r/ChubbyFIRE

We are in our early 50s, living in VHCOL place. We have about $10.5mil liquid assets ($197K Roth, $2.98mil in 401(k)/IRA, $7.5 mil in brokerage), we own ~$1mil home with no mortgage.

HHI is ~$450k.

We are thinking about retiring in few years. We need about $180k to live on.

Biggest concern for us is health insurance. Unsubsidized ACA costs $30k just in premiums for a couple in mid 50s plus $15k+ deductible. We have some health issues so we will eat through this deductible. So we are looking at $40k+ healthcare cost which is a effectively a huge tax on us.

We wonder if we can use some sort of liquid assets backed loan given we have substantial liquid assets to cover our living expenses at least partially to bring our MAGI to 0 and qualify for ACA subsidies and cost sharing for deductibles. Home equity won't work for us since we will need renewable loan for over a decade until Medicare at age of 65. We will also be stuck on our current home if w decide to relocate.

Has anyone done this? Any other possible solution for bring health insurance to a reasonable value?

How many of us have held back on RE because of uncertainty around healthcare? I’m single (50M) with $4.5mil in investable assets ($1 mil in pretax retirement, $400k in Roth, and the rest in taxable brokerage). My home is paid off and I’ll be able to begin taking a $55k/year pension in five years. I also have about $20k/year in rental income. Factoring in taxes and ACA, my annual spend as an individual will be safely under $140,000/year.

The subject of healthcare is the one thing that prevents me from going full FIRE because I’m clinging onto the dream of one day meeting somebody and having a family. If I can hold out and continue to work for five more years, my employer will provide “lifetime” health benefits for myself and my future (albeit, non-existent) family. No need for ACA ever. ChatGPT tells me these benefits are worth $700,000 to $1.5 million in premiums/bills avoided. Curious if anybody else has struggled with something like this and how you approached your decision making. Thanks!

Can I retire at 47?
Married (both 46) with 2 kids (11, 15)
Combined income $260k
Retirement accounts total ($2.7 million, out of which 1.3 mil is roth)
Brokerage $600k
Cash $400k
529 $500k
Mortgage $40k left at 2.65% (Home worth $700k)
One pension at $55k at 55
SS $3500 each at 67

Expenses around $12k per month (incl mortgage)

I am tired of my soul sucking corporate job and want to quit at the earliest and pursue my hobbies and passion(probably go to $20-30k per year). Wife (260k income) plans to work till 55. She has health coverage for the family.

I thought I should share my experience using Daffy for my DAF charitable donations. I am in no way affiliated with Daffy, other than as a user for the past 3 years.

Quick review of DAFs for anyone new to the concept:
•If you regularly donate to charity but do not have enough deductions to itemize, you are not receiving much of a tax benefit. Recent legislation does give a new $1,000 ($2k married) deduction for cash donations even if you take standard deduction. However, it is capped and does not allow for the donation of appreciated assets (investments).

•By bunching a number of years of charitable donations into one year with a DAF, the tax savings can be significant …particularly in a year with a high income event like a Roth conversion.

•Donating highly appreciated stock has a double tax benefit of the deduction for the charitable donation + avoiding capital gains on the donated stock. Many charities are not setup to accept stock directly, so a DAF can help facilitate this.

•The deduction for non-cash donations to a DAF is capped at 30% of MAGI (60% for cash donations).

•Once you put funds into a DAF you make “distribution recommendations” to the administrator for qualified charities. But you no longer own the funds - there is no way to claw back the donation to your personal assets. Technically you “lose control” but in practice the administrators seem to follow your recommended distributions as long as the charitable organization is legitimate. (If they didn’t, there would be outrage in the DAF community as illustrated by a couple of edge case incidents with other DAF providers.)

Criticisms of DAFs:
•High administrative fees. Often 0.5% to 1% of the fund annually. However, Daffy largely solves this with a VERY modest fee schedule.

•Many in the charitable community criticize the fact that a large pool of funds earmarked for charity is sitting on the sidelines in DAFs. While I would encourage anyone to get contributions distributed to their preferred charities, I do not necessarily see large DAF balances as an issue. I am personally prefunding my planned charitable giving for a number of years. (If the funds weren’t in my DAF, they would be in my brokerage account instead.) If anything, the additional tax benefits of a DAF make me more charitably inclined.

My experience:
•Three years ago I decided to test Daffy with a $30k contribution.

•My preferred charity was not on “the list” but since they are a 501(c)(3) charity, Daffy quickly added them in just a few days.

•My “recommended distributions” from the fund have been very quickly processed and sent out to charities. The entire process is often completed in about a week.

•Since I am doing a large Roth conversion this year, (pushing my total income near $300,000) I am combining that with a $90,000 DAF contribution of highly appreciated stock. That removes $90k of income from the 32% tax bracket, plus eliminates $70k in capital gains on the appreciated stock.

•Fees. Daffy fees are based on average annual contributions. Up to $25k in average annual contributions is a $3/month fee. Since this recent donation takes me above that, the fee is now $5/month. If my math is right, I’m paying a 0.07% annual fee - very, very modest compared to the other administrators!

Overall I’ve been quite pleased. A great tax tool for anyone that is charitably inclined. In my experience Daffy has been a low fee, low headache DAF provider/administrator.

Feel free to chime in with any good/bad experiences you’ve had with them or other DAFs.

Hey there,

I need some help in evaluate this scenario:

33F - NO KIDS (Planning to have one)

• Salary: 110k
• Investments NW: 3.3M (excluding housing) - 50% stock/50% deposits (3.5%/y)
• House: Fully paid off
• Spending: 90k/y

Is this enough to RE knowing I could rent my house that would generate 50k/y rent.

With the 90k/y I would be able to rent something simple and live confortably.

thanks for helping me with the calculation

54/52 couple, both working.

HH has 3 streams of income

Job 1: $265k per year (salary plus bonus), no stock

Job 2: $200k per year salary, no bonus and no stock

Side gig: $100k per year, may continue at some level even after jobs 1&2 stop

Savings:

Pre-tax retirement accounts: $2.8M

Cash, post-tax brokerage, 529: $1.3M

Home: worth $3.2M

Liabilities

Mortgage: $1.1M outstanding, 30 year fixed loan at 2.625%.

Expenses: let’s say $20k per month broken up as

Mortgage: $5.1k per month

Property tax: $2.1k per month

All other expenses: $12k per month

Cars: fully owned, no monthly payment

In 8 years, will receive social security and pension from one job totaling $7k per month

In 10 years, add another social security worth $3k per month.

Can we retire now and bridge for 8-10 more years till full SS/pensions kick in?

Or alternately, can one spouse retire and we downshift to single income plus side gig?

As per rule of 55, one 401k worth $1.1M becomes liquid next year. In 3 years another 401k worth $1M will become liquid.

41F / 41 M, two kids 5 and 3 as well as a dog. The eldest is higher needs with high functioning autism, and the younger one likely is neurodivergent without any formal diagnosis yet. Both need OT, physiotherapy, behavioural support - and with them expected to independently live life.

Financial details
Incoming $700k per year, 53% tax rate (likely this will be more like $350k if one person quits). I’m in Canada, hence the high tax rate and no need for health insurance
$1.6M liquid assets and cash across investments
$400k of that is in tax sheltered investments
Home is worth $2M, have $900k remaining.

Monthly expenses $10k/m
Mortgage payments are $5.5k/m
Car payments $1k/m
Lessons and activities $500
Daycare negligible
Living expenses $3k/m food, incidentals, subscriptions

Annual expenses
Car insurance $2k per car (2 cars)
House insurance $4k
Life insurance $8k (whole life, whole family)
Property tax $7k

I’m the 41F and completely burning out. I make $240k/y, and haven’t been promoted in 6.5 years from a director level at a tech company despite significant increase in scope over the years. I’m now operating at a VP level mandate and scope, without the salary or title matching. I’m doing something from 6am until 11pm every day, with weekends 7am to 10pm. I’ve talked to my boss, but the answer has always been not yet. I’m seeing now that I will never be promoted.

I believe I can get a better paying job, but tech is weird with AI, and I’m worried about just leaving without any other plans. I wanted to ideally have $4-$5M liquid assets before quitting but not sure what to do.

Last piece of info: the company I’m at has grown 10x in the time I’m employed, and I have illiquid options that could be $1.5M post tax and share payment on the strike price. This would get me over $3M but not sure when this will happen so am not banking on it.

Have any others as a female left work in tech for 2-3 years then come back with any success? I’m also considering starting up consulting part time as I have a very sub specialized expertise that’s relevant for AI. I’m worried about most options, with a lot of money trauma living in poverty at a young age and working several jobs to put myself through university.

I am 44, with $5M liquid in $3.5M normal brokerage, $700K Roth, $300K 401K, $500K Inherited IRA with 9 years left. About $300K/year in W2 income and maxxing 401k at $30K/year. Dunno when I'll retire, but assume I'll have ~20 years of pre-rmd runway to do roth conversions if it makes sense.

My spend is about $180K/year.

Is there a quick way to understand if Roth conversions will make make sense for me? My 401K balance is so low relative to my other accounts that I don't really see RMDs becoming a major issue as it is currently just a couple years worth of spend.

I am not planning on doing them while I'm working, but just trying to figure out how much I should be planning around them right now?

What is the general strategy here?

45M / married, 3 kids under 8 $6.6M NW, $5.6M investable.
Based on an $18K per month spend (soon to be $16K), my FA says I can quit tomorrow (87% success).

My question:
Right now, I am thinking about doing one more year. Although I hate my job, I feel like I could wrap my head around a “12 month countdown.”
And it would likely mean another $500K (before taxes, but after all other expenses).
But I worry is the market drops 25% in the next 12 months, and all of a sudden, I’m forced to do X more years until it recovers.
Is my plan prudent? Or am I over-thinking it, and I just need to bite the bullet and then figure it out as it comes?

Thank you all! I really appreciate the wisdom of this group.

Additional details:

1. Very low rate mortgage is almost paid off, once done, will eliminate $2K in monthly expense
2. Kids are almost out of daycare which will eliminate $3K in monthly expense
3. The elimination of daycare will likely be offset by private medical insurance

Additional levers:

1. I don’t ever plan on “not working.” Although at some point, I’d like to do some $0 jobs, I think my “first retirement job” might still be be in corporate tech, but at a much lower level with lower stress.
2. My wife and I both grew up without much, I think we could find a lot of flexibility in our budget if SORR started to emerge.
3. Although we’re not counting it at all, we expect a $1-$3M inheritance from my wife’s parents who are now 76 y/o

Apologies for the formatting, I’m on my phone.
35M attorney in California trying to figure out whether continuing the grind is actually necessary anymore, or whether I’m just psychologically attached to maximizing income/career progression.

Current snapshot:
~$3.6M net worth
~$3.1M index funds
~$170k cash
~6 rental properties that are cash-flow positive after debt service (about $3k/mo net profit on average). $330k in equity
~$700k total mortgage debt across properties
No kids
No spouse

One important nuance: I currently live with my parents, and the household expenses are around ~$12k/month post-tax. That figure is not really “my personal spend” — it’s more of a worst-case assumption that I may eventually need to fully support the household financially.

So I’m trying to analyze this conservatively:

1. assume I cover the entire household

2. assume continued market volatility

3. assume I don’t want to rely heavily on selling assets

4. Career-wise, I’m at a crossroads between:

6. moving in-house / lower stress / more normal hours.

7. Continuing to grind in biglaw

The strange thing is that mathematically it feels like the portfolio may already compound faster than our spending over the long term, especially given my age (35). But emotionally it still feels risky to step off the gas while I’m in prime earning years.

Questions for the sub:

Would you consider this already ChubbyFIRE?
Does the leverage/rental portfolio materially change the equation?

If you were me, would you:

1. retire,
2. coast,
3. go in-house,
4. or keep maximizing income?

For people who left high-paying/high-stress careers around this level, how did you know it was “enough”?

How much should I value future earning power at 35 versus current freedom/time?

I suspect the harder part here is psychological rather than mathematical, and I’m curious how others navigated that transition.

37M & 35F with 2 kids 6 & 3 in VHCOL. We are targeting FIRE in the next 5-7 years.

• 3.2M in taxable brokerage
• 1.3M in 401k and Roth IRA. Adding 60k/year to 401k.
• 1.5M mortgage left, 6.125% (500k equity)
• 650-700k HHI. 600k is W2 income, and remaining is from side business income.
• Current annual spend is 220k. 132k is mortgage + property tax.
• No other debt
• After tax savings are going to taxable brokerage. 180k/year.

We’d need at least 5M in taxable brokerage to sustain 220k annual spend. It might be even higher due to health care costs at that drawdown amount.

Does it make sense to aggressively decrease the house principle in the next 5-7 years? That would proportionally decrease the retirement annual spend. Any future gains we lose from not investing in taxable brokerage would be offset by the gains in retirement accounts.

Downsizing our house is an option, but starter homes are still in 1.2-1.5M range, so the home payments do not decrease by that much.

What’s the optimal strategy?

We are hitting our FIRE number 3 years earlier than we projected. We are thinking of upgrading our house now. Is it a bad idea?

We just want a slightly bigger house with better floor plan, and we’ll be happy to live in until we become empty nesters.

Stats:
40M/F with 2 toddlers
2.9M NW (1.6M non-sheltered liquid assets)
Cash $120k
SI2K household ($210k salary— will likely stay this way until we fire in 4 years. formerly 300-450k but stock comp expired 2025, and I got laid off and became a SAHP)

Current house 400k at 2.8% (still owe 270k), going to sell. Will probably sell for 500k

New home max 800k at max 6.5% interest rate

Marked the occasion with a 2006 vintage rare Rolex as a heirloom(2006 is a significant year).Paying for my mother’s flight trip to china and taking my twins and hubby to the sphere to watch backstreet boys and visiting family across Canada in the summer. I will say, it’s hard to spend money like this after leaving a career and investing hard for 20 years.

I now reframe my spends as ‘investments’ on health, time, family and experiences.

What did you do? What purchases or experiences, or other did you celebrate with?

35M attorney in California trying to figure out whether continuing the grind is actually necessary anymore, or whether I’m just psychologically attached to maximizing income/career progression.

Current snapshot:
~$3.6M net worth
~$3.1M invested assets
~$170k cash
~6 rental properties that are cash-flow positive after debt service
~$700k total mortgage debt across properties
No kids
No spouse

One important nuance: I currently live with my parents, and the household expenses are around ~$12k/month post-tax. That figure is not really “my personal spend” — it’s more of a worst-case assumption that I may eventually need to fully support the household financially.

So I’m trying to analyze this conservatively:
assume I cover the entire household
assume continued market volatility
assume I don’t want to rely heavily on selling assets
Career-wise, I’m at a crossroads between:
staying on a high-intensity legal path (biglaw-type trajectory), or
moving in-house / lower stress / more normal hours.
The strange thing is that mathematically it feels like the portfolio may already compound faster than our spending over the long term, especially given my age (35). But emotionally it still feels risky to step off the gas while I’m in prime earning years.
Questions for the sub:
Would you consider this already ChubbyFIRE?
Does the leverage/rental portfolio materially change the equation?
If you were me, would you:
retire,
coast,
go in-house,
or keep maximizing income?
For people who left high-paying/high-stress careers around this level, how did you know it was “enough”?
How much should I value future earning power at 35 versus current freedom/time?
I suspect the harder part here is psychological rather than mathematical, and I’m curious how others navigated that transition.

Hello - as part of chubbyFire, I’m seeking input on how people think about saving for kids college and future.

We have 2 kids under 3, so we have a long time horizon still. My wife and I are mid 30s, our FIRE timeline is loosely 52-55.

Our intention is to cover 100% of college costs for both kids.

*When saving for kids college, are you investing in 529s with the projected cost of in-state tuition or out of state / private school?*

My thinking is, if you put into 529 for “private school costs” but the go to in state, then you end up with too much money in the 529. I know there are ways to handle that (IRA, change beneficiary, withdraw and pay tax etc) but it still is more limiting.

So I’m thinking, you put into the 529 “enough for in state” and front load the investments (let’s say $1000 a month until kid is around age 8), then shift to using a standard brokerage account to save the money for “what if they go to private school?”

That way you’re still intentionally saving to cover any college outcome, but you have more flexibility and can use that brokerage money for anything, such as gifting a house down payment, a car etc.

*So, how are folks thinking about the way they plan and save for college tuition knowing that in state v out of state is such a large delta? *

Plus of course, what if your kid doesn’t want to go to college, college looks different in 15+ years etc

As it relates to FIRE, the amount we save for the kids now, impacts what we can invest for ourselves now (we max 401k, do backdoor Roth, other investments etc), and if we undersave in the 529 so we have to “fund” the out of state tuition from “our savings” that influences things.

Our current situation roughly:

Mid 30s, both working parents. No debt (other than house mortgage), $2.7M+ across brokerage, retirement accounts etc (not including my house in assets)

Thanks!

Throwaway account..

We would appreciate your input on our plan over the next five years as we approach FIRE.

About us:

* Married couple in our early 50s/40s with one child

* About 5 years away from our retirement goal

* Investment target: roughly $6M total, split across taxable, Roth, and 401(k) accounts (529 excluded)

* Planned withdrawal rate: around $200k/year (~3.3% SWR)

* No debt, no pension, only future Social Security

Since we plan to retire before Medicare eligibility, we’ll need to manage healthcare costs for several years.

In the past, I never fully understood why some retirees maintained a relatively large cash position before/during retirement.

However, after researching ACA healthcare costs and Roth conversions during lower-income years, we’ve started to see the value of having a meaningful cash allocation.

Our retirement income would come from:

* Dividends from taxable equities

* Interest from cash/money market funds

* Selling taxable equities with relatively low capital gains

* Cash reserves as supplemental income

* During market downturns, potentially selling bonds and rebalancing into equities within tax-advantaged accounts

Our thinking is that holding cash:

* Helps control MAGI for ACA subsidy purposes

* Creates more room for Roth conversions at lower tax brackets

* Helps reduce sequence-of-returns risk

So over the next five years, we’re considering the following allocation:

* 75% stocks (across taxable, Roth, and 401(k))

* 15% bonds (primarily in 401(k))

* 10% cash/money market (primarily in taxable)

At first glance, one could argue that inflation will erode the purchasing power of the 10% cash allocation.

However, we’re thinking the combination of ACA subsidy savings, tax flexibility, and Roth conversion opportunities may more than offset the drag from holding additional cash.

One important note: this allocation is intended mainly for the pre-Medicare / pre-Social Security years, not necessarily as a permanent retirement allocation.

Would appreciate any thoughts or blind spots we may be missing.

Background: M 52, W 57. We retired about 2 years ago. Net worth is roughly 4 million with a 401k approaching 1 million now, 2 million in an investment account and 4 rental houses. I also have a small pension that will give about 2000 a month when I hit 65, and our SS will be 2000 and 1000 respectively. Option and dividend income has been higher than expected, and I'm getting 100k more than our expenses easily.

So the question - does it make sense to upgrade our house and move into the golf course community? We are in Houston and play golf every day, so we are commuting to the golf course 30 minutes each way. This is still a few years out...I'd like to sell off our rentals ($200k each) first. Then I can get rid of all the house maintenance equipment etc and just have a golf cart.

Reasons to stay: Our small gated community is wonderful, our property tax is still reasonable for Houston, and at a 350K value on the house we can afford to self-insure. (Last year they wanted 3k for insurance and we told them to pound sand). We can also drive by the grocery store every day on the way home. It's also great to walk dogs and we like to work with the local dog rescue rehabilitating dogs. I also just planted some fruit trees in the back yard.

Finally we stay about 4 months a year with my aged parents in Japan. So our house necessarily sits empty for 1/3rd of the year. We have neighbors who keep an eye on it for us. Just talking through this, I'm thinking it doesn't make sense until my parents pass away...but I'm still interested in hearing people's experiences.

35M attorney in California trying to figure out whether continuing the grind is actually necessary anymore, or whether I’m just psychologically attached to maximizing income/career progression.

Current snapshot:
~$3.6M net worth
~$3.1M invested assets
~$170k cash
~6 rental properties that are cash-flow positive after debt service
~$700k total mortgage debt across properties
No kids
No spouse

One important nuance: I currently live with my parents, and the household expenses are around ~$12k/month post-tax. That figure is not really “my personal spend” — it’s more of a worst-case assumption that I may eventually need to fully support the household financially.

So I’m trying to analyze this conservatively:
assume I cover the entire household
assume continued market volatility
assume I don’t want to rely heavily on selling assets
Career-wise, I’m at a crossroads between:
staying on a high-intensity legal path (biglaw-type trajectory), or
moving in-house / lower stress / more normal hours.
The strange thing is that mathematically it feels like the portfolio may already compound faster than our spending over the long term, especially given my age (35). But emotionally it still feels risky to step off the gas while I’m in prime earning years.
Questions for the sub:
Would you consider this already ChubbyFIRE?
Does the leverage/rental portfolio materially change the equation?
If you were me, would you:
retire,
coast,
go in-house,
or keep maximizing income?
For people who left high-paying/high-stress careers around this level, how did you know it was “enough”?
How much should I value future earning power at 35 versus current freedom/time?
I suspect the harder part here is psychological rather than mathematical, and I’m curious how others navigated that transition.

9:28 AM

SS is going away. Healthcare will bankrupt you. Sequence of returns will wipe you out. Civil war. WW3. Live to 120, spend 40 years in a nursing home. Someone posts solid numbers and the comments come back , one more year. Two years. Three. Keep going, it's never quite enough.

At what point does conservative planning become catastrophe planning?

The 4% rule is the worst case in US market history. A robot pulling the same amount out every single year, no SS, no flexibility, never adjusting through 1929 when markets dropped 86%. That's what 4% survived. It's the floor, not the target. Bengen himself now says most retirees can safely start at 5.25% to 5.5% and that people clinging to 4% will likely end up with a pile of money and a lot of regrets.

Someone spending 6% of their portfolio in year one of retirement who skips the big trip when markets are down, holds off on the car, pulls back when things get rough that person likely does better than the 4% robot who never adjusts no matter what. The flexibility is the safety net. You don't need to engineer it into the number, you just need to act like a normal person.

So when someone holds out for 3.5% 28 times spend, no SS — what exactly are you protecting against? Something worse than the Great Depression, while also never collecting a benefit 70 million Americans receive, while also promising to never adjust spending under any circumstances. Does that actually describe you?

The 2025 Social Security Trustees Report says worst case — zero Congressional action you collect 81 cents on the dollar in 2034. Not zero. Congress fixed this in 1983 when it was in worse shape than it is today. Seventy million people collect it. Seniors vote.

Median age of death for men is 81.7. One in five reach 90. Dementia affects 33% of people 85 and older. The years you're working extra to fund may not be years you're fully there for.

For those already retired one year, five, ten or more how bad has it actually been? And for those still holding off are you a catastrophe planner waiting for a number that never feels safe enough?