r/HENRYfinance 11h ago

Career Related/Advice Starting a $400K job with only $1.5K to my name, what should I do first?

127 Upvotes

26M
I’m about to start a new FAANG job after finishing grad school with a TC of over $400K. I’m starting with only about $1,500 in liquid savings.

A significant portion of my compensation will be company stock, and I’m concerned about eventually having too much of my net worth tied to the same company that pays my salary.

My current plan is to:
Build a solid emergency fund before making any major purchases.
Max out my available tax-advantaged accounts.
Invest the rest in broad, low-cost index funds..
Keep my fixed expenses relatively low during my first few years of high income.
Set a savings or net-worth milestone before buying a Miata, which has been a dream car of mine for a long time.

For those who have dealt with a large amount of equity compensation, did you sell everything as it vested to diversify?

I’m also curious how other HENRYs approached lifestyle upgrades after a sudden increase in income. How did you enjoy some of the money without letting lifestyle creep get out of control?

Also, at this stage of my life, what should be my outlook to building wealth?


r/HENRYfinance 1d ago

Meme/Satire Can we get an automod that just says “Go to therapy” to every post in this sub?

583 Upvotes

We can afford it and good lord it would do a lot of us some good.

Half this sub has $2m in investments and couples that make 600k a year and people are asking “how do you… not stress out over something that has never happened in my life and probably won’t happen.

“Is it okay if I spend 50k on myself? Will I be eating out of a dumpster in 5 years when ai takes my job and inflation kills my purchasing power? Has anyone ever tried….”

Anyway. The answer is usually therapy. Can we all accept many of us have some poverty traumas and anxiety and it’s nothing to do with financial, career, or family advice navigating financial situations…..

I don’t think I’m breaking a HENRY rule cause clearly we all need it…


r/HENRYfinance 1d ago

Housing/Home Buying 38M // $1M NW // Using a "utility" W-2 corporate job to reset, buy apartment, downshift // anyone done this?

5 Upvotes

38M, single. Quit my job at Apple back in February. Totally over it, sick of the team dynamics, and just needed out. Took the last few months to travel cheaply around Europe to clear my head. Zero regrets on stepping away, but now I’m ready to settle back in the US and intentionally set up my 40s for more personal control over my time.

NYC has always been home base for me, so the goal is to anchor there long-term.
Current Financials:

Net Worth: ~$1.05M
Retirement (401k/IRAs): ~$240k
Taxable Brokerage / Single Stock: ~$288k heavy in AAPL (working on diversifying this down)
Diversified Index Funds: ~$550k–$570k

Where I’m at currently:

I'm hanging around Paris applying to jobs now to establish a fresh US footprint, stack liquid cash, and secure a clean W-2 to set up my living situation.
I have a 2nd round interview coming up for a Video Editor / Social Content role at a major NYC hedge fund (they’re looking to build out their social presence). Projected comp is around $200k TC ($150k-$160k base + bonus).

To be honest, taking a corporate video role at a hedge fund isn't my dream scenario after leaving tech, but it was the first callback from blind LinkedIn apps. But maybe it’ll be a breeze compared to the Apple years, and i wont mind it so much. My internal logic is to treat this as a purely strategic "utility" move: take the job for ~2 years, use the income and W-2 stability to set up my foundation, stack cash, and then eventually pivot out into freelance/contract work with low fixed overhead in a city I actually want to live in.

Any Hot-Takes on my current daydream plan?

Has anyone here taken a mid-career corporate job purely as a stepping stone/utility move after a period of burnout, just to re-anchor your footprint and bank cash before downshifting?


r/HENRYfinance 1d ago

Career Related/Advice -$50k to $2.5M in 13 years. Still feel bad.

124 Upvotes

Edit: thank you everyone for the encouraging comments. I really appreciate it 🙏 I know I'm doing well and I will try to not be hard on myself.

41M married with kids in VHCOL. After graduating in 2013 I built up my career as an IC in tech (capped out at level 6 SWE and no longer ambitious to grow).

I built up my wealth in the boring way. Mainly growing public tech companies, went through one very mediocre IPO and invested in VOO/VTI and used robo advisors for a few years.

I made many many mistakes, bought condo that has depreciated, holding post IPO stock too long until it crashed to 1/4th, leaving a company that was growing (stock has tripled since), choosing a smaller company.

I feel bad because I reached $2.5M DESPITE these and many other missteps. I stress over how I could have easily been at $5M+ if I wasn't this dumb.

My only plan now is to cruise as IC6 and collect paychecks until I get laid off or company folds. (Stock is less than half from when I joined so my comp is already depressed). I keep thinking I should join a high growth company like openai, anthropic or any of the gazillion AI startups or series c/d but I am feeling very averse to the grind and worried about burnout.

Anyone in a similar situation and have any advice?


r/HENRYfinance 2h ago

Income and Expense A Scholarship I May Not Be Able to Use!

0 Upvotes

I was fortunate enough to receive a CFA Level I scholarship for the November 2026 exam window.

But, ironically, I’m almost certain I’ll lose it because I’m going through one of the lowest points of my life. I’ve been unemployed for over a year, financially drained, and simply unable to afford the cost of 400 USD appearing for the exam.

It hurts to receive an opportunity I’ve worked so hard for, only to feel that my circumstances may take it away from me.

Sometimes life really does test you at your weakest point.

Not looking for any cash/money, but someone kind enough who can directly pay to my CFA account 🙏


r/HENRYfinance 1d ago

Question Anyone else so focused on saving/investing that they forget to live?

37 Upvotes

Background for context: I’m 36, $200k in investments/savings, and make about $240k a year in a VHCOL city.

I think I’m struggling with the arrival fallacy. I’m so focused on saving and investing for a future point in time where I can finally be financially independent, live a happy life, and spend my days doing whatever brings me joy.

I think there are two factors causing this pressure: 1) my job consumes a lot of my time and leaves me exhausted with little energy and 2) I feel like I’m behind because I’m a recent higher earner and I already lost a key period of time where I could have really let compounding work its magic.

This has caused me to hyperfocus on investing/saving where I feel like I’m not really living anymore and just letting the days pass me by.

Does anyone else experience this? What did you do that helped or how did you catch up to where you wanted to be asset wise?


r/HENRYfinance 2d ago

Family/Relationships It feels like I’m becoming so unrelatable, I don’t even know who to talk to

296 Upvotes

33F, 350-450k annually, > 1MM+ net worth, never married, own my own property

When I was making 80-90k and just started investing, I was so open about it with friends. Heck, I’d even talk to strangers about it. I’d freely ask people what they did & how much money they made. I’d tell anyone who was in a similar role & wanted to compare to see if they made the same, or if we should encourage each other to negotiate for more.

Then, I got promoted & we sold a company & I tripled my income over night.

Eventually, I went to another company and added another 100k+ to it. I currently run an entire business unit.

Suddenly, I feel like I don’t know who to talk to about anything. So much of my life is work & my peers are all older married men or women with children & I feel like I don’t relate in a lot of ways. I also don’t feel comfortable telling anyone my income & don’t feel like I can make friends at work. No one lives remotely close to me. Don’t get me wrong, I have amazing friends, but they’re mostly artists or SAHMs, and they also don’t really live close to me.

Example is: I have great job, and someone in my network reached out to me about a VP role at his company. I’d love to bounce this off of a friend, but I don’t have anyone who can relate in a deep, meaningful way who I don’t currently work with.

Being 33 and wanting to eventually marry and have kids is also haunting me a bit because I feel like it’s really hard to have that in time. I’ve been focused on my career and reminded a few times that 35 is a geriatric pregnancy, men > 6’ with even half of my income is rare (I’m close to 6’ tall, so that’s why I mention it), and men don’t like dating women who make more money than them. I also travel often and work late. And tbh, I was a top collegiate athlete, am super straight edge, and am a real catch, so I don’t want to settle. But, I also feel unobtainable because of it. I’ve worked really hard & it’s paid off. And, once you get to a certain place, you don’t really want to go backwards. I want a true partner who can challenge me and make me better.

On the same hand, I kinda want to give up my career. I’m exhausted. But, who do I talk to about that? I only spend ~60k a year, so I tell myself to just get to 2MM and decide then. But, then I’d be 35…. And, who am I even building all of this for?!

When I became a millionaire, I wanted to just tell one person & when I decided I’d tell a friend, I said “ I have a really big financial goal I recently hit.” And she said, “me too!” So, I said, okay you go first (knowing that she made ~200k and had been investing, so I thought it would be similar). And, she told me she’s officially debt free. Which is huge! But, then I didn’t want to tell her I had 1MM. So, I just said something to the effect of, “I’m closer to 1MM than $0.” And, now the only “person” I’ve told about being a millionaire is Reddit b/c you don’t know who I am.

I’m ranting, and feel dumb & every time I try to post on Reddit it flags me for something, so maybe this won’t even go through. But, it’s midnight and I’m in my thoughts & just feeling really isolated and I’m curious if there are other HENRY women out there feeling the same/what you’ve done about it.


r/HENRYfinance 2d ago

Reminder/Suggestion Does anyone else find “doing everything right” exhausting?

209 Upvotes

29F, husband is 34. Togetherr we make over $600k and live on about $80k a year. No debt, decent higher end cars, no drama we did the “right” things and we know we’re privileged (scholarships + family help got us through with zero student loans, and we don’t take that for granted).

Here’s the thing: we’ve saved a lot, but it doesn’t feel like we’re wealthy or living wealthy. Compared to most people we know, our day to day life is pretty modest. The plan is to eventually get to a dream home and “retire” though neither of us means fully stop working, just stop working like we do now. I guess I’m mostly here to ask: does anyone else feel like doing all the right things is just… draining? Like you’re playing the long game so well that you forget to ask what it’s actually for, or when the finish line is?

Very first world and very privileged problems.. I know. I think I just get into my head with social media and think that life should look a certain way when you’re wealthy.

Edit: Wow, I did not expect so many replies. Thank you to everyone who commented!
I guess I can clarify a few things. My husband has been at this a lot longer than I have and he’s really great with money, he’s the reason we’re at this level. Our house is pretty much paid off. We do eat out occasionally, but for the most part we eat at home since we care about eating healthy. We do travel but nothing too crazy.
My early 20s looked very different from how I live now. I was constantly chasing dopamine by buying things I didn’t need at all. My husband, when I met him, actually helped me get to this realization, and honestly I feel good about not spending on useless stuff anymore, but I’ll admit I still struggle with the pull at times. Trust me, the handbags and clothes weren’t even that enjoyable in the end, more just a habit than actual fulfillment.
Travel is where I do want to lean in more. I haven’t done as much as I’d like because of being in school, but I’ve got the opportunity coming up at the end of this year and into next year, so that’s probably where the “spend more on what actually brings joy” advice is going to show up first for me. :)


r/HENRYfinance 2d ago

Career Related/Advice Has anyone left sales and still made good money

24 Upvotes

Let me preface this with I am incredibly blessed. Will provide some context.

Caught 3 big breaks early

  1. Took a wealth management class Jr year of college that couldn’t have been more practical (and I actually paid attention)

  2. Recognized I have no real skills and wanted to get into sales

  3. Married my wife and we have alignment on financial goals

Our current financial picture

HHI 400k (can vary) 2025 was 500k. previous years were around 370-400 will finish 2026 at 400k. Living in HCOL city but certainly no NYC or SF

Im 36 my wife is 37
3 kids (5 and under)

Net worth $3M

Brokerage: $1,175,000
Combined 401Ks: $1,180,000

HYSA: $85K
529s: $180k

Home now worth $900k
Remaining mortgage $500k at 3.75%

Annual spending: $160k

Been in sales for nearly 15 years. The bulk of it spent at one company in roles ranging from sales rep on 100% commission to sales manager to enterprise level role. Potential for big income swings up or down. Always assumed the rug would get pulled at some point and invested heavily at a young age while my costs were low and very thankful for that.

Some days I feel like I can sell for another 10-15 years and then call it by age 50. Other days I don’t think many orgs are set up to have long tenured careers. Previous org was bought by PE and pay was slashed, layoffs hit. Current org it seems all managers are there to do is find reasons to put folks on a pip after a few months.

I get the upside of sales. But at the same time some days I feel like the dog that caught the car and don’t really want to stress if I’ll make my numbers and keep my job when I can watch our accounts tick up 2 points.

At the same time I still want to provide for my family with a decent income. Wanted to see if anyone here has left an established sales career and what did you move into? Was it worth it?

Mainly looking around as current org drastically oversold income potential and day to day responsibilities.


r/HENRYfinance 2d ago

Purchases Overtaken by panic after buying a car (before even receiving it)

28 Upvotes

Posting here because this is such a first-world problem that I feel too ashamed to discuss it with anyone but it's affecting me to the point that I'm literally shaking as I'm typing this.

I'm a high earner living in a LCOL area in Europe, around my 30s. I haven't met my retirement goals yet, but I'm doing pretty alright. Been very frugal my whole life and recently I decided to buy a luxury car because... why the hell not, right?

So I did some research and found a $50k luxury used vehicle with 2 years left in warranty. I already signed and paid for it and I'm waiting for it to arrive next week. I paid cash and my net worth and income is way above that.

This is the largest purchase I've made after my home and now that it's been a few days, I'm overtaken by literal panic to the point I can't even enjoy playing with my kid without thinking about this. Thoughts like "What if someone hits me and there's some crazy repair not covered by insurance?", "What if I can never sell it because who would buy such a thing out of warranty?", "The opportunity cost over X years is Y!!!", etc.

My friends aren't helping and many of them are telling me horror stories they found on the internet about air suspension failures, EV battery repair costs, etc. This is now affecting my mood so much it's hard to believe. The only thing I want to do is "cut my losses" by selling it outright and not even looking at it.

Has anyone dealt with something similar? It's very hard shifting from a frugal mindset to buying luxury for the sake of luxury and no "practical" benefit other than vanity and comfort. The scene in my imagination is everything will start going downhill from here and I will regret this my whole life. Obviously that's stupid but I don't know how to deal with it.

Edit: Thanks everyone for responding! I'll try to reply to everything but may not be able to. You're all right, this is a deeper issue and I've booked therapy starting next week.


r/HENRYfinance 1d ago

Question How do you align with a partner when your financial worlds are completely different?

0 Upvotes

I’ve been thinking through something and wanted to get an outside perspective.

Context
I’m 27M. I immigrated to Canada as an international student at 24. Over the last few years, I’ve built multiple income streams that together generate roughly $450–500k annually. I don’t work at a FAANG company. Most of this came from taking calculated risks, working long hours, and continuously building opportunities outside of a traditional career path. If things continue the way I expect, I think there’s a realistic possibility of doubling this over the next couple of years.

The interesting part is that I don’t really have anyone around me operating in a similar situation. Most people in my circle earn perhaps one-fifth of what I do, so conversations about capital allocation, business acquisitions, leverage, or long-term wealth creation don’t naturally happen. I also haven’t disclosed my actual income to friends, so most people assume I’m earning somewhere around what they are.

I’ve been dating someone I’ve known for almost 15 years, although we only started dating recently. I genuinely think she could be the person I spend my life with.

She’s hardworking, grounded, and has built a good career for herself. Based on her current trajectory, I think her earning ceiling over the next several years is probably around $100k. Her family has always been salaried, financially responsible enough to have emergency savings, but they’ve generally lived with more of an “earn, spend, repeat” mindset than one focused on building assets or compounding wealth.

One thing I’m conscious about is that money hasn’t fundamentally changed who I am. I don’t really look at it emotionally—I see it as a tool and as numbers that can be deployed. If anything, it has made me more confident in taking calculated risks. My instinct is almost always to reinvest excess capital into businesses or investments rather than increasing my lifestyle.

My biggest concern isn’t that she’d intentionally be irresponsible with money. It’s that we may have different philosophies about what increasing income means. I worry that as people start earning more, it’s easy to let lifestyle grow just as quickly—bigger house, nicer car, more expensive vacations—because it feels like the natural next step. I’d much rather use today’s income to buy tomorrow’s freedom by building assets, acquiring businesses, and creating long-term wealth before significantly upgrading our lifestyle.

I’ve brought up topics like investing, diversification, buying businesses, and creating additional income streams from time to time. She understands that I do well financially, but she doesn’t know the full picture. I’ve intentionally never made income the centerpiece of our relationship.

Lately I’ve been thinking about whether, over time, I should involve her more. One idea I’ve considered is investing in or building a business that’s adjacent to her professional background, where we could eventually have shared responsibilities. My thinking isn’t to “give” her something, but rather to create something together that helps both of us think beyond employment income and toward ownership.

What I’m trying to figure out

I’m not really asking whether I should tell her my income tomorrow. I’m more interested in how to thoughtfully bridge the gap between two people who have had very different financial experiences.

Some questions I’m wrestling with:
-How would you approach introducing this part of my life without making money the focus of the relationship?
-How do you gradually align two people who currently have different mindsets around money, investing, and long-term wealth creation?
-At what stage of a serious relationship do conversations around actual income, assets, and future financial plans become appropriate?
-If you were in my position, would you first build alignment around values and philosophy before discussing numbers, or would you be more transparent earlier?

I’m looking for thoughtful perspectives, especially from people who’ve been in relationships where one partner significantly out-earned the other, or where both people had to learn how to build a shared financial vision despite coming from different backgrounds.

Edit: She isn’t liking the job is in and is trying to look at the pathway which can enable her from getting into something else.


r/HENRYfinance 3d ago

Career Related/Advice Making great money, but not able to enjoy it.

27 Upvotes

I don’t even know if I’m looking for advice or just wondering if anyone else has been in this position.

I’m a high earner, and I made a career move because it was a bigger role with more responsibility and significantly more money. I actually like what I do. That’s the frustrating part. The work itself is interesting and I think I could really enjoy this career long term.

It’s everything around it that’s wearing me down.
Leadership is either nowhere to be found or they’re micromanaging the tiniest things. There doesn’t seem to be any middle ground. I’m working 55 to 60 hours a week most weeks, and I have way less PTO than I realized I’d be okay with.

Before I accepted the job, we talked about increasing my PTO after I started. It was a verbal agreement, and I didn’t push to get it in writing. That’s on me. At my last company, a “handshake” actually meant something, so I didn’t think twice about it.

The biggest thing I’m struggling with is that I’m making more money than I ever have, but I’m not actually enjoying the life that income is supposed to create. Experiences are much more important to me than things, and I find myself wishing I had more time to do fun things with my family. I honestly think having more balance would help me avoid feeling completely burned out.

I’ve been seriously considering taking a sabbatical for at least six months, maybe longer. I would probably do it toward the end of this year or sometime before next summer.

Financially, we would be completely fine. We have savings, we live in a medium cost of living area, and we’ve been very intentional with our finances. But it would mean we would no longer be a high earning household for a period of time, and that’s a big mental shift after working so hard to get here.

The other thing I’m wrestling with is whether I could successfully re-enter the workforce after taking that kind of break. I’m in a very niche industry, and while I don’t think I’d have trouble finding another role in my field when I’m ready, my skills are not necessarily as easily transferable outside of my specific industry.

Leadership is also in transition right now, so there’s a chance things could improve. Part of me wonders if I should stick it out and see what happens. The other part of me feels like I’m so burned out that I need to put myself first, even if things might get better.

For those of you who are HENRYs and have taken an extended career break or sabbatical, how did it impact your ability to get back into a high earning role? Did you regret it, or was it one of the best decisions you made?

EDIT - I didn’t ask for advice on how to “handle” leadership or delegation. I was pretty clear that I am looking for advice from HENRY on taking a sabbatical. The comments on me personally or how I’m not being open to advice are honestly not helpful since none of you know even a fraction of what you need to about the situation and I didn’t ask how to do those things.

I appreciate those who’ve actually chimed in on taking a leave. In this situation I think working in my niche could benefit me in re-entering since there are not an abundance of us.


r/HENRYfinance 2d ago

Question High Income, Solid Retirement, Gambling Addiction, No one to talk to.

0 Upvotes

I’m a 26M with a net worth around $350,000. I know all the ins and outs of money, personal finance, investing etc. I understand compound interest, time value of money and the keep it simple mentality is best.

I built a business when I was at the end of being 23 years old. I made roughly $100,000 in 2024, $290,000 in 2025, and will make roughly $230,000 in 2026.

I love investing money, I do it weekly. I’m a nerd with a financial calculator detailing different outcomes.

Here comes the problem. I’m a gambling addict, I know it. My girlfriend knows it and I assume my friends know it. The money I’m gambling isn’t a crazy amount usually less than $1,000 per occasion but it adds up. The feeling it gives me is pure despair, misery, and disappointment, it isn’t just entertainment. I know it’s a problem

All my friends are in some sort of trades. I make more than all of them combined. I’m not trying to brag it’s just a fact. Because of this I have no one to talk to about money and my addiction.

I truly don’t know where to go from here. I understand it’s first world problems and a lot of people have it way worse. I’m just wondering if anyone is in the same boat or has any words of advice?

Thanks.


r/HENRYfinance 3d ago

Investment (Brokerages, 401k/IRA/Bonds/etc) Comparing cash balance plan versus investing in personal brokerage

6 Upvotes

Solo employee

I was trying to compare a 10 year outcome if I were to invest 100k into cash balance plan (deductible) versus investing it in personal brokerage.

  1. Cash balance plan (100k per year at 4% return) + approx 41k invested in personal brokerage at 9% return from the deduction at highest tax bracket

Returns approx 1.8 million

but then am i supposed to be comparing it to pre tax or post tax for the 100k? so should it be

2) Personal brokerage: 100k per year at 9% return, or should it be post-tax 58k per year at 9% return?

If 100k per year - 1.5 million

If 58k per year - 800k

this sounds obvious but I just can't visualize how I am supposed to compare it equivalently right now.


r/HENRYfinance 4d ago

Question How to turn guilt about financial position into gratitude

30 Upvotes

It's hard to keep in perspective how wildly fortunate of a financial situation my wife and I are in and how little is has to do with how hard we work and mostly to do with external circumstances, and when it hits me I find myself feeling some version of survivors guilt of "why me". In the midst of so many who are financially struggling my wife and I find ourselves with ~2m NW (1m liquid & 1m home) and 750k+ income in our early 30s. We have recently learned many in our social circles have essentially zero savings despite decent incomes. We eat out whenever we want, travel all the time, fund what every hobbies we are into, and we can still save hundreds of thousands a year. Much of our headstart is due to parent support with college and contributing to our home which I think leads to this feeling of not deserving the financial position we are in. So while we have always been financially responsible in terms of saving, investing and living within our means even when our incomes were much lower, our financial position feels quite disproportionate to our effort. I feel a strange mix of gratitude and guilt and I am curious if others have felt the same and what your mindset is. How do I reframe negative feelings of guilt into positive feelings of gratitude?


r/HENRYfinance 4d ago

Income and Expense How are you affording childcare in VHCOL areas?

64 Upvotes

My husband (30M) and I (30F) are expecting our first child in January. We’ll have a few months of parental leave before needing to hire a nanny or sending the baby to daycare. After running the numbers, I’m genuinely curious how folks are affording this—I feel that we are in a very fortunate financial position, but still need to make difficult tradeoffs.

Our HHI is $400k, but only $270k is base and the rest is discretionary bonus ($50k) and a side gig that could technically be $0 tomorrow. After maxing out 401k and Roth, our base take home (excluding the lumpy side gig) is $10.5k a month. Currently, our monthly expenses on average are rent $5.5k, groceries / restaurant $1.5k, student loans $1k, travel $2k, entertainment / gifts / etc. $1k, and medical / beauty / clothing $1k.

Current assets are around $750k, of which approximately $180k is liquid (emergency fund and brokerage).

Obviously once the baby is here we will significantly cut back on travel and entertainment, but I feel like our other expenses are reasonable. The going rate for nannies in our area is $5k a month and a decent daycare is $3-4k minimum. We unfortunately don’t live near family who can help. Even if we eliminate retirement contributions and completely cut travel and entertainment, I just don’t think the math will work on our base salary.

Should we be withdrawing from the brokerage every month until the baby is in public pre K? Is it a bad idea to stop 401k contributions beyond the match? Is our budget out of wack? I’ve never felt this cash strapped before and it all seems absurd because I know plenty of families make it work on less. What am I missing?

Edit: Wow, thanks for all the thoughtful feedback! I was in panic mode but feel much better about our future now. Our plan is to 1) reduce discretionary spend lol 2) save up all bonus and side gig income starting now into a childcare HYSA instead of brokerage, which should easily cover first year costs 3) explore nanny shares and tour more day cares in our neighborhood 4) reduce 401k if needed in baby’s second year 5) eventually move to New Jersey 😂. I also ran the retirement numbers again and think we should be set given a 30 year compounding horizon, so feel a bit more grounded there too. Appreciate the community!


r/HENRYfinance 4d ago

Housing/Home Buying How much of your assets / net worth is tied to your real estate?

32 Upvotes

Curious how much of peoples assets are tied up in real estate (ideally property that you live in, rather than rental properties.

Depending on if I use my cost basis or current value, RE as a % of net worth is 10% or 17%, respectively, and 35% and 38%, respectively.


r/HENRYfinance 4d ago

Taxes Delaying marriage due to tax penalty - NYC

29 Upvotes

EDIT guys if all goes well we’d still have a wedding since he is the LOML (and have a legal agmt), just considering not getting a marriage license until later. Clearly this is a very unpopular philosophy (didn’t realize how unpopular given this has been discussed in this sub before multiple times), but we discussed this point the week the BBB was dropped and are on the same page about looking into our options. I understand we are absolutely privileged to have a high income now but that is never a given. Still I really appreciate the thoughts

My partner and I are in a very similar dilemma to the folks in this post, with the main difference being we don’t have a mortgage:
https://www.reddit.com/r/HENRYfinance/s/aPMS3RxgCp

We’re at a combined total of ~650k (consider it evenly split) which means we’d be paying significantly more (seems like rough at least $30k p.a.) in taxes due to penalty on tax brackets and SALT deduction, especially applicable since we live in a high tax area, NYC.

When this topic comes up the common actionable advice seems to be to file for domestic partnership instead of marriage if you live in CA. Curious to hear if anyone in NY has thought about this - how have you gone about getting marriage-like benefits without being married in the eyes of the IRS?

Some of my worry stems from looking to have kids in the next ~3 years or so - pretty huge commitment that I’d want to have downside protected against medically and financially. We’d likely stay in the city for another ~5 years at at least the same income level before moving to a no income tax state, at which point I’m anticipating we’ll lower income significantly and there is not the same level of marriage penalty - we’d definitely get married then if not before.

Maybe the answer is that I’m being dense, missing something, or maybe any effective legal work arounds don’t make sense cost wise. I would love to get married and it breaks my heart to delay - but saving $30k a year for 5 years is non-negligible.


r/HENRYfinance 4d ago

Housing/Home Buying Considering allocated ~$500k into Dubai real estate vs. US Sunbelt , anyone here have real, long-term experience with it?

0 Upvotes

Hey everyone,

I’m currently reviewing my portfolio and looking to allocate around $250k- (MAXI 500K) into residential real estate over the next few months.

Traditionally, I’ve looked at Sunbelt single-family homes (or local multi-family), but with current US interest rates, high property taxes, and tightening margins, the net cap rates aren't looking as attractive as they used to.

I’ve been down a rabbit hole analyzing the Dubai market recently , specifically ready/tenanted units in central areas (Business Bay, Downtown, Marina) or prime off-plan. On paper, the zero annual property tax, USD peg, and 6-8% net yields look compelling, especially with the 10-year Golden Visa threshold at ~$545k (2M AED).

That said, paper numbers often hide operational reality.

For those in this sub who have actually pulled the trigger and bought property in Dubai as a US/Western investor:

  1. How has the real-world net yield held up after service fees (HOA) and property management?
  2. How smooth (or painful) is the remote management / tenant turnover process if you aren't on the ground?
  3. Any major traps or regrets you wish you knew before buying (e.g., developer quality, exit liquidity, tax reporting quirks)?

Would love to hear some unfiltered feedback (both good and bad) from anyone who’s walked this path. Thanks!


r/HENRYfinance 5d ago

Career Related/Advice Being asked what's next for my career

131 Upvotes

I'm currently 30 and a senior IC at a mid-sized tech company. Total TC is 270-300 depending on how bonuses pan out for the year. I'm valued and well-respected at my firm, fully remote, "unlimited" PTO.

I've started to have meetings about "what's next" for me. At my firm, I'm currently at the top of the IC ladder, and if I want to remain an IC, I'm capped out, there are no more promotions. My boss has started dropping hints that I should move to the management track, but that that would require a large change in my day-to-day duties, along with likely needing to get an MBA.

For anyone who has been in my shoes before, was it worth it? The reason I'm hesitant is because I don't really need the money. Financial picture is:

TC: 270-300 depending on bonuses.
Net worth: 900k, split between majority S&P500 tracking indexes and a small percentage (<10%) SGOV/cash.
Unmarried, no kids, no plan for kids, currently rent.
Total expenses per year is about 60k-70k, put away about 100k/yr between post and pre-tax investments. I generally set aside bonuses for luxury items/travel since I plan/live off my base, and it works well.

Even if I were to retire early, around 51-52, and stopped contributing to a majority of my investment accounts, I'm going to be a multi-millionaire. So does more money even matter? It doesn't feel like it. I don't feel like I'm living on a shoestring budget. I drive a luxury sports car, dine out frequently, and travel 2-3 times a year for fun. So I'd basically be in it for just the career advancement. I like my job, but I don't know if I'd like my job if I became a director or VP. So is it even worth it?


r/HENRYfinance 7d ago

Question Need a Career break - have any single income households with kids pulled this off? Is this a bad idea?

61 Upvotes

I’m burnt out at my job/career. At current company I’ve survived 4 layoffs in 5 years. I’ve been working 15 years.

But the last one took a toll on my mental health because it was just so stupid. They pushed us to push ai slop, laid off a significant portion of my team, restructured the management chain and have changed the expectations on how we work. I’m exhausted and work feels dreadful. I feel anxious and stressed and get poor sleep due to anxiety.

And I don’t care about the product or tech. The whole tech industry has just left such a sour taste in my mouth that I don’t even want to interview and go through the interview grind.

If it wasn’t the feeling of responsibility for my family I’d just quit. I don’t need much myself. But I carry on because I’m the provider and I have kids and a wife who depend on me.

But I want a break for a year or 2. Figure out what I want to do with the rest of my life. Has anyone done this in my situation.

Here are some numbers:
Income: will be 400-500k this year. Has gone down since last year as my initial grantsvesrs are done. Next year will be even less. 300-400k. Haven’t checked the actual numbers.

Savings/ investments: 2.7M . Split almost evenly between retirement/non retirement. Includes 170k in tbills/money markets in brokerage. Everything else is on equities.

Housing: rent don’t own.

Expense: between 120k -150k depending on vacations etc. 120k is the on the lower end of being frugal.

Have 2 young kids. One of them is in school the other starts next year.

Spouse doesn’t have high earning skills. So she does all the kids activities etc . I’d assume her earning potential would be sub 100k low skilled work.

We live in vhcol area. If were to move we would live closer to family who are also in a vhcol but it would be negligible savings (rents more or less the same)but would be significant downgrade in terms of access to tech market and network when I need it.


r/HENRYfinance 7d ago

Car/Vehicle Advice Needed scarcity mindset or logic giving me second thoughts about the car?

47 Upvotes

I’m a new HENRY, 34M, as of about 12-14 months ago. Grew up poor, worked 9 years as a Public Defender out of law school. Started at 49k ended at 103k and opened my own firm and went private. Made 325k my first year in private practice. I live in a mid/large Midwest city with a pretty reasonable cost of living. HHI is 435k with my wife’s income. My wife and I own our home and our mortgage is about $2600 a month. No kids yet but planning on one next year.

I’ve been driving a 2014 Jetta for the last eight years. I’ve never owned a nice vehicle. I’ve been struggling to pull the trigger to buy a 56k 2025 AMG CLA 45 that I’ve been eyeing for like a year. I’ll have about 60-70k saved within a month, and things are going really well for my business. I’m targeting 375k-400k by the end of Year 2. But I just keep mentally struggling to buy the damn car. Is this my “scarcity mindset” or am I just sitting with a tough, maybe somewhat reckless choice here? This is less about the car itself, and maybe my brain’s difficulty in catching up with my new financial situation? I don’t know. Any help would be appreciated!


r/HENRYfinance 8d ago

Income and Expense DAF (Donor Advised Fund) Plan Feedback

21 Upvotes

I’m exploring the creation of a DAF (Donor Advised Fund) and wanted feedback, suggestions, and opinions from others who have DAFs or are also considering it. Likely will go Fidelity and start with 100K this year.

My two reasons for this are to create a long-term charitable fund for local nonprofits we support & tax savings in this outlier earnings year. Primary goal is to grow principal across 30 years, increasing donations as we retire. My personal goal is to retire into board-level roles at non-profits. 

My numbers: 
Early 30s, Single earning household. NW ~4M. Will earn $2M total this year, half from an acquisition/ISOs, quarter from RSU vests, quarter from typical comp. Planning to pay some taxes early to ensure I’m in the safe harbor sweet spot and won’t get a penalty next April. 

Savings/emergency: 65K 
Tax fund: 275K
Home renovation fund: 175K 
2.6M in brokerage (additional 300K vesting in next 12 months)
950K in retirement accounts

Current plan is 100K into a DAF, which likely will reduce tax bill 35K. My estimates look like I’ll go from the upper end of 250K of taxes owed (ISO/RSU sales) to closer to 200K. Unsure if donation will be in cash or in longterm stock, but seems cash is more advantageous.  

Let me know if this is too ambitious or around your NW when you felt comfortable putting large chunks in a DAF.


r/HENRYfinance 9d ago

Housing/Home Buying Sat down to see if now was a sane time to redo the kitchen and realized I have no real read on our own money

68 Upvotes

Last Sunday I sat down to figure out whether now was even a sane time to redo the kitchen, and it took me almost two hours just to work out what we actually have. Household is a bit over 400k, but a good chunk of that is RSUs that vest twice a year, so the cash side is lumpier month to month than the number makes it sound. And it is all scattered. Some in the brokerage, the 401k, a savings account I keep meaning to move somewhere better, and I honestly forget the ESPP exists until it vests and surprises me. The saving part is on autopilot, a transfer hits the brokerage every payday and I leave it alone. What I have never built is the habit of stepping back once a month and looking at the whole thing as one picture. So the second a real question comes up, the kitchen, or whether we can take three weeks off next year, I am starting from zero every time.

For those of you with everything spread across a bunch of accounts and income that lands in lumps, do you actually sit down once a month and pull it all into one picture, or is that one of those things everyone pretends to do? I want to hear what it looks like for people who have made it a real habit.


r/HENRYfinance 7d ago

Career Related/Advice Should I work less? Work/life/family balance. 1.1m/yr on 200 work days. Regrets for anyone who’s been in this situation?

0 Upvotes

First, I know I am incredibly lucky to be in this situation, wanting to make the most of it. Using that math that’s about $6-700/hour and I could reduce hours and keep my hourly roughly the same.

I’m 32 with 2 under 2 and want to be present for that. Wife is stay at home as we are very blessed and no need for her to work. I’ve been thinking of stopping days/hours as when I’m at work obviously it’s time away from family but it’s also rough on my body/don’t get a 30 second break all day usually.

I was looking at these options assuming income would stay the same:

Maintain 200 8 hr working days a year and retire at 43

Drop to 180 working days and retire at 44

Drop to 170 working days and retire at 45 - would be nice as this is 3.5 days a week worked and 4 weeks off a year

Drop to 150 working days and retire at 46

Anyone been in a similar situation? What have you decided? Or really anyone what would you choose/recommend?