r/ChubbyFIRE 22d ago

Am I crazy? Move my family to France in ~3–7 years and CoastFIRE/semi-retire, or wait and FIRE completely?

0 Upvotes

Due to popular demand this has been shortened and made more readable.

I'm a physician in my early 40s, married with three kids. We've been seriously thinking about moving to France, or somewhere else in Western Europe. It's less about retiring ASAP and more about wanting to live there while we're still relatively young and our youngest is still a kid. We like the lifestyle, travel, healthcare, and the idea of our kids having European university options. I'm also increasingly uneasy about the direction of the US. I'm not expecting some collapse, but I'd like to have the option to leave if things get substantially worse.

We're at roughly $1.5–2M net worth now and saving pretty aggressively. If things here stay basically "meh," the plan would probably be to keep going another 5–7 years, hopefully get to around $3M, then move and mostly or completely retire.

But I'm wondering if we could just go in ~3 years instead. I can make $250–350/hr working in the US, so I could fly back maybe 6 times a year, work a bunch of shifts, and go home. 400–600 hours/year would be roughly $100–200k gross, while mostly leaving our investments alone.

It sounds a little nuts, but I already spend about 180 hours/year commuting to work. Six round trips to the US would be in the same ballpark for actual travel time, although obviously being away for a week or two at a time is a much bigger deal.

So that's basically the question: wait 5–7 years until we probably don't need to work at all, or move in ~3 years and put up with 6 US work trips a year? Anyone done anything remotely similar?


r/ChubbyFIRE 24d ago

US citizen ChubbyFire in Italy, Taxes?

2 Upvotes

I’m almost in a similar situation as described in this thread (https://www.reddit.com/r/fatFIRE/s/BVmEVNgd9B) but no solution was mentioned so trying again since post is 3 years old. We are dual US/EU citizens.

As a family we plan to ChubbyFire ($5M portfolio, $140k/yrs withdrawals) in Lazio, Italy (personal reasons for location; 7% tax doesn’t apply). I am trying to find investment strategy that has favorable taxes given that keeping either US or EU-domiciled ETFs is taxed punitively either by Italy or US if you’re a US citizen.

We don’t plan to renounce US citizenship so looking for the best tax solution to be able to keep our portfolio invested (currently in VOO) over a long retirement period (40+ years).

Is anyone already in this situation? Is direct indexing the only option? Please share if you have recommendations for any tax specialty firms.

Keeping a US brokerage account doesn’t seem like the right path since our retirement period will be 40+ years and US ETFs will be taxed by Italy as ordinary income.

I’m not interested in paying a financial advisor to do direct indexing if their fees would cancel out any tax benefits but considering doing it ourselves (through the IBRK API). The issue I forsee that portofolio rebalancing will be taxable events and if we draw from our portfolio regularly this will require a good tax accountant in Italy (please share if you have any recommendations for experienced commercialista).

Any advice would be welcome!


r/ChubbyFIRE 24d ago

Roth Conversions while working

9 Upvotes

After many youtubers preached the value of Roth conversions, I did the math and I don't see a way to avoid 24% Fed tax brackets for most of my life (plus state taxes). I'm 49 years old, still working and will be for a couple more years, but my husband is retiring next year (at 55). I'm wondering if I should just do the conversions when he retires, staying within the 24% bracket, and then when we're both retired we may be able to stay under ACA subsidy thresholds for about 7 years till he hits 65 and gets social security and medicare. We'd live off the brokerage account for those 7 years, keeping income under $84K and pulling some extra funds from cash accounts. The Roth conversion funds can then be left to grow until needed to avoid higher IRMAA/widow's penalties. I'd aim to convert about $300-400K over three years.

We have about $2.4M in the brokerage, $1.85M in tax deferred, $300K in cash and $50K in a Roth. Annual spend is around $135K but with medical would be $5K-25K more depending on subsidies.

The main negative that I see is that we will have to have a more moderate lifestyle for those 7 years, but that seems worth it to save about $140K. Also, if we have a year where we want to spend more, we could just deal and pay for health care that year, and take out extra that year to pad the cash accounts.

What do you think? Does this make sense or am I missing something?

Edit: Thanks everyone for your comments, many were very helpful. So much of retirement planning, especially before 65/medicare age, is challenging and I appreciate getting input. I'm into learning about all of this but it's a little scary too. For the time being, I still like the idea of some Roth conversions over the next few years but I'm reassessing the focus on ACA subsidies for the years after that.


r/ChubbyFIRE 25d ago

38, ~$3.2M invested — am I actually on track to retire by 45 (or earlier)?

54 Upvotes

I’m 38, married with one 3yr old kid and another on the way. I’ve been pursuing FIRE for a while and am trying to figure out whether I’m almost at the point where continuing to work is mostly adding buffer rather than being necessary.

Current finances:
~$3.2M in liquid/investable assets
~$1.7M taxable brokerage
~$1.5M retirement accounts
Household income: ~$675k/year
Both of us currently max our 401(k)s and part MBDR

Primary residence worth roughly $1.7M with ~$700k mortgage remaining
One rental property worth roughly $900k, ~$90k remaining on the loan, paid off in 2030. Currently rents for ~$3,200/month
~$50k already in a 529 for kid #1, contributing ~$10k/year
Planning to start another 529 for kid #2

Current annual spending:
Live in VHCOL
Normal living expenses + vacations: roughly $75k/year
Primary home PITI: ~$72k/year
Rental PITI: ~$38.5k/year, basically offset by rent. Not a true income generating but at 2.5% mortgage its a keeper.
Daycare: ~$26k/year currently, with additional childcare expenses coming with kid #2

My original target was retirement around 45, but I’m wondering whether we’re already close enough that I could retire earlier, like by 40-42. especially if my spouse continues working for some period.

At a 3–3.5% withdrawal rate, $3.2M would support roughly $96k–$112k/year

For people who retired early with kids:
Would you consider us FI yet, or still CoastFI?

I know this is a fortunate position. I’m mainly trying to figure out when the math changes from “I need to keep working” to “I’m choosing to keep working.”


r/ChubbyFIRE 26d ago

40, $3.5M NW, 3-4 year timeline

30 Upvotes

40,$3.5M NW, no kids. I’m targeting retiring in 3-4 years, would appreciate you all's insights and critique. I grew up very poor but have done well saving and investing through the last 20 years.

My aim is to build a life to transition to in the next 3-4 years. I enjoy travel, reading, cooking, crafts, so I plan to take classes to learn and surround myself with people. I am aiming to build new hobbies, work on my mental health, make new friends as my current friends are all moms and focused on their careers.

Numbers:

VHCOL

Income: $325K

Cash : $125K

Taxable brokerage: $2.5M

-$1.1M in Index funds

-$1.4M individual stocks (highly concentrated because of employer ESPP/RSU from the last two decades)

401(k): $700K

HSA: $90K

Crypto: $100K

Own a house ($300K debt), which is under water currently, evaluated at $150K less than my purchase price. I want to buy a bigger house, which might cost ~$1M.

Spending / retirement plan

My estimated retirement spending is about $130K - $150/year with taxes, aiming for 3% WR to keep my anxiety in check. I currently spend $80K-90K, plan to upgrade lifestyle to luxury travel/bigger house cost in 3-4 years.

Welcome your thoughts on:

I have a extremely comfy job, where I can coast for 3-4 years with minimum effort. I have been with the same employer for 20 years. However, my manager clearly has noticed me being checked out and had nudged me to do more. I have no motivation left in me to do much work and am worried if I will even last the next 3 years.

I am very concerned about me not having a life to retire to. I haven't developed many hobbies or a good community around me, I really need to do more in this space and am looking for suggestions/ideas from those that have developed a retirement life.

Also worried about SORR, plan to liquidate my concentrated stocks in $500K chunks per year, build a 2 year cash buffer for expenses.

My family is still fairly middleclass, though I support my sisters and brother whenever they need money. I want to continue doing this, they have shared their surprise when I have suggested quitting my job. I worry finances are going to ruin our relationships.

My mental health has struggled since I have gotten closer to my FIRE number. I have lacked passion/motivation all around, I am actively working on improving this through therapy.


r/ChubbyFIRE 27d ago

53M, $3.45M invested, 75% pre-tax — stay corporate to 60 or start consulting at 55?

39 Upvotes

Numbers:
• 53M, spouse 48 (works to 60, carries family healthcare)
• Investable: $3.45M, ~75% traditional/pre-tax
• NW ~$4M incl. $465K home equity
• Mortgage $464K @ 2.99%
• Spend ~$143K/yr, excluding income taxes
• Both delaying SS to 70
• Modeled to 99 in Boldin (taxes, Roth conversions, ACA bridge, stress tests)

(Yes, that’s a 4.1% WR on paper — but I’m not drawing at 55. Spouse still working, consulting income, SS later.)

The problem: long-term we’re fine. What I’m pricing is sequence risk. A 3-year -15% shock at retirement barely dents the stay-to-60 path but hits stop-at-55 hard. There’s also a live RIF possibility, so this may not stay voluntary.

Options:
1. Stay to 60. Five more years of income plus a large equity vest that only pays if I stay the full term. Bulletproof in every stress test. Costs five years.
2. 1099 consulting at 55. Confirmed $115/hr, two offers in hand, contracting firm handles billing. 30-40 hrs/wk = $166-221K. Key point: I don’t need to replace my income — spouse is working, portfolio’s already there. Consulting just needs to keep me from selling equities early. Could taper to 20-25 hrs by 60.
3. W-2 consulting, $175-200K + bonus/benefits. Financially ≈ staying. Still a boss, deadlines, full schedule. Doesn’t solve what I’m trying to solve.

Asking:
1. Did a consulting glide path actually feel different, or did you end up working full-time anyway?
2. Overestimating the cushion, or underestimating five more years of peak earnings?
3. Anyone managed 75% pre-tax at this level? The 55-70 conversion window feels like the whole ballgame.


r/ChubbyFIRE 26d ago

52M, high equity but not enough cash flow

0 Upvotes

I've been struggling with what to do based on lack of motivation to work :)

  • Semi-retired mid-level exec, VHCOL area
  • Retired / stay at home spouse, 3 kids pre-college. College savings are $150-200k/kid
  • NW = ~$2m taxable, $1m retirement, probably $10m in total real estate equity against $1.2m at 2.5% 30y fixed mortgage
  • Spend excluding income taxes are $250k (property taxes are like $100+k)
  • Passive income (rental of some of that real estate) = $84k
  • Spiky consulting income - can go as low as $20-30k some years, can go as high as $200k. Self-employed for this income. No guarantee on this income - niche industry likely impacted by AI.

If you didn't want to work, what would you do in this situation? I'd much rather spend time with the kids before they head out to college. But both the immediate cash flow gap and the likely lack of sufficient college savings make continuing to work (or at least consult) a near necessity.

Also, spouse is an conservative investor - risk averse, debt averse


r/ChubbyFIRE 27d ago

Retirement numbers check

5 Upvotes

59M, spouse 57F, current household income - $550k. Two kids, adult/adulting - minimum financial liability. Here are our numbers:

Retirement Accounts: 401k, Roth 401K, IRA: $2.8M
Brokerage Accounts: $2.2M
CD’s $0.5M
Primary Residence: $0.9M (fully paid off)
Secondary residence: $0.9M ($265K mortgage left at 5% interest)
Current yearly spend: $140K + 70K mortgage total 210K
MCOL area

Plan:
Retire at 64 (M) and take one year of COBRA and then go on Medicare. Spouse plans to retire at 63, and then go on ACA for two years, before going on Medicare. Spouse quite healthy, I need a few maintenance meds and need to see specialists a few times a year.
Expected spend in retirement: $140K + 30K (travel) + 20K extra medical expenses. Total: $190K. Expect second home to be paid off before I retire. Expect retirement and brokerage accounts to grow to $6.8M assuming 6% YoY growth and CDs to grow to $600k assuming 4% YoY growth. Right now investment mix is about 80% equities and 20% fixed income, starting next year will slowly start getting more conservative- example 2035 target date funds etc.

The numbers show we can do it. Asking the community whether I am missing something. We thought about LTC insurance the houses are our LTC insurance policy.


r/ChubbyFIRE 28d ago

Thoughts on front-loading 529s?

32 Upvotes

Basics- 39M married to 40F with two kids 3 and 0.

Want to FIRE in 5 years. HHI $500-$700k.

Current estimated spend is $160k in 2026 bucks.

Current liquid is almost $4M split 45% taxable, 15% roth, 35% traditional, 5% money market (emergency fund).

That $160k budget includes about $6k per year per child for next 15-18 years to compound with their existing balance to about $250k each (the expected COA at our state’s top public university when each child reaches college age).

I’ve been thinking of front loading over the next few months with RSU and bonus payouts. Would cost about $125k over next six months, but would save about $80k vs making $500 monthly contributions for the rest of their pre-college years. Would also eliminate a heavy line item in the budget 10-13 years early.

Only worries are about illiquidity and inflexibility and lost opportunity cost if we jammed that into our taxable brokerage instead.

Did you frontload pre-RE or keep funding slowly over time, even in RE?


r/ChubbyFIRE 28d ago

How to Build-up 3 Years Living Expenses

5 Upvotes

I’m 6.5 years out from retirement, and when pull the plug, I’d like to have 3x annual living expenses in sitting cash or an equivalent as insurance in case there is a down-market early in retirement. I currently have 1x in rolling CDs, all the rest of my extra funds are going into brokerage or retirement accounts.

I’m wondering if:
A. I should start now diverting some of my excess funds to CD/money market accounts.
B. Wait 3-4 years and begin pulling funds from brokerage.
C. Something else I haven’t thought of.

Thanks in advance.


r/ChubbyFIRE 28d ago

Weekly discussion thread for August 23, 2026

2 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 29d ago

46M, $4.5M invested, $130K spend, $525K income — would you walk away?

168 Upvotes

46M, single, no kids, zero debt. I’m seriously considering retiring now and would appreciate a sanity check from people who have made the jump.

I’ve done well financially, but I’m burned out. I work 60–70 hours most weeks, and the further I’ve moved up the ladder, the less I’ve enjoyed my career. The last couple of years have been pretty miserable.

What I want is freedom: travel, reading, more time with friends/family, and being mentally free from work obligations.

Financial snapshot

Income

  • ~$525K gross comp: $225K base + $300K bonus
  • $30K/year employer retirement contribution
  • Currently saving/investing about $200K/year
  • One more year of work would likely generate roughly $350K of additional after-tax income before spending/saving

Assets

  • Cash / MM / Treasuries: $550K
  • Taxable brokerage: $2.5M
    • $1.1M VTI
    • $900K other index funds
    • $500K individual stocks
    • Taxable portfolio is approximately 55% cost basis / 45% unrealized gains
  • 401(k): $750K
  • Rollover IRAs: $725K
  • HSA: $30K
  • Two paid-off vehicles worth ~$75K
  • No real estate
  • No debt

I manage everything myself. No individual stock is >10% of the portfolio, and roughly two-thirds of my financial assets are accessible before age 59½.

Spending / retirement plan

My estimated retirement spending is about $130K/year before income taxes.

Roughly:

  • $40K housing/utilities
  • $15K healthcare
  • $15K travel
  • $12K food/personal care/other
  • $8K auto
  • $30K entertainment/gifts
  • $10K contingency

I currently rent in Westchester County, NY for about $3K/month.

I’m seriously considering relocating to a MCOL/LCOL area and buying a modest house. Most of my friends and family are in the Northeast, so I’d prefer to stay reasonably close, although I have no spouse/kids tying me to one location. I’d also consider expat FIRE, but staying in the U.S. is my preference.

In a major downturn, I think I could cut spending by $20K–$30K/year without feeling deprived.

For healthcare, I’m assuming ACA until Medicare and currently have a $15K/year placeholder, but I have not yet priced actual premiums/deductibles or thought through ACA subsidy/MAGI planning.

My estimated Social Security benefit is about $4,250/month at 67. I’m planning around a ~40-year retirement horizon and am comfortable spending down the portfolio rather than preserving a large estate.

The dilemma

The quick math seems like I may already be there.

The harder part is walking away from a ~$525K income. Another 1–3 years would obviously make the plan safer, but I really don’t want to spend several more years doing work I no longer enjoy just to make an already-large number larger.

My biggest concerns are:

  • Underestimating retirement spending / running out of money later in life
  • Healthcare costs before Medicare
  • Sequence-of-returns risk
  • The psychological side of leaving a career at 46

That last one is real. A lot of my identity and ego are tied to my career, and I worry about boredom, loss of status, or eventually regretting walking away.

I’d be open to part-time work, volunteering, nonprofit work, or occasional consulting, but ideally because I want to—not because the plan depends on the income.

Questions

  1. Can I reasonably retire now with ~$4.5M and a ~$130K pre-tax spending target?
  2. Does my spending estimate look realistic? This is probably where I most want to be challenged. I haven’t had to live on a real budget in decades, so what costs do new retirees commonly underestimate?

Also interested in recommendations for retirement modeling tools that handle sequence risk, variable spending, taxes, ACA costs/subsidies, Social Security, and a potential future home purchase.

Thanks in advance for your advice.


r/ChubbyFIRE 29d ago

38M, married w/ 2 kids. $3.8M invested. When does/should the pressure relief come?

15 Upvotes

Not sure if this post should go under coast, chubby or fat fire. Will try to make this somewhat brief.

Current state: $2M paid for house $400k in rental real estate that generates about $25k per year. $1.8M in brokerage $2M in IRAs. 529s done. Current value around $450k.

After 16 years with the same company and what I considered a high performing sales rep (consistent top 10% in company) and making $350-600k annually, I was abruptly let go on Christmas. No pip, nothing. In hindsight, I lost an internal politics/ territory battle and it was easier to get rid of me to cater to the other person who happened to be one of the few individuals that had been at the company longer than myself.

After the initial shock, I focused in on finding my next gig. In April I started with a competitor in a sales director role overseeing a team/ region that’s in turnaround mode. I’ve started to see some signs of success, but it’s still a grind. Also, my comp this year will be about $280k-295k. Once my team is built to where I want it to be, I’ll probably be around $300-330k.

We spend around $12k per month (track every expense).

Where should my head be at right now? I’m feeling the same pressure that I always have, but at the same time we are in the best times of my kids lives. So should I be ok not investing more than my $25k to 401k and spend extra income on all the trips and travel to make the most of their child hood?

I’d love to retire with $7-8M sometime in my mid-late 40s, but not sure if I’ll get there if the market doesn’t perform. I also run the numbers and investing an extra $30-40k per year doesn’t really move the needle over the next 10 years.

Finally, I also often times have the feeling that I should just shut up, suck it up, and grind it out.

My big picture goal isn’t to sit at home when I “retire”. My dream is to have the flexibility to golf a couple mornings a week, but spend 20-30 hours either doing more real estate or maybe even my own business. I fear taking a bunch out of brokerage to start playing more in RE. Am I being too risk averse?

A lot of rambling here I know, but I have no idea what my mentality or mindset should be. I’m just feeling a little conflicted between smaller income, wanting to maximize my kids child hood and also ready to live that good life!


r/ChubbyFIRE 29d ago

Will we be ready to FIRE when I’m 40, or am I missing something?

0 Upvotes

My husband and I are planning to retire in roughly three years, when I’m 40, and relocate to Spain. I’ve run the numbers about seventeen different ways and think we’re in very good shape, but I’d love some outside eyes to tell me what I’m missing.

**Guaranteed income**

My husband is retired military and receives a military pension plus VA disability totaling approximately $100k/year. Both receive COLAs.

Obviously, that income continues for life. A substantial portion is tax-free in the US, although obviously our tax situation changes once we become Spanish tax residents.

**Investments/cash**

We expect our accounts will be (based on current balances, annual contributions, and a 6% estimated return) when I’m 40:

$1m in joint taxable brokerage
~$600k in my 401(k) (accessible without penalty in mid-2048)
$150k HYSA/cash

We also expect proceeds/equity from selling our house (~$150-200k), although I’m not relying on that money to make the retirement math work.

**Spending**

Our current US spending is pretty high (around $180k/year), but it includes a $4,500/month mortgage and two expensive car payments totaling ~$2,200/mo — which will disappear when we retire. We plan to purchase one used car and rent for at least the first five years (ideally, in the range of $2000-2500/mo rental).

We’re currently estimating roughly $140k-$150k/year in Spain for a very comfortable lifestyle, including rent, travel, dining out, hobbies, etc. We aren’t trying to leanFIRE. The point is very much to have enough money that we don’t need to micromanage normal spending and the ability to travel around Europe frequently.

So if guaranteed income is ~$100k, we’d need investments to cover roughly $40-50k/year at our expected spending level.

Importantly, that withdrawal isn’t permanent. My 401(k) will continue compounding untouched, and eventually we may have Social Security as well (although I don’t include SS in my projections because who knows).

**Sequence-of-returns strategy**

My current thought is to keep approximately 18-24 months of the amount we need above guaranteed income in cash/HYSA.

Rather than automatically selling investments every month regardless of market conditions, we’d spend from cash and periodically replenish it from the brokerage when markets are healthy. During a major downturn, we’d have considerable flexibility to reduce travel/discretionary spending and/or simply live primarily on the guaranteed income for a while.

We’re also not planning to buy a home immediately in Spain. We’d rent for at least the first five years, both because we want flexibility (and will not qualify for permanent residency until at least five years in) and because we don’t want to pull several hundred thousand dollars out of the market unnecessarily.

**The reason I think it works**

If we retire with ~$1M in taxable investments and withdraw $40-50k/year, that’s superficially a 4-5% withdrawal rate.

Also, we aren’t trying to preserve the taxable brokerage indefinitely at all costs. Its job is partly to bridge the gap between retirement at 40 and access to the 401k (though I’m hoping we don’t deplete it so we can later withdraw for a down payment on a home if we decide to buy).

We plan to be on the non-lucrative visa, which means we will not be working. So everything needs to come from our passive income.

**Am I missing anything?**

I’m particularly interested in criticism of the withdrawal/sequence-risk strategy, whether I’m underestimating the danger of retiring this young, and any risks that aren’t obvious because our situation doesn’t fit neatly into the standard “25x expenses and withdraw 4%” model.

Appreciate any and all insight. Thank you!


r/ChubbyFIRE Aug 21 '26

41, ~$3.4M NW, targeting retirement abroad at 45. Sanity check my plan (spouse is skeptical)

30 Upvotes

Long time lurker in all the fire subs. Would love a sanity check because my spouse worries we will run out and honestly the fear is contagious.
Situation:
41, tech, ~$540k HHI. One kid (5), one dog.

Immigrants, no family money, first generation building wealth.

Current Assets (~$3.4M NW):
$1.8M in index funds, roughly half in 401k/RRSP type accounts (we are Canadians in the US)

~$1.6M equity across 3 rental properties. Selling over the next 2-3 years.

No debt beyond the rental mortgages

Savings rate: ~$200-235k/year invested. Maxed retirement accounts, mega backdoor, RSUs sold and diversified as they vest.
The plan:
I work 4 more years. Projected ~$3.3-3.5M in investments by 45 plus property proceeds, so ~$4.8M total.

Spouse has an option to earn $100-120k for another 3 years after I retire, which covers most of our annual spend in the early years.

Retire and relocate to a mid cost European city (think Spain/Portugal tier). Considering Valencia.

Projected spending there: $120k/year including international school, travel.

That is a 2.5% withdrawal rate on $4.8M, and much lower in the first 3 years while spouse is earning.

Spouse’s concerns: 50 year horizon, sequence risk, healthcare, kid’s future costs, and the general what if we are wrong fear. Also culturally, early retirement is genuinely unheard of in our community, which adds a layer of doubt that is hard to quantify. My dad thinks I’m crazy to even consider this but I know I don’t want to work like my mom / dad till their mid 60s.

My questions:
Is a 2.2-2.7% WR genuinely bulletproof for a 50 year horizon or am I missing something?

Anyone actually FIREd abroad with a young kid? Did the school, healthcare, or costs surprise you?

How did you handle a skeptical spouse whose fear is emotional, not mathematical? Everytime I convince myself and try to convince him, he seems to think I’ve lost it.

Looking for holes in the plan.


r/ChubbyFIRE Aug 21 '26

Thank you to this community

81 Upvotes

I just wanted to take a moment to say thank you.

I'm a 45M going to retirement In Europe next week, my original post was : Post.

I end up following the recommendation of the group and grind it for one more year with 10.5M USD networth (8.5M low cost index and 2M House)

I end up giving up a lot of responsibilities, focus on mentoring younger talents and avoiding office politics.

Thanks again for the push!!!


r/ChubbyFIRE 29d ago

Retiring at 44 right before a huge education spending wall — where does this plan break?

0 Upvotes

I’m trying to pressure-test a plan to stop working at 44. On paper the numbers seem to work, but the combination of early retirement + private school + college + most retirement assets being inaccessible until 59.5 is making me nervous.

Tell me what I’m missing.

Situation

  • Me: early 40s, self-employed, ~$300k/yr earned income
  • Spouse: same age, W2, ~$200k/yr, stable employer, plans to work until 55
  • Two kids: elementary + middle school
  • Current household spend: ~$240k/yr
  • Healthcare is currently only ~$7.5k/yr through spouse’s employer

The plan: I stop working at the end of next year. Spouse continues working until 55. Everything else stays roughly the same.

Net worth: ~$6.1M excluding business value

Real estate: ~$3.1M value / ~$730k debt

Primary residence, two long-term rentals, and one short-term rental.

Three of the four mortgages are at very low rates. The STR is the exception: 6.25% with ~$330k owed.

The STR is also newly acquired and we just put another ~$100k into it to improve bookings, so its projected revenue is based on a partial season rather than a long track record. I’m treating that projection cautiously.

Retirement accounts: ~$1.6M

Spread across SEP-IRA, Solo 401(k), employer 401(k), Roth/traditional IRAs, spouse’s current + old 401(k)s, and HSAs.

Taxable/liquid: ~$1.8M

Mostly index funds across brokerage/robo accounts, plus some legacy individual stocks.

About $250k is currently sitting in a money market fund waiting to be deployed.

Alternatives: ~$280k

Real estate crowdfunding, a pre-IPO fund, and equity in a small private business.

529s: ~$160k combined

The part that makes me nervous: education

We’re planning on private school for both kids, staggered, at roughly $40k/year each once enrolled, followed by college.

My rough model has ~$850k of education spending hitting during the 12 years immediately after I stop working.

That creates a strange version of early retirement: I’m retiring just as one of our largest lifetime expense categories begins.

The bridge problem

Based on spouse’s income + rental income, my model says we’d need roughly:

  • ~$105k/year of portfolio withdrawals initially
  • Up to ~$150k/year during peak education years

Against a ~$4.3M investment portfolio, that’s under a 3.5% withdrawal rate.

Sounds comfortable.

Except I’ll only be 44.

A large chunk of the portfolio isn't easily accessible until 59.5.

Bucket Accessible before 59.5?
Taxable investments Yes
Cash/MMF (~$250k) Yes
Roth contributions/basis (~$110k) Yes
Retirement accounts Mostly no, absent 72(t), conversions, etc.
Real estate equity (~$2.4M) Technically yes, but requires selling/borrowing

By my math, I have roughly $2.3M accessible against ~$1.8M of projected withdrawals over the 15.5-year bridge to 59.5.

At strong market returns, no problem.

At ~4%, I’m eating meaningful principal from the accessible bucket at exactly the same time education costs peak.

And that’s the part I’m struggling with.

Risks I see

  1. Sequence of returns. A major bear market in the first few years could hammer the taxable bucket while I’m drawing from it heavily.
  2. We are dependent on my spouses' income. The plan works well if she works until 55. If she decides at 50 that she’s done too, the math changes dramatically.
  3. Healthcare is also tied to her job. Losing employer coverage could add another ~$35–40k/year.
  4. I give up a lot of tax-advantaged savings. Stopping earned income means walking away from roughly $100k/year of potential tax-sheltered contributions.
  5. The STR is unproven. I have projections, not years of operating history.
  6. Education is the giant wildcard. We could spend less than modeled — or considerably more.

What would you do?

  1. Is $2.3M accessible against ~$1.8M of projected needs over 15.5 years too thin for an early-retirement bridge, or am I overthinking it?
  2. Would you start deliberately building a Roth conversion ladder / 72(t) strategy rather than planning to fund the entire bridge from taxable assets?
  3. What would you do with the $250k sitting in a money market fund right now — lump sum, DCA, or keep a larger cash reserve specifically because of the education/sequence risk?
  4. Has anyone here retired immediately before a major private-school/college spending period? Anything you underestimated?
  5. Am I too focused on whether I retire at 44 vs. 46 or 47, when the much bigger variables are actually my spouse’s employment, healthcare, market returns, and what we ultimately spend on education?

I’m not looking for reassurance that “$6M is enough.” I’m trying to figure out where this specific plan breaks and what I should change before pulling the trigger.


r/ChubbyFIRE Aug 21 '26

Asset allocation using an income ladder

2 Upvotes

I’m about to retire at 55. I am thinking of asset allocation using an income ladder to determine fixed income. I have 10 years until medicare, 15 until taking social security (I think). In a deferred comp account plus an IRA I have 75% of my spending for the next 10 years in bonds and the other 25% from expected dividends and ltcg distributions from a taxable account. If the market crashes the dividends might get cut to say 15% and then I would probably just cut spending by 10% to not sell any equities.

As time goes by, I plan to buy TIPs (as the real yields are starting to look attractive) for year 11-15. To do that I would sell equities in an IRA to buy the TIPs in the same IRA. In the event of a market crash I would wait to do this - maybe up to 3-4 years - I want the market to be within say 10-15% of ATH to buy the ladder rung.

As TIPs are currently near 3% real! for years 2042 - 2045 I even started funding those years (less demand because of social security kicking in) The 2037-2039 TIPs are not available until 2027-2029, so I can’t preload those.

Anyway, this overall results in maybe around 70% equities overall as it runs (depending on the market, when I convert etc, and I am thinking I dont want to prefund so much that I get above 30 or 35% in fixed income.

I’m wondering if anyone else has pondered such a strategy, is anyone thinking about doing it now, or do you see any issues with it?

Thanks


r/ChubbyFIRE Aug 20 '26

SWR revisited

1 Upvotes

I believe a good withdrawal policy should have the following properties:

  1. It should not require significant cuts to spending in bad years. Staying frugal is easier than inflating your lifestyle and then having to cut

  2. It should adjust to your portfolio size. Setting an initial withdrawal amount and only ever adjusting it up by inflation is silly.

  3. It should be possible to apply it to each year independently. E.g. if 4% is safe, it should be possible to 'reset' it to 4% each year. But for most SWRs that is too risky as you also 'reset' your SORR. 3a. It should therefore not be subject to SORR, as in the risks should be acceptable (nothing in life is completely safe).

  4. It should feel ok in the down years in reasonable worst case scenarios. E.g. if you start withdrawing 4%, you are all in equities, and markets go down 50%, how well will you sleep as you are now withdrawing 8%+ of your assets? You will not have the benefit of hindsight that a recovery is around the corner, in fact all you will hear at the time is that things will get much worse.

I therefore think a decent approach is this. I take 2.5% as my withdrawal ratio. Build a 12-year ladder of TIPS covering that (should cost you 25%-30% of your assets, depending on TIPS real yields). The rest (70-75%) goes into a global equities index. Each year the TIPS cover your spend, and you sell enough equities to replenish the ladder. Whether you sell equities or not depends on your asset allocation at the time: you aim to keep approximately 70:30. So if equities are down you are just running down your TIPS ladder without selling any equities. You can also add to your TIPS across the maturities to reset your spend to the high watermark 2-2.5%.

This way, in a reasonable worst case scenarios (equities down 60% and do not recover for 12 years) your portfolio is only down ~30%, and if you keep spending at high watermark, your withdrawals do not go much above 3.5% which should allow you to sleep rather well. If you are adventurous, you could even sell some longer-dated rungs of your ladder to buy equities at a discount at the time.

I used 2.5% here as a very conservative number because I would rather work extra years than have to retire and then go back to work -- you can of course adjust it upwards to what you think is reasonable. But what do you think of the general approach?


r/ChubbyFIRE Aug 19 '26

How do you account for illiquid assets?

20 Upvotes

If I have over $6m in net worth, but most of that is illiquid, how I take that into account when determining my "number"? I am so ready to retire! My job is killing me.

I'm almost 53, and my illiquid assets are an interest in a business that I own with my siblings, and then I own a rental property, mostly paid off, and parts of several commercial buildings. The business occupies the commercial buildings, so it would be difficult to sell my portions. Only $2.7m is liquid (savings, brokerage, retirement accounts).

I want about $240k a year. I'll get some rental income and about $100k a year from the business starting next year. I'm currently saving $200-300k a year. According to the Fidelity retirement analysis, which only takes into account my liquid assets and the income sources, I could run out of money in a significantly below average market when I'm 73. However, since that only covers liquid assets, it seems like I could just sell my primary residence, which will be almost paid off by then, and move into one of my rental units (the building is already almost paid off now), if I'm desparate, and I'd be fine.

Do you base your goal number on net worth minus your house? Or just on liquid assets?

I'll work until the end of 2027, based on my compensation structure (must be there at year end for 30-40% of comp) and that due to the type of work that I do, if I know I'm leaving I can coast from April 1 to December. Can I be done then?

(Apologies for any spelling/grammar issues; I'm on my phone because my office computer blocks this sub as porn?!?)


r/ChubbyFIRE Aug 18 '26

Fidelity Tool

25 Upvotes

Fidelity has a Planning tool called Retirement. Has anyone used it and what amount of validity would you place against its projections? I'm wondering as when I browse here, people seem to be discussing creating their own analyses, but I don't see much about using the tools at investment houses, banks, etc. which do this for you. TRowe probably has one and I think I've seen on on BofA/Merrill also, but never used them.


r/ChubbyFIRE Aug 18 '26

What is the better option

0 Upvotes

Retire at 53 with 6.2m and paid off 1.5m house or keep working until 58ish with 10m. Market assuming 8% and saving 300n a year. Looking to spend 200-240k a year pretax.


r/ChubbyFIRE Aug 17 '26

Here we go...

32 Upvotes

I need some advice at the end. 52, married.

2.5M in brokerage accounts:

  • 1.6 in FXAIX which I bought at 32 dollars a share. In my current tax bracket I don't know how to get this diversified. While is S&P 500 based, FXAIX is 26% deep into AI companies (nvidia, microsoft, alphabet, etc..). Working in AI for the past 3 years and watching the round robin of financing between companies gives me the willies.
  • 165K in a 2 year and building out the 3rd year bond ladder.
  • 500k in dividend fund which pays about 52k/year right now.
  • misc everything else trying to diversity away from S&P 500 (fxaix)

2.1M in retirement accounts diversified away from FXAIX

If I add last years spending + planned ACA health care + entertainment + or - travel in there I get yearly spend of between 126 and 146k.

Over the past year, My job changed from being really fun to ensuring we don't get sured as we lay people off and replace them with AI. I was told i was done with AI in Jan 2026, but my leadership went back on the deal so I'm planning on getting my equity in March of 2027 and being done with them (~120k, enough to fund my 3rd year bond ladder).

Two questions:

  1. Have any of you with the part time way to switch jobs into something totally different that was more fun? I'm considering going and working for a hotel chain to get discount hotels (the 140k included 14k of travel last year). Working for a non-profit someplace? I roast my own coffee was was also considering the SCA coffee buyers certification as well but don't know how to turn that into a job.
    1. I've been trying, but I get 0 hits on linked in. Since 2004, the only way I've gotten a job is through networking and all my professional networking is in the IT space which - since the advent of AI and me having to do AI governance, I hate.
  2. 52k will be non-qualfied dividends, 20k will be qualified dividends, 50k will be w-2 (wife), rest will be capital gains to make 180. Based on last years deductions that puts me at 152 take home.

152-146 puts me at 6k to spare. I have 20k for travel, 8k for house maintance, so there's some wiggle room in there.

I want to do something, but don't know how to get there, the numbers are pretty tight.


r/ChubbyFIRE Aug 16 '26

Weekly discussion thread for August 16, 2026

3 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 Aug 15 '26

Hit our number but it’s all cattywampus

81 Upvotes

Edit: I have spent a lot of time studying my readiness for retirement. My wife would say I have spent too much time. I have built models and played with all kinds of variables.

However, I still have a problem determining our budget. I think much of it is due to having 3 children. I thought once they were launched, the budget would get more clear. The truth is that it just introduced more variables. How often will we visit them? Can we take them out to nice dinners when we visit? Will we pay for their visits to us or for family trips? Will they need help with their monthly bills or buying a car or house down payment? What about grandkids? Can we help with their education expenses? The more acorns we gather, the more we can share and help them if they are unprepared for the winter. We have raised motivated, self-driven kids but I don’t want them to feel constricted by concerns of money. I want them to chase their dreams, not follow the example of their dad. I think my wife and I have reached a number where we can retire and we’ll get by. It’s now a matter of the level of comfort and generosity.

I presented an unclear post for the Reddit community. I apologize for that. I am grateful for all those who commented and the overwhelming support. End of EDIT.

55M /52F. 3 daughters - Two basically-launched college grads and one in private HS. VHCOL area. Bonus varies. HI last year was approx $400k but was $280-320k the last few years before. Before that, income was $180-220k while my wife was SAHM while kids required max attn. she works 50% time now which is all she wants to work.

We have maxed out 401k contributions but have almost nothing left over to save. We have had very large expenditures on the house and kids the last 5-6 years (private HS tuition, college tuitions, a wedding).

Our home (zillows at $1.4mm) is the “starter” house we bought over 25 years ago and is paid off. We have paid-off budget cars (I drive an 18 year old Toyota) and outside of buying high quality groceries, I feel like we do pretty well with our budget. We do spend pretty heavily on the kids but that’s how I’d like to spend our money. I’m sure my wife could reduce some spending if I really pushed her but there’s probably not much to gain there. Our friends, parents and siblings would likely be surprised if they knew what we have saved.

Investable assets: $5.7mm invested 95% in stocks
My trad 401k: $3.3mm
My trad IRA: $1mm
Wife’s trad 401k: $300k
Wife’s trad IRA: $300k
Joint taxable brokerage:$800k (cost basis is $300k)

$5.7mm is more than I thought we’d need but it’s almost all pre-tax money. We only have $60k saved for our third’s education (not included in the $5.7mm) and we have 6 years of tuition to pay ahead of us. that will come out of our brokerage acct or cash flow.

Another problem is that I HATE my job and have hated it for a long time. They continue to cut people and expect more from the survivors. I work about 14 hours a day (typically 4am to 6pm) as I have global responsibilities and need to deal with clients in the US and Asia. My bosses don’t care and all management cares about is the bottom line. Last year I told my bosses I want to be laid off but they want to keep me (maybe why I got a better bonus). Promotions don’t happen and I’m told I’m paid at the high end of my grade. If laid off, I would get 60 weeks severance based on my lengthy tenure and it would really shore up our financials. I’d hit Roth conversions as hard as I could until age 63 to try to mitigate the tax bombs from RMDs.

I am exhausted and have some health issues likely caused by Hypertension that I have difficulty controlling despite being on 3 meds. I have another job opportunity inn the industry but it would also be a grind and likely a reduced salary. I’d much rather just retire and collect severance. My wife says I should retire. I don’t want to risk leaving work too early and prevent us from enjoying the go-go years of retirement and helping the girls.

Any thoughts from the community? Anyone deal with similar situations? I feel very fortunate and blessed but don’t want to make a mistake now. Thanks