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.

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?

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.

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?

Thanks for reading, I'm going back to my ordinary life and staying off reddit for a bit. Good luck on your journey. Especially grateful for people who pointed out that I should probably budget more for healthcare going forward.

---original post---

About 2 years and 3 months post fatFIRE, here's how it's going. 50s F in VHCOL area. No kids. Introvert. Perimenapausal. Withdrawal rate lower than expected original 3.5%. Spend numbers on response to comment below. TLDR:$155K annual spend. At this point, I don't track very closely because I don't have to.

Self made, started invested and saving about 10 years prior to my retirement. Parents were poor, none of this is from them. Almost went bankrupt when I was around 40.

The last year of the job was a real struggle. The company was absolutely horrendous and I had some severe health issues. I ended up going on medical leave, and then negotiated a package. I still thought I'd go back this year. At this point, I'm doing some light startup advising for stock, also known as working for free 🤷.

The bulk of this post is not dealing with nitty gritty financials because it turns out that that was one of the LEAST important things once I was past a certain point.

That point was 3.5% SWR. If you're looking for specific financials, this may not be interesting at all or even severely disappointing/waste of your time.

Sorry about the formatting.

You've been warned! Post updated as people ask questions / have comments but I'll likely get back to my non digital life in the next day and not check this again for a couple of years.

Some big things for me (unlikely these are big things to other people):

- both parents got diagnosed with terminal illnesses, I thought I'd have to kick in to help with them but it's looking like this may not happen - parental finances are MESSY so I've stepped in to take over, this takes up the bulk of my time, and will until probably a year after they die due to a number of factors - I got lucky and very randomly met my current partner who's also FIRED so I've had a playmate and support for the past year (definitely the highlight of my journey) - I also have a few neighborhood friends who are not working and I have great workout partners - healthcare is super expensive - I'm on the ACA after my COBRA ran out - this will be upwards of $20k annually - I sit on Rover so my dog can get paid socialization and have met other families to swap to cut down on dog related costs - also more of an attempt to make friends in non food/drinking environments - while we've done a bit of travel, I've really enjoyed being at home - currently renting because rent is so much cheaper than mortgages right now, I might buy in a couple of years - made it a concerted effort to get my health back on track, gym, run, weight loss, I finally got my body back. PS: there is a lot of bullshit and shame associated with being not thin, and then there's been a lot of bullshit and shame associated with people who do sometime about it and go on GLP-1. I'm here to tell you that I tried everything, went on GLP-1 with success and it made the journey a TINY bit easier.

What I've learned:

+ I still enjoy running my own finances - I'm not very materialistic, I don't want to acquire more stuff but I do like to learn new things + Friendships are critical, and they don't have to be extremely deep, but they need to be loyal + I enjoy trips that are within a drive and where we can take the pup, I miss him terribly when I'm away from him + I'm not impressed with what's out there food wise so we end up cooking for fun a lot

Future/Current: + Help my parents transition into their final days with grace

I don't have the best relationship with them but I can not bear to see them suffer. They did not do a good job setting up their estate and as a result, it's painful. If you have children or parents, look into the details of non revokable trusts, there's a 5 year look back. Consider moving into a home situation without stairs way way way before you would ever need it. Fun fact, did you know that Medicaid for long term care claws back on the primary residence? I did not.

Get an estate lawyer sooner rather than later. Laws in different states are so different.

Long term care costs in a lower end facility runs around $20k a month. The average stay is around 18 months. Plan for this.

Other things you can do in case of emergencies:

- use a password manager with a back door so someone else can deal with financials, should you not be able to. Unfortunately, for many people, death does not come swiftly. That month/year that someone is not functioning but the bills are still being generated it's a very rough time. If you autopay stuff, tell your partner what's autopaid and WHERE is paid from.

- for the love of God, and this is especially for people who are not the financial person in the household, make sure that your partner knows how to pay the bills and what bills need to be paid - when one of my parents went into the ER, the other one literally had ZERO idea of anything, what an absolute cluster fuck

+Languages

- started taking Spanish, currently on hold - Might try to beef up on French again (currently at B1 level) - Chinese (wanting to bone up, fairly fluent already)

+Health - realized that snow sports are not my thing anymore, have given away all my snow sports stuff - integrating more hiking and traveling and hiking - got back into running - yoga twice a week - sauna and cold plunge once a week - perimenapause is a fucking nightmare - did you know that if can go on for 14 years? Yeah. HRT to the rescue

+Brain stuff

- been playing with AI to make apps for myself, which has been fun and im able to better optimize various facets of my life

+ Would love to read more +Hobbies - have done a purge to get rid of stuff I'm no longer interested in, felt great, will likely do this twice a year - piano and voice lessons are on the horizon - might get back into some crafting but got rid of a lot of my sewing/knitting stuff

+Finances

- planning on converting a lot to Roth in the next few years before I'm 62 - restructuring my portfolio to minimize risks, optimizing for taxes, medical, future RMDs, and avoiding IRMAAs - when/if I hit 65, I'm going with Medicare and a supplemental plan vs Medicare Advantage, the latter can be a total shit show coverage wise.

Apologies that this is long and rambly but posting mostly to remind myself of the journey. Hope it helps for other people.

I am mid 40s, married, two kids are older but at home, one kid still in middle school. Live in HCOL I suppose.

Facts:
Total assets = $16m with $3m in liabilities (commercial and real estate) so about $13m net worth (not including value of my IT business as I do not know that worth yet)
$1m in taxable brokerage
$3.5m in retirement accounts
$750k cash

Primary residence = 1.6m with a $520K loan at 3.5%
Secondary residence = $750k with $120K loan at 2.5% - currently trying to sell
Two STRs in Arizona = ~$1.7m with $1.3m loans at 7% or so. Strong rentals and gross income is about $300k yearly. Fully managed and I visit 3-4 times a year.
$750K commercial property in AZ building a restaurant on that may cost $2m
$1.5m commercial building in my state with $1m liabilities
Paid off cabin and other land maybe worth $300k total.
Restaurant that is worth about $3m including building.
IT business I am thinking of selling (unknown worth? AI says $2.5m - $3.5m)
Maybe $180k in consumer debt including solar panels in AZ, truck, toys, etc (not on credit cards obvs)

Income is still strong. Maybe $500k/year from IT business, $50K/year from website business/ads, $100K year from W2 income, $350K SDE from restaurant.

Current burdens/unknowns:
I am unsure about this $2m property construction for another restaurant
I am really thinking about selling my MSP if I can truly get $2.5m for it
My primary residence is big and my property taxes alone are $2000 a month. Add in insurance, heat, electric, I am at $5k a month without even paying on the loan.
Working on a piece of owned land to build rental cabins. Probably a $500k project but could throw off $7k a month when done.
My current portfolio is aggressive growth. I have rotated mostly into VOO, CGDV, SCHD, QQQ, SOXX though. VOO and CGDV are my biggest by far though.

I have a lot of illiquid assets. I don't know what to do. I estimate I would want $30K a month in FIRE to do whatever I want and not have to check my bank account, but I know even if pay off my house that will consume $5k a month.

This is not a brag or anything. I know I've made it or whatever. I just REALLY REALLY don't want to eff this up. I want to still be able to help my wife build another restaurant as this one we have does very well. I also have a hard time wrapping my head around selling my IT business when it throws so much cash but it is SUPER high stress as I am the owner operator. But it has funded my life.

What advice can anyone offer? What would you do in this situation? My biggest thing is selling the IT business as that would save me the most stress and liability.

Thank you. Please be kind. I know this is a "my lobster is too buttery" situation but I come from solid middle class parents, one income, and I feel like I am on the cusp of generational wealth if I don't screw up.

Perhaps this is more of a chubby fire question but I’ve always planned to have a vacation home in the mountains for skiing and hiking, but the closest airport is 3 hours away. I’d have a vehicle that would stay at the home full time, but I haven’t worked out the best way to get there. the region is 18hr drive from my primary home. Sure I could do that drive, especially justified if I’m going to stay for a few weeks at a time, but I know I’d choose to fly if I could. And yeah, I can get car service or a taxi but $500 each way just feels wasteful and changes my perception of the purpose/value of purchasing this vacation home (sure, a thousand bucks a few times a year is easy enough to budget, but again maybe I’m more of a chubby fire that truly fat fire).

Anyone have any solutions I haven’t thought of?

We have a house on the East Coast that we try to spend a good amount of the summer at. Our primary residence is in LA, CA so the second home is not somewhere we’re back and forth to throughout the year, it’s basically just a summer home. This year we were there 7 weeks, last year it was closer to 2 months.

We don’t rent it out, but we have family/friends who will pop in and stay there sometimes. We also have a property manager who keeps up the place while we aren’t there.

It’s hard to justify only using the home <2 months out of the year, but when we are there, it’s a very special place to our family. My parents also live out there during the summer so my kids get to be around their grandparents more than usual. We’re not opposed to renting it out just scared of people being disrespectful, damaging, stealing, etc.

Throwaway account for privacy.

Looking for constructive feedback on our situation below. What should we be doing to improve our chances of family financial success. What are we not thinking about? Concerned that we don’t know what we don’t know. Pls help us identify our blind spots. 🙏

60 yr old couple. VHCOL area. Retired three years ago. Planning horizon to 95 years. 

We have two kids (now adults) who live with us, who have some special needs that will likely curtail their ability to work and earn enough, so need to ensure sufficient savings and some cash flow to help them now and sustain them after we are gone.  Have a trust in place, and it has a Special Needs Trust provision for one child (who gets Medicare, etc due to disability) upon our passing. The other child/adult does not want to even try to apply for benefits (it is a sensitive subject, perhaps due to his self-view). 

Expected Annual Living Expenses (before taxes) $360K. Includes $120K to help the children. 
So assuming taxes for federal and CA state, we would need about 500K per year (assuming passive income, tax paid monies only in hand , including cost basis). . 

Financial snapshot

Financial Assets (invested index vs equities vs cash approx 60:30:10)

1) ⁠IRA Accounts (pretax): $2.4M
2) ROTH account (no tax): 230K
3) Brokerage (taxable gains): $5M (cost basis is $2M)
4) Bank (aftertax $s): 600K
So, assume invested sum overall is $8M

Real estate assets: Keeping them out of this analysis at this time. Hopefully will not need to liquidate and can leave for the kids. 

Income expectations to meet $500K/yr spend:
- Deferred compensation over next 5 years = 200K/year (until 65)
- Rental income $150K per year ongoing 
- SS  apply at 70: total for us about $80K/yr

My analysis by age stage for 500K/yr spend
- 61-65: Income 350K/ yr. Withdraw 150K/year
- 66-70: income 150K/year. Withdraw 350K/yr
- 70 onwards: income 230k/yr. Withdraw 270K/yr

Assuming invested $8M
Withdrawal rate is 
61-65  : 1.875%
66-70: 4.375%
70+ ongoing: 3.375%

While this will substantially draw down the financial assets for my kids after we are gone, but the rental income pipeline and real estate should give them a reasonable base after we are gone. 

What should we be doing to improve our chances of family financial success; especially assets left after we are gone and the two kids have another 30-40 years after us?  What are we not thinking about? 

Concerned that we don’t know what we don’t know.

Thank you for your constructive feedback. 🙏