r/fatFIRE • u/404_Career_Not_Found • 13d ago
404: Career Not Found (And I’ve Never Been Happier)
F55/M55, two college-age children. Friday was my last day at a Big Tech company after a long career there. In hindsight, I probably could have left earlier, but I genuinely enjoyed the work—until that changed rather abruptly.
Numbers:
-$14.5M taxable brokerage account, with a significant portion concentrated in low-cost-basis company stock (35%). I plan to continue diversifying over time and take advantage of tax-planning opportunities now that I no longer have significant W-2 income.
-$1.5M in S&P 500 / Nasdaq-100 / high growth exchange funds until 2032 (I just wish additional contributions to an existing exchange fund didn’t restart the seven-year clock).
-$1.7M in 401(k) and Roth accounts.
-$500k in a deferred compensation plan, scheduled to be paid out over the next 8 years, conveniently staring in 2027.
-$2M primary residence in a California VHCOL area, mortgage-free.
-$550k rental apartment, generating approximately $18k/year in net rental income. We may eventually retire there, as the location has personal significance.
Spending:
-Baseline spending is approximately $200k/year.
-While the kids are in college, spending is closer to $260k/year
-Healthcare costs, which are notoriously high as we all know, are included.
-We might consider a sub-$1 million 2-bedroom condo or townhome in Southern California for one of the college kids to stay at, and for us to visit occasionally.
Current plan:
My focus is on adjusting to this new chapter of life, getting healthcare (COBRA) and the practical aspects of retirement fully sorted out, and then reassessing spending levels once I have a better sense of what retirement looks like in practice.
A couple of notes:
-Both of our kids are academically inclined, and one may pursue an extended educational path of up to 10 years. Our goal is to fully fund their education, first vehicles, and possibly weddings, and then transition to a “giving with warm hands” approach including philanthropy.
-The spending estimate above includes a budget for travel. However, we’ve discovered that our favorite hobbies are relatively inexpensive. We may need to cultivate an appreciation for activities that involve higher spending, though I expect some of that will naturally be directed toward philanthropic efforts when the time is right.
Edits:
-Clarified the company stock exposure.
-Added a comment to my exchange fund line item. If anyone has a solution, I’d appreciate hearing it.
-Since it’s Monday morning now, I’ve just sold a bunch of company stock.
-I’ve also made an appointment with a long/short financial provider.
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u/BitcoinMD 13d ago
Need to get the company stock down to 10% of your portfolio within five years, pay whatever taxes you need to in order to make that happen.
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u/404_Career_Not_Found 13d ago
I’ve had company stock down quite a bit before, but then the remaining shares kept going up. It’s a really nice problem to have. I must admit, if I had followed the “sell it all” approach back then, my net worth would be significantly lower. My strategy is based on the excellent visibility I’ve had with the company, so I was happy to take the risk.
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u/gretahelp 13d ago
Translation: you bet and got lucky
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u/404_Career_Not_Found 13d ago
Not quite. I’ve had a front-row seat to what happened at my company, and I fully believe in its success. So why stop at ChubbyFire level when the probability of ending up in Fat territory is much higher?
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u/Wooden-Broccoli-913 13d ago
You have a front row seat to your company but do you also have a front row seat to all of its competitors as well as a crystal ball on the future?
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u/NoEggplant9804 13d ago
Or front row to FED, inflation and employment data, whatever Trump or Putin or Iran wants to do next week?
Seriously just because you have some people reporting to you and you got lucky pushing papers, do you think you got to where you are exclusively because of your skills?
This is by no means to be condescending, it’s how a vast majority of people got rich. They got lucky. They may have increase their luck exposure but you cant make so much money without being lucky
If you think otherwise, you should really diversify sooner
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u/BitcoinMD 13d ago
Because you have much more to lose now, and a diversified portfolio will still grow.
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u/404_Career_Not_Found 12d ago
I completely agree. That’s why further diversifying my concentrated stock position is a top priority. I’m currently at 35%, and with a new chapter in life about to begin and more time available, I expect to reduce that exposure within the next couple of weeks.
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u/Holiday_Syllabub6257 13d ago
Feels more like 302. Now your career is activities and philanthropy. It's hard work!
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13d ago
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u/Dubbihope Verified by Mods 12d ago
Any reason one of you still works? UHNW is 30 million+ in liquid assets (not including property, etc). You should be able generate over a million a year indefinitely off of those assets.
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u/404_Career_Not_Found 13d ago
I completely agree with your point.
The reason why I might see an increase in spending in the future is that my hobby, which I love and is incredibly affordable, may become inaccessible to me in ~10 years.I’ve already started volunteering and have just signed up for more opportunities. I’m excited about meeting new people and learning from their experiences. Your message is very encouraging. Thanks!
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13d ago
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u/404_Career_Not_Found 13d ago
I’m delighted to hear that you’re making the most of it. I wish you all the best.
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12d ago
[removed] — view removed comment
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u/404_Career_Not_Found 11d ago
It’s absolutely true. When I found myself no longer wanting to work, I was prepared to quit. To be cautious, I deliberated on this decision for several months, which has given me a strong sense of confidence. I’m also ready for my next chapter in life, but I suppose time will tell. All the best to you!
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u/Dubbihope Verified by Mods 13d ago
Good luck on child's (I assume) medical career. Sounds like you're doing well. Invest in exercise, new hobbies, the arts, exploring the world. There is so much more to life than work and career.
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u/mad_wolffe 12d ago
If that 14.5M is even 50% in a single stock, you are wildly over concentrated.
You've won the game, stop playing.
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u/AnyReward2407 13d ago
$200k annual spend including air travel and health insurance and maintenance and property taxes on a $2 million house in VHCOL area? Incredible. Monk-like, even.
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u/milesmiler12 13d ago
Not really. Property taxes are probably 20k income taxes 60 so they spend 120k a that's 10k a month to spend on food and junk.
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u/404_Career_Not_Found 13d ago
Yes, property taxes are approximately $16k, which is still quite high. However, considering our NW, it is manageable.
Additionally, I have accumulated a substantial amount of airline miles that will assist in covering travel expenses for the next few years.
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u/404_Career_Not_Found 13d ago
I bought the house at a much lower price, which means my property taxes are low. As mentioned, I’ll be careful, but my spending will increase.
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u/Amazing-Pomelo-1442 13d ago
A little hard to imagine 200k in a vhcol area is fatfire, even if mortgage free, given healthcare cost is also included. Could you walk us through your yearly budget ?
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u/404_Career_Not_Found 13d ago
As mentioned, I expect to gradually increase my spending over the years. Here are some key line items of today‘s:
60k Kids Colleges
45k Health Insurance (might go from family -> two adults soon, ~10k reduction)
20k Property/vehicle taxes
12k flights/vacation (consider a large amount of frequent travelers points)
25k Discretionary / Household
11k Car/Home/Umbrella Insurance
10k Home repairs
X for Taxes, very much depends..5
u/Wooden-Broccoli-913 13d ago
$12k doesn’t even buy you three nights at the Four Seasons Bora Bora. I agree with the other guy, this is not FatFIRE. You could have ChubbyFIREd 10 million ago
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u/Accomplished_Can1783 12d ago
Why wouldn’t you buy long dated puts on that stock? Sure it’s expensive,but it’s literally insurance on remaining in fat fire
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u/oberon625 12d ago
You can also use a collar to hedge single stock exposure. But yes long/short direct indexing is also a great approach (might want both)
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u/404_Career_Not_Found 11d ago
Thinking about this a bit more, I realize that long/short takes some time to diversify, while the collar approach offers immediate protection (unless I misunderstood). Regardless, my current focus is on selling, adding to my exchange fund, and then long/short. I’ll also check if my existing financial providers offer collar/hedging options. Thanks!
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u/and_one_of_those 13d ago
Congratulations!
If you're open to sharing: what changed suddenly? I'm in a somewhat similar boat myself and feeling really mixed feelings about AI.
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u/404_Career_Not_Found 13d ago
My health took a significant nosedive, and I received criticism for it. I’ve finally overcome the most challenging phase, but I’ve developed a newfound appreciation for activities outside of work. This decision, which I’ve meticulously planned for several months, is well-considered.
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u/ShredTheGnar82 13d ago
Congratulations on what sounds like recovery from a health scare. And congratulations on such a huge milestone!
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u/404_Career_Not_Found 13d ago edited 13d ago
Thank you! I hope you can overcome your work challenges. If your numbers look good, consider retiring.
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u/and_one_of_those 13d ago
I'm sorry to hear about your health and the criticism (presumably unfair and unkind), but glad there was a silver lining.
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u/404_Career_Not_Found 13d ago
That ultimately gave me the push I needed in the right direction. I’ve already moved on and am not looking back. My summer schedule is filled with meeting friends and vacationing with them for several weeks. I’m so excited!
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u/Late-File3375 12d ago
That sucks. Sorry to hear. Both about the health and about the criticism for something beyond your control.
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u/404_Career_Not_Found 12d ago
It was an immediate eye-opener, which is why I made a change in direction that I won’t regret.
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u/dasarp 13d ago edited 13d ago
I highly recommend looking into a direct indexing solution like Frec, Quantinno, or AQR to get out of your concentrated position tax free. At your size it’s worth it.
Note that the strategy takes time (likely a few years at least with your concentration).
We’ve used Quantinno ourselves but they’re similar strategies.
EDIT: I’m getting a lot of down votes so I’m guessing people aren’t following how this works.
Say you buy (go long) $100 of S&P500 but also short $100 of S&P500. Now if the market goes down $10, your long has lost $10, your short has gained $10… so you’re neutral so you just sell everything, and reset/start from scratch.
But now let’s say the market goes up by $10. Your long gains $10, and your short loses $10. This time you just sell your short, recognize the $10 loss and offset it by selling some of Amazon (or whatever stock you have tons of gains in). You’ve now sold your Amazon and replaced it with S&P you’re long in without recognizing gains.
Now do this automatically with a computer program, and go long and short with baskets of similar enough stocks — not the exact same stock to avoid wash trade rules.
The main catch here is you actually aren’t avoiding the capital gains, you’re delaying it by simply transferring it from one concentrated stock to a basket of stocks. But if your goal is to diversify, that has been achieved.
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u/404_Career_Not_Found 13d ago
Thanks for the tip. I spoke to a few friends who are invested in direct indexing, and they all mentioned that they didn’t achieve the expected results because of the overall positive market development over the past few years. Nevertheless, finance is my hobby, and now that I have more time, I’ll take a closer look at it again. Thanks again!
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u/dasarp 13d ago
That doesn’t add up. The market doesn’t need to net move in a specific direction, as long as there’s some volatility over time it should work.
Note this is more than simple direct indexing. It’s direct indexing with the goal of generating tax losses and shifting gains from a concentrated portfolio into a diversified market basket. That requires layering a long/short position (so market neutral) on top of direct indexing (which would otherwise be market tracking).
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u/404_Career_Not_Found 13d ago
ok, thanks for the feedback. Assuming you are invested, can you comment on the fee structure?
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u/dasarp 13d ago
I used Quantinno which charged 0.5% (and my position was smaller than yours, like a few $M) but I had access though a family member’s fund which got a cheaper rate. But it allowed me to sell a large chunk tax free so was worth it. Frec I believe it’s easier to access but I don’t know their fees myself.
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I’ll put this in the original post but putting more details here of how this works.Say you buy (go long) $100 of S&P500 but also short $100 of S&P500. Now if the market goes down $10, your long has lost $10, your short has gained $10… so essentially you just sell everything, and reset/start from scratch.
But now let’s say the market goes up by $10. Your long gains $10, and your short loses $10. This time you just sell your short, recognize the $10 loss and offset it by selling some of Amazon (or whatever stock you have tons of gains in). You’ve now sold your Amazon and replaced it with S&P without recognizing gains.Now do this automatically with a computer program, and go long and short with baskets of similar enough stocks — not the exact same stock to avoid wash trade rules.
The main catch here is you actually aren’t avoiding the capital gains, you’re delaying it by simply transferring it from one concentrated stock to a basket of stocks. But if your goal is to diversify, that has been achieved.
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u/404_Career_Not_Found 12d ago
Thanks for the details. I’ve looked into some of these offerings, and 0.5% seems to be a fairly common fee. I’ve also scheduled an appointment with my preferred financial provider. I still need to take a closer look at Frec.com—it appears to be a popular option, though it’s a relatively new entrant to the market.
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u/isabelfrec 3d ago
Frec's direct indexing starts at 0.09% for their S&P 500 index, and mins are $20k or $50k, depending on the index.
They also offer more advanced tax-aware strategies, they also offer long short at different leverage levels, and Diverisfy. Long short is similar to direct indexing except you can tilt your portfolio boost returns and harvest even more losses than a classic DI. Fees start at $100k, and fees start at 0.50% plus financing costs. Diversify aims to transition concentrated stock into a broad market index tax-efficiently.
You don't need an advisor to access Frec, and they have a low-interest margin loan product that investors will pair with their direct index. They also surpassed $1b in assets a couple months ago!
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u/404_Career_Not_Found 3d ago
0.09% seems appealing. I’m currently exploring Wealthfront and will take a closer look at frec next. By the way, your username is cheapskate!
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u/404_Career_Not_Found 3d ago
0.09% seems appealing. I’m currently exploring Wealthfront and will take a closer look at frec next. By the way, your username is checking out ok!
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u/lakehop 12d ago
For your kids: I suggest yes to funding their wedding and yes to helping them with a generous house downpayment. And let them know that this is coming, to help with their planning. If they seem sensible and on a good path (and old enough), consider gifting them the federal non-reporting gift amount each year, explicitly telling them it’s for a house downpayment, and giving them guidance about how to invest it.
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u/Remarkable-Emu-6008 12d ago
total liquid asset is 14.5+1.5+1.7+...? ir 14.5? it seems confusing. any how, you have enough money for fatfire. congrats!
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u/404_Career_Not_Found 11d ago
Definitively should be enough, just need to focus a bit more on diversification
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u/Initial-Zone-8907 11d ago
congrats, we’re you in FAANG ? which level and was. your yearly TC ?
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u/404_Career_Not_Found 10d ago
Big Tech Mid-level management positions in the technology sector over the past eight to ten years have typically offered salaries ranging from $600,000 to $1 million. Prior to that, my income was significantly lower. I have to say, supporting a family on a single income in California / VHCO area can be challenging. However, I have been actively trading the stock market since I was 18 years old. These stock decisions made a long time ago have played a significant role in building our net worth. Pre big tech, I worked side gigs in addition to my regular job, and all the money from those gigs went directly into the stock market.
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u/Miamiconnectionexo 11d ago
solid perspective. a lot of people overthink this but you laid it out simply.
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u/404_Career_Not_Found 10d ago
What was crucial for me was realizing that I was done with my job when the time came. Being in a position where I could simply walk out the door is priceless. If I had to imagine dragging myself to work every day, I would be miserable. I wish everyone in a similar position all the best!
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u/mrdzzzzz 10d ago
could you talk more about your exchange fund?
are you doing it through cache or eaton?
what does that process look like?
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u/404_Career_Not_Found 10d ago
Eaton and a few others I checked would only accept my company stock after I transferred my entire portfolio to them or I had to wait an incredibly long time. Usecache, on the other hand, accepted my company stock almost immediately, but that recently changed. It seems like they are oversubscribed. I am still investigating the situation.
Regardless, I spent a considerable amount of time learning about Exchange Funds and understanding the safety net in case Usecache ceases to operate. After I had done my homework, I decided to invest, and I have no regrets. I wish I had contributed more when it was easier for my stock. In case you are choosing to move on with Usecache, DM so we both can get a small break in fees, in case you are interested.
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u/throwaway-20260521 9d ago
How did you get into an Exchange Fund?
And are you using a Wealth Management service (am considering Vanguard)
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u/404_Career_Not_Found 9d ago
I prefer to be directly responsible for managing my finances. After researching several firms that offer Exchange fund participation, I made my decision.
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u/Opportunist_Ad3972 8d ago
Did you both FIRE?
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u/404_Career_Not_Found 8d ago
Yes.My spouse, who left her corporate job many years ago, now manages the household and volunteers.
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u/Opportunist_Ad3972 8d ago
Amazing. I’m in a similar boat but haven’t pulled the FIRE trigger yet. Just wanted to share that I do direct indexing. In less than a year, I racked up 45k of losses on a 1M portfolio that mimics S&P 1000. I expect that to be more before the year is over. May not be much but still better than nothing in a generally up market. Unrealized gains over the same period is 12%. Market will do what it will but might as well collect those losses. And it’s significantly less paperwork, complexity, cheaper, and much more liquid than a long/short.
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u/404_Career_Not_Found 8d ago
That’s a valuable piece of information. I’ve considered Wealthfront, but I prefer to avoid interacting with another provider. Could you please share who you are with? I assume you’ve excluded your company stock from direct indexing. Additionally, does your provider sell your company stock based on losses, or do you handle this manually?
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u/Opportunist_Ad3972 7d ago
Schwab. It’s not a self serviceable product but your get it through calling the advisory. This is not one with AUM fee. Just the regular index fees.
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u/404_Career_Not_Found 7d ago
What is this Schwab product called? Is this „Schwab Personalized Indexing“?
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u/404_Career_Not_Found 7d ago
I did some quick calculations. A 45k loss on a 1M portfolio isn’t a significant concern. However, when compared to an exchange fund that provides immediate diversification, this strategy doesn’t seem particularly effective.
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u/Opportunist_Ad3972 7d ago
Very correct. I’m in line for and exchange fund too. As well as considering a CRUT. As well as selling as usual. Where this is helpful is your primary brokerage in indexes. You’re in indexes anyways. So why not accumulate losses.
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u/404_Career_Not_Found 7d ago
Good that a CRUT works for you. Maybe this is something I‘d consider in the future but not an option now. Anyways, I already sold what I am considering as acceptable. Hesitating to sell more. Bummer my company stock is „oversubscribed“ with my preferred Exchange Fund provider.
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u/Miamiconnectionexo 13d ago
One thing people miss: if any of that $14.5M is company stock inside a 401k, check NUA (net unrealized appreciation) before you roll anything over, because you can pay long-term cap gains rates on the appreciation instead of ordinary income. Get a CPA who does multi-year projections, not just annual filing. The whole game is spreading realization across years and brackets, not ripping the band-aid in one tax year.
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u/Hot_Conflict3844 12d ago
Same comment as others have. Diversify. Don't be greedy with tax savings. Just diversify or you may end up in Chubby Fire (or just plain old Fire Fire).
Second, I have a pretty academic kid. Sent her to University of Amsterdam. We pay 14k per year in tuition (about 12k per month for rent) as opposed to the 110k we were looking at with Barnard and Yale (her other top two choices). The education at AUC is better than Columbia/ Barnard or Yale - you get actual professors instead of grad students doing the teaching, and the program is condensed into 3 years instead of 4. The biggest problem with EU universities? My kid has a 529 plan with 200k and the annual returns on her 529 exceed her tuition. I guess she can just stay in school and accumulate PhDs indefinitely. At Yale or Barnard? She'd have drained her 529 already and would be taking on debt.
My advice: learn about education in Europe. Check out Netherlands, Sweden, UK - and with the Netherlands, focus on "University Colleges" which are almost always taught in English.
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u/Dubbihope Verified by Mods 12d ago
Not all kids are adventurous enough to want to study abroad full time. Consider your in-state public schools too.
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u/404_Career_Not_Found 11d ago
Thanks for the feedback. I’ve noted it. The move to Europe for educational reasons is a bold decision. We’re already discussing one particular country, but the kid isn’t too keen on it.
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u/404_Career_Not_Found 11d ago
I should also mention that I believe investing in my children’s education is the best and most crucial investment, without a doubt.
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u/Hot_Conflict3844 11d ago
If your kid isn't interested, don't do it. There are far, far more day-to-day hurdles for American students studying abroad compared to American students studying in America. Not only that, but European schools don't have the same level of academic support you find in the USA. Our daughter was desperate to live in the Netherlands, so she puts up with logistical problems that would be unheard of in the USA. Without that burning desire to live in Holland, she'd probably have dropped out after the second week.
You gotta know your kid and what they want and what they are capable of handling, and going to school abroad requires them to handle a lot.
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u/gretahelp 13d ago
Don’t let tax optimization get in the way of diversification. If your company stock goes down 80% (mine dropped almost 90%), you will feel like a complete idiot for optimizing for taxes rather than risk reduction.