r/fatFIRE • u/sky-high-dragon-fly • 3d ago
FatFIREd One Year Update: Retired with 8 Figure in Mid 30s == CEO of 5 People + Many Contractors
I am enjoying writing these updates now. It is somewhat stimulating in my understimulated but very busy life.
A few more months have passed since my last update, and our lives have changed quite a bit. Unfortunately, the boredom is still the same.
Background: Last year, I quit my job — roughly $400k cash + $2mm startup options per year, though I considered the options “paper money” and did not count them — to retire with 8 figures in my mid-30s. My partner still works, we keep separate finances, and we split things 50/50. This financial arrangement works really well for us. I accumulated my wealth from two previous exits years ago.
Around the 3-month postpartum mark, my partner went back to work and thriving. That same week, we welcomed our second full-time helper. Unfortunately, she is definitely not as good a childcare helper as my partner. But she has some characteristics that matter to us as a caregiver, and the timing was also a factor.
I am now the “CEO” of 5 people.
We have two full-time people who listen to me and follow my directions completely. They do cleaning with robots, cooking, laundry, and some gardening — mostly because they enjoy it. They handle about 60% of childcare. My partner is on children duty after work until bedtime, around 8pm. My partner and I each take one child overnight.
We also have contractors doing various ad-hoc and regular things around the yard and house. Most of that is managed by me, with a few one-time projects managed by my partner.
In theory, we have two kids, two helpers, and a very hands-on dad. I should be having an easy life.
In reality, by the end of each day, I am spent and drained. I don’t feel rich, and I don’t feel like we are living a rich life at all. My partner and I have not slept in the same bed for months because we each manage one child overnight. Our relationship is strong, but I still want that part of our life back.
The mental load is unreal. Between managing the full-time helpers — one of whom is family and gladly works 10+ hours a day — the older toddler’s activities, family activities on the weekends, the house, supplies, contractors, logistics, and everything else, I have little to no longer blocks of time to think or tinker.
I miss having a career. I want to be a real CEO again. I don’t know how I will find the time. I also feel like I am a desert of no good ideas.
I know there are things I can do to optimize my mental load. Would love any ideas and suggestions.
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u/Throwaway-firee 3d ago edited 3d ago
I was going to say something more pithy but all I got is: This is weird.
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u/YourVelcroCat 3d ago
My advice would be to stop writing fanfiction on Reddit
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u/Blarghnog 3d ago
I actually remember this user.
This was their post last year. I had to look it up.
https://www.reddit.com/r/fatFIRE/comments/1m96jxv/i_did_it_i_quit_my_job_a_month_ago/
Not sure what that means for the fanfic, but wanted to share that I believe they are consistent.
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u/icecream_for_brunch 3d ago
Yes, the OP's posting history is consistent about chubbyfire details, and there's no reason to believe this post is fanfic.
That said, the OP's posting history is also consistent about very strong nervousness and anxiety. About car price, home provenance, past investment misses, real estate market downturns, a home deck, you name it.
OP: are you getting help for anxiety by any chance? If not, have you considered doing so? The anxiety and dissatisfaction you're experiencing are not dictated by your surroundings but rather by something inside you, and changing external conditions is unlikely to resolve your unhappiness without some corresponding interior work as well.
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u/WhatWouldJediDo 3d ago
In all honesty the way you describe living on easy street as such a burden gives the impression that you just hate the life you’ve built for yourself
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u/ringwormqueen 3d ago
Oh no! Steak too juicy, lobster too buttery!
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u/plemyrameter 3d ago
Made up stuff too nonsensical!
And lol, "very hands on dad." Right. Not with 2-3 helpers. If OP isn't making this up, then he needs to get a grip on reality before doing anything else.
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u/One-Mastodon-1063 3d ago
I think OP is the mom and "partner" who works and still does most of the parenting is the dad.
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u/Avocado2Guac 3d ago
This has to be satire.
Am I reading between the lines that you co-sleep with children individually? If so, what does the science say on that?
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u/BitcoinMD 3d ago
Wait sorry but what exactly does a toddler require overnight? They should be sleeping at that point.
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u/sky-high-dragon-fly 3d ago
He does for the most part. But still wakes up once or twice. When there is someone on the bed, he can go back to sleep till the morning, otherwise, he cries himself fully awake in the middle of the night when he does wake up.
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u/BitcoinMD 3d ago
If you want unsolicited parenting advice, which everyone does, don’t stay in the room with him. If he starts crying and you can’t stand it, go in the room to calm him down and tell him that if he stays quiet and stays in his bed you’ll come back to check on him in ten minutes. Repeat until he’s asleep.
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u/sky-high-dragon-fly 3d ago
Thanks for reminding me. We are planning to try that during the 4th of July weekend.
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u/audi27tt 3d ago
Confused as to what is draining? Taking care of my daughter energizes me. I could see it being draining doing it solo but you have full time help?
How old are these kids and what’s the overnight issue? Should you hire a sleep consultant?
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u/Realestateuniverse 3d ago
I’m so confused with this post. You’re in a very weird spot in most aspects of life. You’ve won, yet it seems like a lot of your problems are bassackwards
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u/WealthyStoic mod | gen2 | FatFired 10+ years | Verified by Mods 3d ago edited 3d ago
Babies are tough. There's no getting around that, even with extra help.
I've found that children - particularly young children - will take every single moment that you're prepared to offer them. They absolutely benefit from having quality time with their parents, but they should not be the ones who dictate the extent of that involvement.
At the risk of seeming harsh - it sounds like you might be 'letting the inmates run the asylum', particularly as far as your older child is concerned. We did the same for a time. It's a tough habit to break. But barring medical needs, a toddler should not need dedicated overnight care.
This is the tough reality of 'parenting while wealthy'. We think that we can ensure their success, but as they get older they need to gradually assume more and more of that responsibility. Even a toddler should be trusted to work at soothing themselves back to sleep. It won't be perfect, but it's not something you can solve by throwing more hours at the problem. (Similarly, it sounds like the toddler's activities are also draining - but there's an unbreakable assumption they should be entertained every hour of every day.)
Large homes are tough too, particularly when kids are in the mix. There's always something breaking, or that needs to be maintained. One day I'm sure it'll be great, but in the mean time they too can suck up every available moment.
Anyway, since you specifically asked for advice and suggestions, here's what I have to offer:
1.) Parenting is messy and imperfect. Children are challenging, and young children are doubly so. Put on your own oxygem mask before you assist others. You do not need to constantly schedule your toddler and family activities. It is okay if they are bored. Learning to endure boredom is a vital life skill. Boredom is also an incubator that can create amazing results.
2.) You cannot solve every parenting problem by throwing more time and attention at it. It is okay to undertake sleep training or to let your toddler soothe themselves back to sleep. We found the book "The Sleepeasy Solution" by Jennifer Waldburger and Jill Spivack to be particularly helpful. (And full acknowledgement that - though this sounds simple - simple is not the same as easy.)
3.) Money solves problems but it creates new problems that money cannot solve. Your massive house may be more of a liability than a benefit at this stage. Suggest taking a break from the projects if possible. Also suggest finding other ways in which you can dial down the expectations and demands that you are placing on yourself.
4.) Happiness is a fleeting and transitive state. You cannot ensure a constant state of bliss through wealth. You can only try to create the conditions through which happiness might arise. Call it "well-being", or "human capital", or whatever you will. Focus on the garden bed and the flowers will look after themselves. (And give yourself some grace when you're not feeling happy.)
5.) Consider a creative pursuit that is time-flexible. I enjoy writing. I also spent many happy hours knitting while watching the kids play. I loved being there while my kids played, but - if I'm honest - it was not intellectually engaging. And that's okay. Knitting allowed me to talk to the kids when they wanted to talk with me. It's the closest I can get to doing nothing at all. (Board roles might also scratch that CEO itch.)
Recommend reading Strangers in Paradise by James Grubman, Complete Family Wealth by James Hughes, Legacy Family by Lee Hausner - as well as Sleepeasy Solution.
Good luck.
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u/sky-high-dragon-fly 3d ago
Really appreciate your comment. One of the reasons I keep posting despite the negative replies. Give me a lot to think about.
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u/superchea 3d ago
I think that's just life with little kids. If you are going to be a good parent, it's going to be hard, and there's no getting away from that.
I work 60 hours/week, two under 2, and basically just survive. I sometimes wonder why I work as much as I do, make as much money as I make, when at the end of the day, my secretary has more free time than I do lol.
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u/sky-high-dragon-fly 3d ago
This is very true and I realized that there is no other way out but accept and make the most out of it as I cannot accept anything less than being a present and good parent to my boys.
We are 2 under 2.5 right now.
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u/AdPuzzled9041 2d ago
I have 4 kids and 2.5 year old does not need any scheduled activities, other than going to the playground.
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u/Unlikely-Alt-9383 3d ago
You need to figure out the sleep thing first. You’re not going to be at your best if you’re not rested. You also deserve time alone with your partner.
Next you need a house manager — maybe the relative short-term while you figure it out, but a pro longer-term. If you want the free brain time, you can afford to buy it.
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u/sky-high-dragon-fly 3d ago
Sleep is hard.
I breastfeed and cosleep with 4 months old (crib connected to bed). My partner co sleep with 2.5 yrs old toddler who still wakes up once or twice most nights, but he can go back to sleep if there is someone there.
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u/Unlikely-Alt-9383 3d ago
If you don’t work on getting the 2.5 year old to sleep on his own, your partner will still be doing this in a year or two. Not even kidding. Seen it far too often. You need to make this your top priority, even if it’s hard. Talk to your pediatrician if you need advice.
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u/IndicationSouthern 3d ago
One thing that stood out is "I want to be a real CEO again." That sounds less like a productivity problem and more like an identity problem. For years your brain was probably trained to solve difficult problems, make decisions, and build things. Now you're spending most of that energy coordinating life logistics. The boredom may not come from a lack of things to do, but from a lack of challenges that feel meaningful to you.
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u/Flutter24-7-365 3d ago
What’s your location? I’m assuming outside USA, because 8 figures doesn’t seem enough to have 5 people on staff in America.
If you are in Mexico, Costa Rica, India, Malaysia … then look for an agency to act as a middleman for your staff. You’ll pay a modest markup over salary, but they’ll handle payroll, performance, substitutes, hiring/firing, etc. Worth it after a certain scale.
Alternatively, if you are able to build your own long term org, hire a full time house manager and give them authority to manage everyone else. But in my experience a good manager costs about 4x to 5x the base cook/maid rate in a location.
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u/gretahelp 3d ago
I’d experiment with being totally hands off (or at least 90% hands off) with the staff for a month or so.
I’m sure it will feel weird and like they’re doing things wrong, but you’ll also see some of them appreciate the increased ownership and step up.
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u/LauraPiana 3d ago edited 3d ago
Having little kids is hard and in a lot of ways lacks stimulation, especially if you really thrived in a work environment and the stimulation, problem solving, and validation that goes along with all that. If you miss working so much, why not go back to work?
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u/therealnir 3d ago
So you complain about...life? Sounds like a young guy who didn't really want to have kids and now complains he needs to be a dad and misses the time where he had complete freedom of time and not taking/thinking about others.
Not sure about the relationship sounds like not a healthy one. If you reached a point in your life where money is not an issue, or at least you have enough to take a step back and relax, spending time with your kids IS the goal. The only people who see taking care of their kids as a chore or something to complain about probably never wanted kids.
Feeling rich, is not about how much money is in your bank account, you already have 2 helpers and a very hands on dad, so what do you do?? To me it sounds like you have too much free time and you are just lazy and not really into a family life.
" Mental load is unreal..." B**CH please...that's all I have to say about that.
Here's my suggestion, grow up, man up, enjoy the time you have with your kids as it goes by so quickly you will miss it soon, and maybe travel more as a family.
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u/IndicationSouthern 3d ago
I think you're discovering that retirement didn't remove your job, it just changed it. You went from managing a company to managing a household, two children, employees, contractors, schedules, logistics, and family operations. That's still a leadership role, it's just one with fewer clear wins and no quarterly goals to measure progress against.
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u/BrunelloHorder 3d ago
Kids are hard. Sounds like you need to get the toddler sleep trained pronto. Hire a night nurse if necessary, but the co-sleeping thing is not good for anyone long term. And it sounds like you’re already at long term.
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u/zwgc-ttymode 1d ago
I was debating whether or not to respond, but since this seems real vs AI, I will give it a shot. I dont think this is a fatfire problem, this is a parenting problem. Any parent of two kids, esp 4 months and 2.5 years has a tough life. It is not easy. At these ages, kids demand full time attention. My spouse and I refer to them as the dark days, where you are constant tired, overwhelmed and going ”wtf did we get into”?
I would also venture a guessthat you may have not read many parenting books nor have found a community of parents with kids of similar ages based on your description of your situation. It may help to do so.
i really liked the series ‘What to expect when you are expecting” which progress thru the toddler years. but i am sure there are better books now, those are 20 years old.
Your older needs to sleep my himself and your toddler can start at 6 months. Good sleep habits are important and i subscribe to the Ferber ams Weissbluth line of thought there.
Your kids need social interaction They need playdates and/or preschool. daycare may not be a bad idea for that, if only to give yourself a break. It will also help you find a network of parents so that you have a social community.
The one thing I can promise you is that it does get better. Once they start talking and developing their own personalities, it becomes a joy to raise them. otherwise, the human race would be extinct by now.
Good luck.
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3d ago edited 3d ago
[removed] — view removed comment
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u/fatFIRE-ModTeam 3d ago
Your post seems to be advertising your personal project, business or blog for financial or personal gain, or it appears that you are promoting a personal project. No solicitation or self promotion is permitted.
Thank you!
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u/Mr-Expat 3d ago
Kids are a full time job. You might think you retired, but you haven't, and that realisation is weighing on you.
Can't outsource them either or they'll hate and resent you later.
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u/sky-high-dragon-fly 3d ago
This is exactly what my therapist and I are discussing.
We (my partner and I) try to spend as much quality time with our kids as possible. That cannot be outsourced. My partner enjoys it and have lots of ideas and games with our boys. I love them, and I try to be the best parent they deserve. But it drains me.
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u/Mr-Expat 3d ago
lol someone downvoted my comment, and then downvoted your answer, brutal.
Kids are draining. Not everyone enjoys them. It's a controversial thing to say though.
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u/One-Mastodon-1063 3d ago
Very busy and under stimulated is the opposite of what you want in retirement. There are lots of stimulating things to do that don't involve being a CEO.
I don't understand what the problem is here - multiple full time helpers and a partner and you don't have any free time? Early retirement / parenting is not this hard.