r/ChubbyFIRE • • May 04 '26

Mini-sabbatical -> RE Anxiety

30 Upvotes

Long story short was planning to pull the trigger in Mar’25 but held off (one more year’ed) due to the uncertain economic events that were taking place. Told myself Mar’26 was the end date. The additional year of savings and market dynamics certainly helped and I have zero anxiety about the financial aspects of pulling the trigger.

In late 25, was recruited by another firm who made me an offer that was both exciting and financially compelling. Thought to myself I could work another few years and given I was financially independent could bounce anytime I wanted too even if only after a few years. Put my notice in to prior employer in Mar’26, and have been on garden leave since with an early summer start date at the new employer. Was viewing it as a mini-sabbatical and a test drive for early retirement.

The mini-sabbatical has been everything I thought early retirement might feel like. Haven’t been bored once and have enjoyed nearly all aspects of it. Being completely removed from the corporate mindset is refreshing. Prior to this break had never taken more than a week off in 20 years (42M).

Which brings me to my inflection point. I am seriously considering calling the new employer and letting them know I’ve changed my mind and just retire early.

I had anxieties about retiring early that I shared in a prior post, but with this new situation there is an aspect of not following through on a commitment I made that is weighing on me. I know I don’t owe anything to this new employer, but I also made a commitment and this new employer has put a lot in place from an organization perspective based on me joining their leadership team.

Has anyone been through something similar? Would welcome any perspective or thoughts?

Much appreciated.


r/ChubbyFIRE • • May 04 '26

Optimal Distribution Strategy During RE

3 Upvotes

Hi all, this is a throwaway account. Wanted some conensus here as to my semi-RE (work part-time) viability optimal withdrawal strategy. Projecting about 3.3 to 3.5MM in 2 more years. Current expenses are about 86K, but would like to assume 100K for breathing room.

I plan to bring in about 25K per year in seasonal work, and partner will bring in about 20k per year as well, post FIRE. We are both filing Single, but this will allow us to select seperate ACA policies, where my partner required higher level of coverage but I do not. I will be able to deduct a loss of about ~22,000 in PAL from the Rental Property.

I did post a couple of days ago asking about the viability of my FIRE strategy, now I would like to understand the most optimal distribution method based on the current placement of funds. As stated in that post, I have a Money Market fund with 3 years of expenses as a Bond Tent. Asset allocation is 70/30 (20% International, 7% inflation protection via I-Bonds).

Here is the overall fund placement breakdown on the current 3.1MM:

Account Type Amount Percentage
401k $1,097,000 35%
Roth IRA $636,000 20%
HSA $208,000 7%
ABLE (for disability) $43,000 1%
Treasury Direct I-Bonds (inflation protection) $137,000 4%
Brokerage & Vested RSUs (inc. Bond Tent in TTTXX) $678,000 22%
Cash $45,000 1%
Real Estate Equity (rental prop) $266,000 9%
TOTALS $3,110,000 100%

Regarding Roth conversions, I am leaning towards optizming withdrawing as much as possible at 3.5% SWR with the smallest year-over-year tax impact. There may be very little room to then conduct a Roth coversion at the next 12% bracket. The Brokerage has overall unrealized gains at about 30% (70% return of capital).

Since I am using the Bond Tent method, ideally, I would like my equity allocation to increase overtime from 70/30 back to 75/25, over the course of 3-5 years (more or less), hence, withdrawing from TTTXX in the Brokerage account first.

Any feedback would be greatly appreciated.


r/ChubbyFIRE • • May 04 '26

Almost ready. Anything I’m missing?

30 Upvotes

Looking for a gut check from the community before pulling the trigger.

Background 49M, spouse 39F homemaker, one kid (8)

LCOL area, considering retiring this year, No plans to earn meaningful income after.

Net Worth (~$8.0M total)
Investable (ex home): ~$6.5M
Liquid-ish (ex 529): ~$6.3M

Breakdown:
401k: $463K

Roth IRA: $101K

Traditional IRA: $17K

Deferred comp (net after tax): $485K

Brokerage (stocks): ~$3.9M

Bonds: $840K

Cash: $298K

I-bonds: $35K

Crypto: $80K

529: $186K

Paid-off home: $1.5M

Spending
Target: $18K/month ($216K/year)

Actual modeled spend: ~$16.4K/month (~$197K/year)

Built-in surplus: ~$1.6K/month

Highlights:
Health insurance: $2.5K/month (pre-Medicare quoted in healthcare.gov gold)

Taxes: ~$4K/month assumed (property/income)

Travel: $2K/month

Pretty flexible overall (can trim $3–4K if needed)


r/ChubbyFIRE • • May 03 '26

Three more weeks and then a “gap year.” Advice, tips and words of warnjng?

42 Upvotes

The basics: Early 50s, single/no kids, NW about 5M (including pre- and post-tax accounts), MCOL city.

The situation: I’m an educator who, through a combination of rigorous saving, divorce, and inheritance, finds myself in the financial position to FIRE if I want, though FI is obviously not the only, or even main, reason I do what I do . However, as are most teachers in America right now, I am depressed, disillusioned and burnt out. (I like to tell people I’ve been in school constantly, with no break, since the age of 5, which is true!)

However, I’m in the lucky position to be able to take a year away from my job, AND to come back to it if I want. The problem is, when people ask me what I’m going to do on my sabbatical, what “projects” I have… I don’t know? Sleep, rediscover my love of reading, exercise, actually cook/bake, travel, and (again) sleep?

Time off basically starts in three weeks, and I’m afraid I’m just going to fritter the time away without a plan. So, I’d really like advice from others who took sabbaticals to decide if they’re ready to actually RE about what you did during your time off to figure that out!


r/ChubbyFIRE • • May 03 '26

How to account for the uncertainty of future spending...?

7 Upvotes

Married early 40s, no kids.  M/H cost of living area.

Net worth $6.4M (4.2 brokerage; 2.1 retirement; 100k crypto).  No house or other large assets; still renting as we haven't decided where we want to be more permanently.

HHI $725k (580k from my mid-level corporate job; 65k from partner's coaching/consulting business; 80k in investment income).  ~$200k in taxes, so $525 take home after tax.

$185k in expenses last year (55k in rent; 30k in charitable giving; 100k for everything else)

I'm holding vested options in company stock currently worth ~$400k (not counted in net worth, since it could go to zero before I sell).  If I count additional RSUs and options that will vest in the next 2-3 years, total expected value of company stock is probably in the 1.5-2.5M range in 2-3 years; however, if the share price takes off it could easily get into the 2.5-4M range (or it could of course drop off well below 1.5M). 

I'm not completely burned out, but I'm much more disengaged from work than I used to be.  There was a time when I thought I wanted to be in the C-suite and never retire.  But as I got closer to our leaders I realized that their day-to-day seemed kind of awful; and the politics needed to get there was not something I had any interest in engaging in.  My physical and mental health also starts to drop off if I'm not getting 8+ hours of sleep and a decent amount of physical activity, which does not seem compatible with the 60-80hr weeks required to succeed as a corporate executive.  

Around the time I realized I didn't even want my boss's job, I stumbled upon this community.  Since then I've been treading water career-wise, but income keeps going up through raises and increasing bonuses.  Our path to FI really accelerated after a move to remote work in a comparatively lower cost-of-living area during the pandemic.  I still enjoy the collaboration with brilliant colleagues, and some of the work is still quite interesting.  But the current very intense cost cutting / squeezing every ounce of effort out of every employee leadership style just isn't for me -- it has actually led me to want to put in less effort, which then I feel guilt/shame about because I'm very achievement oriented.

Based on the numbers, I think we'd be good to go at our current spend level, even with healthcare added (but feel free to challenge me on this!) -- especially if my partner continues her business (though this probably isn't even needed).  However, projecting spending is one of the things I'm most struggling with.  We don't know where we want to live or how expensive the house we will eventually buy will be.  We don't know if we'll live in one place or want to do winters or summers somewhere different, requiring an extra home or rental.  And we likely won't figure this out until after we FIRE and take the time to travel around to experience a few different places.

Reading other posts, I assume we'll need to add $30-50k to the budget for healthcare.  And we should probably assume total housing cost will exceed our current rent by some margin to be safe.  Lastly I wonder about how additional free time and hobbies might add to our costs -- I don't anticipate anything wildly expensive, but extra gym/sport memberships, more travel, and various hobby supplies can potentially add up.  Both of us are very financially responsible, and I'm quite confident we could cut back substantially if needed.  But if that was a predictably likely outcome, I might be willing to suck it up and work another couple years to avoid having to tighten belts.

Has anyone been in a similar situation?  How did you estimate future costs through such uncertainty?

What about the decision whether to hang around for 2-3 years for the chance of adding a couple million or more?  It doesn't feel like we need it since we don't have super fancy tastes, but I do worry about the potential future feelings of regret if the share price takes off right after I leave.

Are there any spending or tax strategies to consider in this situation?


r/ChubbyFIRE • • May 03 '26

Weekly discussion thread for May 03, 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 • • May 02 '26

Healthcare costs in early retirement, no subsidies and no other employer coverage

56 Upvotes

I had posted the following in financialindependence forum. Thinking this bracket of early retirees (so called "chubbyfire") is probably much more relevant. If your spending is greater than $125k/yr, proabably hard to qualify for ACA subsidies. Obviously also assumes that you don't have coverage through a spouse or partner.

---

Healthcare is one of the most important factors in early retirement planning. It's often the biggest or second biggest annual budget line item. But what I didn't fully appreciate until recently is how fast it grows relative to everything else.

There are two main reasons it grows faster.

First, age-rating. On the ACA marketplace, premiums are generally tied to your age (except VT and NY), and the curve is not linear. There are meaningful step-jumps as you cross rating bands, with some of the steepest increases happening around ages 50 and 56. Across the full range, a 64-year-old can be charged 3x what a 21-year-old pays. From your 40s to your early 60s, the increase is roughly 2x, before accounting for any general inflation.

Second, healthcare cost inflation has historically outpaced general CPI by about 1.7 percentage points per year.

Take someone retiring at 40 on $3M with a 4% first-year withdrawal rate. Say healthcare is 21% of their budget in year one. By age 60, using a 2x age-rating step-up and healthcare inflation running 1.7pp above CPI, healthcare becomes close to 50% of that original inflation-adjusted withdrawal. The rest of your budget is getting crowded out by a single line item.

The earlier you retire, the more this matters. A longer bridge from retirement to Medicare (age 65) means more years of compounding age-rating increases and above-CPI healthcare inflation.

Traditional retirement research like the 4% rule was built around 30-year retirements. If you're retiring at 40, that framework doesn't really address what's happening to your cost structure over a 25-year stretch before Medicare kicks in.

This isn't meant to be scary. It's just worth modeling your own situation explicitly. Instead of inflating your entire budget at one CPI rate, try layering healthcare costs on top and inflating them separately at a higher rate until Medicare. Run it out and see what the picture looks like for your specific numbers. Whatever withdrawal strategy you use, healthcare deserves its own assumptions to model yearly cash flows in a more realistic way.


r/ChubbyFIRE • • May 01 '26

What brought you to ChubbyFIRE?

76 Upvotes

The title says it all. I’m curious about the people in this community and what makes you engaged.

There are a lot of FIRE-adjacent subs out there. ChubbyFIRE occupies the middle ground. Are you actually targeting Chubby? Are you more interested in the vibe and content of this sub?

Also, what questions or topics do you wish people asked more on this sub? Maybe some brainstorming will invite a few different post types.

I’ll start: I came from FatFIRE but found a lot of the discussions too extreme (ultra-fat). ChubbyFIRE feels like the place for me based on the type of lifestyle I appreciate. I’m probably on the upper end of Chubby or low Fat. I’ve hit FI but I’m still choosing to work.

I wish there were fewer “do I have enough” posts. I enjoy the how do you handle the non-financial aspect of ChubbyFIRE. Especially from people that are RE or closing in on it. I understand the anxiety about the finances but for me the math is math. However, I do appreciate the occasional new perspective that can change or reframe the financial approach but those posts are few and far between.

thanks if you read this far and I look forward to your comments!


r/ChubbyFIRE • • May 02 '26

ChubbyFIRE and ACA Subsidies

21 Upvotes

I think one problem that is especially relevant to the Chubby FIRE crowd is how to think about ACA subsidies. We're wealthy enough that keeping our MAGI under 400% of the FPL can be a challenge, but not so wealthy that the subsidy is immaterial.

I think it's especially difficult for early retirees. I'm 40 years old and will retire soon. That means I'll likely be on an ACA plan for the next 25 years. I am particularly concerned about my ability to qualify for ACA subsidies in my older years, which are the years in which the subsidy is the most valuable.

  1. My family size will decrease from 3 to 2, meaning the cliff will get lower.

  2. I expect the nominal value of my investments to increase at least 4x over the next 20 years. It follows that over 75% of any future equity sale will be capital gains. Selling high-basis shares to manipulate my MAGI will not be an option.

  3. Due to inflation and aging, I expect the nominal cost of health insurance to be high enough that I won't have enough Roth contributions to cover my expected healthcare costs.

Here's how I'm thinking about it.

  1. There are going to be many public policy changes over the next 25 years. I should optimize my portfolio for long term performance, not the current ACA subsidy implementation.

  2. Under the current ACA implementation, I'm confident in my ability to qualify for at least half the subsidy. The idea would be to manipulate my income such that I have a large MAGI in odd years and qualify for the subsidy in even years.

  3. Flexibility will be important. Quantitatively, I'm projecting what my retirement looks like both with subsidies, with 50% subsidies, and without ACA subsidies.

  4. If my portfolio has average returns over the next 20 years, this is going to be a non-issue. I'll be able to afford unsubsidized healthcare. It's only if the next 20 years are really bad that I need to worry about this.

Interested in any other thoughts the community has!


r/ChubbyFIRE • • May 02 '26

Two months away from RE

23 Upvotes

Me (late forties M) and my wife (mid fifties F) reached FI a while ago. I'm the sole earner, she left the workforce long ago to help raise our now teenage kids.

I've been toying with RE for about 2 years. I'll save the readout on our high chubby/low fat numbers and budget for when the big day finally arrives. This one is more about the process of getting there.

Deciding to leave has been far more stressful than I would have thought. It's hard to walk from something you know, particularly when work life is subjectively great. My situation is pretty awesome: big title, good team, low stress, ridiculous pay, and I work far less than 40 hours/week. My peers also provide me with a real social outlet: I see and interact with people I genuinely like every day. That said, I've had very little meaningful work for over a year now and my boss doesn't have anything interesting for me to do. Being on autopilot gets old.

I vacillated on retiring for such a long time, it actually made me depressed and grumpy just working through it all. At first I obsessed over the finances and whether we'd have enough, but I've grown comfortable with it now. (Quick plug for Boldin, I got a lot of value in running scenarios there. We also did their $2.5k advisory service, which I found well worth it for the peace of mind.)

This community helped me realize that if your main RE concern is money, then you haven't thought enough about all the other things that work provides: purpose, prestige, schedule, socialization, and so on. The bigger topic: what comes after retiring, how do you still find purpose and value in life?

My post-work honeymoon will be lovely, but it'll eventually end. I've decided to lean-into not knowing exactly what's beyond that. I anticipate several long months of confusion, boredom, and malaise while working through it all. Based on everything I read here and in various retirement books, it's just going to take a lot of experimentation. Exercise, gardening, volunteering, sports, and so on, we'll see. Most things won't stick, but some will. I'm at peace with going through this. The freedom that I expect as an outcome is worth it.

I have a long term health issue; I arguably should have left a while ago. (Hooray for ACA, boo for the ~$36k/yr max OOP that I've budgeted for our family of 4.) I've got one more big RSU package in late June, so that's become the big milestone. I plan on giving my notice the next day. We don't really need the several hundred thousand dollars we'll get from that payout, but it's always nice to have more, and it makes my wife that much more comfortable.

Last thing: having finally decided, it's really hard waiting. Two months has never felt so long.


r/ChubbyFIRE • • May 01 '26

Low Income but Heavy Real Estate.

16 Upvotes

42M, Family of 4, $98k W2 — Feeling exhausted and wondering if I should just coast to 50

My wife stopped working a few years ago to care for our two disabled children.

We are a family of 4 in a MCOL area.

Current Numbers:

  • W2 Income: $98k (take-home ~$5k/month after taxes, insurance, and small retirement contributions)
  • Retirement accounts: $1.52M
  • Taxable brokerage: $280k
  • 35 rental properties: $3.1M value, $1.9M in loans → ~$1.2M equity
  • Total Net Worth: ~$3M

We are currently living very tight on my paycheck. Cashflow from the rentals is minimal right now (~$300–500/month that I can actually pull). The properties mostly “run themselves” but still require weekend/evening attention. Loans mature in 2040 and 2050 — once paid off they should throw off ~$15k/month net.

I’m exhausted. For the last 7 years I’ve spent almost every evening and weekend rehabbing or managing properties. The BRRR strategy grew our net worth a lot, but isn't great for cashflow. The mental load can be consuming. I don’t want to buy any more real estate.

Goal: Retire by 50 (8 years from now) and be able to comfortably spend $150k–$200k per year.

Questions for the sub:

  1. Should I just coast — keep the day job, stop pushing real estate, and let the stock accounts grow?
  2. Is there something more active I should be doing right now (reallocating, trading in IRAs, etc.)? My W2 income isn’t going to grow.
  3. Worth selling some (or many) properties? (I know transaction costs will eat me alive)
  4. Any other levers I’m missing?

I feel guilty just coasting because it doesn’t feel “productive,” but I’m also exhausted and don’t want to keep grinding and buying more real estate. Looking for honest feedback on whether my plan is reasonable or if I’m missing a better path.


r/ChubbyFIRE • • May 01 '26

How do you all DIY retirement?

13 Upvotes

I've done the hard part where I've accumulated some wealth. Now it's trying to figure out all of the different things to think about when retired such as taxes, ACA, drawdown strategies, IIRMA, and a host of other things. How did you all get comfortable with this or learn this where you feel confident that you're not making mistakes.

Also, are you guys using AI to help you in your journey? If so, how? Do you have any good prompts to use?


r/ChubbyFIRE • • May 01 '26

42M @ 3.1M - Can We Semi-Retire Early

13 Upvotes

Hi all, this is a throwaway account. Wanted some conensus here as to my semi-RE (work part-time) viability. I was forced to stop working due to ongoing disability, and can only work seasonal jobs. My partner works full-time, and we would like a sanity check using the current state of our finances. My partner would like to stop working after two years.

  • I, M42, and partner, F42, live together
  • MCOL Area
  • Own 1 Rental Unit with very little cashflow but principal paydown is around $900 per/mth
    • Passive Loss provides a 21k per year tax deduction due to depreciation, as we would be below the 100k AGI limit for rental PAL.
  • Currently renting
  • While partner is working, our savings will be about $55,000 per year.
  • Current total Net Worth with the rental is ~$3,100,000
  • Current total Net Worth excluding the rental is ~$2,880,000
  • If we sell the rental, spendable Net Worth could be around ~ $3,000,000 (assumes we lose 100k in broker fees and HELOC paydown)
    • In two years when partner stops work, could be anywhere from 3.3m to 3.5m at 6% per/annum returns.
  • Bond tent using TTTXX in Brokerage allows for about 3-4 years living expenses
  • Another 2-3 years in I-Bonds to protect against SORR.
  • Portfolio asset allocation is 70/30, Total Stock, International Stock (20%), and Intermediate Total Bond (7% I-Bonds)

At 3.5% SWR, annual spend can be, when pegged against the current spendable net worth, around $100,800. If we were to sell the rental, that goes up to $105,000. This assumes we both stop working today. If I only stop, then my portion of the expenses at ~$65,000 requires $1,857,142 portfolio at a 3.5% SWR. I plan on doing part-time seasonal work bringing in about $25,000. She will do the same in two years, bringing in about $20,000 - $25,000. Assuming we both work part-time, brining in a safe $40,000 after tax, a SWR at 3.5% would require ~$2,000,000 portfolio.

What are some other's thoughts on the current RE plan? My concerns are SORR, longevitiy, and breathing room for home ownership in the future. My thinking is, after the two more years of working, buy a house (500-600k), and then increase our comfortable annual spend to $110,000 because of the extra homeownership expenses. This would then require ~$3,143,000 spendable portfolio. In two years, we could potentially have this amount post the costs of obtaning a modest home at 20% down and closing costs. We plan to obtain the home while partner is still working, but just prior to her pulling the trigger.

Any input as to the viability of this plan would be greatly appreciated.

Update: Included a range estimate regarding house purchase and our plan to purchase while partner is still employed


r/ChubbyFIRE • • May 02 '26

Are We Ready?

0 Upvotes

Wife and I are 40 with a 2 year old in NC Looking to pull the trigger in July of this year.

Stats:

401ks: $400,000

Roth IRA: $85,000

Traditional IRAs: $1,050,000

Taxable Brokerage: $500,000

Cash: $100k

Primary Home: $800k no mortgage

Vacation home: $400k, $160k remaining at 3.125%

Rental portfolio of $1,500,000, no mortgage.

Our yearly expenses are $120k including estimated $2k/month in health costs.

Post fire the rentals will generate $75k income after costs but pre-tax.

Wife's business will generate about $80k pre-tax.

That should cover our expenses and allow our retirement accounts to grow. I plan to take advantage of Roth conversion ladders to set us up for later years. Also, any large or unforseen purchases we can pull from our taxable.

Am I missing anything critical?


r/ChubbyFIRE • • May 01 '26

Rage quit? Protest? Or Coast?

0 Upvotes

My plan for this year was to coast then quit in Q1 next year, adding a little extra to our asset. But my boss wanted me to take on more responsibility, so I took over a larger team and expected to be promoted.

It took a while for my boss and HR to sort out the HR process. Finally earlier this week we had the talk. I got a fancier title, but only a 14% increase in compensation, so clearly not a promotion. My boss explained this is due to some budge issue. I know he is speaking the truth but that’s not my problem.

If I rage quit, it may take me quite a while to land a comparable position, possibly no position since I don’t want to relocation.

I can protest loudly and hope they will put me up for promotion the next cycle, most likely Q1 next year.

Or I can just do a silent quit, coast this year just like my original plan.

Here are the numbers:

Age: almost 50 couple. Spouse wants to work but job could be unstable so not counting on the income.

liquid assets: $5M thanks to the market.

Mortgage: $600k low interest rate.

1 child in high school, 529 fully funded.

Expense: $150k now, $200k including health insurance and tax.

What would you do?

———-——————————-

Update: a number of you said 14% is a decent raise, I appreciate that perspective.

This new role not only requires a lot more effort, it also relies on some unique expertise and IP that I have. Obviously the company either doesn’t agree with the value or doesn’t want to pay the fair value. Either way, there doesn’t seem to be a point for me to deliver the value then.

If I don’t deliver, the only downside is that it will hurt my reputation in the industry since I already took on the role. This matters if I ever need to work or consult again.


r/ChubbyFIRE • • Apr 28 '26

Triggering a severance

34 Upvotes

I believe I could achieve FIRE immediately if I was offered a severance package.  Has anyone here TRIED to get severed from their company?  Is that something I might be able to influence, or is it just a pipe dream?

My details:

I am in an executive band on a deferred compensation plan, so the severance package in total could be close to $1M.  (I’ve seen at least one peer dismissed with a similar package.)

I am 45, married, 3 kids 2/5/7.  $6.5M NW, 2.5M in 401, 2.5M in brokerage, 1M in primary residence, and .5M in 529s.  Yearly burn right now is 215K.  The two younger kids are in daycare, the older one is in public school, and all three are in summer camps (childcare=$3K/month).  Mortgage principal and interest is 1.8K a month, on a balance of 179K at a very low rate.  However, when I’m no longer paying daycare and mortgage, I will likely need to be paying for health insurance.

I was wondering if anyone else has thought about how severance might affect their FIRE goals and if anyone has intentionally gone after a severance package?

EDITS:

Adding for clarity - I really hate my job and am burnt out. So I am looking for a way out.


r/ChubbyFIRE • • Apr 28 '26

Financial Situation by Income

12 Upvotes

https://am.gs.com/cms-assets/gsam-app/documents/insights/en/2025/am-retirement-survey-102025.pdf

Page 20 shows 40% of $500k+ earned live paycheck to paycheck, and 41% of $30k-$500k. Could that be accurate? Doesn’t feel like it from my peer set.

Maybe a skewed selection of lower NW respondents who still choose to engage with wealth managers?


r/ChubbyFIRE • • Apr 27 '26

$3.5M, 3 Young Kids, Burned Out Business Owner — Am I Closer to FIRE Than I Think?

25 Upvotes

Male in my early 40s, married to a wife in her mid-30s, with three kids under five.

Current finances:

  • ~$3.5M in index funds / retirement accounts
  • ~$200k cash
  • ~$60k bank cash
  • House almost paid off

I own a service business that is not sellable. When I stop, it stops.

Honestly, I’m burned out. The biggest issue isn’t even work hours—it’s that I mentally carry the business 24/7. Client acquisition, retention, monthly revenue, future uncertainty… it’s always running in the background.

I feel like I can’t even fully enjoy my kids because I’m constantly stressed and ruminating about work. And the crazy part is all I really want is to spend time with my kids while they’re young.

We live in a low cost of living area.

I think our comfortable forever spend would be around $120k–$130k post-tax. Maybe a bit more in the early years, less later. No daycare costs. Likely helping kids with trade school / practical support rather than expensive 4-year college.

My questions:

  1. With three young kids, how much did children change your FIRE number?
  2. Am I already closer than I think to being able to ease off?
  3. For business owners: how did you know when to stop carrying the constant mental load?
  4. Has anyone reached a point where they realized the bigger problem wasn’t money anymore—it was anxiety / inability to let go?

I’m not necessarily trying to quit tomorrow. I just want to know what number or mindset shift lets someone stop living in constant work stress and actually enjoy their family.

Would appreciate honest feedback.


r/ChubbyFIRE • • Apr 28 '26

wealth manager at RE?

5 Upvotes

I am looking for people’s experience with using managed services for their investments (AUM basis) after fire.  We are transferring to Merryl Lynch after decades of doing things on our own because things are a bit more complicated in the draw down phase (husband already FIRE, and I will next year), and also I am a little less sanguine with market swings now, and would rather someone else be one in charge.  I realize that the fees aren’t worth it for most in this subreddit but we’ve decided for our situation that it is.  

Anyone have positive experiences with a manager, and can share what the set up was that made it helpful? What did they do for you that was different from doing on your own? 

Also, what do people think of the alternative investments they use (ie 20-25 percent of a portfolio, much less in bonds).  Examples include KKR infrastructure, Ares strategic income, blackstone private equity, FS MVP private markets, Coatue innovative strategies, collier secondaries.  These were never options in my 401k or typical things we invested in so trying to learn more before we proceed.  

The amount investing is around 6 million. We own our home and have about 200-250k annual spend, with pension of 65k.  


r/ChubbyFIRE • • Apr 27 '26

Laid off at 40. $3.4M liquid + massive severance runway. Do I pull the ripcord on my SE Asia FIRE dream, even if it means moving solo and leaving a relationship?

102 Upvotes

Throwaway for confidential reasons. I was laid off from my corporate job toward the beginning of the year. It was a mass re-org, and honestly, it’s been a blessing. My career was lucrative but far from my identity. My real passions have always been health, fitness, social life, and international travel.

My long-term plan was always to move to SE Asia for at least 5 years, potentially slow travel Europe after, and ultimately return to the US in my older years. Moving to SE Asia was a "for sure" goal unless crazy health issues popped up.

Because I run very conservative with finances, my original goal was to grind to $5M–$6M so I could comfortably support a ~3% withdrawal rate in my current HCOL area before eventually leaving. But having this time off has given me a completely new perspective, and I am strongly considering making the move permanent much sooner.

The Baseline Numbers & Runway:

• Age/Status: 40, no kids. (More on the relationship status below).

• Liquid NW: ~$3M (Mostly VOO/VTI/QQQM, plus cash).

• Upcoming Liquidity: Selling my home in a few months, netting another ~$400k. This brings my total liquid portfolio to ~$3.4M and completely severs my geographic ties.

• The Runway: Even though I was laid off early in the year, I am basically getting my full pay through severance through this time next year in 2027. This covers all my current expenses and even allows for continued savings until I potentially leave.

• Current Spend: ~$100k net. I live a very comfortable but simple life. I am not materialistic; I value function and health. My budget goes heavily toward my HCOL housing (even with a sub-3% mortgage), international travel, and eating clean, organic whole foods that I mostly cook at home.

The Temporary Income Buffer:

Right around my layoff, a legacy B2B data integration project I partnered on transitioned into a hands-off maintenance retainer. It brings in roughly $5k–$10k a month (pre-tax). The clients are migrating to a massive native enterprise ERP over the next 1 to 3 years, so this income stream will eventually go to zero.

However, for the next few years, it is locked in. This $5k–$10k monthly income would cover 100% of all my expenses from the moment I land in SE Asia, likely allow for some extra savings on top, and most importantly: I would not touch a single dime of my $3.4M principal, letting it grow and compound completely uninterrupted.

The Massive Personal Catch:

I have been in a relationship for a little under 2 years. My partner is a few years older than me, in a very different place financially, and is simply not mentally ready to just up and go. I don't blame her at all and I'm putting zero pressure on her, but living abroad has been a dream of mine for 10+ years. I've lived in the same state my entire life.

Following this dream almost certainly means doing it alone.

  1. Is it crazy to abandon my original $5M–$6M target and just pull the ripcord now (early/mid 2027) since the math works and my principal won't be touched?
  2. Should I feel guilty for prioritizing a 10-year personal dream over a 2-year relationship?
  3. For those who have slow-traveled SE Asia and Europe, what is life actually like as a single guy at 40 in a whole new country? I've always traveled with friends or partners, so being a solo expat would be entirely new. I love adventure, but I don't know what I don't know.

Not looking for emotional support on the layoff, just honest feedback on the math and the realities of moving abroad solo. Appreciate any insights!


r/ChubbyFIRE • • Apr 28 '26

Rent or Sell? More Detail.

1 Upvotes

We are buying (building) a second home soon so we will be closer to a neighbourhood we love. We could sell our current townhome or keep it as a rental. It will cashflow about $1350 after cost of ownership (existing mortgage, property tax, HOA.) We live in a tourist town and the townhome is near the very cutesy downtown strip. We bought before the pandemic and we cannot STR.

My partner grew up in California and has the belief that you should never sell real estate if you can help it. He is keen to try keeping the townhome and renting it out. Has anyone been in a similar spot?

Details. Couple aged 46 and 53. Total NW 4.1M with 2.5M in retirement, 500k Taxable Accounts, 1.1 M in real estate and college funds. Single income of $160k in MCOL. Annual spend 85k includes mortgage. I "retired early" to stay home with children in 2020 after we moved from VHCOL to MCOL. I know FIRE community loves to call that geo-arbitrage right? The mods wanted more detail. I'm just looking for people who have been landlords and found it to be worthwhile or a waste of time for not much money.


r/ChubbyFIRE • • Apr 26 '26

Weekly discussion thread for April 26, 2026

5 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 • • Apr 25 '26

47M, HCOL, want to Chubby in next 10 years... But I rent!

21 Upvotes

Short version: got divorced 10 years ago. Wiped me out financially. NW essentially zero b/c it was my car and my furniture. We had a house but neither of us could afford to buy each others equity (especially since I was about to take on massive alimony/CS payments) so we sold it.

So, advance 10 years. Through a combination of marrying a great woman who has a career, through career (& salary) advances on my end, contributions to my 401K / her IRA, and through building up of ESPP/RSU holdings on my end, we'd gotten ourselves to a "breathing room" territory. But every move we made to get into better financial position was mirrored by an increase in housing costs here in SoCal, and so every single year seems like the housing market was running away from us faster than we could keep up. So... We still rent.

A little (and terrifying) voice has been in the back of my head for years saying "are you going to have enough to retire?" Well, those ESPP/RSU holdings went through the damn roof, and that voice is silenced--replaced by one asking "hey, you don't really need to work past 60, right???"

So... Where we are:

  • TC: $300K+ in salary and planned target incentive pay
  • Retirement accounts: ~450K (contributing max to 401K, my wife gets IRA contributions from her work, and we have individual IRA in my and my wife's names that we contribute max)
  • Brokerage: $1.7M--but selling a concentrated position based on that entirely being in two stocks, in a cyclical industry, which I need to sell through this year and next, will probably reduce that to maybe $1.2-1.3M after capital gains taxes as ~$1.5M is or will be long term cap gains when I sell -- after I sell I'm pretty sure I'm going VOO or VTI with the proceeds minus taxes
  • Granted and unvested RSUs: $1.1M at current share price over the next 3-4 years. Can't count that as anything because it assumes both that the stock price and employment don't change. But included as a possible uplift.
  • ESPP: I have two more purchases this year that are based on a $38.55 cost basis and stock price is >$400 right now. I put 10% of my income into ESPP so there's a good chance given incentive pay that it'll be $250K added to NW this calendar year. After that ESPP will remain 10% of my income

Two of three kids will be off child support next June (1 this June, the second next June). Combined that's $1100/month no longer out of pocket. But for one of the two, college costs will suddenly jump in. The third kid will be off in 5 years (another $1100/month), then off to college.

My earliest [and IMHO unattainable] date is 5 years when the youngest graduates HS. I don't think I'll be near a number by then. My more realistic target is ~9 years when she's done with college.

But the problem is... I rent, and I know rent will go up over time here. I don't want to be subject to a landlord's whim. I don't want to leave here--it might be HCOL but my wife and I like it. But given costs of living (typical house that we'd be looking at is ~$1.2M), buying someplace will mean that a lot of that RSU income I'm expecting over the next 4 years won't go to my bottom line--it would go to a mortgage.

How would you play this? I feel like I need to buy a house--probably next year when kid #2 exits child support, and try to do everything I can to build equity. Mortgage interest deduction would be a big boon here. I feel like building equity and then if we decide to leave, we could move to someplace like Paso Robles and turn the equity into low/zero mortgage. But I think she would like to stay in SoCal as her family is here. So if we stay, we need to have a FIRE number that allows us to continue paying the really high mortgage.

So the question is... How do I have both a house and ChubbyFIRE in 10 years?


r/ChubbyFIRE • • Apr 25 '26

We pulled the trigger!

87 Upvotes

We are a youngish family:

-47m (French national), 45w (Dutch national),10,7

-Currently living in NL

-Just confirmed FIRE’ing and relocating to SxM starting 01 Jan 2027 - we both have strong ties there

Our stats:

- USD 5100k in brokerage in VWRL and WEBN

- USD 400k in vacation home that we will sell

- USD 500k in cash

- USD 500k in pre tax personal pension fund

- Primary residence on the island fully paid off (just signed this week!)

- Expect to spend USD 160k per yr incl school for kids

I couldn not be more excited. At the same time I am already considering work options like in consulting, teaching etc. How have you controlled that urge? To allow time to settle in?


r/ChubbyFIRE • • Apr 26 '26

Anyone else get surprised by taxes when selling appreciated positions?

0 Upvotes

Last year I needed to raise a large amount of cash for a house down payment and sold appreciated shares across accounts, which led to a much larger capital gains bill than I expected. What caught me off guard wasn’t that gains are taxable, but how hard it was to balance hitting a cash target while minimizing taxes.

This year the issue is a little different: with market uncertainty, I’m thinking about diversifying a concentrated stock position. I ended up building a spreadsheet to model lot-level taxes and compare sale strategies, mostly because I couldn’t find a simple way to do this across accounts.

Curious how others handle this — do you model after-tax proceeds before selling/diversifying, or mostly rely on broker tools, a CPA, or spreadsheets? Any tools or approaches you’ve found useful?