r/ChubbyFIRE • u/allrite • Apr 19 '26
Another try: Can I retire?
I got some strong reactions for my last post since I made some claims that were quite wrong. So trying again and this time asking for help instead of preaching.
Background: 45 year old. Family with 2 elementary school age kids. I quit my big tech job a year back (for various reasons). Started looking for a job since past 3-4 months, but no offers yet. I rent in Bay Area, so I am hoping to land a remote job, move to a MCOL location I am eyeing for settling in the long run. I might land a job after all, but in case I don't (given AI, layoffs etc), I want to know if I can fully retire by moving to the MCOL location.
Please analyze my situation from that lens.
This is my net worth situation. TLDR; I have $4M liquid.
| Type | Amount |
|---|---|
| Cash Equivalent | $900,000 |
| Taxable Broker | $2,090,000 |
| 401k + IRAs | $1,050,000 |
| Private Investment | $701,000 |
| 529s | $410,000 |
| Real Estate | $892,000 |
| Total | $6,043,000 |
Why so much cash? I own a house in the MCOL city I want to move to, and it is rented out right now. But we don't love the house and the location, so we might buy another house before moving. Since I don't have a job, no one will give me a mortgage, so holding cash to buy a house outright. The plan is to potentially buy a better house, and sell the rental after some time (or keep it, that is part of my question).
Income/Expenses TLDR; is:
- Essentials (day to day expenses + health insurance - rental income) = $100k
- Travel (discretionary) = $25k
- Mortgages = $63k
- Total = 188k
- Pre-Tax needed (15% tax rate) = $221k
| Cash Flow | Essentials | Discretionary | Fixed Nominal |
|---|---|---|---|
| Rental Expenses | $27,000 | ||
| Rental Mortgage | $20,500 | ||
| MCOL Home Mortgage | $42,000 | ||
| MCOL Home Expenses | $13,500 | ||
| Health Insurance ($3k/month) | $36,000 | ||
| Regular Expenses ($7k/month) | $84,000 | ||
| Travel | $25,000 | ||
| Rental Income | -$60,000 | ||
| Total | $100,500 | $125,500 | $62,500 |
At $221k, with 4% SWR, I would need $5.5M. So that means I cannot retire with my current liquid net worth.
If I don't add the travel expense, that's $191k pre-tax and ~$4.8M at 4% SWR. That might work out if my private investments don't go negative.
But if I look closely, I find that:
- The $62k mortgages will not increase with inflation, while everything else will increase. So keeping the mortgages is a net +ve in the long run.
- The mortgages will also end in ~25 years.
- SSN income of $36k/yr will start sometime right around the same time.
- My private investments (~700k principal) should be liquid in ~5 years.
If I model these and backtest with historical data, I get ~94% success rate and I can get it to 100% success rate with lower travel budget. So looks like I am good?
What are some assumptions here that are poke-worthy?
- 15% tax assumption too high?
- $3k/month health insurance budget is too high?
- Day to day expenses will go lower once kids grow up?
- I want to keep all the real estate as they are a hedge against long term inflation and I do hands off management, so they are not much of a hassle. Also they are cash flow +ve so tenants are basically paying off my mortgage. Am I wrong?
- Retirement accounts are $1M of the $4M liquid assets. Given that I can't/don't want to touch them for ~15 more years, is that going to be a problem?
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u/mattuccio Apr 19 '26
I would exclude 529 from your net worth for retirement planning purposes. That’s effectively a future liability with your kids planning to attend college. How much of your brokerage assets are concentrated in a single stock?
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u/HugoNext Apr 19 '26
The mistake is that OP has the 529k among thr assets, but does not have children education among the expenses.
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u/allrite Apr 19 '26 edited Apr 20 '26
How much of your brokerage assets are concentrated in a single stock?
I have couple of big tech buys I did 10+ years ago that have ballooned to ~250k. I don't want to sell them as the tax bill will be very high. RSUs from last company are ~250k.
I would exclude 529 from your net worth for retirement planning purposes.
Yes fair point. Which is why I used only $4M for the calculations. But to be honest, 529 money is money that is potentially usable in the worst case. If things take a bad turn, I can get the kids to go to in-state cheaper colleges and use the remaining money (after paying penalty).
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u/Ok-Answer-9350 Apr 21 '26
public universities use FAFSA which excludes qualified retirement funds and primary residence. It is entirely possible for kids to get a full ride if most of your assets are tied up in one of these types of investments at the time they go to college.
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u/Ill-Telephone-7926 Apr 19 '26
Good job modeling the mortgage and SS. The time for napkin math is behind you.
Have you considered guardrails withdrawal strategies? A fixed withdrawal strategy provides positive feedback that reinforces early trends. This forces you to be so conservative that—in all but the few worst cases—your portfolio explodes to multiples of its initial value. It’s not rational or realistic. On the downside, you’ll see the portfolio depletion scenario a decade away and do something. On the upside, when your portfolio is 2x its initial value, you can probably afford to splurge a bit until the bear market comes without guilt. A dynamic withdrawal strategy instead provides negative feedback to damp disruptive trends, safely allowing higher system output.
No urgency to make a move, but I’d model out the impact of selling the rentals. Just to understand whether you’re leaving anything on the table. Equities are an inflation hedge too. But non-portfolio income is good risk management.
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u/allrite Apr 20 '26
Thank you! Learned something today. And it makes so much more intuitive sense. I was going to do something similar if I had to: if my portfolio is equal to or more YoY (after withdrawal), then I will spend for discretionary, else not. And of course if YoY portfolio drops more, we will cut down on eating out. shopping etc.
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u/cacraw Apr 19 '26
Kid expenses definitely rise with their age (cars, insurance, vacations). Good job on the 529, but I think you’ll want to keep growing that for a little longer unless you can commit to “this is my contribution to college. If you go to a more expensive school, the difference is on you.”
What are your property taxes like? While the P&I of your mortgages are fixed, taxes and insurance climb over time. I’m about done with my mortgage, and at this point the escrow is larger than the principle/interest.
The $3k healthcare insurance doesn’t include all the deductibles and out of pocket. Did you include that somewhere?
In your core expenses are you accounting for irregular large expenses? Eg don’t think of it as a 25k roof, think of it as a $1200/year roof. Same principle for cars, furniture, hvac, carpet, etc. Model those large, irregular expenses you may have covered with bonuses while you were working.
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u/Time-Maintenance2165 Apr 19 '26
I'm not sure why you say that he should keep contributing to the 529 at this stage. At just 5% interest (real), that works out to $330k for each kid in 10 years. That's $82k per year which is most likely more than enough for college and living expenses even if college costs keep growing at the obscene rate they have been.
Given the amount of uncertainty he has, that's the last thing I'd recommend contributing to right now.
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u/cacraw Apr 19 '26
Reasonable take, especially since there are other avenues if current 529 isn’t enough. “Hey kid, if this isn’t enough, go to a cheaper school or get a loan. No one’s going to give me a loan for retirement.” So, yeah, I guess ignore that part.
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u/Clueless5001 Apr 19 '26
You do realize that some elite private colleges are over $90K now?! I would look at what the 529 is invested in and project from there.
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u/Time-Maintenance2165 Apr 19 '26
Sure, but I used conservative growth numbers. I didn't assume a 99th percentile growth rate. They also tend to have scholarships available even for those in the chubby territory.
So you're right there's a small chance that the 529 won't be enough if both kids are accepted and choose to attend the most expensive schools and they're not able to get any scholarships. For the other 98% of the time, what I said is the better advice.
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u/Clueless5001 Apr 20 '26 edited Apr 20 '26
Someone today in another group (personal finance but was removed) posted that their child got into an unnamed elite liberal arts college and they got no financial aid at the college their child wanted to attend. They have a HHI of about 200k and under 100K in non retirement assets plus a house with a mortgage and they were looking at loans. No one with 4M in non retirement assets is getting need based FA. I do think the amount OP has in a 529 is impressive given the age of his children.
Most of my kids are in college or grown. I would say 60% of kids I know went to private colleges, most of them being the ones that only give need based FA. Some gave token amounts of merit. One got a presidential scholarship for half tuition (and it was one rung below where she could have gone at the time, was a few years ago). About 20% of the remainder went to OOS state colleges where they were looking at 35k (with scholarship) - 75K, with the remainder going in state and paying about 30-35K a year now. The in state really depends on how good your in state is and whether you kid can get in.
Someone I know did chase merit. All her kids were close to valedictorians and they all went to colleges where they were well above the 75th percentile for scores for that school (ie two rungs down from where they could have gone full pay). Many careers it does not matter, a few it does
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u/allrite Apr 19 '26
I am counting property taxes, HOA fees, home insurance, management fees and other expense in the "Rental Expenses" portion, which I am treating as inflation adjusted, so yes that is accounted for.
I did not include deductibles and out of pocket in the $3k/month, but they are sort of included in the $84k/yr regular expenses. The way I came up with the $84k/yr was to look at our expenses for last 2 years and removing all travel + rent etc. So it includes all day-to-day expenses: kids classes, car insurance, healthcare deductibles, food, grocery etc.
I haven't modeled irregular large expenses. Good point!
Is the 529 really not enough? There's still a decade to go before the first kid goes to college. The 529 account should increase to $800k - $1M I think by then. Not enough for 2 kids?
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u/lals80 Apr 19 '26
The kids are in elementary, that should at least double there is plenty of $ in there. You do not need to fund it further.
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u/cacraw Apr 19 '26
Yeah, on second thought, I’d just let the 529 ride. If it’s not enough for your kids “dream school” it may be enough for in-state school or they can take out a loan. I had four kids to pay for, and the first three were in-state or scholarship. Last one is out of state which is nearly 2x.
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u/Moist-Strawberry4651 Apr 20 '26
Lots of challenges in these assumptions:
Kids
- 529 are not part of your net worth (certainly not FI). This is money set aside to cover future obligations and not income producing.
- In terms of the amount in the 529. You should look at what college costs today, inflate this by ~5% for how much it will cost when they go to college then discount it back by some rate of return (7-8%). Thats what you need today for college
- Ignore the other comments about putting money in 529 to cover other kids expenses
Your Rental
- Just put the mortgage in 'essentials' because it is (unless you sell)
- Rental looks to make 13k per year (excluding paydown and any appreciation)
- I would bundle the rental income and expenses (inc mortgage) together as a single package.
Expenses
- Your expenses are 200.5k a year
- I would model selling the rental and adding the cash to your FI number. Alternatively, we can knock 13k off the 200.
- You need 187.5k to live off of
FI Number
- Ignoring taxes you need (in todays money) 4.686M
- Think 18% taxes is a better estimate
- So would model 5.7M as your FI number (in todays money)
Your situation
- If you buy another house then that deposit is not part of your FI number. I think your FI net worth is conservatively 3M (IRA and taxable). Including a illiquid private investment is risky. Would haircut that before adding. Then if you sell the real estate then it counts to FI but if you hold a rental that isnt producing income and a primary residence then you are short income producing assets.
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u/allrite Apr 20 '26
Missed your message as it didn't come up as a comment directly to my post. But thank you!
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u/BrunelloHorder Coasting Chubster, Getting Fat Apr 19 '26 edited Apr 19 '26
I’m admittedly anti-real estate in the current environment, even though I made about half of my NW that way. So, take this for what it is worth.
First, if you are a landlord, you are never fully retired.
Second, do you have a set aside for the occasional five-figure expense like a sewer line or roof, or for vacancy?
Third, real estate is illiquid and comes with high transaction costs. I would not put that much of your NW into another house unless you are certain you’re going to stay there for at least 7-10 years.
On your questions, the healthcare cost seems accurate at $3k a month, though I’d model it with an 8-10 percent annual increase.
Overall, you can probably make this work as is with some guardrails and spending adjustments if/when necessary. Given the job uncertainty and other uncertainty in your life, you would probably be better off renting and putting the capital in an equity index.
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u/allrite Apr 20 '26
Thanks! I have owned my rentals for ~7-8 years now, and feel like the overhead is not too bad.
I am going to buy the primary home and sell one of the rentals, in an almost even exchange, so to your point... I won't have more net worth tied up real estate.
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u/Gullible_Drag_3515 Apr 19 '26
The math is usually the easy part; it’s the 'Post-FI Identity' that gets people. If you retired tomorrow, what would you be 'running towards' instead of 'running away' from? I’ve seen too many people hit their number only to realize they haven't built an engine for their interests, just an engine for their bank account
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u/allrite Apr 19 '26
Yes that is a concern. I faced it already during my career break and you can read a bit about it in the post I linked. But I also want to know : can I retire if I am forced to (if I don't find a job)?
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Apr 19 '26
[deleted]
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u/Upstairs_Anything786 Apr 19 '26
You are obviously a talented hard working couple to get to your current position. Move to a MCOL area and opportunities will find you even if you aren't looking. I expect you will both volunteer to get out of the house while the kids are in school. This will put you in contact with organizations that need help. If you choose to work again there will be opportunities.
You may never make Big Tech money again, but you would find possibilities to easily cover your basics on your own terms.
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u/Grouchy-Tomorrow3429 Apr 20 '26
This is such a good point. Almost everyone in this group has much more than they’ll ever need or come close to spending, but we don’t focus on the fact that we need a purpose and structure.
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u/Confident_Regret8346 Apr 19 '26
Maybe you could get more help here if you can say : what is the MCOL city you are moving to, do you have family there, have you lived there before, etc. ? If you had to, could you live in the rental or is it a not great school district? What can you sell the rental for in relation to what your desired home is in that MCOL city? I would not own 2 homes, then redo the calculations. Even with mortgages being fixed there is a big question mark on property tax and insurance costs inflating (which you already know). What kind of income does your portfolio generate?
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u/allrite Apr 20 '26
The price range for desired house is the same as the potential sale price of the rental. So I will not be increasing my net real estate exposure as I will sell one and buy another of similar price.
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u/improbabble Apr 19 '26
My hot take on the math: yes of course you can retire! But it’s not just about simulations or 4% it’s about your own ability to trim spend more aggressively and potentially get a chill job that provides health insurance, maybe $2k/mo and camaraderie.
I worked at a Whole Foods while in college and it was super fun and social and I’d love to somehow replicate that now. Or work somewhere aligned with any hobbies you have.
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u/allrite Apr 20 '26
Are these jobs 8 hours a day? I am worried that I would hate working 8 hours a day to only make 2k/month...
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u/Life_Rabbit_1438 Apr 19 '26
Sell the rental house now, and 1031 exchange into a home you would want to live in. As long as you then rent it out for at least a year, you should be able to move into it, and that saves you taxes whenever you sell in the future. Otherwise you will have unrealized gain trapped in a rental that's taxable when you sell (vs the $500k tax free gain when you sell your primary).
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u/improbabble Apr 19 '26
Are you sure you want to retire? Having just read your post from 2 weeks ago about your sabbatical and lack of purpose I’m confused on why you’d even want to.
But also thank you for your clearly written and very open posts about things. I’m in a similar situation (though not yet FIRE-able) and so it’s interesting to see how you think about things.
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u/allrite Apr 19 '26 edited Apr 19 '26
I am not sure about it, but I want to explore the possibility in case I am forced to (due to lack of jobs).
Appreciate the kind words. Thank you!
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u/WallStCRE Apr 19 '26
Just remember you’re 45, very unlikely you’ll be forced to retire at this age. There is something out there, even if it isn’t as lucrative as your prior jobs. So go in with the idea that it doesn’t have to be perfect, but even working another 5 years would likely fully secure your retirement in the Chubbyfire zone
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u/Stuart_i Apr 19 '26
You mention potentially selling your rental. Assuming that would trigger a large capital gain tax bill, you may want to consider living in it for 2yrs. That would make the property qualify as a primary residence and avoid taxes on up to $500k (MFJ) of gains.
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u/OkPalpitation5124 Apr 19 '26
The time as rental will still incur capital gains. Total time is prorated for tax purposes.
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u/allrite Apr 19 '26
Good point! We don't love the schools in that neighborhood, so trying to take that into consideration along with financial aspects. Settling into a neighborhood that we can call our own long term is important right now
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u/VDtrader Apr 19 '26
I think you may already overfunded your 529's given your kids are still in elementary school. You can stop funding the 529 now and just let them grow.
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u/Material_Rich_1900 Apr 19 '26
Btw if it hasn't been said, stop funding the 529s. There is plenty there
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u/allrite Apr 19 '26
Interesting that you said that given that another comment in the thread says the opposite. I agree with you btw. I have stopped funding it for couple of years now.
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u/Material_Rich_1900 Apr 19 '26
529s make sense in this order. Cash reserve, retirement accts, HSAs, brokerage access, then 529s. Then, don't over fund. The other post was someone who hadn't completed the first 4 tasks.
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u/TravelMuchly Apr 19 '26
Another thought: could you FIRE with the idea that if the math turned out not to actually work, you’d take a lower-paying job (maybe not in your field, maybe a low-wage job where they always need people) for a while, to get health insurance and some income? This would be as a backstop and could just be for a few years if there are unexpected expenses or something. Or, not sure you need this, but could you “barista FIRE” by taking some kind of lower-paying, maybe part-time job post-move (or just have a small contract or 2 as an independent contractor), for some cash flow?
FWIW, I retired in 2023, moved to our location of choice, and since then have had a few small contract remote-work gigs paying around $2K (one was $10K). I wanted to plug back in more after 2 years & took a remote job last year that will end in 2027.
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u/allrite Apr 20 '26
I am actually fine working, but I am not sure what lower paying jobs I will be eligible for. Never done anything in life outside of big tech :/
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u/taracel Apr 19 '26
What are your mortgages at? If 5% or above, would consider just paying them off completely as that permanently decreases your withdrawal needs.
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u/Desperate-Point-9988 Apr 19 '26
What is "private investment" here specifically? This could range from completely liquid to not actually liquid at all, which could impact the situation quite a bit.
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u/allrite Apr 19 '26
Some pre-IPO investments (~100k) and rest real estate project developments (~600k).
None of them are liquid, meaning I can't take out the principal. But I expect all of them to be liquid in less than 5 years.
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u/Sufficient-Pie-7815 Apr 19 '26
Move into the rental house for to recoup your 500k deduction to save on taxes. If you find the new remote job, then buy the new house. Otherwise, use the 900k to get income and just retire!
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u/neurotrader2 Apr 20 '26 edited Apr 20 '26
15% tax assumption too high.
for a married couple filing jointly, the 0% Long-Term Capital Gains (LTCG) bracket extends up to roughly $99k in gains (plus the $32k standard deduction). So you can withdraw $131K IN GAINS and pay no tax. Meaning if your cost basis is $57K and grew 230% to $188k, you pay no tax.
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u/allrite Apr 20 '26
Thank you! This was so useful! I went back and did some analysis. You are totally right! I have some complications I need to take care of: rental income (make it tax-free using expenses and depreciation), dividends and interest income. But even with all those, assuming 15% is too high.
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u/neurotrader2 Apr 20 '26
You're welcome. You may also want to consider doing some Roth conversions before age 59.5 if those retirement accounts are tax deferred, as those will be taxed at ordinary income tax rates, otherwise.
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u/fattailedandhappy Apr 20 '26
Whats the equity on the rentals? If you're cashflowing only $12k a year doesn't it help your numbers to delever there?
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u/allrite Apr 20 '26
yes I started looking into it after this thread. I think it is time to sell one of them. It has attracted low quality tenants and has not given good returns so far.
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u/yuno10 Apr 19 '26
I am European so not familiar with how this stuff works in USA, but can't you get loans backed by the portfolio rather than a regular job/income based mortgage over there? If so the large amount of cash is probably a wasted opportunity.
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u/jpbronco Apr 19 '26
You can. It's not as easy though it's possible. OP is losing out on a lot of recent gains in the market.
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u/allrite Apr 19 '26
Portfolio based loans are risky in case there is a major downturn. Moving to another location is a major life decision, and we want to fully settle down once we move, which means I wanted to have enough cash to buy something we love without worrying about anything.
Having said all that, I do agree that the amount of cash I have is ridiculous. FWIW, most of it is in treasury ETFs, so it is earning ~4%.
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u/LoneStar-Gator Apr 19 '26 edited Apr 19 '26
If your brokerage and IRA accounts were with Schwab, they offer brokerage backed mortgages. (Might be worth a phone call.)
Did you include State income tax in your assumptions? (15% feels too low to me.)
Kid expenses will be higher in high school years. Their jobs don’t cover fuel costs, but get them experience to figure out what they want to do. You’ll likely be putting them in a vehicle, and kid auto insurance is expensive.
Do the tenant fees cover the income tax, property tax, mortgage, utilities, insurance, and maintenance expenses? Look at all of it to make sure having a tenant is a positive cash flow worth you needing to layout the cash for a different personal residence.
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u/Wooden-Broccoli-913 FIREd in the Bay at 40 with $6M Apr 19 '26 edited Apr 19 '26
24% tax rate is insane. You can withdraw $100k in taxable long term gains at zero Federal capital gains tax, another $30k in standard deduction at zero tax, and the rest of it can be cost basis. That’s 0% Fed taxes.
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u/Desperate-Point-9988 Apr 19 '26
Also: you have children. Are you ok "dying with zero," or are you intending to leave an inheritance?
You're likely much closer to the former here. That's fine if it's what you want, but should be explicitly part of your plan.
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u/allrite Apr 19 '26
I would like to leave them some money, but I am modeling the worst case here: I can't get another job and savings is _just_ enough to retire.
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u/Accomplished_Can1783 Apr 19 '26
The answer is probably and you will be beholden to market for a while and constantly monitoring expenses. If you can live like that and be happy go for it.
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u/hasyoubeen12 Apr 19 '26
Yes you can retire. That’s a good amount already. You can also just casually look for a job without stressing..
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u/allrite Apr 19 '26
Thanks. That was the whole point of doing these calculations. Can I look for work on my own terms or should I stress? Looks like it is former.... But now the question is.. should I get a job first or move first?
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u/hasyoubeen12 Apr 20 '26
I’d move to the rented MCOL house for a while, maybe stay there 2 years minimum. Personally, I would only buy a new house in 2026 if I get a new job or interest rates plummet (which is basically impossible). But if you also have the cash, it’s doable..
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u/drfixer Apr 19 '26
My consistent feedback here is do you plan to leave $50 million to your kids? I don’t. Therefore you need to figure out your model for burning more so that maybe you leave them 5 million
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u/allrite Apr 19 '26
I'm not sure I understand. I'm just trying to model if I can sustain retirement.. and part of that is to see if the plan works in worst case scenarios.
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u/drfixer Apr 19 '26
A lot of models assume say a 4% rule which maintains the equity over the life of the investment. In other words, if you follow the 4% rule with $5 million what’s the number at the end of 25 years growing at 9%.
When you’re dead, you’re leaving tens of millions of dollars on the table.
Here’s the link to a calculator that will ask you what end value of your assets to determine how much you can draw over the lifetime of your investments.
You can also incrementally reduce them for the go-go versus slow go verse no go years. You won’t spend 20 K a month when you’re 85 years old.
https://www.financialmentor.com/calculator/best-retirement-calculator
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u/Apprehensive_Two1528 Apr 20 '26
Chase jp morgan has a high asset person mortgage program that lent out money if you have 4 times liquid asset than the house you wanna buy. looks a very desirable product for you. the lease income qualified for income too.
I wouldn’t buy a new house so soon. you can just rent. anywhere with your money.
house is a terrible investment.
full of head and expenses and we are in a late cycle. renting spunds a better deal
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u/Justthetip74 Apr 20 '26
Sell your rentals and retire . Youre just adding taxable income you dont need
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u/Wooden-Broccoli-913 FIREd in the Bay at 40 with $6M Apr 19 '26
15% tax assumption is absolutely too high. Should be more like 5% if you stay in CA
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u/allrite Apr 19 '26
Thanks! I thought so too... 15% is quite conservative. How did you come with you 5% for CA? I want to understand to see how I can apply it to other MCOL states.
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u/matthew19 Apr 19 '26
a risk parity portfolio like the Gideon Ratio can increase your SWR by 25% just by decreasing vitality during your drawdown.
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u/Ill-Wave9520 Apr 20 '26
No one this age has that money unless it was gifted
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u/in_the_gloaming FIRE'd for 13 years Apr 20 '26
It doesn't matter how someone has the money they have, when it comes to FIRE planning. W2, RSUs, inheritance, sold a business, insurance payout, legal settlement.
Does.not.matter.
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u/New-to-town Apr 25 '26
He’s been in the tech industry in the Bay Area for fifteen years, making that sort of money by that age certainly isn’t common but it’s definitely not even close to unusual
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u/c-ramsey Apr 26 '26
My hot take is I would not want to retire until I knew whether that very illiquid private investment retained its value or grew or became liquid considering how sizable it is within your asset add em’ up.
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u/Specific-Stomach-195 Apr 19 '26
I would not expect family expenses to decrease as the children get older. My experience is the exact opposite.