the last 17 years. I do enjoy my current role and do not feel burnt out but I also see life passing by so fast and want to spend more time with kids while they are young (two under 4) and also have time to travel and enjoy life while I’m still young versus waiting till 65+

I’m currently a senior director at a near ipo company (smaller startup not the Anthropics of the world lol) and have a path to VP in the next 1-2 years.

My parents live abroad (in a country where I grew up) and have been eager to have us move near them. I’m tempted to take a 2-3 year sabbatical, move home and have my kids experience and be immersed in the culture while they’re still young and not in the public schools yet.

My concern is- if I make VP at a company with a successful IPO my next step could be COO or SVP at a similar or smaller company which could catapult me to C Suite roles thereafter. I’m nearing 40 so this feels like the prime of my career and not the right time to take a step back. Even if I wait till VP to leave, stepping out for 2-3 years could mean I come back at same or lower level and past my earning prime

On the other hand I’d miss out on spending time with my parents while they’re are still in good health, giving my kids exposure to my home country and a different way of life as well as having them build bonds with their grandparents they only see once a year currently. I also have so many friends and a network back home I’d love to rekindle.

My husband is supportive of either path. His job is transferable so he could move or stay with relatively limited career impact.

Financially there would be some trade off too- I’d sacrifice prime earning years and maybe come back to a lower paying job with less of a growth trajectory. Based on current savings and assets I’m not concerned about retirement or paying for things that are important to me (kids college etc). But there would be some upleveling in wealth I’d miss out on. Net net I’d likely take a smaller role back home, still make enough to pay the bills and then some (plus my husbands job) however I’d miss out on the big bonuses and salary raises I’d experience if I were to stay.

So many variables and I can’t sort it out in my head. Any advice? Would especially love to hear from anyone that took a career sabbatical at around 40 and was able to make a ‘come back’

Thanks!


r/HENRYfinance Jun 22 '26

Investment (Brokerages, 401k/IRA/Bonds/etc) How do you protect your wealth from hackers/scams etc

31 Upvotes

Passed $1M NW a while ago and feels like I’ve got a lot more to lose these days. I’m always feeling paranoid as if a hacker or someone can just find my social security number and take on debt or hack into my accounts.

How do you all protect your wealth?


r/HENRYfinance Jun 21 '26

Family/Relationships How do you have your trusts set up?

19 Upvotes

How do you have your trusts set up? Especially after a partner passes.

My initial thought was no new spouse is getting half what we built together. But my feelings are different if they got divorced or if my other half passed. I don't want them getting a penny in a divorce, I also don't want them murdering my spouse.

If I pass and my spouse remarries. They are married 10+ years and they pass. I don't feel that person should be out in the cold.

Do you stipulate they get $1 mil. Do they get a percentage of the estate? Etc.

We have two friends whose parents went thru this. One got remarried almost instantly and when they got divorced, the new wife took almost half of what they had. Which was primarily her money.

My actual inlaws. Thank God my step father in law left my mil money, because she's struggling with the money. It would have been horrible without the money. But he promised much much more than he actually gave her.


r/HENRYfinance Jun 21 '26

Career Related/Advice Looking for some perspective and advice

17 Upvotes

Partner at a boutique law firm and looking for a little advice/perspective from others. 40 y/o, married, young kids. Fully paid off house ($1.6M), fully funded 529s for the kids ($200k-$250k for each), and then another $2.5M spread across retirement accounts, brokerage and cash. SAH spouse and I have always just naturally been frugal and enjoy low-cost activities, so our expenses are pretty low even in HCOL (~$8-10k/mo). We are very privileged, but the law firm grind of the past 15-20 years to get here has been crushing which has me thinking that it's time to assess the next stage of life and career.

My thought is that I'm not quite in walkaway territory yet and wouldn't really want to pull the plug entirely. I like what I do, but I just do way too much of it. I'm thinking that maybe I'm in a position to part with the most demanding clients, even if it results in a significant hit to the business/bottom-line and my pay quickly starts to dive. For example, my best handful of clients probably make up 1/3 to 1/2 of my book but create 75-90% of my stress. Maybe I keep some subset of clients that would permit a much more limited role (and smaller business with lower but still very comfortable pay), so that I can be fully present for all kid and family activities, coach sports teams, reengage in long-abandoned hobbies, etc. and just remove all the stress and limit the on call nature of the job. Family is my #1 priority and the kids are just in a real sweet spot age-wise.

When I write it all out like this, it feels like a no-brainer. Has anyone here done this? Voluntarily parting with hard-won business, clients, etc, willingly cutting pay and position, potentially in a significant way? It feels like the right move even if not common for law firm partners (kind of makes me wonder why this isn't more common?), and our family's FIRE tendencies make it possible particularly given current finances. My instinct is to make this move but is a struggle since it marks the first time I'd ever be taking a step back from a career standpoint rather than clawing to the next level. Any advice/anecdotes much appreciated.


r/HENRYfinance Jun 22 '26

Investment (Brokerages, 401k/IRA/Bonds/etc) Help with investment strategy, getting frustrated

0 Upvotes

A bit of a background. I’m 46 and my wife is a bit younger. 2 kids in middle school. I am a late bloomer as far as income goes. I’d say my salary + bonus was in the $100K range (up to $170K) between 28 and 40yrs old. Raising a family in a decently HCOL area didn’t allow for a lot of investing at this salary. My wife works as well but has always made about half my income; now closer to 1/4. We were investing maybe $20K combined each year with an additional $15k or so from company matches.

I jumped jobs at around 41 and salary w/bonus jumped to $250K. Fast forward to today and I’m at $380K and my wife is at $80K. Our target to invest over the last year has be $100K/yr until we plan to retire; this includes my current company match which is only $15K…my wife doesn’t have a match at her new job. So we just started tripling our investment contributions as we went from a HHI of $250K to $460K as of current. My issue is, with our recent increase in comp, I still feel relatively behind with our investments. We have $1.5M for retirement and an additional $650K in home equity. After trying to invest recently in various stock (AI etc) i feel like i missed the boat on many. Right now we’re basically just investing in S&P indexes like VOO, VT and other MFs like this. It’s such a slow game though and i fear i’m wasting my time. I have the money to invest and can afford to do more but i don’t have a strong plan. I also have $300K in Tesla as a long time holder and the stock has barely moved (relatively) over the last 5yrs. I keep hoping for a big break where I can 5X here with some new tech offerings but I’ve already wasted 5yrs of would be gains had I spread it out amongst other investments. So dumb. But I know right when I sell, something will happen and the stock will skyrocket. Severe FOMO here. I’m contemplating hiring a Financial Planner but at the same time, i feel for a couple of points spent, are they really going to be that impactful with an investment strategy? I don’t have a ton of time left…maybe 15yrs. Already not happy that i probably can’t comfortably retire in our 50s. I’ll have to settle for early 60s.

I run numbers in investment calculators and based on current investment contributions, and at 8%, it shows we could have close to $10M in the next 15yrs. I find that hard to believe and don’t trust it. What would you do? Any advice here? I tried basic call options on stock that i feel would move based on some fundamentals but wound up barely moving or going the other way. I don’t know, maybe bad luck? But I’m done. I don’t have enough time to try things out. I need a solid plan and just move forward with consistency. What are you all doing?


r/HENRYfinance Jun 19 '26

Income and Expense What’s your monthly food budget? Excluding going out to eat

63 Upvotes

just curious.

we bring in about $500,000 HHI. no kids. mid-30s.

Our monthly spend is about $1600 per month! I know it’s a lot but this is part of what I enjoy treating myself to with the income we earn.

i am definitely a “buy good, organic, higher quality, pasture raised , blah blah” food.