Earlier this week I saw the breakdown of what different tiers of breathing-room money vs "fuck it" money... at what point would you say you earn "frictionless-life" money? Like, having most services or costs on autopilot so you can seamlessly transition from task to job and self care and life with as little obstacles as possible? Im looking for any number and ideas - automatic blinds on a timer, personal gym trainer, robot vaccum, accountant, whatever works for you that makes you go "ahhh"!

[EDIT] It sounds like what would be most helpful is another person managing the household and errands to buy back more time. Thank you for all the responses everyone!

Hi everyone. Apologies for this question is not a usual HENRY finance question. I am, however, looking for the advice of HENRY individuals given my unique situation.

For reference, I am a university student and I am going for a donor scholarship interview soon and wanted some advice on etiquette. Most of this donors are HENRY, if not rich individuals. So, I wanted to get the perspectives for those in this community.

Additional context:

- Scholarship interview is in a dinner setting

- Around 10 donors interviewing multiple students

- Donors all worked/working in the same industry and company. Donors all influential figures, potentially partners in firm.

- Dinner is hosted at one donor’s house (retired but, former C-suite)

- Food and alcohol are being provided

All interviewees are lower-income students, so I’m not sure what the social expectations are here.

Would it be appropriate to bring something for the host? Or would that be unnecessary / potentially awkward in this context?

If so, what would be considered tasteful and appropriate without seeming excessive?

Also, would appreciate any tips for the interview. It is a group interview over dinner as mentioned above.

Thanks in advance!

Edit: Thanks for all the help and advice I receieved. I will most definitely not bring a gift, and instead would write a short handwritten note to the host.

Would really appreciate any advice on how to overcome the feeling of intimidation when meeting/talking to the donors and interview process in general!

Hi everyone,

I'm in mid to late 20's. For the past several years (and now), have always based my residency in tax-free jurisdictions. My NW has been growing 40-50% each year and my income is increasing proportionally for now.

My partner has received an offer and is about to move to a VHCOL city in the US in terms of taxes. Due to her visa type, it is unlikely she will be able to leave the country often (previously she would travel with me often when I was in my second residencies). I can be in that city half the year without becoming a tax resident; if I wanted to stay longer, I could sponsor myself for a visa but then would be subject to the tax rate.

My plan has been to keep compounding in the tax havens for the next 4-5 years, and then have the option to enter the US if it makes sense. If I were to enter the US now, it would set back my goals but I could just try and make more money. Not really sure how to think about this, seeking the advice of more experienced people. Maybe there are more creative ways to structure this? I own interest in all my income sources. Any non-Americans here who had the option to be in a tax-free place but chose the US anyways, can you chime in on your reasons.

And should mention, want to keep everything above board.

Thanks

My wife's employer recently started allowing Mega Backdoor Roth. She currently has about $100k in a 403(b). Should we convert all of it to Roth? What are the tax implications?

I just started doing Backdoor Roth's for myself in Schwab. HHI is around $400k. Happy to provide any numbers if needed.

I’ve seen a post of someone asking if they’re considered rich and it got me thinking. Is “rich” here supposed to be a specific milestone, or is it more of a mindset/feeling?
Is it based on income? NW? FI? At what point does someone stop being “not rich yet”?

NW is close $2.5M across various accounts. Plus about $1M in home equity with a low rate and monthly payments (stretched to buy in a VHCOL area in 2011). HHI is around $600k each of the past 4 years.

So on paper, we may have crossed the Rich threshold, but we don’t live a Rich lifestyle in our community. I actually find it difficult to assess NRY status before we pay for the kids’ educations.

We are finishing year 1 of the most expensive 10 years of our lives- one kid in Catholic grade school ($11k annual) and one kid in Catholic high school ($30k annual). Soon we’ll have both in high school, then the older one will go to college, and at some point we’ll have two in college for 1-2 years.

So in total, we still have 6 years of private high school to pay for and 8ish years of whatever college costs (529 should cover about 50-75%, depending on where they go).

Despite that, I’m about to downshift into a less stressful job. HHI will drop somewhat to $500-525.

I’m consciously prioritizing these last few years with my kids in the house, and as we get close to 50yo, who knows how much longer we’ll be healthy enough to enjoy this all. Hopefully we only have to work another 10 or 12 years. If the market doesn’t crater too badly during that time, lol.

We’re feel NRY (maybe were naively conservative in this assessment), and maybe will never be Rich. But we’re comfortable and going to lean into enjoying our kids while they’re home, and our 50’s, which start this year! We just bought e-bikes so that we can tackle the hills again like we did when we were younger and in better shape :)

This is a perspective that I’ve just recently come around to, and it’s liberating. Admittedly, this may be due to achieving some financial milestones that I never considered possible growing up very modestly.

Sharing here in case this vibes with anyone else. And I don’t have many people around me who I can discuss this with.

Context: I make 400k, wife makes 100k. We have 3 young kids.

Retirement accounts look good, we are in our forever home, college funds are on track. No debt outside the mortgage.

The last piece of the puzzle was the Emergency Fund. I finally got it to 30k (3 months expenses) because I always prioritized getting into this big home over the last couple years, and diligently filling my tax advantaged accounts. I also make a lot of comp in RSUs that get tied up for a while.

I have not really selfishly spent on myself since my kids were born. This year I loved taking my family on vacation, getting access to the beach club, signing up for summer camp, installing a nice big swingset + furniture in the backyard. I love seeing my wife and kids happy.

But now I think I want to finally do it - my dream - the big empty room in the basement can become my Media Room! 83" OLED LG! Sonos surround sound! Big comfy sofa! A place for me to call my own and unwind after the kids are asleep.

But it would require: dipping into Emergency Fund or delaying backdoor Roth contributions or simply waiting until March 2027 when I'll either have enough cash saved up, or a big bonus to more than cover it all.

Am I losing discipline? Am I being irresponsible? Or if I'm on track to be worth 7-10 million at retirement, is it OK to have a nice happy set up 6 months earlier than I would have and take on a little risk with a slightly underfunded Roth / light emergency fund til my 2027 bonus hits?

I’m in that classic HENRY phase where my base + RSUs put me in a high tax bracket, but my net worth isn’t quite at the FIRE level yet.

Every time I look for portfolio advice here or on other finance subs, the consensus is always: "Max your 401k/HSA, liquidate your tech RSUs immediately, dump everything into VOO/VTI, and don't look at it."

While I get the logic behind passive indexing, it honestly feels like we’re leaving alpha on the table. We’re literally working in or around the industries driving the modern market, yet we're told to invest with the risk tolerance of a retiree.

I’m not trying to be a WallStreetBets degenerate, but I refuse to believe everyone in this sub is just happily cruising on market averages.

For those who actively manage a portion of their liquidity:

Do you keep a separate "playground/active" brokerage account? If so, what % of your net worth goes there?

Are you actually picking individual tech stocks, running macro swing trades, or using options (like covered calls) to hedge your company equity?

Curious to see how many people here are actually chasing alpha versus just doing the standard index-and-chill. What’s your take?

Title says it all. Posting my stats below. Curious to hear feedback/thoughts from this group. Want to know if I’m considered “Rich” or still “NRY.

For additional context, I’m very burned out at my job and would love to take a step back and find less stressful work, be more present with my family, take care of me mental and physical health.

Really appreciate this sub and love reading it. Thanks!

Stats:

• Age: mid 30s
• Marital Status: Married, 1 kid under 3. No plans to have any more.
• Location: VHCOL. Right outside NYC.
• Finances:
  • HHI: estimating ~$750k in 2026. Inclusive of bonus + RSUs. Spouse and I both work. My income is 60% of HHI.
  • Investments: $2.15M. Split roughly 60/40 between brokerage and retirement.
  • Cash: $200k
  • Debt: $984k. All mortgage at 5%. Home Value: $1.3M. Assumes zero appreciation of the home since purchase 3 years ago.
  • Home Equity: $314k.
  • NW:  ~$2.6M. Cash + Investments + Home Equity.

My questions:

• Am I considered rich? My investments have eclipsed $2M+, but the returns do not cover my monthly expenses, which are high due to childcare and mortgage.
• Can I take a step back career wise and look for less stressful work? I’m torn as my equity is very valuable and feels bad leaving money on the table. We could get by with less, but I busted my ass to get this job which I kinda hate. It’s a money job, nothing else. Zero passion for the work or company.

Really appreciate this community and all the perspectives here. Thanks in advance!

Now I make way more and am broke. It’s like I went nuts and don’t want to stop dumb spending. I do have 4 kids still in the house. 3 driving age and pay for private school. It feels like everyone in my house is static except me. I’m just mad at myself for letting spending get out of control. Besides 2 401k’s 100k ish and a small investment/crypto account 8k I don’t have anything in the way of savings.

I (30M) have around $1.9M NW (no house, only cash and stocks) ~$500k TC, basically max out all retirement accounts, etc. but my savings rate (after tax) is around 65% after expenses. I probably spend around 25% on necessities and 10% for fun. When did you guys feel that you could ease up on the savings level and more freely spend. I think logically, I could spend much more and it wouldn't make a difference long term, but maybe I'm wrong? I'm also not a very materialistic person, but sometimes I'll see like some tcg boxes or w/e and want it, but 99% I just don't buy it, because I know that there'll be guilt afterwards thinking it's a waste of money.

Maybe because my wife and I are about to start trying for kids, or maybe just feeling a bit of job burnout, but my wife and I are seriously considering (after 4-5 years of just moderately considering) moving from a world class city to my hometown (think 100-150k metro area). Am in big-time-biglaw and doing well after 4.5 years (if getting pretty tired of it); I'm sure I could find either a good remote job or an interesting-enough regional law job, but I can feel my brain chemicals start to shift and other priorities start to take over. My wife is less career-oriented than I am but also doing well in a job she likes enough; she could find a new job easily I am sure.

Anyone done the same (or nearly done the same and pull back) and have thoughts to share?

For context, I have no intention to actually retire early, but at the end of this year we'll probably have 12.5-15x our current annual expenses in liquid/"financial" NW, in addition to a separate fully loaded down-payment fund. Very early 30s.

So I (27M) and finance (27F) have a HHI $550k, DINKs, liquid invested NW $650k, 70/30 brokerage vs retirement since early in our career we were considering a bigger house and went after tax heavy instead of retirement. We also have $150k equity in our home, 12 month emergency fund at $80k on top of my liquid NW number.

To be as quick as possible, I’m considering suing my HOA of which a large and reputable law firm in our area has won against this specific HOA/management company . Without getting into the exact issues, it sums up to HOA is enforcing rules that aren’t listed and strong case for bias from board.

The cost all in range anywhere from $10k-$25k of which if we win, I can likely recoup 40%-60% of costs. Consult and information shared to the firm they believe we could likely win. I have a contract from the firm sitting in my inbox, waiting for me to sign.

So here’s the thing, the cost isn’t that big of a deal to me because in my mind, I’m spending the money for the principal that my HOA can’t keep bullying me which is worth the money and well spent imo. But I’m afraid this is the equivalent of someone posting they’re gonna go buy a brand new Porsche. Am I just being silly and trying to act like I have F*** you money before I’m there, or is this the exact reason I saved up aggressively is to be able to fight things like this I care about?

Edit: single family home in an owner friendly state. This is a rental property. HOA is under 100 homes, but management company is a top 5 nationwide in size. I’d rather not sell-again it’s the principal. Owned for 5 years no issues. New prop management company and now there’s issues.

TLDR: At my income $550k and liquid NW $730k including 12 month E fund, does spending up to $25k to fight my HOA to back off worth it or just stupid?

I’m 45 and make around $300k a year. Which I know isn’t terrible money, and honestly I feel guilty even complaining sometimes because I know people are struggling way harder than I am.

But man... I really thought by this age and income level I’d feel more stable than this.

Instead it feels like every year gets more expensive faster than I can keep up with.

Rent went up again this year.

Groceries are insane now.

Car insurance jumped for no reason.

Every company wants a monthly subscription for something.

I’m not living some crazy lifestyle either. I don’t travel much, rarely buy anything big for myself, don’t go out partying or anything like that.

And yet somehow I still feel behind all the time.

Then I go online and see people my age talking about maxing out retirement accounts, buying second homes, investing nonstop, etc. and I honestly can’t tell if I completely screwed up financially somewhere along the way or if this is just what normal life feels like now.

Mostly just wondering if other people around my age feel this too.

Probably subjective, but I have never done churning. It probably made sense for us when our HHI was $200k (never did it then cuz I am lazy), but now at $800k HHI, it doesn't make sense. My sister is big into the churning game. She does not know how much we make given our modest lifestyle, but she knows we travel a lot and believes churning will give substantial rewards.

Each time I look into Chase CSR, Amex Plat or other reward cards, I zone out quickly on the many hoops you have to jump to maximize the rewards and justify the high annual fee. Or may be I am leaving a few $$ on the table. Our HH CC spend each year is roughly $150k out of which $50k is travel, I do the combo of Citi Double Cash + BofA Preferred rewards + Chase 5% rotating categories cash back. Our cashback is roughly $4k/yr. If I am being generous, I am probably leaving $2k on the table?!?

Thoughts? At what income level does it NOT make sense to play the CC game anymore?

I’m in my mid-to-late 30s, married with kids, and I’ve been thinking a lot lately about the trade-offs between different life paths.

I love my family and I wouldn’t trade them, but I’d be lying if I said I don’t sometimes wonder what life would look like if I didn’t have the responsibilities I have now.

I’m in a decent/high-earning career path, but because I have a family, high rent/cost of living, kids, bills, and all the normal adult responsibilities, it often feels like the money disappears before I ever get to feel “ahead.”

I see people around my age without kids or without family responsibilities and I sometimes wonder if they’re quietly living a very different life- more savings, more travel, nicer clothes, nicer car, more freedom, less guilt spending money on themselves.

For me, even buying myself something small can come with guilt because I immediately think about savings, the kids, the house deposit, the next bill, or whether I should be putting that money somewhere more responsible.

At the same time, I know the bachelor life probably has its own trade-offs too- loneliness, lack of deeper purpose, no family milestones, no kids running around, no real “home team” behind you.

So I guess my question is:

For men in their 30s and 40s, especially those earning decent money, do you ever compare these two lives?

Do family men fantasise about the freedom of being single with money?

And do single/high-earning men ever look at family men and feel like they’re missing something deeper?

Is it basically a trade-off either way?

I’m looking for advice on how to approach our finances now that I’ve run into health issues.

I am 32F and earn $400-600k+ year at investment job with significant carry 7 figure upside. $2MM+ net worth, HCOL area. Housing is our largest expense with $10k / month in mortgage + property tax + insurance. Renting would be at least $7k and lower quality, so we accept the higher cost to own. Husband earns closer to $150-200k.

I recently gave birth to our first child and had a rough labor and delivery that led to postpartum complications that included heart failure and serious lung issues from severe fluid overload. Prior to that, I was very fit with a perfectly clean bill of health. While the immediate complications were treatable, I will not know for another few weeks the long-term impact and have been advised by a family friend cardiologist that I should prepare for this to be a lifelong cardiac risk I need to monitor.

All of my financial planning had been predicated on a long, successful career for myself. I now worry about something happening to me that impairs my ability to work or worse and leaving my husband and children without the life I have planned for them otherwise.

I had asked my husband for us to both get life insurance when we bought the house together, but he thought it was morbid, and I never got around to looking at it seriously. I suppose we took our health for granted because we are both young and fit. Now I assume it would be prohibitively expensive to insure me.

I am looking for advice from anyone who has navigated financial planning after an unexpected health event, particularly at a young age. As an example, I had planned to max out 529 contributions over the next few years, but now would it be better to build a more significant liquid rainy day fund first? Should we still prioritize securing life insurance, even if premiums are high, or look at other products or structures? If you’ve been in my shoes, what would you do differently if you could go back to before or after the health event?

Family and I are going to CA in October. Wife + 2 kids.

We haven’t done an actual family vacation in a while, so I’m not sure if this is just what things cost these days or if I’m …idk.

Flights are 2500
Hotel + Airbnb is 2300
Car rental is 1000

And then we’ll have food and activities and all that, so maybe that’s another $1500ish.

So let’s say that’s $7500 in total for 7 days going from MA to Monterey, CA.

It feels like a lot, but is that just what travel costs now?

ETA: this is reassuring. I think maybe it’s just that the only time we spend that amount of money at once is like when we bought a house so it feels maybe outsized.

Also, on the car, we did get a bigger car. Our kid are 5 and 1yo and both of us are 6ft tall, so we did prioritize the extra space for a bigger SUV. That might also explain slightly higher plane costs because we tried to make the travel for a bit with waking up and naps.

Looking for advice on our college savings approach.

We have two children, ages 3 and 4.5. Education is extremely important to our family, and our goal is to fully fund undergraduate education with the ability to help fund graduate or professional school as well. We are not especially impressed with our in-state public options, so we are planning around a potential cost of $100k/year for undergrad.

Current situation:

• Kid 1, age 4.5: $120k in 529
• Kid 2, age 3: $85k in 529
• Currently contributing $1,750/month per child, or $21k/year per child

Assuming 7% annual returns, this would project to roughly $765k per child by age 18.

We recognize this creates a meaningful risk of overfunding the 529s. For any overfunded portion, we would plan to use the allowed $35k per child Roth IRA rollover if eligible. For the remainder, we would likely use the 529s as a generational wealth-transfer vehicle for future descendants. We realize we are very fortunate to even have this option.

That said, we are considering whether it would be better to reduce future 529 contributions and instead split contributions among a 529, UTMA, and parental brokerage account for more flexibility.

One possible monthly contribution structure per child:

• 529: $750/month
• UTMA: $750/month
• Parental brokerage: $250/month

Projected age-18 balances per child, assuming similar returns:

• 529: ~$500k
• UTMA: ~$200k
• Parental brokerage: ~$65k

For education planning, this would still allow us to fund approximately $100k/year for four years of undergraduate education from the 529. Assuming the remaining 529 balance continues to grow at a more conservative rate during college, my rough estimate is that there could still be around $150k left in the 529 after undergrad.

That likely would not fully fund professional school, but the UTMA could potentially be used at that point. My understanding is that by age 24, the child would no longer be subject to the kiddie tax, so withdrawals from the UTMA could potentially be made with little or no long-term capital gains tax depending on the child’s income and the size of the gains. If that is correct, then for meaningful annual withdrawals, the UTMA seems somewhat similar to a 529 from a tax-efficiency standpoint, while offering more flexibility.

The main appeal of this approach is flexibility if one or more of the following happens:

• Child does not attend graduate/professional school
• Child receives scholarships
• Child attends a lower-cost school
• Child pursues a different path entirely
• 529 rules change over time
• We want to avoid having too much locked into education-specific accounts

The downsides I see are:

• Some annual tax drag from dividends/capital gains in the UTMA, especially under kiddie tax rules while they are younger
  • Tax-efficient ETFs should minimize this, but not eliminate it
• The child gains control of the UTMA at age of majority, which is a real risk
• This strategy assumes responsible children who would use the UTMA for education or another intended purpose

Curious how others would think about this. Would you keep aggressively funding the 529s given our education goals, or would you start shifting more toward UTMA/parental brokerage for flexibility?

Any other potential pitfalls that I am missing here?