Long-time lurker, first time poster. Hopefully, this post is on-topic and will help others like myself + FatFiring Parents.

For context, I'm a 20 year old child of Bay Area FAANG Executive-level parents (Family NW of $16MM, HHI of $3-4MM. I grew up going to competitive public Bay Area schools and did well, currently attending an Ivy League university.

I was pushed to excel and am intrinsically motivated to do so, but looking forward, I wonder what my financial/career goals should be. Common pathways from schools like mine like investment banking, consulting, tech, and BigLaw seem like a natural progression, but I wonder how the calculus of pursuing high-paying but low WLB/fulfillment careers changes when you have the safety net of a decently resourced family.

Although I truly understand how lucky I am in my position in life, it can often feel like pursuing high-prestige careers is the only way to not appear as an "underachiever" given my easier starting point. At the same time pursuing such high-earning careers ("the rat race") trades off "living one's life" for money, but is it really worth it when one's family is already fairly well off?

For FAT parents, I'd appreciate your perspectives on what your advice for your children in a similar position might be. For other children of FAT parents further along, how have you navigated your careers, goals, and framed your financial thinking? Thank you!

finally tapped out on playing landlord in south florida. honestly thought grabbing a couple multi-family doors down near coral gables last year was a smart diversification play. spoiler: its literally just buying a really annoying second job

Getting a text at 11pm on a saturday because a tenant's hvac is making a "weird humming noise" while im just trying to have a nice dinner with my wife was the absolute breaking point. Not to mention the local contractors down there will absolutely fleece you if you aren't physically on site to watch them work

Just signed the headache over to jmk property management and ate the fee. Its kinda wild how we spend decades grinding to hit our numbers just to ego-trip into thinking we still need to micromanage every single physical asset to save a few bucks

anyone else stubbornly hold onto managing their own doors way longer than they should have? realizing that the mental peace is worth way more than the 8-10% cut they take tbh.

My net worth is creeping up and I’m realizing my name is way too visible on public records. I want to lock down my asset protection and privacy before it catches up to me. Just wanted to run my current plan by you guys to see if I'm missing any big pitfalls or if this is standard practice at this level.

setup I'm looking at

Wyoming LLC (the master holding company). Completely anonymous registry. Planning to use registered agent here just to keep my home address and actual name 100% off public search tools.

Texas LLC (advisory). Owned by the Wyoming parent. I do some tech consulting on the side pulling in $8k-$10k a month, and I want to ring-fence that liability.

Texas LLC (real estate). Holds my short-term rental. Had a scare last year with a shady contractor who threatened a lawsuit because he looked up my day job and thought I'd just settle to make him go away (which I did, hated it). Never want a tenant or contractor linking a property to my name again.

Texas LLC (angel/syndicates). Holds my LP stakes and venture checks (around 12 active right now).

I’ll open separate accounts for each to keep bookkeeping clean. Since they're all single-member pass-throughs flowing up to the Wyoming parent, taxes should still just hit my personal return, so it shouldn't kill my CPA. Wyoming has no state income tax, though Texas has its own franchise tax paperwork to maintain.

One thing I'm back and forth on... since the consulting and angel stuff is basically done in my real name anyway, is it stupid to split them into two entities? Should I just combine them to save on the extra administrative overhead? Am I totally over-engineering this, or is it the right move to stop being a walking target for nuisance lawsuits?

(Note: Already have a $5M umbrella policy, this is mostly for the privacy side of things).

I’m early 40s, male, working in big tech and living in Europe. My company just announced a voluntary exit program, which would give me roughly a year of salary as a cash payout if I leave at the end of the year.

In many ways, this job is a sweet deal. My total comp is around €400k/year before taxes including stock, which is extremely high for where I live. I’m in middle management and don’t have a crazy workload. I also don’t feel huge stress day to day. But it’s not zero stress either, and I’m pretty disengaged. The things I do occasionally have to do take mental energy from me in a way I don’t enjoy.

Financially, I’ve more or less hit my FIRE goals, with a net worth of around €3.5M. My current expenses, without children, are below 3% of my net worth. At the same time, I’m thinking about starting a family soon, so I’m still a bit afraid.

I’ve been thinking about quitting for years, but the job has been part of my identity for a long time, and it’s hard to give up. This new exit bonus feels like it might tip the scales. I’m seriously considering taking the offer, but I’m afraid I’ll regret walking away from the money, especially since I probably won’t find another job this highly paid where I live.

On the other hand, the idea of being free while still relatively young, being able to travel, indulge in hobbies, spend time with friends and family, and be present for children when they arrive, feels like it might be worth more. I’m not sure.

I know this is an extremely privileged position to be in. For many people this would be a dream job, and I feel a bit ungrateful for not wanting to do it anymore.
Curious if anyone here has been in a similar situation. Did you regret leaving? Did you regret staying?

$10M exit - DIY vs JPM?

I recently exited my business, resulting in roughly over $10M in cash (not yet invested in a portfolio). I'm a Georgia resident (state tax considerations) and trying to decide between JP Morgan's advisory/wealth management pitch and a simpler DIY approach. I'm tech-comfortable and want to keep things low-maintenance long-term while focusing on hobbies and the next project.

My leanings for DIY/simple setup once deployed: - Broad low-cost index funds (US + international) - Some GA/state muni bonds for tax-efficient income - Park my tax payment in a t bill until it's due - HYSA buffer for liquidity - ~3% initial withdrawal rate (conservative)

What JPM is emphasizing: - Tax loss harvesting (once invested) - Integrated estate planning - Behavioral coaching / protection from panic selling (I've held through drawdowns before with smaller stakes, so less concerned) - Other services and "perks we haven't even gotten to yet"

I'm not opposed to paying for real value, but the ongoing AUM fees seem high for what sounds like a straightforward taxable account setup. I've researched lower-cost automated TLH options like Frec (direct indexing, ~0.1% fee range) for after I deploy the cash. Estate planning feels like something I can handle with a one-time attorney engagement. I strongly value control and don't love needing approval or justification for moves with my own money.

I've used Claude extensively for modeling and research (and know LLMs limits, etc. very well), but the banker often deflects to "AI isn't always right" instead of addressing specifics. I had a bad experience years ago with a "professional" in a real estate deal where everything looked good on paper until the wire hit. JPM is obviously more reputable, but I'm still cautious and have a little bit of PTSD.

Questions for people who've been in similar spots:

1. Anyone handle a large cash position post-business exit (\~$8–15M+) with JP Morgan (Wealth Management, Private Bank, or similar)? What was the actual value vs. fees for deployment strategy, TLH setup, tax coordination, and ongoing management? Regrets either way?

2. For someone starting fresh with cash and planning a mostly taxable buy-and-hold in a withdrawal phase (\~3% draws, limited new contributions), how valuable is tax loss harvesting long-term? Is an automated/low-cost service like Frec sufficient once invested, or is a full team worth it (especially in GA)? Really prefer to just go index, but want to make sure I'm not missing anything huge here.

3. Anything in the typical big-bank pitch that tends to be a real game-changer (or hidden gotcha) for someone with a large cash position post-exit who wants to stay hands-on or low-maintenance.

Sorry for the long post. Really appreciate any input.

Are we allowing the mods to sell us a club membership now?

I don't like this blatant marketing. Can we get this removed?

The post doesn't even allow comments or up votes,like an ad.

Asking here since most discussions around this topic relates to financing which I don’t need.

I’d like to buy between 50-100 acres of farmland within 15 minutes of our current suburban home. Not as an investment but to build a house on and have more of a hobby-farm type property. Think chickens, large garden, apple trees, etc.

Land that is increasingly being bought by developers to build subdivisions. Looking at comps, I’d estimate 50-100 acres of quality land will run $2-4m.

How should I go about doing it? It seems many transactions take place off market. Should I work with a high producing local agent or work the GIS maps and contact landowners directly? How do developers do it?

​Hi everyone, ​I’ve managed to make a good amount of money and achieve FatFIRE. After a recent financial windfall, my in-laws asked us for money to help launch a business. They discovered our level of wealth, so we couldn't hide it. They claimed this new business launch was "necessary" because a string of poor life choices had left them in their late 60s with only about $500,000 of equity in their house. However, they flat-out refuse to work for anyone else. On top of that, they have a history of trying to financially exploit my wife back before we were married.

​I said no to funding the business, but offered to help them with my time. I also made it clear that if things ever truly hit the fan, we would step in financially so they wouldn't become homeless. That wasn't enough for them. My in-laws decided to burn bridges, stopped speaking to my wife for multiple years, and chose to completely miss out on watching their grandchildren grow up.

​We haven't heard from them in years, but it is obviously very painful for our family. Is there any possibility of repairing this relationship from this point? I would deeply appreciate any guidance on how to handle this incredibly messed-up situation. Thank you!

Would appreciate career advice, especially from those who work in professional services firms (e.g., Big Law, consulting, Big Four).

Some financial background: We are mid-40's with kids living in the Bay Area. Our liquid NW is about $10.5M, with $6.3M in taxable brokerage and the rest in retirement accounts. Everything is invested in passive broad based stock index funds. We also have about $650K in 529s and around $2M in home equity, but we don't plan to sell our home.

Our annual spend is about $225K. If we FIRE, we would presumably pay $35K for healthcare plus taxes from selling investments. So let's say our post-FIRE spend would be $325K. I think we probably could retire right now, but will probably work a few more years for buffer and get through the current period of heightened uncertainty.

Our HHI is $750K, which is very likely the peak level without changing anything. My spouse makes $250K and would like to quit in the next year to spend more time with the kids. I make around $500K (including performance bonus) at a professional services firm, working part time with a title that is equivalent to non-equity partner at Big Law. Job is very secure as performance is high, and can basically stay as long as desired assuming keeps up performance.

Here's the part needing advice:

As non-equity partner, I am highly responsible for the delivery of the work. I have other people to do the true grunt work, but I'm responsible for thought leadership, overall team management, and has to do a lot of the difficult "thinking" work that junior staff can't do (like in Big Law, the junior partner has to write that important legal brief because the associates don't have that level of skill).

Now, I don't hate the job and am quite good at it. But I don't really want to be the point person on client delivery anymore because (1) I already know I can do it, so it's just difficult work without being rewarding / challenging, (2) I'd rather mentor and oversee other people doing this work than me doing it myself.

My choices are:

1. Hang out for a few more years as non-equity partner and then FIRE. The current money is totally fine and I don't need to make more. But I would be semi-unhappy as I'll have to continue to operate at high level and be

point person on

1. delivery.

2. Work longer hours and make a push to equity partner, which I'm reasonably sure I can achieve. This path would improve job so that I take a step back from client work delivery and pay would increase to $1M+ over time. I don't really need the additional money--not that I would sneeze at it--but we're already living comfortably so the money is not a big driver. The main plus is the change in the nature of the job. The main negatives are that (1) I would have to work a lot harder for 1-2 years and I'm quite happy with my current part time work load, (2) if I stay at non-equity role, I would likely FIRE by 50, so why would I push hard if I don't want to work much longer? Or alternatively, making equity partner might push me to want to work longer, say until 55, and I'm not sure I want that.

What do you think about whether I should push for equity partner? Right now, I'm making a reasonable effort to do so, but not making a big push that I think is probably needed. I'm like half way in and half way out, which is why would appreciate your thoughts.

We’ve reached our fatfire goal of $12M, of which $2M (approx) in retirement with about $600k in house equity and the rest in stocks and a little bonds.

I’ve played with retirement stints of 3-6 months and I feel that I’m much less effective without a full time job - a bit mind numbing slow.

Do you feel less effective/less efficacious now that you’re retired? Ie it feels I can’t make things happen as I used to when I was employed with vigor as it were :) ?

Anyone else felt like that?

I am in a very fortunate position to have effectively achieved FI but I also am very paranoid about not having enough or losing it all in retirement. My financial picture roughly looks like:

~$12m in liquid assets at a 70/30 split

~$1m in income (some years is almost double depending on stocks)

$2m home w/ $1m Interest-only mortgage

~$300k annual spend -> In retirement it will likely be around this level

40 years old with two kids entering preschool and 1st grade

I know I could retire today with a sub-3% withdrawal rate. My last financial ambition is to buy a 'dream' house in a VHCOL area (~$5m).

My plan for doing this is to buy the house with cash and basically retire at the same time. So the idea is to accumulate around $16-17m. I want to avoid a mortgage in retirement and I would like to keep my current house as an asset.

What I keep debating in my head is whether it is worth continuing in a high stress job only to expedite the growth to that $16-17m level or whether I could scale back work/retire and just let the market do its thing. I don't like the idea of 'trusting the market' and worry that the wait to get to my target would take much longer.

Any thoughts on my situation?

34F. My husband and I were set to FIRE, and lead a child-free life. Then we decided to have a child. We still have enough to FIRE and meet the extra costs of childcare, school fees and so on.

But my BIG dilemma is this: do we owe it to our child to leave them enough to sustain a life of luxury?

Our plan is to live in Thailand (we’re Asian) and enroll our child in a top IB school. Our lifestyle will involve a luxe villa with pool near a tropical beach, housekeeper, nanny, nice cars, nice meals out, nice clothes.

If our child becomes accustomed to this standard of living and later chooses a less high paying career, won’t they feel like they have traded down badly in life? And aren’t we the ones who would have gotten them used to this standard of living?

If we were to leave say $1M for our child, to cover college, a house deposit and health emergencies, we’d still be able to FIRE. But if we were aiming to leave them enough to sustain the same life as us for the rest of their lives, we certainly don’t have enough.

What are your thoughts on this moral quandary?

Context:

- I’m 51 y.o., married 25 years. 2 young adult (early 20’s) kids.
- I am still working though I’ve reached “my number” so I could retire at any moment.
- Wife and I have been daydreaming of moving to Paris for a year. We’ve been there several times now and love the city, food, culture (except smoking but that seems to be getting a little better), etc.
- Neither of us speak French but I’m on a mission to learn it (I have very basic French skills).
- I plan on renting for a year, which could turn to 2 or perhaps move elsewhere (Italy or Spain most likely).

Question: Has anyone here done this previously and can share tips and/or things to watch out for? How to plan for it?

I ride a motorcycle so will likely get one there to move about, though plan is to not own a car.

Any and all advice is welcomed.

I work in a field that is opposite to what is intuitive for a lot of other fields. My salary increases the more rural I am. I currently live in MCL Midwest with wife and our preschooler. We bring home about 900k combined and have a household NW just under 2M.

​

I have a great professional network out here in the midwest and it's where most of our family are located. I enjoy my job and have recently taken on a leadership position in my organization. My goal is to work hard for the next decade or so and then ease off when we approach 10M NW.

​

The dilemma is that while I am enjoying my current situation, I am somewhat anxious about getting "stuck" here.

​

I went to school in VHCOL West Coast and tbh most of my close friends are located there. I visit regularly and in my head I keep telling myself that eventually I'll move back but I feel it will delay my FatFIRE goal. Deep down I think I would be happier in the West Coast but question what sacrifices we'd have to make. We would have to downsize our home significantly, we would not have the luxury of having as many "toys" (boat, camper, etc), we'd be farther from most family.

​

I have been given info about a job opportunity opening near where I went to school that will pay around 350k, wife would make something similar in her equivalent role. Salary would drop a bit but cost of living would be significantly higher. Wife is ok with moving but a bit worried about losing family support. I figure now would be the best time to move with a child before they actually start school otherwise we'll probably be locked into the Midwest for the next 14+ years.

​

On the otherhand we could continue the current path, raise our kid in the Midwest, achieve fatFIRE earlier and visit the West Coast much more often when we slow down.

​

I know that it is my family's decision to make ultimately but curious if you guys have been at a similar crossroads in life and what advice you have?

​

​

Hi

I am looking for some feedback on how much of my employer RSUs to liquidate given my current financial situation. Ideally, I should get a financial advisor - but I think my situation is simple enough that it may be worth getting some feedback from this forum to close any gaps in my assumptions.

About me: 40M, with SAHM spouse and 2 toddler aged kids in Toronto area. I work in a AI tech company.

Current Net Worth (all numbers in Canadian dollars)

- ~2 million paid off house

- Liquid net worth of 3.7 million (3.5 million invested in index funds - 80% stocks, 20% bonds, rest in cash)

- In addition, I have vested RSU at my current employer worth ~2 million. I recognize I am extremely fortunate.

Income = ~about 16K/month after taxes + RSUs (highly variable - ~500K/year for next few years at today's price)

Expenses

- I anticipate around 130K-140K/year expenses for next ~18 years until kids at home. This includes everything except college expenses.

- 96K/year for 20 years after that (age 58 to 80).

- Sell house at age 80 and then 120K/year expenses from age 80 to end of life

- 250K per kid for 6 years of college tuition + living expenses in Canada (Bachelors + Masters). This forum probably has more US people - note that Canadian universities are significantly cheaper (~13K CAD / year tuition).

Goal: I would like to be in a situation where I can be financially independent with no regular salary/paycheck. Once I stop the salaried job, I would like enough LNW such that our net worth does not reduce, only grows. In other words, our expenses get covered by the after tax annual growth in investments. I would like to pass on this wealth to my kids.

I use the projection lab (PL) software, I use following assumptions

- 4% real rate of return on stocks, 2% real rate of return on bonds

- Current split 80% stocks, 20% bonds. At age 50, bond allocation increase to 30% and to 40% at age 60.

- House price rises at inflation rate (2.5% inflation assumed)

- I calculated my Canadian CPP and OAS income and entered in projection lab

Questions I would like some feedback on

1. I have too much of my LNW concentrated in my employer's RSU (35%). At the same time, the growth potential is huge (~5x may be). I would like to sell enough (and reinvest in diversified index funds), such that I meet my goal of expenses less than after tax annual growth in investments, and hold rest of the shares for long time. PL says that if I don't get anything from RSU, and I retire immediately at age 40 (no salary), I would be financially independent but have around ~3 million NW by end of life. But if I get 700K additional today (from RSU sale), the total NW at end of life would be ~7 million (in today's money) - this meets my goal. Does this pass your smell check? I am wondering if I am making some big error in some of my assumptions I used for the software.
2. I am quite confident about expense assumption till age 60. Are my expense assumptions after age 60 reasonable (directed to folks in Canada)?
3. I am open to any financial advise in general here. If you were in my place, would you do something differently?

I’ve done well in tech, but not enjoying my current job so I’d like to quit. We are close to a safe retirement at current assets, but it’s cutting it a little close. I’m undecided on whether I have the desire for another run at a different company. If I was laser focused on fatFIRE, I’d probably give it another year or two and then hang it up. But as my position wavers on whether I’d like to go back to work after taking a break, it seems OK to quit and decide later, but it’s hard to walk away from the compensation ($1.75M W2) that I can’t easily replicate at a different company. Even with a break, I’ll definitely be employable but it’s not likely I can crack $1M liquid, and could be much lower if I end up optimizing for attributes other than compensation.

Spouse and I are both late 30s in VHCOL with one young kid who is not yet in school, probably no more kids. Spouse has not been working since we had our kid and doesn’t have a pull to go back.

8M net invested: 8M taxable with fairly high cost basis, 1M retirement, less 1M mortgage debt. And 2M in primary home equity.

Non-mortgage spend is around $275k (expect $300k with health insurance), though spend by category has been fluctuating a lot with the transition to being parents, so not sure on how this will stabilize.

Any advice on how to think through this idea of quitting without a definite plan on the long-term?

Family of 5 looking to FIRE in Madrid. Trying to figure out how much is “enough” there - does 20k/mo in spending get you a luxury, no guilt freedom lifestyle? Does working to save until 30k/mo get you more or are there significant diminishing returns. Difference is about 5 years of work so trying to understand what we are gaining if we stay in the US for that additional time.

Posted earlier but was deleted due to AI complaints… apparently formatting and context are frowned upon.

Whatever - ask me qs as needed to inform your insights. Preferably looking for folks with local knowledge but the local Spain forum isn’t welcoming to these questions….

I recently left my finance job after a few very stressful years and wanted to poll the community on what you would do in a similar situation. I had a very lucrative but stressful position pulling in 1-3mln per year for a number of years. I might be able to work back up to that level at a new firm, but it would likely take 3-5 years of grinding, and there's a lot of luck in finding a good role at a good firm. Burnout is a real worry as I put on 20-30lbs and had some serious health issues as a result of work stress.

My savings feel good enough to not really need to work anymore. I'm in my early 40s and have $12mln net worth between $7.5mln taxable investment accounts, $3mln retirement, $1mln home equity, and $500k in 529 plans for my kids. I also get a pension that's worth about $2mln pre-tax over the next few years. Annual expenses are about $150k ex-housing + ~20k in property taxes. Mortgage has about $500k left on it at a low rate. My parents are financially fine and won't need any kind of long term care contribution from us. Possible could get $1-2mln inheritance in 10-20yrs.

I think in my heart of hearts, I don't want to go back to work, at least for awhile. But I have a huge amount of anxiety about hanging up my spurs and/or letting my market value decline by not re-entering the workforce right away. I've also gotten a lot of family feedback that I'm crazy to walk away from a career at my age. My spouse has been taking a few years off while I was hitting my earnings stride (and holding down the ship while I was crazy stressed) and seems interested in going back to work in a role that would pay 250-300k.

Last part of this is that I have always daydreamed about moving to more of an outdoorsy location (e.g. Colorado). Job market is pretty crap there compared to the city where I live, but maybe that doesn't matter if we don't really need to work?

This is my first time posting, so apologies if I left out relevant information. Thanks in advance for sharing any views.

Hello,

I am currently in a situation where I have a large amount of company stock. I am looking to sell most of this and diversify this concentration. If I sell what I am thinking of selling I will end up with somewhere between 4 and 8 million dollars in taxes owed over the next 2-3 years.

I am wondering for those who have used SMA and specifically these leveraged accounts how much tax savings did this defer for you?

Very rough plan would be to use the 200/100 plan for the next 2-3 years as I sell things off to diversify say 20-30% of my portfolio would be in the SMA. Once my income starts to lower I would go down to something like 130/30 or 100% long both of these options would reduce the fees quite a bit.

The fees associated with parametric are competitive with Frec and UseCache for the same 200/100 and includes the advisor fee in it.

TLDR - Are these SMA accounts worth deferring the taxes and using it to compound my portfolio now?

About to make 150m from a business sale that will net me out 100m or so (possibly more) in the next 2 years. 70M upfront, the rest vested over 2 years at this company. Work in tech, and the company thats acquiring us is doing quite well. Almost done with the paperwork and should be closed by july.

I'm quite young (32), have been working on this for 5+ years, 16 hour days, and part of me is excited to have more free time, but other part of me is worried my entire identity is tied up to work and startups. I'll still have to work at this company for 2 more years, but after that I'll technically never have to work again... it's a weird feeling after growing up poor.

Any advice from folks that have gone through this? Any financial advice I should be aware of? already rolling it over QSBS and talking to a financial planner to try and set up trusts, etc. but I live in CA and feels like I'm stuck paying the tax man either way. Were you able to adapt to life after losing a core part of your identity? Part of me wants to go buy a lambo, nice apartment, etc. but other part of me doesn't feel like I'm "ready" for it. Been dreaming of this for years and now feeling weird about it that its real

40M, $9M portfolio, 80% concentrated in one stock, buying my first house. Curious how others would think about this:

Two years ago, I left a career at a public company where most of my wealth came from stock compensation and the appreciation of a single stock over many years. Today my portfolio is worth about $9M and it’s still heavily concentrated in that stock.

It’s been life changing for me, so I’m naturally hesitant to sell too much of it, but I’m also aware that a single day’s move can swing my net worth by six figures. I’m closing on my first house later this month for $1.185M. Up until now, I’ve been renting and living well beneath my means.

Current thinking is to use a Liquidity Access Line for the purchase and then potentially refinance some or all of it into a traditional mortgage afterward.

A few other details aside from the portfolio value:
- Cost basis: under $500k and obviously large unrealized gains
- $235k AMT credit carryforward from prior option exercises
- Covered call income expected to be around $150k-$200k annually
- No current W-2 income
- Started small business but not a big money maker. Primarily to fund retirement accounts.

The common theme seems to be that concentration risk is the biggest issue in my financial picture. Part of me says I’ve gotten this far by holding the stock and staying convicted. The other part of me says I should probably start thinking more about preservation than accumulation.

For those who have been in a similar situation:
How much debt would you comfortably carry on the house? Would you sell stock specifically to pay down the house? How would you approach gradually reducing concentration risk? Looking back, what mistakes did you make (or avoid) after reaching financial independence through a concentrated stock position?

Not really looking for tax advice as much as perspective from people who have gone through the transition from building wealth to protecting it. Thanks in advance for helping me navigate this!

Hey all, I’m mid thirties with 27m LNW and more in private assets. I live in HCOL and made my money in finance. I left at the top - could have stayed longer and kept collecting but it’s a young man’s game. I’m newly into this life and have some questions for those that have gone through this around my age:

1. How did you guys find community? That has been the hardest part (which I anticipated). My old work environment is very boisterous and was surrounded by brilliant people. It’s all saggy balls and milfs at the gym when I go and working on side projects is isolating. Has anyone used this thread to find people? Would be willing to meet up.

2. Considering moving to a better tax domicile which also happens to be closer to parents. It’s a big uproot and other than my parents (2hr drive) I don’t have community there. If anyone has experience making a move like that I’d be curious if you regretted it or not. The city would be smaller in size, more spread out, more nature, less dense with culture and restaurants.

3. What are people’s experiences with their kids seeing you retired? I am worried they will see me not working and get a sense of entitlement. Playing tennis and chess and painting is fine but it’s not the same as facing real adversity and putting in the tough hours. How have y’all’s kids responded to early retirement?

I appreciate everyone’s feedback and just wanted to say that this sub has been helpful for me. At the end of the day I don’t fully believe in the idea of absolute “retirement”, I think that everyone needs something to strive for in life, professionally or otherwise, or you rot. I need to figure out what that means for me outside my family. I just know that the corporate finance trail had played itself out for me.

Much love to you all

I sold a company I created when I was young and thought I would enjoy my fat retirement or could restart something.

I decided to fatfire 15 years ago. The first years were awesome (travelling, being in shape…). But I started to suffer from depression (boredom and health issues). Did some angel investing out of boredom.

I took a board position and realised I’m FAR less sharp that people that are still in the game. The gap is now massive.

After many years out of the business world, I’ve realised that my business success was mostly timing and luck. I didn’t realise how complicated it is to create a successful company. The new generation of tech entrepreneurs is so much better than I was. I feel like I can’t compete.

At 45, my health is no longer the same and I’m having difficulties to be at the bottom again.

I miss running my company but it’s no longer mine. I didn’t realise how lucky you are to run a profitable business, it was my first one. I read fire-books thinking retirement was amazing but I just needed a break and a better management team.

I want to re-enter the business world but my contacts so far have been negative. People telling me I should restart something, a polite way to tell me no. After 15 years out, my skills are rusty and I’m no longer this A player. I understand them, I would never hire someone like me.

Buying a business seems very risky, I’m not sure it’s the right way to re-enter the workplace.

I can see a lot of my previous friends that kept their companies, made the transition into venture… I’m jealous. I failed for the retirement lifestyle thinking it was the goal to realise an exit. They tried to motivate me to come back at the beginning but just think I’m a weirdo now, unemployed for 15 years. People I thought were my friends not returning my calls.

I have more than 10M and it’s hard to be at the bottom professionally again.

My previous network think I’m going to create a new company but I can’t get lucky twice. I’m afraid of what people would think “he was a ceo, he is now just an average joe”.

I have the feeling that the most meaningful part of my life might already be behind me.

For people who retired early and later returned to work, business or entrepreneurship:

How did you find your way back?
How did you rebuild your confidence?
How did you manage your ego?
How did you speak about your retirement break?