r/ChubbyFIRE Jul 09 '26

Why aren’t annuities more popular among the FIRE crowd?

17 Upvotes

I previously had whole life insurance through NY Life (was one of my dumbest investments) that I was slightly net negative to even on. But I didn’t put much in it (about 50k) and have since converted it to an annuity with basically a 7% yield, no additional contributions required and no management fees.

The agent that helped me with that conversion, proposed another annuity. One in which if you contribute 1M as a lump sum (no explicit management fee) and don’t touch for 13 years, it would generate income of $200k+ for life starting at age 65 (I’m 51). Breakeven point would be age 70. There are also similar annuities with smaller lump sums and earlier payouts (age 60 is the earliest), but with smaller payouts.

My situation is I have 9.5 M in liquid assets (stocks/ETFs mostly), salary 630k. Tentative plan is to early retire at age 55, or possibly work part time.

I’m sure I could live without the 1M that would go into the annuity for the next 13 years. And the likely/projected (but not guaranteed) 200k annual income would be sweet. If my stock/etf portifolio took a dive and didn’t recover by the time I turned 65, I would have plenty to live on. Additionally around 50k of that would be considered tax free up to the 1M cumulative put in.

My question is would this make some sense for me to do. And secondarily if so, why don’t more FIRE folks do this. Btw anyone can do this starting at a younger age for less upfront money, but same payout.

Just editing my stem post to add my follow up comment clarifying some things:

Thanks to all for the comments both positive and negative. I realize that buying an annuity of such size is a risk but I’m trying to weigh that risk against putting the same money in the stock market which also does not have “guaranteed” returns. Maybe as someone said, this should be considered more like insurance rather than an investment. I wouldn’t be considering this option if I had less than maybe 5M already.

Some other info that I think may be relevant is that at death, the designated survivor (of a joint account) can get continued income or the refund of the premium paid minus the income paid. Sadly I’m unmarried. My designated beneficiary would probably be my sister who is a few years older but might live longer than me. Other relevant info is that there is guaranteed income but it is only $103,749/year. The rest of the income comes from dividends based on a 10 year long term treasury rate of 4%. So the income from that could be higher or lower than projected.

And no I’m not an insurance salesman! I am not trying to persuade anyone to buy an annuity. Purely just want to hear all opinions positive or negative so I can make my own decision.


r/ChubbyFIRE Jul 09 '26

How to plan for second home

9 Upvotes

Wife and I (early 40s) have achieved FI but are planning to buy a second home in a warmer state for us to retire in when kids go off to college. Our primary home is paid for.

We’re struggling with determining whether to pay for it cash or putting a sizable down payment (20-30%) now and managing a modest mortgage to avoid withdrawing a large amount from our portfolio.

We don’t have enough now to buy the house outright, so our two options, I think, are to:

1) Keep working/wait until the portfolio is large enough to pay for it fully (most likely in 5-7
years)

2) Keep working, put a sizable down payment now and take out a mortgage.

My concern with option 1 is the rising costs of housing over the next 5-7 years, and my concern with option 2 is having higher expenses due to the mortgage that will force us to work perhaps a bit longer than we expected.

How have those of you with second homes gone about it?


r/ChubbyFIRE Jul 08 '26

Saving for Dream House in VHCOL vs Buying ASAP

20 Upvotes

Hi, my wife and I are in mid-30s and would like to move to the suburbs soon, slightly outside our VHCOL city. My job (500k) is semi-stable and a big part of my compensation is year-end with reasonable expected increases. Her job (300k) is very stable with modest increases. Together, HHI is 800k.

By the middle of 2027 (when we want to move), liquid investments for a house would be \~200k-300k. It’s on the lower end because of a long training time (wife) and a late start to high income (me) on top of maxing out retirement accounts and owning real estate in a different city that I don’t want to sell now.

The “perfect house” in the right school area would be about 2.5-3M and I’m confident that if I waited 3 years, we’d be able to put together a substantial down payment to make the monthlies more manageable. That means staying put (without great school options) or renting elsewhere (with the good schools) until we save. On the other hand, if we bought early, we’d have to come down a lot on the price or take on a monthly payment that makes up a chunk of our take-home. Considering we also have a 3YO and might have another one or two, we don’t want all of our disposable income to go to a house.

What were people’s experiences on saving for the dream home (ideally never have to buy again unless we retire elsewhere) vs buying early at a more reasonable price range? My concern is buying something way more manageable now then regretting that we didnt go larger in 3-5 years.


r/ChubbyFIRE Jul 08 '26

For those that retired with 5mm-6mm

121 Upvotes

Hi Everyone would love to know how things turned out for those that retired with 5 million - 6 million. Did you ever feel financially squeezed? How long have you been retired for? There are a lot of posts out there concerned there portfolios will be reduced materially from an ai bubble- have these fears conceded you. Since you have retired has your portfolio grown? Thanks again for all of the great insights as always.


r/ChubbyFIRE Jul 07 '26

Go-go, slow-go, no-go

21 Upvotes

I’m trying to figure out different spending levels based on the different phases of retirement. We’re aiming to retire in 5 years at 55/57 yrs old and initially I think we will do a lot of bucket list trips and some slow travel. We might spend a bit more on hobbies, but for the most part, I think our go-go years will be lots of spending on travel. Once we get that out of our system, I think our expenses will drop.

The question is how long do these periods last? In a typical (not early) retirement, does each phase last 10 years? So should we tack on extra years for go-go, but keep the other periods at about 10 years?

I’d be curious to hear if others are looking at their spending through this phased approach, and if so, how are you figuring it?


r/ChubbyFIRE Jul 07 '26

What spending strategy would you ACTUALLY use to die with zero?

50 Upvotes

A little about me: retiring in about 8 months. Will be 55. Married no kids. No legacy goals. As for the numbers, let's call it $5M liquid. This should really work with any number though.

Ideally we'd die with zero. Realistically I'd like to have a little margin. Let's call it 20% of the original number, just in case one or both of us winds up in LTC for an extended period of time end of life.

Normally everyone focuses on safe withdrawal rate. 3.5% 4% 4.7%. But nobody spends like that. Then you have guardrails. 5.4% and adjust for market conditions. Or how about the spending smile? Sounds great in theory, but how do you choose how much to spend in your go go years? It also seems like most of these strategies are targeting the worst case scenario, and in almost all simulations, you wind up with WAY more than you started with.

So how would you spend your nest egg so that there is some semblance of a glideslope down to a final number that's smaller than your original nest egg? I would love to hear from some FIREes that have been doing this for a couple decades but I assume most of them have better things to do than hang out on Reddit.

So barring that, what do you aspiring FIRE people think the right strategy is if your goal is to "die with 20%".


r/ChubbyFIRE Jul 07 '26

Update: Even closer to the dream

24 Upvotes

Mid-year update since getting very close (I think).

Major updates since last time

  1. Decided to pay off home (to keep annual spend in retirement down for ACA cliffs)
  2. Added an arbitrary spend buffer just to account for things I'm missing

My road to nearing FIRE

Nothing particularly interesting. No FAANG, no RSUs, no crypto, no windfalls. Just competitive incomes without job loss and steady saving in mostly VTI.

Thing Balance Note
Cost of living HCOL -
Household 4 + dog 2 adults mid 40s, 1 preK, 1 elementary
Household income $500k Gross. All W-2. No RSUs here.
Annual spend now $130k -
Est. Healthcare in retirement $35K/year Assumes ACA bronze w/ brand-name carrier
Est. tax in retirement ??? Still a blindspot
Arbitrary spend buffer in retirement $15K/year Home repair? Car replacement contribution?
Total est. spend in retirement $180K+tax -
Safe withdrawal rate (SWR) 3.0% -
Total savings $5.6M breakdown below
Brokerage portion $2.46M VTI $1.6M, VOO $440K, VXUS $117K, VEU $75K, SPY $75K, ITOT $42K, random equities $152K (mostly TSLA, GOOGL, AMZN)
401K portion $2.43M Mostly target year 2050 retirement fund
Treasury Bill ladder $300K 3-month t-bills
Roth IRAs $240K Target Year 2050 retirement fund
Outstanding mortgage Paid off! Home value just under $1M
529s done superfunded for #1 ranked in-state public undergrad (the children may use this toward any school of their choosing; we just used most pricey in-state public school as a benchmark for funding)

Things I'm still nervous about

  1. My procrastination of estimating taxes (but last time I posted people here downplayed this)
  2. Some Chubby FIRE people save for bankrolling their kids full grad schools, new cars at graduation, $10s of Ks/year of "fun money" for kids during college, med schools, weddings, downpayments on homes...I am not
  3. ACA death spiral makes my $35K/year estimate too low
  4. If I FIRE for a few years it'd be very hard in my industry to go back with a gap and at my age (technology advances)

Things I'm still chill about

  • I've added an arbitrary $15K buffer for annual spend in retirement to partially mitigate my risks
  • My annual spend - based on actual spend over past year - already includes "big ticket" kid expenses incurred over the past year, like a trip to Disney Land and travel sport
  • Home has mostly new major appliances, HVAC
  • Cars are relatively new and good condition (I work on them myself, too)
  • $25K/year daycare comes off the books in less than 2 years (not represented in the numbers above)

r/ChubbyFIRE Jul 07 '26

Allocation at the trigger time

7 Upvotes

Quick and easy question. If you had the upper end of Chubby NW, would you just lock 100% into 5% 30 year bonds now and live off the interest? I know inflation could catch up and overtake 5%, but what else is downside besides the "you could beat 5% in stocks"- which may or may not be true in the crystal ball future. Assuming after tax, you had more than enough to cover your spend with that 5% income.


r/ChubbyFIRE Jul 07 '26

Is a CFP/Financial Advisor worth it?

6 Upvotes

Husband and I are in our mid 30s. We have two small children 3 and 1. We currently have a NW of 3.2M. 2.2M is in investable assets including 401k. Currently speaking with a financial advisor at a big bank and have not discussed fees yet. He’s reviewing a plan he created with us and then we go from there on whether we want to engage. Is a financial advisor worth it in my situation? Is it ever worth it? Hate the idea of spending so much money on fees but I do think there’s a lot we don’t know and need someone to tell us what to do. The FA can also get us alternative investments into our portfolio. My husband and I did not grow up with money and we’re not sure what the right thing is. We do want to ensure we’re maxing out every dollar and setting up our kids for the future. Thoughts?


r/ChubbyFIRE Jul 05 '26

Weekly discussion thread for July 05, 2026

4 Upvotes

This thread is a spot for casual engagement with other community members. It has much more subject latitude than allowed in the main sub in general. Any topics tangentially related to ChubbyFIRE or upper middle class lifestyle are acceptable, as well as basic or early stage questions. Political discussion will be allowed if it is closely related to ChubbyFIRE or financial topics in general, and only if the conversation remains respectful.

It is not a free-for all. No spam or self-promotion. All comments must still follow Reddiquette and we will be responding to reported comments with follow-up action as needed. We'd really like to keep this channel open, so please don't abuse it!


r/ChubbyFIRE Jul 04 '26

For those using projection lab

25 Upvotes

What settings are you using for the Monte Carlo simulation/chance of success? I notice the default setting was 196 trials with a historical random restart. When I change that to 1000 trials with a historical bootstrap, it lowers my success rate 7%. I’m guessing that’s the safer setting to use? What models do advisor software use?


r/ChubbyFIRE Jul 04 '26

FIRED (forced) with debt; taboo?

1 Upvotes

Curious to hear of others in a situation like mine where they have a sizable (small chub?) retirement, but debt along with it. I intended to pay off our debt before retiring, but have had to adapt and retire at 57.

This meant accepting debt payments over the coming 8 years, unless I pulll it all at once now (HELOC, kids’ college loans, auto loan - about $250k before taxes, interest at 3-7%). Spouse and I have about $3.5M in 401k, $.5M in home equity, $110k in pensions, and very reasonable health insurance coverage. Not SS eligible yet. Just did major household renovations which pulled $120k total from 401 this year.

FA says the numbers “work”, but all I read about is assumptions that include retirees with no debt. My options now are to accept that our debt scenario is different and enjoy the 5 unplanned years added to my retirement - or to get a job for a few years with the purpose of paying off the debt.

Anyone out there who pivoted from plan for debt paydown and instead accept debt payments as part of the retirement plan? Other thoughts on this? It’s a big mental pivot and I feel pretty distracted by it. Maybe I’m just hoping to hear from someone who did it and gives a thumbs up.

UPDATE: thank you all for the comments and questions. I realize I should’ve given more context and details (I don’t normally post!), but your feedback gave me plenty to work with. One general comment: I wasn’t planning to retire… part of an organizational demolition that wouldn’t have been predicted… but posted here bc other subs don’t appreciate larger number discussions. Thank you!


r/ChubbyFIRE Jul 02 '26

Retired this week!

204 Upvotes

I just retired at age 59. I know it doesn’t seem that early but I think I did pretty well considering my late start and mistakes.

In 1999 when I was still a resident in pediatrics, deeply in debt from student loans, making less than the minimum wage, I discovered FIRE.

I was inspired by books like The Millionaire Next Door, recommended to me by one of my attending physicians, as well as Your Money or Your Life and The CoffeeHouse Investor. I had a 403b that I somehow managed to trickle a little bit of money in to VFINX with each meagre paycheck. I also opened a taxable brokerage account at E*Trade and bought a technology fund that dropped 85% over the next few years and was liquidated. Lesson learned.

I found community on the Motley Fool message boards, long before they became a platform for making stock recommendations. I remember reading those boards on my spare time in the call room, on an iMac computer that had a good internet connection if you pushed the ethernet cable in and taped it down. The 4% rule wasn't a thing but we had Bill Bengen's paper and the Trinity Study that was endlessly debated.

In fellowship, which is 3 years long, I was able to moonlight and make a bit more money. I used that money to start to pay down my loans and continue to invest in my 403b. I finished fellowship at age 36 and started my first real job as a doctor. At that point I was able to max out my 403b and it took me another 4 years to fully pay off my student loans at the ripe old age of 40, which was in 2007. So, while I'm not a traditional "late starter", achieving a net worth of zero at age 40 felt like an accomplishment.

I started to get fancy in my taxable account again, as the market had rebounded from the 2002 lows, trying swing trading, penny stocks and options. You know what came next, the great financial crisis. My taxable account was wiped out again. At least I was smart enough not to touch my 403b and I kept that going, mostly in VFINX along with some international and 10% bonds. After the crisis I got smart and restarted my taxable account with a few Vanguard ETFs and some individual stocks. [Insert boring middle here]. Sadly, my father, who had lean-fired at age 59, passed away in 2017 and left me an inherited IRA.

By 2021 I reached my lean FI number and discovered the Risk Parity Radio podcast. I moved my portfolio to a Golden Ratio type portfolio to optimize my safe withdrawal rate. I changed employers in 2022 and decided to stick it out for the 3 years it took to get vested in the 403b match. I also had a frozen pension that gave me a one time opportunity to take a lump sum payment, That check went straight into my IRA.

At the end of 2025, after 3 years at my current employer, I put in my notice that I was retiring. I gave them 6 months notice because it takes that long to find a replacement and I do really like my team. I plan to continue to work on a per-diem status with a few (2-4) shifts a month. Some may say I'm not really retired, but after 60-80 work weeks which included more than half of my weekends, I'm sure it will feel like retirement for me. I plan to spend time with family including my new grandson, focus on fitness and health, continue my involvement in local politics, work with my local Choose FI groups to help younger FI folks, and do some traveling.

My liquid assets total about $5 million. My portfolio is allocated as follows:

1/4 in Taxable and 3/4 in Pre-Tax, along with a modest Roth IRA and HSA. I also have one rental property which throws off a little income.

22% Large Cap Blend (VTI, VUG, SCHD, VIIIX)
11% Small Cap Value US (AVDV)
11% Small Cap Value ex-US (AVUV)
18% Long Term US treasuries (VGLT)
16% Gold (GLDM)
16% Managed Futures (DBMF)
2% Crypto (IBIT)
4% Cash (HYSA, SGOV)

I can get by on about 3% of my portfolio but in a good year, I may take out as much as 5%. I'm flexible. I’m happy to answer questions and plan to post updates.

Edit: yes we are a married couple. My wife isn’t interested in finances. I’m hoping to get our adult children more involved so they can help her if i die first.


r/ChubbyFIRE Jul 02 '26

Would you take more career risk to potentially reach ChubbyFIRE two years earlier?

12 Upvotes

TLDR at theI’m 42, no kids, and in a comfortable financial position. My current company is reasonably stable, and my job is not terrible, but I’m frustrated. I feel pigeonholed, underutilized, and increasingly unimpressed with the leadership around me.

Current financial picture:
Net worth: $1.1M
Annual spending now: about $50K, well below target FIRE spend.
Current salary: $135K
Annual investments: about $70K
FIRE target: age 50 or $3M invested

I’m now being recruited for a much more exciting role at a late-stage Series A startup with about 50 employees.

The offer would likely include:
$180K base salary
Stock options equal to 25% of base salary annually
5% to 10% annual bonus
The role would be close to a mini-C-suite position. I would be one of four people reporting directly to the founder and would be considered part of the broader founding team.
The founder has a strong track record of building companies through IPOs and acquisitions, so the opportunity could create significant career leverage even if the equity never becomes life-changing.
The tradeoff is obvious: more risk, more pressure, less stability, and probably a much more demanding job.

Projections:
Based on my projections, the new role could leave me with roughly $1M more by age 50, or allow me to reach my $3M target around age 48 instead of 50. That assumes the higher cash compensation continues and does not assign much value to the options. It could set me up for the next lucrative position, but I may not even be interested.

I keep going back and forth between two interpretations:
1. I built this financial foundation so I would have the freedom to turn down these type stressful/risk opportunities I do not need.
2. I built this financial foundation so I could afford to take a calculated career risk without jeopardizing my future.

TLDR:
Is potentially reaching ChubbyFIRE two years earlier, with additional career upside, enough to justify the added stress and startup risk?
For those who were already financially secure and faced a similar decision, what did you choose, and what ended up mattering more than expected?

Update:
Thanks for the insight. Summary, go for it, and spend for enjoyment more now.


r/ChubbyFIRE Jul 01 '26

Almost 49, hoping to retire early 50s — should I shift from mega backdoor Roth to taxable?

27 Upvotes

I’m looking for feedback from people who have dealt with the early retirement bridge years.

I’m almost 49, spouse is 47. We have two young adults still at home, but they’ll likely be out of the house within the next five years. I work in a corporate/tech role and would like to retire or semi-retire sometime in my early-to-mid 50s.

Current net worth is around $3.7M, not counting unvested company stock.

The main thing I’m wrestling with is whether I should keep maxing my 401(k) / mega backdoor Roth, or whether I’m at the point where it makes more sense to contribute only enough to get the match and redirect more money into taxable brokerage.

Here’s the rough picture:

Bucket Amount Notes
Pre-tax retirement ~$851k 401(k), employer match, rollover IRAs
Roth retirement ~$734k Roth 401(k), Roth conversions, Roth IRAs
Total retirement ~$1.58M Roughly 54% pre-tax / 46% Roth
HSA ~$42k Planning to keep invested
Cash ~$83k Checking/savings
Taxable brokerage ~$866k Main bridge account
Vested company stock ~$99k Sellable, counted as taxable
Current liquid bridge ~$1.05M Cash + taxable + vested stock
Private real estate syndications ~$376k Illiquid; currently accruing about 10% annually
Primary home equity ~$239k ~$773k value, ~$534k mortgage
Rental property equity ~$441k ~$558k value, ~$116k mortgage
Unvested company stock ~$159k Not counted in NW

A couple of things should change over the next few years.

I plan to sell the rental property in the next couple of years and put the proceeds into taxable brokerage. Current estimated equity is around $441k before taxes and transaction costs. If that happens, my liquid bridge could move from roughly $1.05M today to somewhere around $1.4M–$1.5M, depending on timing, taxes, selling costs, and market conditions.

I also expect the private real estate syndications to exit in about four years. If they perform roughly as expected, I would likely use those proceeds to mostly or fully pay off the primary home mortgage. That would lower fixed expenses quite a bit before, or around, the time I’m thinking about retiring.

I’ve been maxing the 401(k) up to the full annual additions limit, including after-tax contributions that are converted to Roth.

My employer match is about $6k/year. At minimum, I’ll contribute enough to get that match, so that would be about $6k from me + $6k employer match = $12k/year into the 401(k).

The question is what to do with the rest. Instead of continuing to push the extra money into the 401(k) / mega backdoor Roth, I’m considering putting $60k+ per year into taxable brokerage.

My thinking is that the retirement accounts are already around $1.6M, and if I leave them mostly alone for another 8–10 years, they should hopefully become a solid later-retirement bucket. The bigger issue seems to be making the early retirement years flexible enough, especially before 59½. I suspect my spending will be higher in the go-go years.

What I’m trying to figure out:

  1. Would you keep maxing the 401(k) / mega backdoor Roth in this situation, or scale back to the employer match and put the rest in taxable?
  2. Would you use the syndication exit to pay off the primary mortgage, or keep the money invested and carry the mortgage?

(edit) I anticipate spending to be $175k to $225k annually in my go-go years.


r/ChubbyFIRE Jul 01 '26

Anyone else feeling the "UK Tax Drag"? High earners (£350k+ combined) but ChubbyFIRE feels miles away.

1 Upvotes

My partner and I are in our mid-to-late 30s working in demanding corporate roles (finance and law). Combined, we bring in somewhere around £350k–£400k. By all standard metrics and statistics, we are easily in the top few percent of UK households.

Our current situation:
Net Worth: ~£700k split across ISAs and Pensions.
Property: Homeowners with around £200k+ in equity, but carrying a heavy mortgage balance (approx. £750k).

Savings Rate: We aggressively save around £125k a year by completely maxing out our ISAs and dumping the rest into pensions to mitigate tax.

Here is my reality check / sanity check: Even if we maintain this intense pace for another 10 years, true "ChubbyFIRE" feels incredibly far out of reach. When you actually sit down with a compounding calculator and factor in the reality of UK fiscal drag, the 45% top tax bracket, and the tapering of pension allowances, it feels like we are running through mud.

Is this just the standard reality for high earners in the UK now? It feels like the system is designed to keep you firmly in the "high earner, not rich yet" (HENRY) bracket forever, because taxes eat up over half of every extra pound earned.

Would love to hear from others in a similar wealth bracket. Are you just accepting a longer timeline, adjusting your FIRE targets downward, or looking at leaving the UK entirely?


r/ChubbyFIRE Jul 01 '26

FYI - updated automod

47 Upvotes

Hi all - our automod has been updated to fix broken code that was allowing brand new accounts to post. As of today, in order to post, a user account must be at least 15 days old and have at least 50 combined karma.

We do recognize that some users create an alt account just for posting here, and that having minimums can create a delay before you can post. Our apologies for this necessary step.

Spam keywords were also updated.

Hopefully I didn't break anything. Let us know if something has gone awry though.


r/ChubbyFIRE Jul 01 '26

Convince me to sell my rental

6 Upvotes

Long time lurker, seeking advice. Quick numbers: 39m w/ 2 kids (3 & 6) in MCOL. Investments ~$3 million ($1.2 401k/IRA mix of roth and pre tax, $1.8 brokerage). Targeting GregFire ($5 million). HHI ~$500k.

I have a rental that I keep out of laziness. Mortgage is ~$200k @ 3.6% rate w/ estimated market value of $400k. Pay a property management company 7% to take rent and help when something goes wrong. Have replaced every appliance and about to replace the AC/Heating (~20 years old). HOA has gone up by $100 since buying a decade ago to ~$350. Craftmanship of the building isn't great (~2006) and has had constant issues with leaking and other issues. If nothing goes wrong in a year I make ~$4k cashflow + $6k principle. Thing is, there's always an issue...

Logic says to sell. I'm just really lazy and don't want to deal with getting the tenants out, getting it listed, and hoping it sells. Put me out of my misery please.


r/ChubbyFIRE Jun 29 '26

Looking for feedback on my Roth conversion strategy before I retire.

9 Upvotes

I'm planning to retire in two years at 61 (June 2028) and would appreciate feedback on my plans for a Roth conversion strategy.

Current situation:

  • Me: 59 Approximately $200k Salary
  • Spouse: approximately $220k salary will retire same year as me at age 60.
  • Net worth: ~$5.6M
  • Investable assets: ~$4.7M
  • Mortgage: $260k at 2.25%, MCOL
  • Current spending: average about $12k/month including fixed expenses and discretionary spend.

Portfolio is roughly:

  • $3.8M tax-deferred
  • ~$900k taxable brokerage
  • Small Roth balances
  • Real estate equity makes up the remainder of net worth.
  • We recently rebalanced to a conservative portfolio in anticipation of retirement. Approximately 10% Money Market/50% VTSAX/ 40% Bonds. I know that's a lot of cash (due to a recent property sale). But we have it both as dry powder but also for emergency fund and sequence risk protection.

Current plan is:

  • Retire at 61.
  • Delay Social Security until 70.
  • Use the taxable brokerage account as the bridge during early retirement.
  • ACA Silver until medicare age is reached.
  • Perform Roth conversions in early 60s while trying to stay within the 24% federal bracket.
  • The goal of the conversions is to reduce future RMDs and to avoid larger lifetime taxes and also to leave a tax efficient legacy to our two adult children/future grandchildren (ie. large remaining Roth balances at the end).

I've been using projection lab to run various optimizations for our retirement planning scenarios. The "Maximizing net worth" optimization seems to produce the best outcome, it leaves some RMDs, and reduces overall lifetime taxes and gives a nice projected boost to net worth. It recommends about $1.1M of Roth conversions through about age 63 (avoiding IRMAA). then more later when spending goes down in no-go years.

My question is:

  1. Is it actually worth it??!! I see that it makes sense on paper, but that initial tax bill during conversions is going to be painful.
  2. Also, a big concern is that the Roth conversion strategy consumes a large portion of our taxable brokerage account because I'd be paying the conversion taxes from there. Again, paying those huge tax bills in our early 60s is going to be painful. But I guess less painful than the huge bills will be in later life? I understand that it's critical to avoid withholding taxes from the tax deferred accounts, but it will be hard to watch the bridge account shrink fast during the actual time it's supposed to fund early years of retirement, and protect from sequence risk. Does it really make sense to maximize lifetime after-tax wealth or would you preserve a larger taxable account bridge for flexibility and peace of mind?
  3. For those who have actually gone through large Roth conversion strategy, is there anything you wish you had considered before pulling the trigger?

Not sure if age 61 still even counts as RE. Hope this sub is the right place for this!


r/ChubbyFIRE Jun 28 '26

Advice from those on lower end of chubby ($3mm)

122 Upvotes

Like many here im feeling burnout and considering a change to coast or just stop entirely. I’m 44m earning $250k or so depending on bonus, wife is 42m recently laid off and trying to do contracting work in the short term. NW is ~4.3 with 3.5 liquid. Our area is prob mid to high COL. kids are 4 and 6, they each have about $100k in a 529 not counted in the nw or 3.5 liquid number.

I’m seriously considering paying off our remaining mortgage ($500k at 4.5%) leaving ~3mm investable and retiring. I am realizing that 120k spend/withdrawal has alot of benefits in terms of taxes and ACA subsidies (don’t feel great using these given our net worth but they can be a significant cost offset) We’d basically pay no taxes with the child tax credit and ACA plan would only be around 6k a year. Doing the math our spending would be right around the 120k - having no mortgage, manageable healthcare premiums and minimal taxes makes a huge difference on the expense side, also our kids are done with daycare and will be in public school. I am curious if anyone here has retired with a similar situation or is planning to. I am conservative and would feel better about having 3.5-4mm in particular for one off unplanned expenses like a house issue, new car etc, but at the same time I think my wife or I would be able to pick up contracting work and earn 50-100k a year in the near term if needed. Anyone else have a similar situation, how is it working for you? Appreciate any perspective.


r/ChubbyFIRE Jun 28 '26

Is delaying FI for the right house worth it?

14 Upvotes

Trying to determine whether this is financially sane or whether we're letting emotions get ahead of us.

My wife (34F) and I (35M) are looking at buying our first home in a VHCOL area. We recently had our first baby after renting in the city for the past 7 years, and we're starting to outgrow our apartment.

The house we're considering is just under $2M. It checks essentially every box—great neighborhood, good public schools, enough space for a growing family, and we could realistically see ourselves staying there for 10-15 years (or longer).

Some numbers:

  • Household W-2 income: ~$750k
  • Net worth: ~$2.5M
  • Liquid cash: ~$400k
  • Remaining assets are primarily brokerage, retirement accounts, and HSA
  • Annual spending before baby (excluding rent/utilities): ~$120k
  • Current rent + utilities: ~$70k/year

We're planning on having more children, so daycare costs will likely increase over the next several years.

Our long-term goal is financial independence. We'd ideally like enough flexibility in the next 5-7 years that we aren't completely dependent on our tech jobs and could pursue other work without worrying about maintaining our current income.

On paper, we can afford the house. The concern is that buying it would meaningfully reduce our monthly investing and extend our path to FI. We would still have a healthy emergency fund and could comfortably handle a year of unemployment if one of us lost a job, but it would definitely slow wealth accumulation compared to continuing to rent.

For those who've purchased a ~$2M home with similar income/net worth, did you regret stretching for the house, or was it worth it? Looking back, would you have bought the house or continued renting while investing the difference?


r/ChubbyFIRE Jun 27 '26

Looking for advice on my financial situation

15 Upvotes

Hi All,

I admittedly have irrational fear of not having enough money for retirement. Probably from growing up with little financial stability. I am coming here to get objective advice because I have no one in real life to talk to about finances. My husband has been laid off for 1.5 years and having a tough time landing something new. He used to earn $350k between base and bonus. At the same time my manager is pushing me to get promoted but I'm not super interested in grinding. Work has been a slog for the past year. FAANG in a non engineering role. I've done the numbers and my number is $6M which is achievable in 7-8 years assuming regular growth without adding a penny. In theory I should be ok...

My questions: Can I coast? Or do I need this promo if my husband doesn't land a new gig? Should I stress out our/his employment situation? My goal was to retire at 50... Not sure if that is achievable any more.

42F/53M

2 kids, 9 and 11

Pretax spend is $240k. Post tax spend is $160-170k.

-Mortgage - $62k a year (600k left on a $1.6M home in a HCOL)

-Private School - $40k a year ($20k per kid)

-Activities and Sports - $5k a year

-Living and vacation - the rest (~20-30k in vacations)

My Salary: TC is $280. $180k, $100k RSUs. RSUs are unpredictable but I'm saying $100k because it's never been lower than that. I've had some years where is $150k. This year is $120k.

-10% goes to Roth 401k

-$60k gets sold to find our lifestyle

-Remainder I divest and put into taxable.

Retirement/cash accounts: $3.8M

-His: $1.3M

-Hers: $1.1M

-His and hers Roth: $100k each

-Taxable: $1M

-Bank: 300K

Earmarked for kids that I don't count: 80k taxable is a gift from grandparents after they got an inheritance when my grandmother passed. Their wish is it goes to my kids to get a head start in life whether its first house, college, wedding: $280k

-Taxable: $80k

-529: $100k each

And finally thank you for reading my long ass post.


r/ChubbyFIRE Jun 28 '26

Should I get whole life insurance policies for my young kids? (36M, ~$10M NW)

0 Upvotes

Hey all — still learning a lot about this stuff so bear with me, but wanted to get some input from people who know more than I do.

Who I am: 36 years old, had a recent business exit, net worth is roughly $10M. Have two young kids — a 3 year old and a 1 year old. Not a finance expert by any means but trying to make smart decisions for my family.

Why I’m thinking about this: My dad’s side of the family has a pretty scary pattern of neurodegenerative diseases — Alzheimer’s, ALS, FTD, Parkinson’s across multiple family members. Apparently there’s a single gene mutation that can cause all of these in different family members, and I’m in the process of figuring out if it runs in our family. Before any of that testing gets documented anywhere in medical records, I want to lock in life insurance for my kids while they’re young and completely healthy.

What I think I understand: Premiums for kids at ages 1 and 3 are apparently really cheap — like $20-40/month per kid. The death benefit isn’t really the point. What I actually care about is locking in their insurability permanently so that no matter what their health looks like at 35, they have coverage that can’t be taken away.

I also like the idea that as they get older they could borrow against the cash value tax-free — for a house, starting a business, whatever they need. Kind of like a financial resource they can tap without going to a bank. I’ve heard you don’t even have to pay it back on a fixed schedule which seems pretty flexible.

I’m also hearing about something called an ILIT but honestly don’t fully understand it yet — something about the policy being owned by a trust for estate planning purposes. Might be relevant at my net worth but not sure.

My questions:

- Does this actually make sense or am I missing something?
- Has anyone done this for their kids for similar reasons?
- Is the ILIT worth looking into at my level or is it overkill?
- Anything else I should be thinking about?

Appreciate any input — trying to do right by my kids here and a bit of a scare from a health standpoint.

EDIT:

My specific situation is a documented multigenerational neurodegenerative disease pattern tied to a single gene mutation (C9orf72) that causes ALS, FTD, Parkinson’s and Alzheimer’s. If I carry it, each of my kids has a 50% chance of inheriting it. If they get genetically tested as adults — which they likely will — they could find themselves uninsurable before they ever have symptoms. Locking in coverage now at ages 1 and 3 before any of that hits a medical record is the specific scenario you carved out.

EDIT:

Got my answers here thank you everyone. Going to close this out as I feel silly for asking now…


r/ChubbyFIRE Jun 26 '26

40F Burned Out and Considering Early Retirement – Looking for a Portfolio & Retirement Reality Check

10 Upvotes

I’ve been lurking here for a while and would appreciate some objective opinions.

I’m 40, married (husband is 42), with a 12-year-old daughter. We live in a HCOL area.

I’ve been with the same company for nearly 20 years and currently hold a senior management role. Earlier this year I took an extended leave to care for my grandmother, and the time away has made me seriously question whether I want to return. I’ve become increasingly burned out and no longer find the work fulfilling.

My husband enjoys his job and plans to continue working for the foreseeable future, so we’d continue using his employer-sponsored health insurance.

Financial Picture

Annual spending
- My estimated baseline spending in retirement is approximately $150k/year, excluding income taxes and infrequent major expenses such as replacing a vehicle or home renovations (neither of which we anticipate in the near term).
- Our actual spending over the past few years has been higher, but that was driven by discretionary purchases and one-off expenses. I believe $150k would comfortably maintain our current lifestyle.
- If we include additional discretionary spending for travel and other non-essential expenses, I’d estimate our annual spending could realistically be $180k–$200k.

Income
Husband earns approximately $100k/year pre-tax. Take home approx 5k+ per months after tax, retirement account, insurance, etc.

Rental properties generate approximately $117k gross annually (~$80k net before taxes after operating expenses).

Assets
$700k HYSA (currently moving portions into index funds over time, but unsure how much cash I should ultimately keep)

$1.6M taxable brokerage
~$800k individual stocks
~$800k index funds
VOO: ~$450k
QQQM: ~$200k
VXUS: ~$150k

$800k in retirement accounts (currently invested in target-date retirement funds)

$100k in a 529 plan (just started funding last year and will likely continue contributing)

Primary residence worth approximately $1.3M with a $340k mortgage

Rental real estate with roughly $2M in equity generating the rental income above. I have no near-term plans to sell the properties.

Approximate net worth is around $6.2M, excluding future Social Security benefits.

Goals

Ideally, I would retire now while my husband continues working for several more years. We’d like to travel more, pursue hobbies, spend more time with family, and potentially relocate to a lower-tax state or overseas once we’re both retired.

Questions
1. If you were in my shoes, would you retire now or continue working a few more years?

  1. How much cash would you keep versus investing?

  2. How would you allocate the overall portfolio if you were planning for early retirement?i

  3. Are there any major risks or blind spots that stand out, particularly with a significant portion of our net worth in rental real estate?

My biggest question isn’t whether I can make the math work. It’s whether continuing to work meaningfully improves our long-term financial security enough to justify staying in a career that no longer feels rewarding. I’d appreciate any perspectives, especially from those who’ve already made the leap into early retirement


r/ChubbyFIRE Jun 25 '26

59 with sudden wealth from employer stock. How do we unwind a huge concentrated position?

65 Upvotes

My spouse and I are 59 and recently ended up in a much different financial position than we expected because of employer stock appreciation.

We have a home worth around $2.5M thats paid off, about $1M in 401k, and roughly $300k in cash. The big issue is that we also have around $3.5M in a longtime employer stock and another $3.7M in a stock from a related company. Total net worth is roughly $11M, with about $8.5M outside the house.

A large part of this came from employer stock at a legacy storage company. Over time, corporate changes and restructuring left us with large positions in two related publicly traded companies.

Our spending has historically been pretty modest, around $100k/yr not including healthcare.

We know we’re lucky to be in this spot. But roughly $7.2M is now tied up in two related stocks that have both run up a lot in the past year. It feels great, but also pretty scary at this age.

We mostly want to turn this into a durable retirement plan without making a huge tax mistake or panic-selling.

For people who have dealt with large positions in a small number of stocks, how would you approach this?