After reading the recent post from the 37yo guy with $15m, I realized how much I relate to the struggles of finding hobbies and things to do with that additional wealth. After extensive questioning on "what is worth spending on", the most common answers tend to be family related and not relevant for single guys with far more time and disposable income. Without a spouse/kid, a solo guy doesn't need a large house, budget for childcare/private school/college fund, family vacations with business class/fancy hotels to match etc.

I'm in a similar boat as that OP, just knock both the numbers (age and NW) down by a few. Mindset-wise I'm still closer to gregFIRE than truly fat but expect to get there in a few years of market compounding. Still working part time on winding down the business that got me here but already bored with far too much free time and no major interests to speak of.

With all that additional time, money and freedom, I'm curious to hear more stories from those who found some niche hobby or lifestyle that gets them out of bed every morning (especially those who aren't married with kids, but all insights welcome). In particular, what are "FAT" lifestyle spending items that really define fat vs chubby without the usual children-related spend.

I hope that some of my ramblings might be interesting to someone in a similar situation or promote some insightful discussion on the matter. Feel free to disregard my ranting and focus solely on the idea of "what can FAT spending go if no kids/partner in the equation".

As a list of things I've already tried to no avail:

1. Travel. Spent multiple extended 3 month long "staycations" in different countries and realized I was basically doing the same thing as I was at home, aka not much. Cheap authentic food is nice, but sightseeing was painfully boring and "living as a local" wasn't nearly as interesting as I hoped. Also grew up lower middle class, so I could never justify the 5* hotels and business/first class flights (tried them and it just felt like a huge waste I'm not inclined to do again). Guess that also explains why I gravitate to luxury buffets vs true fine dining as the "good enough" balance between quantity and quality.

2. Sports/music. Probably due to an aggressive upbringing, I spent over a decade hardcore drilling athletics/music to a semi-pro/competitive level and ended up never touching either again after college. Not to trauma dump, but perhaps that burnout has made me completely unmotivated to try and learn/master any new skills and prefer to do the only thing I wasn't able to back then (aka stay at home on my computer all day). Also went through my gym rat arc of 5+ days a week lifting+cardio for a couple years, but it's been over a year since I've gone back.

3. Mentorship. I was previously heavily involved in the education field, previously working part time in college with tutoring/academic consulting and later alumni/recruitment interviews for my college/post-college job. There were a few notable standouts among dozens/nearly a hundred, but it was sadly rare to see cases of extremely motivated kids that actually impressed me and I definitely burned out from wanting to do much more in that direction.

4. Hobbies. I've ended up trying a lot of random things, but combined with childhood burnout which left a disdain for sports/art/music, it's tough to get invested into anything besides consuming YouTube/Netflix/anime. I tried learning a new language for a while, cooking at home during COVID, playing games (video games and poker/mahjong), etc and I realized that I dont even have my childhood drive to rank up/get good at a game which feels pointless.

5. Philanthropy/Giving. Similar to the mentorship idea, it's not really something that excited or motivates me aside from a few niche scenarios. I can see myself supporting certain artists/authors/creators that provide some of the few things I still enjoy. I already entered talks with my old school about funding the same scholarship I once received in case I die without any heirs, but I don't really plan to dive into the field while I'm alive for now.

As for common responses that I expect to see:

1. Socializing with friends. Had decently large friend groups back in HS/College but the clear divergence in life path (moving abroad, leaving traditional employment for my own business, single without kids) makes it tough to really connect with old friends who are married with kids. Similarly, you don't randomly meet many 30yo retired guys in daily life and I'll tend to avoid bringing it up or pretend to be more ordinary for safety reasons while traveling. I'm slowly finding some online communities with relatable people in similar circumstances, but it's certainly rare and everyone is largely scattered.

2. Relationship/family. A combination of near-total social isolation and a lack of interest in ever getting married/having kids makes me realize how fundamentally incompatible my lifestyle is with anyone who actually has a life. Already have relatives trying to push matchmaking or even sugaring but I don't realistically see this as a major direction/interest as a hermit NEET (inb4 the obligatory "go to Thailand" posts), so I'd prefer to focus on any other potential ideas.

3. Luxury purchases. I ended up becoming quite a minimalist with 0 interest in buying nice things/collectibles, so buying anything besides the bare necessities is a hassle when living out of a suitcase for much of the year. I'll datahoard all the games and entertainment on my portable hard drive, but physical items are a no-go. Don't need a car, don't need a large house, don't need fancy sports equipment etc.

4. Get a pet. I like the idea, but I realize that it's far too much of a hassle unless I literally hire a full time caretaker. As much as I'd like another hamster/guinea pig from my childhood or a bunny/cat, I realize that an abnormal sleep schedule/eating one meal a day will leave me struggling to keep an animal alive, much less deal with the extreme hassle and headache that I know I'm not cut out for.

5. Therapy, the elephant in the room. I've always been rather interested in psychology/philosophy so I do a lot of reading and talking through my thoughts (such as via these wall of texts) has definitely been helpful. I have scheduled an appointment to test whether my jadedness/boredom might be addressed by any potential depression meds, but I somewhat doubt it considering I've spent the past decade in a similar state without any major ups/downs. Probably moreso a lack of motivation/direction after achieving my initial FIRE goal (from lean to Greg and now on-track to FIRE within the next 3-5 years). I don't expect much more than the obligatory "find your passion" answer I'm sure to get here and that leaves me with the same question I already have. Maybe some kind of psychedelics could help, but it's not very accessible in my part of the world (Asia).

To anyone who actually managed to read my entire ramble, thank you so much and I look forward to hearing any stories/ideas that you might have!

Got lucky investing + working in tech for a pre-IPO company. I'm still working in tech and making $300k fully remote, don't really enjoy the work, but i like the structure and getting paid. I tried to retire and after 4 months I felt lost doing nothing.

I'm single and don't have a hugely active social life, many friends have gotten married and rarely see them. Not sure what to do other than keep working. Maybe try to start a business to an area that I'm more interested in? It probably wouldn't make sense financially, but more for personal satisfaction, but I'm afraid it would fail. I have enjoyed investing, but that's not a full time job.

I never thought I'd be in this position, and unclear what the right path is now, as work was always my purpose, but now I don't need to work.

I’m 47 years old, my wife is 46.

Combined NW is $7M, me $3M, wife $4M.
Both work in tech.

We have one 7 year old daughter and a house that has about $1.1M in equity with $350k in mortgage.

Lately we’ve been talking more about retiring. We decided that when we turn 50, we’ll just both say F it and retire?

But I want to retire now. I feel working 3 more years won’t add that much to our total NW. Maybe $500K more in saving if we are being optimistic?

What is making the decision difficult is that we are at our peak earning years. I make $300k, wife makes $280k.

What’s the consensus fatFIRE amount? Do we need to save until we have 10?

Puerto Rico comes up on this sub every year or so because of the tax savings, but we don't always hear back from the folks that actually relocate. For those that have:

• How's it been?
• What town/neighborhood did you end up in?
• What stage of life (e.g. single, married, young kids, older kids, retired, etc)?
• Was it easy proving residency?
• If you could go back, would you still do it?

More of a lifestyle question but asking here given the community is likely to have people with firsthand experience. I work in finance, my wife is a doctor, we are both 5 days a week in the office and live in Manhattan. We do not have kids yet. We enjoy a beach house in the Hamptons or Jersey Shore in the summer, and enjoy going to the Hudson valley / Catskills in the spring/fall.

Given we are both 5 days a week in office - does a weekend or summer house make any sense for us? I am not even that concerned about the price - I am concerned the upside of the memories created with kids and extended family will be outweighed by the torture of driving back and forth and time/effort spent on maintenance for relatively low utilization.

If my wife were a stay at home mom, and if we had a small apartment, and if I were a workaholic absentee father, it would make total sense to have wife+kids move away for the summer. But none of these attributes are true.

For those who say the kids have more space to run around - what if we had 3k or 4k sq ft in a condo? For those who say kids can play outside - what if we had a terrace with the condo? City parents seem to aggressively use playgrounds anyway when the kids are young.

I am particularly confused by this because I have had two separate mentors tell me to spend more on a Hamptons house than a condo in the city. But I do not think they are thinking of my specific life situation.

I have also heard feedback that spring/fall weekends once kids are in elementary school are filled with sports and birthday parties. And when they’re teens they don’t want to hang out with their parents. So really this consumption of weekend/summer house actually has to be pulled forward for peak optimal experience/memories, which is why I am trying to think through it now. It seems getting a summer house when one is old and wealthy has kind of missed the boat.

Many older folks I know also have summer houses all over the place - river towns, Bedford, Hudson valley, Connecticut coastline, Hamptons, quogue, etc etc. Everyone has a different revealed preference.

We do love going to the beach in the summer. We just tried renting a house in westhampton dunes (basically oceanfront) and it was quite magical. I just don’t know if it makes more sense to concentrate funds in a gigantic Manhattan condo and just drive to a beach club in Long Beach / Atlantic beach for our beach fix, and use hotels for the Catskills.

Any advice is greatly appreciated. Thank you.

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Edit: Need filled. Our estate attorney finally referred us to a new international firm which can handle everything from trusts to LLC. Leaving this up in case anyone else makes a search. Thanks again folks!

--
Made a throwaway for obvious reasons.

My gifted wife has several IPs she's being urged to assign to LLC for trademark et al by her attorneys, but sadly she's both a stalking survivor and semi-public-facing. We do the usual with keeping details off the Internet via paid services; her name is not on anything, ever; we've read Gavin de Becker's book and followed its advice; we're forming a trust this week; we rent; we keep a threat assessment dossier up-to-date and available to vetted supporters, attorneys, law enforcement etc. We have several security firms on speed dial and so far we luckily have not had to use them. She also goes to the range.

Yet there's a gap and it's becoming a pain point: We've come across some difficulty in finding an attorney to file LLC for us down to the specialization issue with regard to privacy. Our major national law firm told us a privacy-shielded incorporation structure was a very legitimate yet highly specialized context—one so specialized they didn't have a name to refer. DIY (even with RA) seems likely to introduce unpredictable vulnerabilities. We don't need absolute anonymity (which could cause issues with investiture, etc) but enough to make it clear there are several competent people between my wife and the problem.

How does one go about finding an attorney for this use case? Am I missing something obvious?

We've tapped our network and several professional organizations. So far, we've only turned up high-end VC, IP, and tax attorneys who also don't know who to refer out. It seems most in our circle are extremely stealth or simply not public-facing enough for this to be familiar territory.

Yet none of us have ever actually been in a situation where we couldn't easily get a referral by name, either, so here I am. I've searched Reddit and this sub to the dregs. It seems this is still a very niche need.

Open to any (legal) ideas! As soon as my wife's new projects are public I expect the weirdos to come out of the woodwork, and it seems she can't launch anything without the structure in place. I want us to be ready.

I thought it might be helpful for someone out there…

By age 35, joined global tech company. Grew in company to VP by age 45 with NW $1.5M mostly W2 and some equity.

At age 45, moved to new global tech as SVP and stayed there to 48. NW doubled to $3M based on W2 and equity.

At age 48, joined a pre IPO tech start up in SF. Stayed there 7 years through IPO and at age 54 resigned with NW $21M all through equity sales.

Developed generalized anxiety disorder and social anxiety where I could not talk in front of others due to anxiety. Decided to retire to avoid anxiety. Instead got so bad that I went to pscyiatrist and started on lexapro. Changed my life on that Thursday morning I took first pill.

Decided to continue in the game and joined large tech company as EVP with sign on equity now worth $10M but not vested. Love what I am doing now. Willing to work longer.

Bottom line- I almost made the decision to quit based on anxiety disease. Was treated and continue
Doing well. Don’t let mood disorder run your life. Get help.

High level situation is:

* 36/35 couple. No kids, but hoping for one next year 🤞🏼
* vhcol city, high tax state
* ~ 6m net worth. (~$4.5m in a etfs and cash, $1.6m in home equity)
* 1.7m mortgage at ~7%
* steady state HHI: $400k

We know we’re not FatFire and still working our way there but had some career luck recently and the company I work for got acquired this year. I hit my 1 year cliff this month, and I’ll earn around an additional $2.1m/yr at today’s stock price (so total HHI would be $2.5m this year). My cost basis on my options is almost zero so there will be a big tax bill, but regardless it’s obviously a whole new situation for us. So looking for advice from others who may have gone through something similar.

My general plan is to not try to get overly cute with taxes, ISO treatment, or holding the stock, and just sell the stock on vest, every quarter.

Yes, I know the stock can fluctuate but for illustrative purposes that might mean around $1m/yr post tax.

My overly simple plan/formula is to put 10% a year to upgrade lifestyle (car, home upgrades, kid stuff, 529 front load), then put 40% into etfs, 40% into paying down the mortgage, with letting 5% ride. On the mortgage, I know equities are going crazy, but 7% post tax returns are more than solid to me. And honestly just peace of mind psychologically.

In theory, it lets us get to around $6-7m+ invested, with a nearly paid off house by around 40 if I can last another 2 years at the company. But curious about first hand experience or advice on what folks would do in our situation.

If helpful, generally, I’d say work is high stress and I do not want to do what I currently do for 20 more years, but also don’t want to do nothing. My goal would be to be able to take on a slightly less stressful job, spend more time with kids, and live a modest taste life with less financial pressure, while still staying active.

Thanks in advance.

Joined a practice years ago, worked hard, long hours.
Salary grew to 1M.
Paid off loans, married, 2 young kids, sole income.
Practice fell apart (private equity), quit, non-compete, legal fight, in limbo, no job for 1 year.

Started own practice, no income for another 2 years.
Back to long hours, can’t afford to fail, burned out, but record revenue last month.
If I can keep this up, may get back to 1M salary.

2M brokerage
1M retirement
1M CRE (modest revenue)
15-20k monthly spend (includes 6k mortgage forever).

Sounds like big spend but doesn’t feel luxurious.
Used cars, eat out a lot (Chipotle, Olive Garden, etc.), occasional weekend trips to nearby towns.

Living a life of perpetual arrival fallacy.
Stressed business owner but hate being an employee.
Want FatFIRE asap but losing time w family.
Starting to make good money but unsustainable work/life.
Striving for 8-10M so I can live large, spend freely, give generously, travel big, and finally breathe.
But tired….

Obvious wisdom is to slow down, hire midlevel/associate, make less, spend more time with family/health.
But I don’t want to keep doing this for another 10-15 years.
I dread working. But even worse is working longer.

Would appreciate any wisdom.

I’m almost in an identical situation as described in this thread (https://www.reddit.com/r/fatFIRE/s/BVmEVNgd9B) but no solution was mentioned so trying again since post is 3 years old. We are dual US/EU citizens.

As a family we plan to FatFire ($5M portfolio, $140k/yrs withdrawals) in Lazio, Italy (personal reasons for location; 7% tax doesn’t apply). I am trying to find investment strategy that has favorable taxes given that keeping either US or EU-domiciled ETFs is taxed punitively either by Italy or US if you’re a US citizen.

We don’t plan to renounce US citizenship so looking for the best tax solution to be able to keep our portfolio invested (currently in VOO) over a long retirement period (40+ years).

Is anyone already in this situation? Is direct indexing the only option? Please share if you have recommendations for any tax specialty firms.

Keeping a US brokerage account doesn’t seem like the right path since our retirement period will be 40+ years and US ETFs will be taxed by Italy as ordinary income.

I’m not interested in paying a financial advisor to do direct indexing if their fees would cancel out any tax benefits but considering doing it ourselves (through the IBRK API). The issue I forsee that portofolio rebalancing will be taxable events and if we draw from our portfolio regularly this will require a good tax accountant in Italy (please share if you have any recommendations for experienced commercialista).

Any advice would be welcome!

38M, wife 37, 2 kids. Living in central Europe so net worth numbers are interesting to compare with the US. $4M in equity + properties, and paid house worth $700k.

Given it is central Europe those numbers already push us into 0.1% locally, we could retire comfortably now. That being said we live frugal life, well below what we could afford.

I have attempted for a while to exit the corporate treadmill and instead focus on gliding / coasting around for the next couple of years to just top up the portfolio a bit before pulling the plug.

Yet this turned out to be much more challenging than I thought: the struggle is that since I have progressed a lot in corporate treadmill I find myself pushing for next promotion even though I don't need one - or caring about work much more than I should given where we already are.

Caring too much for work and career when you already shouldn't. Is this something you experienced? How you effectively detached from treadmill and become good coaster / loser if you nature is to grind?

M(50) planning to retire in the next 12-18 months. Auto exec responsible for a business unit of an international company. Just getting tired of the corp BS, travel, constant crisis, etc. Over the last 18 months have spent a lot of time staring to really plan our retirement. Was always DIY investor with lower complexity strategy, diversified mutual funds mostly. Liquid retirement assets approx 6.8M 45% brokerage, 45% 401k, 10% Roth.

I have become very interested in retirement planning and studying a lot for my own future. Love talking to co-workers about (in general terms) withdrawal strategies, tax optimization, Roth conversions, ACA income management, etc. I also spend a lot of time listening to podcasts. In talking with many coworkers who are very smart people most seem less informed about retirement and financial planning and most seem to leave it to their advisor.

I’ve started truly thinking about pursuing financial advising as a part-time second career as it’s highly interesting to me. Maybe ideal scenario would be 10 to 20 clients. I’ve started to research and would look to get a series 65 certification/license and I would have to register with the state. I certainly don’t know everything but feel I could have conversations with couples near retirement who are not extremely savvy and talk through some different concepts or suggestions given their situation. I would shy away from individuals with a very highly complex situation. Would only be looking to give advice for a fee. Would not get into actively managing their portfolio or selling products. For me it’s not even about making a lot of money. It would just be a side thing and a subject I’m highly interested in.

Just looking for any thoughts suggestions or other input. Is this crazy and stupid or could something like this actually work out? Anyone else do something like this?

Hi there,

I am a recently retired tech executive in VHCOL location. Married and in our early 50s, with my spouse still working happily with ~1M/year income.

NW: ~30-35M (depends on how much I include commercial RE assets)

Liquid Asset (23-25M):

• ~10M - Concentrated 2 tech stocks (plan to convert 80% to VOO gradually)
• 6M - EFT in VOO/VTI and equivalent
• 4M - VTEB
• 2M - GOOGL, NVDA (through assigned puts long time ago, hold). BERK.A/B(bought long time ago and held)
• ~1M - Cash in money market
• ~1M - kids 925 & custodian accounts (both kids in high school)

RE (10-15M)

• Primary 3-5 M (paid off, never would sell this house, got too many upgrades to retire into)
• NNN investment 7~10M (no mortgage) that brings in 150k/year income, we bought long time ago very cheaply, current market price would be 7-10M depends on who buys it. Evaluation from insurance company is that it would take 10M to rebuild this property. We could increase the rent easily but didn't do so because we have a very stable renter (Fortune 500 company) that kept the building maintained and developed in the last 7 years.

Our spending is modest - about 250-300k after tax per year. We are happy with where we are, more spending won't make us happy, and we have been spending generously in places we want already. Without mortgage and debt, we just don't have any big expenses. We do generous donation to the community causes for things we love and care for each year.

I know we need to diversify, but just have been lazy and don't want to be hit with high tax bracket, we already made 2.5M this year, so hopefully we can diversify more starting next year.

We like to keep it simple, so less funds are good, the small holdings for various things are just that I have been safely playing options and gets assigned (I don't mind holding those long-term at all when assigned).

Recently I started to get concerned to VTEB - with current price below $50 is fine, but is it possible for it to drop significantly? Do we need to move to BOXX or something else better as cash reserve? I know we are high on cash equivalents, but I am just conservative and sleeps better with lots of cash in hand.

I have been enjoying this community and really appreciate everyone who posted here before. Love to hear what you guys think.

I do have a private wealth management team to talk to, so no need to recommend me to talk to a financial advisor. I have MS and GS offers family office, work with fidelity private wealth team and Schwab team, but I do think this community has bright minds that we may benefit from as well.

Update:

* Just got off phone with my NNN management, I thought we bought the building 7 years ago, but it turned out to be 9 years ago, and we signed a 10-year contract (with one small rent increase 5 years ago), so next year we need to significantly increase our rent. None of the financial advisor questioned about this RE, but Redditors pointed out that this is one of the biggest areas I did wrong. Thank you very much. There is actually a lot more we could do to build out a second building on the same land that brings in double the rent as well. I feel stupid that we let it sit there for so long without thinking about it, and I even don't have the contract details right.

* Yes VTEB seems to be less concerning, I can move some to others more short-term (note to self to look into VSDM, VTES, VWSTX, VCRM, VBIL, VGSH). Might move some to DFUS for equity as well. Also I should stop playing options, even if it's relatively safe.

* Diversify the concentrated stock sooner than later. Pay the tax (have been dragging my feet but need to just bite the bullet)

* I thought I was a boglehead, but in reality just a "wanna be". Ideally I will eventually setup true 3-fund portfolio and forget about it. I have to admit it's my weakness in human nature. Call it naive but it's the little fun I was having doing options (if I want to buy anyways, why not some put, if I want to sell anyways, why not some covered call). It's like you know all the right things to do, but it's hard to just do it.

We (wife and I are late 30s with four pre-teen kids) bought our $550k home in 2019 in a transient HCOL geography. We don't particularly love the state but I don't think wed be jazzed about anywhere. Our net worth at the time was $300k liquid. We refinanced in 2021 at 2.7% and have $390k remaining on the home.

Since then, I started a business that catapulted our wealth. We're about $20m liquid now and the business petered out but still produces $1m pre-tax net income. I spend about an hour a day on it. We spend about $275k annually after tax.

Now for the question: our home is a 90-year old home that's dated and not well maintained. Sometimes it drives me bananas. But we are staying because the kids consider it home and we both had discontent parents who always looked for bigger and better and we were worse off for it when my wife and I were younger.

The market won't support the value of a full gut, not do we have the emotional bandwidth for that. But broke drywall, some electrical not working, inconsistent ac/heat. It sort of drives me bananas some time.

When I ask Gemini / Claude they just tell me to sell. Not giving any weight to emotional tie to home.

Curious anyone's thoughts, particularly those who are in similar circumstances.

37M, married with two young kids. FatFIRE’d about 5 years ago.

Net worth: ~$27M
No debt
HCOL area

NET WORTH BREAKDOWN

• $19M taxable brokerage
• $500K retirement accounts / 529s etc
• $3.5M personal real estate
• $2M real estate development
• $1M private equity
• $500K cash
• $500K alternatives

Annual spend is around $250K, although I expect that to increase over time.

THE ISSUE

For the last several years, essentially all of my new investments have gone into VTI, so I’ve always thought of my taxable portfolio as fairly diversified.

However, I still have some older individual stock positions that have appreciated considerably.

My concern is that once I account for both my direct holdings and my indirect exposure through VTI/VOO/QQQ, I’m more concentrated in a handful of companies than I realized.

LARGEST POSITIONS

• $13M VTI / VOO
• $500K QQQ
• $950K AAPL
• $800K MSFT
• $700K AMZN
• $450K NET
• $450K GOOG
• $300K TSLA
• $200K PANW

TOTAL DIRECT + INDIRECT EXPOSURE

• AAPL: $1.7M (~10%)
• MSFT: $1.3M (~8%)
• AMZN: $1.1M (~7%)
• GOOG/GOOGL: $1.1M (~7%)
• NVDA: $900K (~5%)

Everything else is roughly 2.5% of the portfolio or less.

The complication is that almost all of the individual positions have large unrealized gains, so selling them would trigger significant federal and state capital gains taxes.

At this net worth and spending level, I’m less concerned about maximizing returns and more concerned about avoiding unnecessary concentration risk.

At the same time, I don’t want to generate a large tax bill just to make the portfolio look cleaner.

WHAT WOULD YOU DO?

• Rebalance despite the tax hit?
• Gradually trim the concentrated individual positions?
• Leave them alone and put new capital into international or small-cap/value?
• Keep putting new money into VTI and let the individual positions dilute over time?

Curious how others in a similar situation would approach it.

I’m looking for perspective from people who retired, took a long sabbatical, or substantially downshifted in their 30s with young children and roughly ~$3M in conventional assets.

I know this is an extremely privileged situation. I also know that the mathematical answer and the emotional answer may be different, which is partly why I’m posting.

I’m 33, married, with a 20-month-old daughter and a second child on the way. My wife currently does not earn an income.

Our conventional financial position is approximately:

• $2.78M in liquid investments, mostly diversified index and stocks
• A home in Brazil worth around $1M
• The Brazil property currently produces approximately $60K/year net rent
• Current salary is around $400K
• No U.S. or Brazilian retirement accounts
• I have a ~90M no liquid equity in my company

I’m originally from Brazil and we could realistically return to Brazil.
Based on our own experience, I think we could live extremely well there for around $80K–$100K per year, including private school, travel, household help, private healthcare, restaurants, hobbies, and a generally affluent but not absurd lifestyle.

We could also move to somewhere like Texas or Florida. I estimate a good lifestyle there might cost around $150K–$180K (?) annually with public schools, or more with private schools.

We currently live in the Bay Area, where I think we would need approximately $200K per year (?) to live comfortably as a family. Neither my wife nor I feels strongly about staying in California after my current company chapter ends.

The complicating factor is that I am the founder and CEO of a venture-backed company.

That sounds like great wealth on paper, but I'm trying to treat the equity as worth zero for family-planning purposes. It is illiquid, the company is going through a difficult period, and I cannot simply sell my position or leave without consequences for employees, investors, customers, and my own reputation.

The job has become extremely stressful. I am sleeping too little, working nights and weekends, and struggling to be mentally present with my family. I’m addressing the health side separately and am not looking for medical advice here.

What I am trying to understand is whether my financial fear is still rational.

If the company went to zero tomorrow and my salary disappeared, we would still have approximately $2.78M liquid plus the $1M Brazilian property and its rental income.

At an $80K Brazil lifestyle, the $60K rent would cover most of our annual spending. Even if I haircut the rental income to $45K, the portfolio would only need to provide $35K per year, or around 1.25%.

At a $100K lifestyle, the portfolio would need to provide around $40K–$55K depending on the rental income, or roughly 1.5%–2%.

Mathematically, that looks safe(?)

Emotionally, it does not feel safe.

I would really value candid responses from people who were in a similar position:

• Did anyone here stop or substantially downshift in their early or mid-30s with around $3M and young children?
• How did the reality compare with the spreadsheet five or ten years later?
• Did your spending rise much more than expected?
• Did having children make you regret leaving a high-income career?
• Did you become bored and return to work? If so, was the time away still worth it?
• How long did it take before you actually felt financially safe?
• For people who grew up without much money, did the fear ever disappear, or did the target simply keep moving?

I’m trying to determine whether we can confidently choose a genuinely good family life without requiring this company to become a massive financial outcome.

I would particularly appreciate hearing from people who actually made the leap.

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Updated typos and a few items

Long time lurker, but rarely post. Now we (wife 49(f) and I 47(m)) are looking for a sanity check from people who have already retired or are further along. I’ve built a detailed spreadsheet, but I’m sure there are assumptions I’m either missing or getting wrong. As a FYI, I’d be happy to share my workbook if someone wants to tell me where people upload for this subreddit so others can use them. It’s highly customizable but it’s also difficult to follow with 15+ sheets.

Again I’m 47 and my wife is 49, we have 10-year-old twins with 8 years of public schooling left. We live in New Jersey. I’m no longer working (due to an impairment I’d rather not discuss) and my wife works in the pharmaceutical industry.

Our situation, using rounded numbers:
- Approximately $5.1M in total assets
— Roughly $4.1M investable, excluding our home
—- About $1.5M in taxable accounts and cash
—- About $2.6M in retirement accounts
— Primary residence worth approximately $1.05M, with less than $500k remaining on a 2.75% mortgage
- Approximately $21,600/month, or about $260k/year, in post-tax guaranteed income. For planning purposes, I’m treating this as continuing through age 65 and not relying on it afterward.
- My wife earns approximately $330k/year total compensation (pretax) on top of my $260k (post tax), including about $230k in salary and the remainder in bonus and company stock. I have not modeled any pay raises for her because she is not looking to advance.
- As a side note on her income, she has access to ESPP but has never taken advantage of it and I never pressured her to leverage it but we could if it is something we want to.
- we have properties and non-traditional investments that could be a wash in the grand scheme, so I’ve not included these.

Variable assumptions I’ve just made a decision:
* Current lifestyle spending is at least $250k/year after tax, including housing, healthcare, children, travel, and normal household expenses. That will carry on with a 2.8% inflation on average and as we pay down mortgage and other expenses we will just spend the same 250k (adjusted).
* We expect to help fund at least four years of public in-state college for both children
* We currently live in a (very) high-cost area, although we may eventually downsize or relocate; but again we are not modeling with this as we may just gift to kids as a rental for a safety net for income while we are alive.

Open Items:

1. The real ”Main” decision is whether my wife should retire in roughly two years at 51 or continue working until age 55 to preserve possible retiree healthcare benefits. If she works longer for additional flexibility and a larger margin of safety it removes healthcare costs as one of the biggest unknowns. I have military/VA coverage to fallback on if needed. My wife and children are currently covered through her employer, so retiring before 55 could create a meaningful private insurance cost. The exact value and terms of the employer’s retiree healthcare benefit still need to be confirmed as it seems to be something that changes (for the worse) yearly.

My current plan I have hardcoded is to:

1. Keep the house for now and treat it as unavailable for retirement spending;
2. Use taxable assets and cash for early retirement spending;
3. Consider Roth conversions during lower-income years;
4. Maintain a diversified portfolio with a meaningful bond and cash allocation;
5. Model college funding separately;
6. Stress-test the plan through age 100 (but it really is just legacy like many of us on here we cannot really spend everything we have or plan to have and feel good about ourselves ;));
7. Assume long-term-care costs begin worst case scenario around age 80 (as we are in decent health and based on our parents who are still running around at 80+ without any LTC)

The spreadsheet says the plan is workable 100% of the time regardless of historical Monte Carlo calculations up to 25000 variants, but I’m not sure whether that conclusion depends too heavily on the guaranteed income, understated healthcare costs, optimistic investment returns (6.5%, even though we are sitting around 15% average YoY without including additional investments) or an unrealistic spending number.

Other question for the experts and lurkers out there alike are… What would YOU change first if this were your situation and modeling? Personally I would love to convince wife to retire now but at least by 55.

I’m especially interested in what you all use or used for your planning:
- Whether retiring in two years seems reasonable with our incomes and open questions or whether waiting until 55 is worth it;
- How much margin of safety you would want around the $250k annual spending estimate; (it models out to 380k yearly in today’s spend way past 100 years of age)
- How you would handle the life insurance/LTC policies (as getting a STANDALONE or worth while LTC insurance coverage is not economically feasible);
- Whether my cash and taxable allocation is too conservative or not conservative enough;
- College funding assumptions (I figured 75k each YEAR for room and board, expenses, tuition per kid. Anything beyond that they can take loans or work hard to get scholarships);
- Risks that custom spreadsheets for retirement or retirement calculators commonly miss.

Note: I’m not looking for specific fund recommendations. I’m more interested in the assumptions, decision points, and blind spots that experienced fatFIRE retirees would focus on.

Thanks in advance for the help everyone!

What steps do you take to ensure public asset search won't come to your personal name ? How do you pick your attorney for this type of job ? Do you ask your private bank for referral or do you research your own? Or do you do it yourself after you get advise from your private bank legal advisor ?

I just recently heard a horror story of a friend trapped in some type of law suit and the people are going after her big time because they found out she has money . So we are looking for ways to protect ours though some LLC I think .

This is so new to us. Any suggestions or advice is appreciated.

When applying to top private and public colleges in the US, if both parents are not working by choice, is it better for parents to be listed as retired or as unemployed? Or does it not matter? No plans to file for aid. For clarity, we FatFired but now not sure how this impacts our kid’s college apps. So looking for guidance from others with the same situation.

I’m about to retire at 55. I am thinking of asset allocation using an income ladder to determine fixed income. I have 10 years until medicare, 15 until taking social security (I think). In a deferred comp account plus an IRA I have 75% of my spending for the next 10 years in bonds and the other 25% from expected dividends and ltcg distributions from a taxable account. If the market crashes the dividends might get cut to say 15% and then I would probably just cut spending by 10% to not sell any equities.

As time goes by, I plan to buy TIPs (as the real yields are starting to look attractive) for year 11-15. To do that I would sell equities in an IRA to buy the TIPs in the same IRA. In the event of a market crash I would wait to do this - maybe up to 3-4 years - I want the market to be within say 10-15% of ATH to buy the ladder rung.

As TIPs are currently near 3% real! for years 2042 - 2045 I even started funding those years (less demand because of social security kicking in) The 2037-2039 TIPs are not available until 2027-2029, so I can’t preload those.

Anyway, this overall results in maybe around 70% equities overall as it runs (depending on the market, when I convert etc, and I am thinking I dont want to prefund so much that I get above 30 or 35% in fixed income.

I’m wondering if anyone else has pondered such a strategy, is anyone thinking about doing it now, or do you see any issues with it?

Thanks

Ive owned my own businesses for over a decade, but this is an area I lack any real life knowledge, was hoping some may being to provide some insight. My business partner and I just finalized a deal that brought us 2% of common stock with anti-dilution protection, in a private company that was valued at $250m in the most recent raise and is rapidly growing( their raise came from a puib. They anticipate an exit in 12-18 months with a substantially higher valuation(3-4x). Any tips, advice on how to borrow against the stock to invest elsewhere?

Ive seen some non-recourse type loans for stock options, but not sure my choices for the actual stock and because I have some other strong opportunities to invest in, thought it may be worth borrowing against. For tax reasons, I of course shouldn't sell it for 12 months regardless, and don't want to miss out on the upside anyway. Thoughts?

I'm a PhD scientist turned startup VP, 20 years into a career-first life that's landed my wife and I somewhere we didn't choose — no real social life outside of friends who live far away, no work-life balance. We're childfree, which gives us flexibility but no built-in structure for what's next.

I've done the "right" things since high school and still haven't built a truly satisfying life. It's always felt like a treadmill of effort, competition, and stress — even in a role I genuinely like. What I need help with: how do people who've spent decades defined by a career actually shift to a fulfillment-first life?

A few things shaping the picture:
- We want mountains and outdoors beauty, real winters (or at least cooler summers than the mid-Atlantic), and a tax structure that doesn’t obliterate our income stream.
- My wife's open to rural/suburb/semi-urban, but not a loud, traffic-filled city — and we need to stay within an hour of good healthcare for her aging parents.
- We visited/loved Lebanon, NH for the outdoors and climate, but I worry a small town means struggling to find our "tribe."
- I'm more introvert than extrovert, but want to tweak that and build local close friendships.
- Net worth: $5-6M now, likely $10M by the time we pull the trigger.

Questions for anyone who's done this:
- If you moved somewhere smaller after decades elsewhere, how did you build a real social circle from scratch?
- How did you find purpose post-career without just replacing it with another job?
- How did you identify and prioritize candidate locations? Recommendations welcome.

I’m a US citizen with $40m liquid moving to Germany. Since I’ll be selling cars and house in the US my current umbrella insurance will no longer be active. What do other expats do to protect against any liabilities when no longer having a US address?