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

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

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

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

Quick note: we're Canadian. Everything converted to USD with US account names so it's easy to follow. Tax details won't map 1:1, so don't sweat those.

Us: 39M / 40F, 2 kids (7 & 10), VHCOL. House paid off (~$1.4M).
Income: me salaried ~$195k; wife owns a growing business netting ~$210k (draws ~$33k/yr personally).
Spend: ~$160k/yr. Net worth: ~$4.46M.

Invested (~$2.9M):

• Taxable brokerage: ~$1.37M
• Business / holding-co account: ~$700k
• Tax-deferred retirement: ~$400k
• Roth-style (tax-free): ~$225k
• Kids' college (529): ~$56k
• Private mortgage/credit fund (8-12%): ~$180k

Asset mix: ~47% equities (broad index, VTI/VXUS-type), ~45% cash ETFs @ ~3.5% (SGOV/BIL-type), ~6% mortgage fund, ~2% crypto

Here's the contradiction I'm living in. At ~$4.5M with a paid-off house, the headline number says we've made it. But ~$160k spend against the ~$2.9M that's actually invested is a ~5.5% withdrawal rate, which says the opposite. And the reason for the gap is staring at me: a seven-figure windfall I parked in cash ETFs "temporarily" and have been too frozen to deploy at all-time highs. If it's deployed and compounding, it could close the gap in a few years, but sitting at 3.5% it kinda never does.

Meanwhile our two incomes cover spend with room to spare, so there's zero pressure forcing a decision, which is exactly why I've made none.

For those who've been in the gap:

1. Did you count home equity and a working spouse's income when you called it, or strictly the liquid portfolio?
2. What finally got you to deploy a big idle pile: lump sum and look away, or a fixed DCA schedule?
3. Would you downshift the salaried job now and let the business + portfolio carry it, or grind until the liquid number clears on its own?

WWYD?

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

I ve seen it mentioned by financial planners and it seems good to model the guide rails approach. However it is not targeted for retail subscribers.

Posted this in fatfire and got some very interesting comments, some recommended I post here too.

Me (32M) and wife (32F) live in HCOL city and are planning for kids in the next year or two. My current role is demanding, but due to RSU appreciation very high paying. The company is not public, but has given liquidity opportunities the last several years. My wife works for the state part time, but gets full benefits and a pension after 20 years of work. She enjoys the work and sees herself doing it for the foreseeable future. I have questions around kids, concentration risk, early 30’s retirement, and opportunity cost risk. 

Job situation

Me - 50hrs/week, $250k base + $1.4M/year in RSUs. (The RSUs will reduce to $600k in July of 2027). 
Wife - 20 hrs/week, $50k/year, only two years in but enjoys the work

Current plan - continue working until July 2027 (when compensation decreases) and then leave to take a break and care for the kids in the first few years before primary school starts. 

Current Net-worth breakdown

Total - ~$6M 

1. Investable total - $5.3M 
   1. Cash - $100k
   2. Taxable total - $3.8M 
      1. $1.6M in semi-liquid pre-IPO company which does yearly tender offers. 
      2. $2.2M in liquid brokerage accounts - Index funds - this is from regular tender sales of the above.

       

   3. Traditional retirement - $670k (me + wife) 
   4. Roth retirement - $650k (me + wife)
   5. HSA - $50k

    

2. Home - $1.1M - this is a pretty modest home in a nice part of town in our city. 
3. Debt - $340k on 15yr mortgage at 2.125% with 9 years left on note.

 

Expenses Total - $170k / year

Essential - $100k/year

• Mortgage - $50k
• Home repair - $10k
• Groceries - $15k
• Transportation - $5k 
• Utilities - $5k
• Pet care - $5k 
• Health - $5k
• Etc - $5k 
• Not including health insurance because my wife is planning on continuing to work part time with benefits.

 

Discretionary - $70k/year

• Vacation - $26k 
• Gifts - $10k
• Fun fund - $10k
• Dining out - $10k 
• House cleaners - $4k
• Etc - the rest - $10k

 

Thoughts

If we count the private equity, we are able to RE given our current nest egg ($5.3M) and expenses ($170k)  - roughly 3.25% withdrawal rate. If I don’t count the private equity, the math works out closer to a 4.6% withdrawal rate, but we will have my wife’s income until she doesn’t want to work, and some discretionary spending flexibility. I've read "Tax Planning to and through early retirement" and think between a bit of work, wife's work, and roth withdrawl shielding I can keep tax cost fairly low. I think the math mostly works with kids if we assume ~$15k/year in cost per kid (assuming I’m doing child care) - we’d like 2. 

If I add the kid cost in - total costs rise to $200k / year for a while - which is still within the 4% rule counting private equity, and less if my wife continues to work. 

I would love to stop working my current job in July 2027. I find the job very stressful, and it has impacted my health (high blood pressure, overweight, etc). July 2027 would be after a large equity cliff, if I stayed, comp would drop to ~$850k/year which is still an insane amount of money, which is part of why I'm second-guessing leaving.

I have a few worries: 

1. Unexpected child costs - I’m worried that I’m underestimating the cost of having kids, or the risks associated with leaving work just before having kids. Am I thinking about the total costs correctly? 
2. Concentration risk - The company I work for is not public, and historically only gives liquidity opportunities once per year. It has been very successful and I take every opportunity in tender offers to diversify, but my current plan is still to leave with a significant portion of my net worth invested in the company. How would others value this equity? 
3. Opportunity cost - my current compensation is insane. I don’t think I will ever strike it this lucky again, would I be nuts to leave this job? 
4. Wife work dependency - my wife working and providing benefits feels like an important part of the plan (is this true)? It feels safe because she is working part time already and enjoys it, but I’m also thinking about how much to depend on this. 
5. Very early retirement - I am perhaps overindexing on money in this situation, I’m curious how many folks actually never earn another dime after they have left work, especially in early 30s. 
6. Anything else I’m missing?

 

Some options I’m considering: 

1. Work my last year and leave July 2027 (current plan) 
2. Work until kid 2 arrives. 
3. Leave now 
4. Work until the Lord takes me.

 

For all of these, I'm considering some work after "RE" - so am curious how folks who have stepped back from high stress tech have done it.

Thank you in advance! 

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

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

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

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

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

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

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

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

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

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

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

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

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

We recently crossed the $4M mark (mostly split between equity, VTSAX, and our primary home which shot up in value), and I’m starting to feel like our risk management is lagging behind our net worth.

Right now, we just have standard home and auto policies with Geico/State Farm, plus a basic $1M umbrella policy we tacked on a few years ago. But looking at our total exposure, a bad lawsuit or a major incident at the property could easily jeopardize a huge chunk of what we built. I was talking to a colleague who’s also on the FIRE track, and he mentioned that once you enter chubby territory, staying with mass-market retail insurers is a bad move because their claims departments drag their feet and their policy limits are full of loopholes.

He suggested looking into a proper high net worth insurance policy through an independent broker who can set up a structured asset protection plan (stuff like un-capped replacement costs for the house, worldwide liability, and actual private client claims handling).

For those who are already chubby or coasting, did you stick with standard retail providers and just max out your umbrella policy to $3M-$5M, or did you actually migrate your entire portfolio to a private client/HNW broker? At what asset level does making the switch actually justify the higher premiums?

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

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

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

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

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

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

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

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

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

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

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

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

Here’s the rough picture:

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

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

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

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

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

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

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

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

What I’m trying to figure out:

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

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

The age-old question, but I'm looking for validation (or words of caution) - Can I retire with my current setup?

Expert (or just knowlegable) opinions would be most appreciated because I'm a bit lost.

Current situation:

• Me: 53. Laid off after decades at the same company (not excited about what I'm hearing from middle-aged friends looking for work in the tech space).
• Spouse: 53. Earning about $30k a year at two part-time jobs she enjoys. Plans to work until age 60.
• Net Worth: ~$3.5M (not including home/property)
• Cash: ~$887K (this is unusual, I know)
• Investments: ~$2.6M
• - ($1.7M are in CMA accounts so I should be able to access those without tax penalty).
• - ($155K is in ROTH contributions, not earnings).

Costs:

• We live in our forever home. No mortgage. (Housing and land assets not factored into Net Worth for this discussion).
• Two cars paid off. No debt.
• 20-year-old kid is in college but expenses are fully covered by 529 (not factored into the numbers above).

Spend: [THIS HAS BEEN EDITED WITH LESS STUPID INFORMATION]

Current non-benefits spending is chubby [edit: less chubby than I thought], even without having a mortgage:

• Around ~$13,300/mo ($160k/yr) if we keep in a home improvement budget intact for emergencies and projects. ~$10,000/mo ($120,000/yr) if we remove the home improvement budget.
• I have the option to keep paying for my own health benefits (which are good and we like them) but likely $2,500/mo (on top of the $13.3K monthly spend above).
• Monthly spend including fancy benefits is more like $15,800 ($190K/yr). Can reduce to ~$12,500/mo ($150k/yr) if we keep fancy benefits but lose the additional home improvement budget.
• Around $16K/MO (some of this is medical, some is upkeep on an historic farmhouse and barn, some vacations and splurges).
• I have the option to keep paying for my own health benefits (which are good and we like them) but likely $2,500/mo (on top of the $16K monthly spend above).
• Actual monthly spend (including benefits) is closer to $18,500 ($222K/yr)

The Future!

• Planning on Medicare (12 years from now).
• Plan to hold off on Social Security until we're 70 years old. Estimated to receive about $6,500/mo.
• Plan on spending from our fat cash pile for the next four years, then pulling from CMAs until I'm age 59½.

All of my calculations (at 7% return on investments/2.5% increase in cost of living) have us covered at this rate until we're 85.

That's a tough roll of the dice. [edit: This actually makes more sense with my less insane and duplicative costs]

If you were us, would you:

• Reduce spending where possible?
• Ditch the good benefits and go for ACA Silver?
• Get a full-time job for the next decade?
• Plan to CoastFIRE?
• Get familiar with Roth convcersions for "the bridge" years?
• Invest some of the cash surplus to goose gains until I'm 59½?

This forum has been super-helpful and blissfully non-toxic. Thanks in advance for any advice.

Our family has two goals: (1) early retirement and (2) upgrading our home.  There is obvious tension between the two.  My own thoughts on how to balance/prioritize are below–but I also wonder whether this community can help me think through things from a different angle.  

Family is: 45M, 44F, two kids 12 and 3.  4.9M in investments (roughly 2.5M of this is taxable).  Outside of the 4.9M, we have 500k in home equity and 400k in 529s for the two kids.  

Higher earner (44F) wants out ASAP (earning roughly 450/year).  45M makes around 170k and plans to go for another 4 years to earn pension credits.  When 44F retires, she will continue contributing to family expenses at the same level as before from retirement savings.  45M will provide family with medical benefits until he retires and continue funding his qualified accounts until RE.  Spend is roughly 14k/month (not including preschool tuition, which we have set aside).  

We’ve gotten this far, like many of you, by keeping expenses low/moderate.  We’ve been in our modest townhome for 11 years.  We would love to upgrade to have one more bedroom and a large yard, but we don’t want to give up RE for it.  

Here are our thoughts/constraints:

• We’d prefer not to sell our townhome.  As a rental, it’s a decent investment for our long term future cash flow.  The core expenses (mortgage (3%), taxes, insurance and HOAs) are $3500.  It would rent for appx 4400-4500/month–we would set aside all of the cash flow for at least two years for a maintenance fund.  Since this house has been our primary home, it’s in great shape (new roof, new windows, new hot water heater, etc).  From an investment perspective, I understand it’s not a great return, but for future cash flow, here is our thinking:
  • Cash flow in retirement would be more or less solved if we kept the rental:
    • At age 60, a 2.6k/month pension kicks in
    • 67/70, our social security kicks in, for about 52k (conservative estimate for both partners)
    • Late 60s, mortgage on townhouse will be paid off and it will cash flow at least 3k/month.  
    • Total cash flow late in life: about 10k/month.  With kids fully launched, this likely covers all of our essential expenses.

    

• This means our investments have to carry a very heavy load for about 15 years (between second partner’s retirement and cash flow kick in).  Roughly 200k (expenses will go up once we lose medical benefits and during kids’ peak expense years (late teenage/early 20s).   The burden on the portfolio will be lighter before and after that 15 years.
• When I model this out using projectionlab or AI, I believe we have a good 1.2M ish that we can spend now on a house while still allowing the plan to work.  We would pay cash for the upgraded home.  But, 1.2M is not really enough.  We need at least 1.5M in our area.  I can’t go that high without wrecking the plan.  Do we:
  • Sell the townhouse, even though we’d love to keep it
  • Have 44F work longer to afford the higher price tag
  • Stay in the townhouse and practice gratitude for the flexibility and security that the low expense provides us
  • Wait a couple of years to see if market performance gives us the extra 300k+
• I know this is very much a “what do YOU really want” type question.  But, I welcome thoughts/opinions or different ways of approaching this problem.

 

[EDIT: as I'm answering comments, I realize that I'm more defensive of the RE plan than the house plan, so maybe that answers it? TL;DR is that most commenters say keep working to fund home purchase and liquidate the townhome because who needs the hassle? Good feedback, but I think we're leaning towards RE first priority, if we end up finding a SFH that we can afford, great. If not, we're fine in the townhome].

Y'all are trolls (especially the chat requests). Sorry I asked for help!

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

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

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

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

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

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

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

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

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

Couple 38 (me) and 35 years old, no kids.
Annual Expenses projected in retirement: $239k
Paid off house $800k worth
Invested assets+cash: $6.5M

I love my job but I have had TMJ/upper back/hypermobility issues for years that might benefit from retiring from my desk job.

If you were me, would you retire from my $1M+ a year job and let my husband get me to fire? (Husband makes $500k a year and is ok with this).

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

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

Current situation:

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

Portfolio is roughly:

• $3.8M tax-deferred
• ~$800k taxable brokerage
• Small Roth balances
• Real estate equity makes up the remainder of net worth.
• We recently rebalanced to a conservative portfolio in anticipation of retirement. Approximately 10% Money Market/50% VTSAX/ 40% Bonds. I know that's a lot of cash (due to a recent property sale). But we have it both as dry powder but also for emergency fund and sequence risk protection.

Current plan is:

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

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

My question is:

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

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

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

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

Looking for perspective from people who have been through a similar transition.

I'm 28 and recently sold my business.

Current situation:

• Net worth: approximately $2.6M
• Married, no kids... yet
• No debt
• My wife works and earns $100k+
• Annual household spending is relatively modest ~ $90k
• Goal is long-term wealth creation and reaching $10M+ net worth

Current assets are a mix of public markets, cash equivalents, and private lending opportunities. I'm also building relationships with local operators and business owners.

The challenge is that I'm struggling to determine what game I should be playing over the next 10-15 years.

I don't want to:

• Build another agency
• Work 60+ hour weeks
• Create another job for myself

I do want to:

• Work ~30-35 hours per week
• Have flexibility for family, golf, travel, etc.
• Continue building wealth
• Stay in coastal NC long-term
• Own assets rather than sell my time

I've been exploring:

• Public market investing into VOO, VXUS, and AVUV
• Private lending (currently evaluating loans around 12% secured by real estate)
• Buying minority stakes in local service businesses
• Eventually acquiring another small business outright

The question I keep coming back to is this:

If you were 28 years old, had a recent liquidity event, ~$2.6M net worth, wanted to stay in a mid-sized NC market, and wanted to build toward $10M+ without returning to a 60-hour work week, what would you focus on over the next 5-10 years?

Would you:

1. Stay mostly invested in public markets?
2. Participate in private lending?
3. Buy an AI resistant small business?
4. Buy minority stakes in operators?
5. Something else entirely?

Interested in hearing from people who have actually gone through the post-exit transition and what worked (or didn't work) for them.

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

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

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

Some numbers:

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

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

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

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

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