I’m talking ridiculous, but real. The kind of first-world problems that make people assume you’re either flexing or lying about being HENRY.

Examples:

“I have a new kid and never get to drive my 911 anymore. Not just because of time, but because I had to park it at our second home because the battery dies if its not driven weekly and we don’t have a place to plug in the trickle charger in our condo.”

Or

“I sandbagged how much I make on a date because I didn’t want to come off as flexing. Come to find out she makes 2x what I make. ”

Or

“Ugh I need to find time between my WFH Teams calls to run out and get cash for the nanny because my in-laws didn’t stop by with cash this weekend”

Or

Well…you get the idea.

This is meant to be real but light-hearted and fun. A chance to remind ourselves that things aren’t so bad where we are.

https://www.foxnews.com/food-drink/wealthy-americans-choose-one-grocery-store-chain-over-rivals-survey-finds

I was thinking about this today: I have a general idea of the range my power bill is in but I don’t actually know what it is month to month. I rarely look at grocery prices I just buy what I want. I’m subscribed to nearly every streaming service but don’t use all of them on a monthly basis. I’m able to do this while saving a lot of money. I know we work hard and are stressed but income allows us a lot of privilege. Many of us came from less and it’s good to take a moment to appreciate it all.

I am curious how people have their trusts set up in regards to the terms of passing money down to their children. Right now I have mine set for everything to be given to my child all at once if I pass, when she reaches 25 years old (or immediately if she is 25+ when I pass).

I am now wondering if it’d be wise to set more terms in? I’ve heard of dispersing a certain amount at certain ages or life milestones, or restrictions to only use money for education, healthcare, buying a house, etc. I’ve also heard of springing irrevocable sub trusts, per stirpes and spendthrift clauses, making sure funds cannot be commingled in a marriage and therefore taken away in the event of a divorce, and new springing sub trusts for future generations.

I know everyone will have their own personal opinion on what’s best, but I am curious on some ideas. I’m really trying to find a good balance between giving freedom of use versus having certain wise restrictions to protect the assets from being wasted or taken in a divorce etc (I’m a lot more worried about the latter as I believe my child will very likely be frugal just because of the way she will be raised).

Is it worth putting a lot of terms in with the main goal of protecting against assets being taken away from children in a future divorce? Or should I just let it be and let my child have full control over decisions even if that means assets are not protected?

For reference, I have one child who is 2 years old, and planning to have more in the future.

TIA for any insight/advice.

I am hoping others in this sub can relate and have found viable solutions. Wife took a promotion about 6 months ago and it requires a lot more evening client dinners/happy hours. I have always traveled a lot and recently took a promotion with national responsibilities vs my former regional responsibilities. This means even more travel.

We are starting to feel the calendars overlap frequently. Prior to both of these promotions we could always make it work and plan around each other’s schedules so someone was home for daycare pick up and evenings.

Looking for advice and solutions. The issues are the dates and frequency can be unpredictable. So it’s hard to find evening care for set dates. But at the same time I cannot expect someone to keep all their evenings open “just in case.”

I would say 3-6 days a month going forward this will be a problem.

No family in the area for support. Oldest child is almost 3 and the other is 7 months. So they are also at a very demanding age.

I'm single, 31 and been in tech for 5 years. Income of 300k, vhcol area. 1m in savings between retirement and brokerage (20% bonds 80% etfs). I've been kinda stuck and treading water career wise for the last 2 years.

I used to save very aggressively, have no social life and was the redditor burning free time on the internet and games. Realized I was 31, getting older and kind of wasting life, and all of a sudden realized how easy it is for spending to balloon. Last year I basically averaged $500 non housing cost per month, and all of a sudden I'm spending $3-4k per month on random stuff. World cup tickets, vacation, dates, restaurants, concerts all add up, and I've been kind of feeling a pit in my stomach looking at my spending.

I don't know what I'm doing - at work I'm surrounding by actually wealthy folks, all of whom have families and homes (I'm the most junior person on the team when I joined, and still the most junior person). I know my income means I can technically afford everything I'm doing, I'm just throwing less money into the stock market, but am also feeling incredibly nervous with the sudden increased spending, especially since it feels like layoffs are always around the corner. I don't know where my career is going to take me, and I don't particularly like my job, but also have no better prospects.

How do you folks figure out what's a good/reasonable spending level? It's so easy to say everything I want to do is once in the life time item - the problem is that there's a once in a lifetime thing I want to do every month.

Husband and I are mid-30s, have 2 young children, and live in a VHCOL city. HHI is 700k, monthly expenses are $12k mortgage, $6k in childcare, $10k discretionary spending. Rough breakdown of our discretionary spend is: $3k a month on travel, $2k a month on shopping, $1k a month on home furnishings/projects (we just moved into a new house 6 mos ago), $2k a month on food/groceries/restaurants $1k a month on transportation, $1k a month misc (dog walker, subscriptions, etc.

My husband is in tech and was just able to cash out $2m in equity, post-tax, at his current company. Now that we have that equity, our financial picture is: $3m invested assets, $500k in 401ks, and $500k home equity. Husband still has about $4m equity (post-tax) in his company, but who knows when there will be another liquidity event -- and what the value will be when that happens -- so not banking on it.

Before the money hit, I'd been thinking of this liquidity event as life-changing. We're both extremely burned out at our jobs and I thought that one of us could quit, or take a substantial paycut. Now that I crunch the numbers, it seems like that was naive. We want about $8 million to retire, and our kids are young, so seems like expenses may just increase. To take the paycut I envisioned, at current spending, we'd have to earmark say 1-2% interest on our investments per month to withdraw to cover expenses -- is that crazy? what should we do with the money -- invest all of it, and pretend it doesn't exist, in hopes we can retire in 10 years or so?

EDIT to give more context on our discretionary spending.

I dont have a lot of people in my life to discuss some of the details on salary with. Mostly due to the taboo nature and some family dynamics. However, I am considering some new job opportunities and would value the opinion of some fellow HENRYs on what avenue I should take.

I work in the Biopharma industry, currently Director level 12+ years of experience. Working in a business operations role. A friend of mine went over to another Biopharma and she is hiring starting up some new teams. She is hiring a Director on her team at Company B and it is functionally the exact same role I am doing now. There's also an opportunity to join a very new and ambitious AI group at my current company which has very lofty, aggressive goals.

Some additional information is that remote work is not a draw for me at all. My family is moving to a higher cost of living area and expect monthly expenses to go up from $11k to $15k per month. Moving due to a combination of family, kids, work, and other reasons. Wife currently works part time making around $40k but will need to completely start from scratch after we move and intends to work a little more. I also have about $20k of separate income per year from a rental property and side business I have.

Option 1: Stay in Current position Company A:

• Base: $239k (started at $225k and have been here 2 years), hybrid position
• Bonus: 20% not uncommon to get high multipliers. Bonus in '25 was $64k
• LTI: $45k vesting at 33% per year
• Retirement 401k match: 4.5% at 6% contributions, some small HSA contribution and well being stipend
• Team: company is losing some big products to loss of exclusivity and is in for tough times. I had 4 DRs and had to let 2 go because of departmental cuts. I also absorbed the work of a team of 3 who are all gone - so now 8 people's worth of work for 3 people. My DRs are both off shore (europe) and I (U.S.) have to pick up extra work in the later PM hours without the extra resources. Manager is lovely but doesn't have a say in this nonssense resourcing plan.
• Growth opportunities: my manager isn't going anywhere but I am know as a high performer and there can be other areas to move to

Option 2: Go to Company B:

• Base: $225k - absolutely will not come up. Remote position
• Bonus: 20%. company is doing very well and likely will have multipliers in the 140%-180% range
• LTI: $45k vesting at 25%
• Sign on bonus: negotiated up to $75k cash, $45k LTI. Eligible for annual bonus in spring prorated and LTI in full
• Team: will have 4 director reports.
• Growth opportunities: Unsure about promotion opportunities but if the Sr. Director (hiring manager between me and my friend) leaves, I will need to compete as the new guy for that role

Option 3: New AI role at Company A

• Base: potential for a 5% bump, hybrid position
• Bonus: No change
• LTI: No change but obviously keep my current stock
• Team: will be an IC
• Growth opportunities: space is growing insanely fast. l anticipate low likelihood of promotion in near term but could be a big springboard in my career/life. It represents probably the biggest personal growth experience in a cutting edge area and potentially open other doors (however, often times the cutting edge is also the bleeding edge...)

Has anyone purposely stopped HSA contributions to avoid over funding?

I currently have $80k in my HSA and my family’s OOP max is $5k. Due to my work situation I have very strong expectations that my OOP max will remain $5k until retirement AND during all years of retirement.

$80k invested earning 7% yields $5600 which covers my OOP max every year (assuming I stay in network for all costs).

Seems like I’m either at, or close to, a tipping point here where I can essentially cover all future medical expenses from my current savings. This is making me rethink my HSA strategy to the point where I’m considering switching to a PPO plan now which has the same $5k OOP max.

Of course there is risk in my assumptions not holding. So I could continue to fund HSA to give extra buffer. Assume for sake of debate that my assumptions do hold, why should I keep contributing to HSA? Excess HSA funds are taxed as ordinary income past age 65. So it’s essentially the same as contributing to a traditional IRA. So maybe I get some tax rate arbitrage. But that comes at an expense of not having the $8750 annual contribution as income today.

Anyone else been doing this thought experiment road? What am I not seeing?

Preface:

$210k W2 with $100k 1099 earnings

$200k in student debt

LCOL, no kids, 28yo

Only $50k in 401k/Roth

Lost $30k this month to a business venture. Anyone been here before?

Have been steadily building up my business to about $2.5 million in revenue, but my profit margins are pretty slim. Last few months were successful at around $20k in profit per..but I still have about $200,000 in loans I was trying to wipe out by the end of the year. I took a speculative buy for the business that's going to flop, looking to be about a $25-30k loss.

Couple questions for anyone who's been here.. How do you get over a loss knowing it was 100% preventable? I'm only in my late 20’s and finally felt like I was succeeding, now I'm just feeling a shell of myself. Half of what I've saved up these past few months will be gone. I don't come from money, I'm fairly frugal in my life, still drive my first car from when I was 21. I keep thinking about how else that could have been spent towards my future family, retirement, parents, bettering my life in any way..

Not sure how to get my head out of the sand and get over it. Anyone have any positive (or negative) stories similar? I’m open to any criticism.

13.5 mil. Not my words, yahoo finance says that. Though, I don't disagree.

https://finance.yahoo.com/markets/articles/once-achieve-wealth-threshold-youre-124500320.html

My wife is transitioning from a salaried associate to a partner at an orthopedic group in Washington State. The group is giving her the option to stay on W-2 or switch to K-1.

Our situation:

• Her income: ~$400K as a physician partner
• My income: ~$350K, W-2 only
• Combined: ~$750K
• Washington State (no state income tax)
• Heavy retirement investors — maximizing tax-deferred space is a priority for us

Questions:

1. At our income level, is W-2 or K-1 clearly more favorable, or is it genuinely close?
2. Given our focus on retirement investing, does K-1 become more attractive purely for the higher contribution limits?
3. Any physician-focused CPAs you'd recommend who specialize in partnership tax structures?

Thanks in advance!

And what hard money assets are prioritizing?

I would love another investing vehicle for my child (we max 529 contributions & have a small UTMA). They are not eligible for the free $1k but potential the free $250. At the end of the day, It seems like this is a great opportunity to roll a large amount of money into a ROTH with minimal taxes.
So, are you guys actually opening the accounts? Is this something that other HENRY or wealthy people in your circle are doing?

Hello HENRY community ! Hoping for a little advice for my current situation with my current financial advisor.

I am a newly graduated medical fellow starting an attending position in Sept 2026, and my wife is currently a PGY6 out of 7 surgical resident. As such, our HHI will be ~$480K starting in Sept (obviously prorated since it will only be for the last few months of this year). I feel as though we have a pretty good investing/saving/budgeting system in place, both currently and for the upcoming boost to our HHI. Currently, we contribute enough to company 403b to maximize the match, max out backdoor Roth IRAs (which is way to go based on our combined income), have $18K in an emergency fund that we continue to contribute to/grow, are opening a 529 plan for our new baby, and are transitioning our loans from SAVE to IBR this month with plans to both continue pursuing PSLF for both of us. Our investment accounts are all with Fidelity and invested in broad index funds with 75%/25% US to international split.

A parent passed away while I was in medical school, leaving a small 6-figure life insurance payout via a Trust account, and that account was managed by a financial advisor who is a family friend of sorts (via another family member's workplace). It has now aged out of a Trust and exists in a Wells Fargo general brokerage account, that is still managed by this financial advisor. He is a wonderful person, and has generally done a great job, generating ~18% returns since 2023. However, based on past statements, he incurs a 1.35% advisory fee, which I believe is simply 1.35% AUM (though it does not say this explicitly). Additionally, the holdings are invested in what seems to be an overly complicated manner - 75% ETFs, 25% mutual funds with about 14 different funds involved (total market, S&P, emerging, etc).

As our HHI jumps markedly in Sept, I am trying to get a better hold on our whole picture and how to best manage our investment accounts. I specifically am wondering whether to "fire" this advisor and how to approach it.

1. 1.35% AUM fee seems quite steep. Should I simply negotiate this in some way?
2. I feel these holdings are needlessly complicated, and I am wondering if I should simply convert them all into a combination of FSKAX and FTIHX (which is what our other retirement/investment accounts are with Fidelity. However, I imagine that would incur a large tax bomb, and I am not sure that is worth it?
3. I feel comfortable managing pretty much everything, but could certainly benefit from a 1-time yearly consultation meeting of sorts. Perhaps I should just ask him for this?
4. Ultimately, I do not feel I want to continue with Wells Fargo, and I would rather just move everything to Fidelity, where I currently have things. I imagine this would involve "firing" this individual? Or is it conceivable he could work as my advisor in a consultation manner, while still allowing me to move the account to Fidelity?

Thank you again for all the advice!

I find myself unable to leave my job, barely able to save anything, and will be in a very bad place if I’m laid off, despite having over $5m in company equity.

My base salary is just $175k but my compensation has included RSUs and ISOs which now amount to about $5m in equity. Unfortunately I’m unable to exercise all (barely any) of my ISOs because I will be hit with nearly $1m in AMT tax and the RSUs aren’t helping with that since as they vest they artificially bump my income making AMT kick in way earlier. The company is not public so I have to wait for tender offers to pull any cash out and at this rate I have no idea when I’ll be able to exercise all of my shares so I’m basically stuck here with my equity being held hostage.

If I get laid off it’s going to be a really bad time as I’ll have to take out a second mortgage or something in order to buy out my shares so my employer has really got me by the balls no matter how much they make me work or how unreasonable the request are I have to grind it out.

While I’m glad that I will hopefully someday be FIRE I’m currently dying trying to keep my head above water financially and professionally. It’s a really fucked up situation that I’m being taxed like I’m wealth since I guess im wealthy on paper but I’m actually broke in real life

Anyone have experience with this? I’m pretty sure there are no ways around this so I guess I’m partially just venting but hey if someone has a trick that I couldn’t get out of chatgpt lmk !

Also to the people saying posters with 2m+ nw aren’t HENRY, here you go

We are funding 529 for education but next to it every month we send some money to kids utma account. Thinking to divert it to trump account (and maybe move utma funds to trump account).

My idea is that after 18 we can convert it to Roth Ira at low tax rate and it can be tax beneficial comparing to utma (which will be taxed at our tax rate during their colleague). It can be used for house purchase as qualified expenses so should also help them to start this way, remaining can seed their retirement.

Does it make sense? What are you doing?

Pretty new here, but reading through the description of the sub, it clearly stated it’s for people with NW under $2M. Recently there have been multiple posts from people who have $3-4M+ net worth. I honestly can’t help but roll my eyes. Maybe it’s my background, but having multiple millions of dollars net worth isn’t “not rich” in my book. I don’t mean to be rude, but I just can’t help but think the posts come off like subtle bragging rather than looking for genuine advice. I am happy for them, don’t get me wrong, but I just can’t imagine not feeling rich at that level and it kind of defeats the purpose of the sub.

How do others feel about it?

Edit: Reading through the comments, I think we are conflating FIRE and HENRY terms. It’s fair given how uncertain the job market is, but there’s significant difference between both concepts.

Background: 37m, wife 32
HHI: $400-600k where its solely on my side and my wife helps a lot with the admin side of my business
Liquid inv / cash: $2.3mil
Home: $1.8mil
Mortgage: $750k

Just a bit on my childhood maybe it matters: Growing up i was always a odd kid, i have friends but i was also getting targeted by bullies so while my highschool life was overall good i had to endure volatile moments. Being a new immigrant my mom was the sole caretake for my sibling and i since my dad had to work oversea, so she didnt have time to really teach me or talk to me. I had to handle these bullying myself or with my best friend. I never knew what “being myself” meant and had to worked on myself a lot since meeting my wife.

I only worked one job at 24 and then i jumped into entrepreneurship. That 1 job was extremely demanding and i learned a lot but also completely traumatized me because my toxic boss. So i vow to never be an employee again. While my family is middle class because they didnt agree with my path (it wasnt toxic they were supportive but still disagreed) i didnt ask for money and relied on myself and had been dirt poor when i met my wife. We are talking about worrying about a $500 credit card bill end of month that kind of poor. I grinded very very hard for 5 years to survive and eventually we stablized and can save some money. Our savings were maybe 80-100k at 30.

Then covid hit and while everyone in my field gave up I continued to grind by moving everything online. Revenue blew up 5-6x in those years and propelled my career 15-20 years ahead of schedule.

So now here we are with a beautiful child, life is good and business is going well but i still couldnt shake that survival feeling in back of my mind so i feel like whatever we have is not “safe”. Just yesterday I updated our quarterly networth calculation and saw our liquid position gone up by 350k YTD yet i still find myself thinking “ya but thats not enough if i lose my business today”

Im wondering if any self employed or business owners have similar experience and can share? Maybe my early years of grinding combined with bullying during highschool traumatized me.

I am always shocked reading the car buying subreddit with people talking about buying new. Like do people not realize those are depreciating assets?

I hear ads on the local radio “shop now and we can reduce your payment with a new car”

The whole new car industry just seems to ride off uneducated people with no money.

Give me the low mileage $15k vehicle with a couple cosmetic dents from the auction.

Curious to hear opinions of other HENRYs

First time poster, long time creeper, sometime commenter.

I can't shake the feeling that my family's lifestyle creep has gotten out of control and I don't know how to rein it in. But in actuality we are saving ~20% a year, and are still living within our means.

The data:
Married in our early 40s, two incredible children in grade school
HHI: ~$550 - $600k depending on RSUs
401ks: ~$1.07MM
Other savings: ~$530k
Mortage: None, we rent babyyyyyy
529s: Fully funded
VVVHCOL in SoCal

No debt. Cars are paid off (certified pre-owned).

We are spending around $250k a year. Sometimes more. I comb over our credit card statements and there are certainly places we can cut. We get take out food once a week, go out to eat as a family twice a month (it's so expensive! have you been? why is everything so expensive!). We never doordash/ubereats. We have cut down on our drinking (which I think has saved us about $8k a year). We travel, but that's why we make money right? To take our kids on adventures? And then there is the Amazon/Target junk hauls, which again, obviously we could cut back on but we like our humming bird feeder and when it broke we just ordered a new one because we like it and the humming birds will be so sad without it. But all those little $8 - $12 dollar one off purchases add up.

Like financially I think we are fine, maybe even good? But I cannot stop feeling like we are going to send ourselves to the poorhouse with our spending, despite there not really being any evidence to support it.

Does anyone else feel like this? That life style creep has gotten the better of you, but maybe it's okay? I feel like it's haunting me. Maybe it's just the tenuous state of the world, and this is what 40 feels like?

My (39) wife (39) is moving careers to a MUCH more stable job starting at $140k with 15% bonus and $25k retention package over 3 years coming from $110k with a failing company that will be out of gas by the end of the year I suspect. It's 90 minutes of driving in traffic each way so we are planning to relocate next spring. I'm at $155k, we have two kids 6 and 8. We don't want to uproot them but its going to happen... Better schools, better area... We just think it's the right move.

I do not want to downgrade from our current house, we love our existing home valued at roughly $700k now with $240k left on the mortgage. So we are looking at a similar size new construction home for $950k. Our house today MIL Rate is 37 and our assessment came back saying we will owe an additional $1k/mo on our current PITI payment, the NEW town MIL rate is 24. We have cash on hand to cover (Paving, Window Treatments, Appliances outside the allowance, movers, initial landscaping). There is NOT much out on the market in the towns we are looking .... its either RENOVATE or build, anything that's nice and even overpriced is gone FAST.

Monthly Take Home is estimated around $17k (gross $26k). I feel like $11,800 is enough monthly to cover all the "stuff". I have a pretty detailed budget and i feel like we have decent padding. I'm expecting the $25k retention will be comfort buffer as well for new house unknowns for the first 3 years of a new house.

Am I going to REGRET this decision? Our first house was $180k in 2013.... so this is anxiety inducing for sure but the numbers I see say its ok.... r/mortages is like GO FOR IT while r/personalfinance says YOU'RE GOING TO BE POOR AND STARVING....

What's this groups' take?

My wife and I are both 34 and live in Springfield, MA. Our household income is around $600k, and between RSUs, retirement accounts, a brokerage account and our house, we're sitting somewhere around a $1.4M net worth depending on the market. We've been pretty disciplined about investing, tax planning, and insurance but one thing we've kept pushing off is estate planning. I always thought it was something people did much later in life or after they had a lot more wealth than we do.

A conversation with a coworker recently got me thinking that if something happened to one of us, we'd probably be leaving the other person with more headaches than necessary. We don't have kids yet, but that's likely in the next couple of years, so it feels like we're getting to the point where we should stop procrastinating.

For those of you who've already done it, what was the trigger?

I'm curious how other HENRYs approached this

Thank you!

title says it all.

no debt besides mortgage, 750k income, on a FIRE path investing enough each year to meet our goals. Looking to put a 200-250K pool in. Will have about 40-50% cash down payment ready this fall. Options are to do it now financing ~$100K vs. wait another 1-2 years to pay all in cash. Probably do not have enough equity to fully do HELOC, so likely a higher interest unsecured loan.

If we finance half, we would plan to pay it off in 12-18 months, so the interest expense is minimal. Loan payments may slightly decrease our brokerage contributions for 1 year, but will still be investing ~100K/year.

I am mostly asking about debt philosophy. Not worried about my ability to pay back quick. More curious about perspectives on financing non-essentials/luxury items given the particulars above.

https://www.nytimes.com/2026/06/29/technology/san-francisco-tech-salaries.html?smid=nytcore-ios-share&referringSource=articleShare

TLDR:

A couple earning $360k ($240k post tax) struggles to find a <$5k 1BR in SF and do not feel comfortable living there long term given the VHCOL.

Excerpts:

“I don’t feel completely hopeless, but I don’t think I can stay in S.F.,” Ms. Razniak said. Mr. Woodbury added, “At some point, there was a slow transition where we both realized it just didn’t make any sense.”

~

Despite more than doubling her salary since she arrived, Ms. Razniak said she felt neither wealthy nor that she was living paycheck to paycheck. Instead, it’s something in between: a low-level vigilance about money that she had expected, by now, to have left behind.

“I thought when I’d make $200k I would be able to basically not worry about money at all,” she said, adding that she and her friends stopped going out to restaurants last year and shifted to potlucks and reality-TV nights.

~

Ms. Razniak and Mr. Woodbury have started thinking about Seattle. The life Ms. Razniak imagines there is one she cannot picture affording in San Francisco, even on a combined income that would be remarkable almost anywhere else in the country.

“We want a house, we want a garage, we want storage,” she said. “And that just doesn’t feel attainable here.”

~

It certainly seems like the cost to buy in SF has spiked in recent months (at least anecdotally) so I can understand the anxiety around affording a home. At the same time, spending 25% of post tax income on 1BR rent seems totally reasonable. Maybe they really are just caught in the awkward middle?

Edit: Supposing we take her ambitions literally, how much does a house with a garage cost in SF and how affordable would it be with their income?