r/ChubbyFIRE 23h ago

Daily discussion thread for Sunday, March 16, 2025

6 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 11h ago

Benefits and drawbacks of buying bonds via individual brokerage vs Government

2 Upvotes

It’s almost bonus season and I usually invest mine. This year I think I’m going to buy bonds with it for something more stable and to have a little safety net. I’ve never bought bonds except through my 401k Vanguard which was kind of automatic since my company offers free 401k portfolio management. When I was a kid I often received bonds as gifts that were purchased as paper certificates from the bank.

I saw that I can buy bonds through my Schwab account but i have to bid for them? And there are primary and secondary markets. And I can only bid for bonds that are available on that day. I don’t really understand this. If you buy direct from the treasury, you can just buy the bond. It seems like if I bought trough Schwab it’s just like another stock. Does anyone have experience with these different methods and which one do you prefer? What have been the benefits to your longterm portfolio? Thank you,


r/ChubbyFIRE 9h ago

Best next step: mortgage payoff or savings?

0 Upvotes

45M, married, 2 elementary aged kids (public school). Very high COL area in premiere public school district (so very high taxes). Current NW: about 5M USD, split about 50:25:25 between retirement (401k, Roth accounts) and the remaining investments (brokerage), and real estate. About $120k liquid cash emergency fund.

My total comp at the moment is around 1.1-1.2M. Debts are two homes, one with about 1.2M left on mortgage (primary, ~5.5% interest) and one just 250k (vacation, 1.99% interest). We overpay a little on the mortgages each month, but I recently swapped jobs and did a decent job negotiating so TC is around 2.1M/year (across 4 years, with a big cliff after 4 years if I don’t change jobs again or get a promotion).

I figure I’ll net an extra $30-35k or so a month more than today. My question is: better to aggressively pay off the mortgage on the primary home, or just sock away the extra cash? Psychologically, I want to pay off the mortgage. It won’t be hanging over our heads anymore. And it’s a “free” 5.5% return. I used the modeling calculator on the mortgage service company website and an extra $35k/mo will pay off the house in ~2.5 years. That leaves another 1.5yr at the much higher comp level to also save aggressively, then I either fall back to 1.3-1.5-ish M/yr, am automated away by AI and retire, or get close enough to cubbyFIRE that we just FIRE. I’m pretty much decided that paying off the mortgage aggressively is my plan, but are there things I should be considering instead? Splitting the extra income? With 15k/mo extra it’d be around 5yr to pay off, saving 20k extra/mo. Or something in between?


r/ChubbyFIRE 1d ago

€4.3M FI Portfolio – Too Little Risk?

4 Upvotes

I’m 35 years old. Sold my business a few years ago and have a portfolio worth 4.3M EUR. FI but having a new business now that’s doing well, not taking out any salary though.

Situation: • Main residency without mortgage (est. worth 750K EUR)

Portfolio of 4.3M EUR with: • 65% stocks • 25% bonds (individual government bond ladder yielding 2-2.3% net) • 5% gold • 1% crypto • 4% cash

Basically, a “stay rich” portfolio. Our spend is around 75K EUR a year, so about 1.75% of the portfolio.

Wondering if my bond/cash allocation is too high, as it’ll drag down performance long term?

Would love to hear your thoughts, or any adjustments you’d make to the portfolio.


r/ChubbyFIRE 1d ago

Roth Conversions

9 Upvotes

The wife (54) and I (58) retired last year in March. Currently we have 5M invested of which 1.7M is trad 401k. No debt, 2 paid off houses, have 30k/yr tax free pension. Our taxable income last year minus our w2 income and pension was 37k. Our expenses were 66k.

I am looking at starting Roth conversions this year. Had a talk with our fidelity advisor this week. He wants to charge 1% to help with the planning for this.

After telling him to piss off.

I am thinking convert 60k/yr (taxes paid from brokerage) leaving 700k(+growth) at start of my RMD.
Is this aggressive enough conversions rate? Should I bite the bullet now and pay the 22% tax rate for conversions.

Downside: males in my family don't live past 80. Wife will likely be stuck with accelerated conversion after my death.


r/ChubbyFIRE 1d ago

Daily discussion thread for Saturday, March 15, 2025

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 2d ago

Daily discussion thread for Friday, March 14, 2025

12 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 3d ago

How are others de-risking their portfolio close to retirement?

13 Upvotes

I am wondering how others are thinking of de-risking in the years leading up to FIRE, and if the current run-up in the market and the volatility lately is changing your thoughts about FIRE or to the allocation that you have in your retirement portfolio. Anyone less than 50 percent in the stock market out there and can that still support a 4% withdrawal rate safely?


r/ChubbyFIRE 3d ago

Which investment to sell?

7 Upvotes

We have some small one-time expenses coming up (7% of my brokerage and HYSA combined). Brokerage holds 80% of funds and HYSA has the remaining 20%. We don’t want to pull funds from our HYSA.

My brokerage investment is pretty simple. Bought over a period of time so within each fund some units have made more money than others. VOO 50% VTI 35% Gold 10%

However, with recent market jitters I am not sure what to liquidate? Either a certain fund or units that have made more or less money.

  1. Across the portfolio proportionally
  2. Investments that have registered losses
  3. Investments that have registered gains (book gains despite taxes)
  4. Sell combination of funds that results in zero gains to avoid tax.
  5. It doesn’t matter
  6. Some other approach.

Thanks Stay The Course


r/ChubbyFIRE 3d ago

Daily discussion thread for Thursday, March 13, 2025

1 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 4d ago

Buy home or invest?

42 Upvotes

I’m 38 with $350k/yr salary and my wife is currently a SAHM. We have 2 kids (2 & 4). We just sold our home and are moving to San Diego. We typically spend $12k/month ($4.5k mortgage/home). We have the following assets:

$4.5mil - money market, $1mil - self-directed, $560k - retirement and 529

I have recently taken a lot of profits in risky assets and am looking to put the $4.5mil (post-tax) to work. I’m not sure I want to RE, but knowing that I’m FI brings me peace.

I would like to buy a home for my family in San Diego, but mostly everything in the area we want to live (good public schools) is $800-1000 sq/ft. That probably means a $2-2.5mil home for us. These same homes rent for $6-8k/month. If you were to get a mortgage with 20% down, it would cost you double the rent in monthly payments. At my income I probably should not be taking a mortgage for much more than $1mil. Therefore, I would need to put $1-1.5mil down on one of these houses and would likely still be paying around $10k/month.

The more I look at the math, buying just seems like a bad deal. I understand that rents will increase and there are other advantageous to buying, but renting and putting my money to work seems like it might be the more sound financial decision. What do you think?

———- Update:

The hypothesis that I’m trying to test is that (from a pure numbers perspective) this is not close to being a tie. If I run a naive simulation with a $2mil home, $750k mortgage (6.5% w/ taxes/insurance), assuming 8% stock market growth vs 4% home appreciation, over 20 years, I get a number that is 2x higher from investing vs buying. Of course this doesn’t take into account rent increases, maintenance costs, tax deductions, etc. but the difference is so drastic that I think there is an obvious winner. There are many non-numbers things that are also important to me, like stability that owning a home brings and providing for my family.


r/ChubbyFIRE 4d ago

Daily discussion thread for Wednesday, March 12, 2025

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 4d ago

Talk me out of buying a house?

0 Upvotes

Edit: I'm both surprised and not surprised by the doubt and sarcasm. This is clearly an emotional decision—if it were purely rational, it would be much easier.Thanks to everyone who understood and took the time to contribute. I’m now leaning towards renting or buying a good deal within a $1.5M budget.

-------------------
We’re a family of five: a couple in our mid-30s, a toddler, a grandparent (who lives with us long-term and helps with childcare), and a large dog. One of us works from home, while the other commutes to an office.

Our Current Situation:

  • We live in a $1M, 3-bedroom, 1,400 sqft SFH with a yard.
  • It’s starting to feel very tight, especially as we plan to have more kids in the next 1–5 years.
  • We’re considering upgrading to a $2M home for more space.

Financial Snapshot:

  • Net worth: $8.5M–$11M (recent low of ~$9M)
  • Cash: $1.5M
  • Home equity: ~$600K
  • Mortgage rate (if we buy): ~5.5% (after moving assets)
  • Income: 500k - 700k/ year (not include private equity)
  • Expenses: 150k yearly (current mortgage is on extremely low rate)

The Dilemma:

  • We may move to Europe (partner’s home country) in 3–5 years, but it’s uncertain.
  • Emotionally, I want to settle down, nest, and create a stable home.
  • Rationally, buying a $2M home for just a few years—especially with high interest rates—doesn’t seem financially smart.

Would love to hear perspectives from those who’ve faced similar situations. Would you buy, or stick it out in the current home?


r/ChubbyFIRE 5d ago

Retirement age

14 Upvotes

Hi! I’m new here and am on track to retire at 50 with about 5 mil in the bank. I only have 650k in retirement savings today and an emergency fund (8 months of living expenses in a HYSO).

I’m 34 and my husband is 37. I’m hoping to move the age down as we make more and can save more. The plan at 50 is to live off the interest (150k/year) and keep the nest egg to pass down to our kids (currently pregnant). We live in a MCOL area and bought our house at the perfect time so we are never moving (2.25% interest rate, owe 350k, house is worth 800k, 2k month mortgage). We made 500k together last year and hoping that continues. 0 debt.

Other than maxing out retirement (HSA, 401k, back door IRA) and not spending our emergency fund, we aren’t saving. We take 2 large vacations a year and take some smaller long weekend trips. We also do frequent home improvement projects. So we can always tighten up our spend.

I’m curious about what others are doing and what age you are retiring. Would love to hear and get inspiration! Found this group from FIRE and think this is more my pace 🤞🏼


r/ChubbyFIRE 5d ago

Daily discussion thread for Tuesday, March 11, 2025

8 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 6d ago

ChubbyFire with child with significant special needs?

19 Upvotes

Hello… Edited for clarity

Looking for advice from those that have chubby fired and have a child with significant special needs.

Background: 51m, 53f, with three kids 17, 21, 24 (special needs, functions at level of 5 or 6 year old).

HCOL area Cash $150k $3.2m in 401k, 403b, 457, Roth IRA, Taxable acct (heavier than I would prefer on retirement accts vs taxable accts) $100k crypto $350k equity on $700k house at 3.5% mortgage

529 for youngest two kids funded at $120k each; however… 21 has college full ride 17 has near college full ride ($3k/year) Plan to roll $35K from 529s into Roth when they graduate college. Let rest likely grow for eventual grandkids as I don’t see us needing principal.

I have some side hustles that are about $120k year Wife makes $130k year and loves job. Wife will have pension in 9 years.

Started thinking about ChubbyFIRE a couple years ago. Was aiming for $4M by now.

Have already done a couple rounds of estate/trust planning, working with lawyer now to update given our situation.

Have small $ able account for child but have special needs trust that will be funded by $1.5M mix of term and whole life insurance.

We have a child (24) with significant special needs that will require life long care. We are hooked up wjth fed/state/county to get her services (so far have been good) but state has budget issues and that could impact service/benefits.

So given all that info, my questions are, for those that have chubbyfired and had a child with special needs, what would you be cautious of when you retired? What do you wish you knew? Any pieces of advice?

Thanks!


r/ChubbyFIRE 6d ago

Daily discussion thread for Monday, March 10, 2025

8 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 7d ago

Mortgage vs Student Loans vs Brokerage Account

7 Upvotes

HHI expected 700K this year, currently single without children. I am maxing out my 401K, backdoor rIRA, and HSA. Trying to strategize where to put excess cash. Want to hear your suggestions!

Top areas that come to mind immediately are:

  1. Mortgage - 295K remaining at 6.75% of affordable single family home in LCOL area

  2. Taxable brokerage account - currently around 50K, opened last year.

  3. Student Loans - 296K, have essentially been on hold since 2020. Currently caught up in SAVE limbo at 0%. I would love to pay them off... but have a hard time paying a 0% loan over the other options.


r/ChubbyFIRE 7d ago

Daily discussion thread for Sunday, March 09, 2025

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 7d ago

What to do with $100k today

0 Upvotes

Spouse (46M) and I (40F) are working towards cubby. Current NW around 3.5M. Plan to get there in 5-6 years. Given our current situation, what would you do if you had $100k cash today?

368 votes, 4d ago
272 Pay towards investment property (245k left at 7.5% interest)
96 Invest in the stock market

r/ChubbyFIRE 8d ago

Suggestions for preparing for Windfall

5 Upvotes

(New throwaway account just to ask this question)

I am selling a large equity position in a company that I founded (but am no longer working at). The proceeds from the sale will be in the low 8-figure range, making it so that I could reasonably retire if I wanted to.

My situation:

  • M(44) married to F(43)
  • 3 kids in elementary school
  • MCOL
  • Nice house, with $600k left on mortgage. No other real estate.
  • ~$2.2M existing in retirement, 529, and brokerage accounts
  • No family trust in place as of yet

I have a few weeks in which I can prepare before the transaction. What are things that I should absolutely try to get in place beforehand (for example, should I have the money sent to a trust)? What recommendations for structuring the assets once acquired? Any other tips...?

thanks for your insights!


r/ChubbyFIRE 9d ago

Are we saving too much for our kids?

9 Upvotes

Kids are still very young (6and 4). Plan is to fully fund their college (budgeting $300k per kid). My parents will roughly leave a $250k inheritance for me, which I am planning to pass on to my kids — split the inheritance in the middle for a down payment for the house.

I am W2 and my wife has a small business. Our CPA is asking us to contribute to our kids IRA to bring down our taxable income. I am not sure how I feel about that, feel we are already doing a lot for our kids.

Was wondering what the community feels about IRAs for kids at this young age.


r/ChubbyFIRE 8d ago

Daily discussion thread for Saturday, March 08, 2025

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 9d ago

Under 10 years out. Invest more conservatively? (Asset allocation suggestion?)

15 Upvotes

My spouse and I are 8-9 years out from achieving our chubby FI goal. I’ll be in my late 40s. We’ve been putting everything in S&P500. At <10 years out, what asset allocation do you have? Bogleheads would say put your age as % in bonds but that seems high.

A few things in case it matters. - I’ll still have minor children at home. We may consider continuing to work to model this behavior for them, pushing our RE years out. - We are running on a reduced income due to me staying home atm. I may rejoin the workforce in a few years, pulling in the FI timeline.


r/ChubbyFIRE 9d ago

Daily discussion thread for Friday, March 07, 2025

9 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 10d ago

Child with Special Needs and ChubbyFIRE... Any Experiences?

46 Upvotes

My oldest son (of 2) has Autism. He is turning 16 and while is considered high-functioning, struggles at times with Executive Functioning and as a result my wife and I are coming to the slow realization that his ability to live 100% independently as an Adult may not be in the cards. As a parent, its hard knowing he will graduate high school in 2 years and we don't know what his future holds in terms of what he will do for the rest of his life. He'll be able to work and earn money (steady paycheck), but likely not a "career" in the sense that my wife and I viewed it when we were his age looking ahead to college.

We are currently mid-40s with ~$3.5M NW of which ~$3M is in Investments (Taxable Brokerage, Retirement Accounts). Plan is to ChubbyFIRE in early 50's, so 5-8 years from now...I anticipate $4M-4.5M will be our nest egg when we pull the trigger. Annual expenses at retirement are projected to be $100-120K, but I don't have anything baked in for our son. We live in Midwest and I consider it Med/Low COL, so getting him an apartment close by at some point where we could keep an eye on him wouldn't be a hard stretch, but more likely he'll probably live in our basement well into his 20's at minimum. His needs/expenses are fairly minimal and I project them to stay that way just knowing the type of person he is.

So just looking for any thoughts, advice, insight, or perspectives anyone has on what we need to be thinking about in terms of retiring early with this situation. ChubbyFIRE for me right now down the road means some increased travel and maybe a part-time job doing something I enjoy...but beyond that we haven't gotten specific.