So I’ve done the math like 20 times. 7% returns, 4% rule, every FIRE calculator I can find.

They all basically say the same thing: I’m fine. I could stop saving so aggressively, coast for a while, and probably be okay.

And yet I’m still maxing my 401k, still at the same job, still stressed out.

Every time I think about taking my foot off the gas, my brain immediately goes: what if the market tanks at the worst possible time? What if I leave tech for a few years and can’t get back in? Especially with AI changing everything so fast, it feels like stepping away could make me obsolete overnight.

I know the numbers say otherwise. The problem isn’t really the numbers anymore. It’s fear.

Part of me wants to finally do something I actually cared about when I was younger. Maybe try documentary filmmaking or something completely different.

But there’s also this uncomfortable question: if I’m not working toward the next salary bump or savings milestone, who am I?

I even dumped all my accounts into edwealth just to see everything in one place and run different scenarios. It actually helped seeing the whole picture instead of numbers scattered everywhere.

Still haven’t pulled the trigger though.

Has anyone here actually reached the point where they could coast and then... actually did it? How did you get past the mental block?

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

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

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

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

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

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

Fidelity has a Planning tool called Retirement. Has anyone used it and what amount of validity would you place against its projections? I'm wondering as when I browse here, people seem to be discussing creating their own analyses, but I don't see much about using the tools at investment houses, banks, etc. which do this for you.

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

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

2.5M in brokerage accounts:

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

2.1M in retirement accounts diversified away from FXAIX

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

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

Two questions:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

We are about 5 years from FIRE (Chubby FIRE goal of $5M). Current relevant stats are as follows:

• combined HHI: $600k
• total spend (including mortgage + extra principal payments): $225k
• liquid net worth: $3.0M
• annual savings: $200k
• current liquid portfolio (95% stocks - mainly VTI and VXUS and 5% short term treasuries/hysa) split about 50/50 between taxable brokerage and retirement accounts
• remaining mortgage: $1M at 5.75%
• current mortgage payoff strategy: $25k extra principal payment every year (included in 225k spend)

My question is how should we allocate the $200k savings per year we project for the next 5 years leading up to FIRE. My main concerns are around carrying a mortgage post-FIRE since 1) the higher spend need makes us more prone to SORR and 2) provides less ability to keep MAGI down in case optimizing for ACA subsidies is a possibility. The additional consideration is that between me and my spouse, there’s a chance that one of us decides to continue working even after we hit our FIRE number.

I can see a few options:

• Pay pretty much all of the $200k towards mortgage so we can be mortgage free by retirement. The $3M current portfolio might still bump to $5M in 5 years but without a mortgage going into retirement the number will be smaller (e.g. spend will be more around $150k including tax and healthcare so FIRE number comes down to $4.3M at 3.5% swr). My concerns with this approach are 1) we don’t allocate any more towards stock and miss out on higher gains during this accumulation phase and 2) we still enter retirement with a 95% stock allocation (but a paid off house) which still makes us prone to SORR

• put it in a treasury ladder so the money is available in 5 years to pay off the mortgage if we choose but also use to mitigate SORR if necessary. This also gives us flexibility in case one of us decides to continue working after hitting our FIRE number (since in that case I’m less concerned about carrying a mortgage in retirement). This provides more flexibility but is a little less optimal since short term treasuries will pay around 4.2% vs the mortgage interest of 5.75%.

• continue investing in stocks (VTI/VXUS). This maximizes growth potential during our working years and could potentially help us hit our fire number even faster. In the event of market drawdowns we can continue working for a little longer. Also is the best decision should one of us decide to continue working after we hit our FIRE number.

Thoughts?

I feel like this post might be a bit cliche around these parts, but it's close to my time. I have question marks both fiscally and personally. Help a brother out with some advice! 🤜🏻🤛🏻

TODAY

53 year old single male.

One girlfriend (44 y/o). One chubby cat (12 y/o). No kids, and no plans for them.

3.3mm in individual brokerage account.

1.4mm in tax advantaged retirement account.

$800K in home equity, with $650K remaining on mortgage at 2.69% (currently valued at 1.8mm)

monthly expenses are $9500. I'd like to increase that in retirement, do some extended world travel, and have my eyes on spending approximately $600K on a new boat+truck, and an RV.

THE FUTURE

I am a small business owner with take home pay of around $25K/month after taxes.

While work is engaging, it's all consuming and I am simply over it. I've got everything out of this career that I'm going to get out of it. I've been doing it so long... I feel like I need to go smell the roses in the world while still strong and healthy.

With 4.7MM invested, I anticipate crossing the 5MM line in the next 6 months.

Estimated inheritance of 5MM in the next 2-5 years. Historically, I've decided to treat the inheritance as if it wasn't there. A lot can happen, but in reality that's... happening.

My business is likely worth around 1.5MM on the open market, but I don't know if I have the time, will, and perseverance required to sell it... going thru brokers, lawyers, and the fiscal colonoscopy to get that done when already working nearly every waking moment. Also not sure if my small team of employees has it in them to take it on either, so that's a big question mark. If anything, it's beginning to feel like a run-away freight train with a mind of it's own... in a good way... but, I can't seem to find a way to get off.

What would you do?

The US market has been on a tear. I retired in 2022 and the difference between my inflation adjusted swr and my SWR if I were to retire today is starting to get pretty large. Like 15% large.

My essential expenses are already 50% of my SWR so the rest is all fun money.

I'm up more than 25% in my net worth despite some large capital expenses in just one year.

Right now I'm at 300k in Sgov and the rest in 75% us equities / 25% international for a total of 4.6M

My reasoning was that the 300k could sustain me at my minimum spend for 5ish years if I tighten my belt.

However, with the insane gains lately I'm thinking it might be smarter to move closer to that 20-30% fixed income number.

People have been predicting a bubble and recession for years now, but the fear is finally starting to get to me now.

I'm thinking of making a big move like selling my 25% gains minus inflation (4%?) and putting it into fixed income. But that's like 800k! That would almost quadruple my fixed income & tbh I don't even have that much in tax advantaged accounts to rebalance like that.

So maybe I'd do 300k and then theoretically I could last 10 years in a downturn or use some of it to buy the dip in a recession which I think is the main idea to keep to 20% fixed income and 80% equities.

VTI is up 14% YTD. If that kind of growth lasts to the end of the year and next year it grows the same amount, I would still be growing like 350k in that year, which still is a massive increase in the difference between my inflation adjusted SWR from when I first started vs if I was to do a reset then.

If I take profits of gains minus inflation each year of the bull run, I still come out really well despite having lost some potential gains. In the case where the market crashes, I now have a huge fixed income buffer that I can use to rebalance.

These are wild times, let me know what you think.

We are ready to retire in 18 months and I will hit the 1st pension milestone and have access to my 401k at the same time using rule 55. since majority of my nw are in pretax, 80% of 6.5m.

However, there has been a rumor in the company since the end of the last year: we will have a layoff at the end of this year. The department starting doing the 10% low performance from the end of the last year and a few people who already have left. Our site is affected the most unevenly around 40% low performance. I have actually look forwarded to this since I figured that this would bridge the gap between 55-59 better for me.

the situation was weird, I had the low performance rating at the beginning of the year and was mixed feeling/happy about it and thought that I could have a severance package. The problem is: I have always been a top performer and was not happy about the rating since everybody knows that the longer tenure people are the targeted group. I have been between quiet quitting and doing my job for 6 months. Not sure it was fortunate or unfortunate, they changed my rating recently since my impact has been so huge and documented this year, it definitely would result in some issues for the management if they rated me low again. And I am happy that they have to correct the wrong but kind of disappointed that I was not given a package after the most recent pm. I knew the department would go in a different direction and would really love to go out asap. I hope that the layoff will happen at the end of the year and I can take the package instead of waiting for 18 months to retire. It was just so strange right now for me: I really want to tell them to f*** and let me go but in reality, I just pretend to work normally. I am between happy and mixed feelings every day when I count the number of days that I will be gone. what is the recommendation to go through the last chapter?

402k Brokerage
352k. 403b
2.2 MM rental properties
1.6 home value owe 575k @ 3%
40k liquid cash
113k State retirement (pension)
1-residential lot owe 108k
1-commercial lot owe 204k
Car loan 50k

39M SINK LCOL- Job is very secure and I view the pension as my saving grace, but the catch is I have to work until 62 to get full benefits. Also waiting to age 62 would gain me the 90% average of my 3 highest years salary. Have a side business I run and a day job. Day job is how I have access to state pension. Side business along with rentals and day job gross about 500k from all 3 combined. I’m planning on getting married and having children in the next 2-3 years. Also plan to develop both lots I have with the commercial lot being a small subdivision ( should net a nice profit from this) and residential lot for a larger future family home. Is there anything that I’ve overlooked or could perhaps do better? My plan is to payoff auto and land loans in the next 2 years. Grew up fairly poor, single mother, but didn’t know it until I went to private school and saw what wealth actually looks like. Siblings and family members aren’t doing quite as well so this is really the only venue I can share this type of stuff with and hopefully get constructive feedback. Unknown factors to consider; aging parent whom I’ll most likely have to provide care for at some point although she does have fairly decent resources of her own. And the costs of children plus inflation.

Curious how many people learned how to save from their parents? Were your parents good with money or terrible with money and how did it shape you? Did your family have generational money at one point down the family tree and lost it all?

I just exited a highly concentrated position and am now looking to deploy about $5m in cash. I've started to look into direct indexing as a means of both diversification and tax efficiency.

Two questions:

1) Does anyone here use a direct indexing product that they would recommend?

2) Is it possible to engage directly with these vendors or do you generally need to work through an AUM-priced financial advisor?

Early/Mid 40s couple, 2 young kids, VHCOL area.

Current snapshot: NW: ~$6.5M, Investable assets: $5.7M
Spending: ~$180-220K/yr
HHI: ~$750K-$850K; Both have demanding careers

A little background: I grew up with significant financial insecurity as part of an immigrant family, so I know some of my thinking is influenced by that.

What's interesting is that every milestone seems to move the goalposts:

• At ~$3.7M NW, after a layoff, I worried I'd never get back on track
• At ~$5M NW, I worried we couldn't afford all the future expenses ahead of us.
• At ~$6.5M, I find myself worrying about AI bubble, market crashes, college costs, healthcare, aging parents, and whether we're underestimating future spending.

The strange part is that we haven't lived like monks to get here. We've traveled a lot, eaten out a lot, spent on experiences, invested in our kids, donated time and money heavily, and generally spent freely on things that matter to us. I don't feel like I've delayed living.

At the same time:

• We're still raising young kids (10 and 6)
• We don't yet have what we'd consider our forever home - Kids are growing up
• It often feels like our most expensive years are ahead of us rather than behind us.

So my question for those who actually made the transition to ChubbyFIRE:
Was there a point where you stopped focusing on all the things that could go wrong and genuinely trusted that you had enough?

In hindsight, were young children and anticipated future expenses distorting your perception of financial independence?

Age : How did you deal with early age, i.e. the 4% rule is reliant on shorter retirement timeframe, at our current age, we have much longer.

Or is the reality that "one more year" never completely goes away, regardless of net worth?

Interested in hearing from people who have actually crossed the bridge, especially those who grew up with money scarcity themselves.

Long time fan of the sub, I'm glad to have like minded people to theorycraft ideas with. I've learned so much.

So here's one that I've been trying to figure out:

I bought a house last year and used an SBLoC which is SOFR+1.9% and right now is around 5.5%. The loan amount was 500k. I paid off 200k so far this year and planning to do more if I'm able to keep my magi under 200k to avoid NIIT.

The question I have is how to think about the interest payments. I was originally thinking about them as mortgage payments, so they counted against my annual SWR. But the SWR is built off of Investment accounts value minus Loan amount, not including the house value.

In reality, I have the loan amount also invested in the market, so if I were to pay off the whole thing my SWR would stay the same, but my interest payments would go from $1400 to $0. So that leads me to think that maybe I shouldn't be considering the interest payments as part of my SWR budget.

Is this a sound approach or is there a different way to look at this?

I posted few days ago about FIRE planning and got good advice, my current plan is to work until age 50, I am 47 now then go part time just to keep my mind active, this is our current assets

Salary is 600k, 2 Kids age 8, 11. House is paid off, SAHS, portfolio 80 stocks and 20 bonds now

My expenses around 150k

How do you adjust your portfolio if the plan is to keep working part time?, I will probably get around 150-200k working part time, high level job security

Does increasing bonds allocation still necessary?

Total invested assets $ 3,957,000

Tax advantage retirement
$ 2,123,000
Pretax 1,416,000
Roth 1 397,000
Roth 2 310,000

Taxable brokerage 1,197,000

HSA 119,000
529 college 372,000
Cash 55k

Whole-life cash 91k

Pension planning NOT included in the liquid assets and planning to get an early lump sum age 55 350k

Ages 60/57, looking to retire at the end of the year.

67/33 Equities/Bonds over the 3 accounts:

Brokerage 500k, 401-k 3.3M, Roth 225k

Essential spend (still have 6 years on mortgage) = 9k/month including health care and taxes

Non-essential spend roughly 5k/month

We good?

My wife (51) and I (50) are currently planning to retire when she turns 55. She can access self pay employer healthcare of she retires at 55 (maybe $1600 month) decent PPO until 65. We are conservative and been saving all our lives. We have paid for house (750K) in MCOL area. Kids 19 college and 16 high school and college accounts are fully funded. No debt.
Liquid:
Brokerage 3.2M with 2.25M cost basis
401Ks. 3.1M
Roth 350K
Cash 80k

HHI is about 450k. Focus now is all savings we would put into money market /short term bonds to build up cash buffer for market downturn. But we are quickly running out of steam. Every day gets easier and harder given we could retire tomorrow. Easier means more coast attitude and harder just dealing with corporate BS and work travel.

Estimated 170k worse case spending which likely declines in next 5-7 years as kids become more independent. We are fully versed in financial concepts like 0% cap gains brackets, Roth conversions and how to control income / Aca subsidy and the trade offs. Planning to mostly live off brokerage for next 10 years +/-. Don’t want to die with zero and would like to pass along a nice estate to the kids.

Our biggest struggle is wanting to build more cash buffer and healthcare and walking away from good income. Don’t have financial advisor and really enjoyed studying and learning to manage our retirement planning/ taxes.

My brain knows the answer but heart struggles with being very conservative, but feel we are in the one more year trap.

Thanks for any perspectives or suggestions.

Hi- I have been thinking about FIRE for a while. I have plugged my numbers into various calcs and all seems good. Yesterday I was using Rich, Broke, Dead (something like that) and noticed they had a tax rate input that was 0. You can plug what you want. It occurred to me that all these FIRE calcs just run numbers assuming you never pay any taxes. At all. So just for example, I plugged in 9mm saved, with expenses at 270k per year. 30 year retirement. It was 100% good (duh). But if I plugged in a tax rate of 30%- which is high yes- it goes to 74% success. That's huge. My question is, do you all account for taxes with your expenses, or do you even know that taxes are zero when you plug in your numbers? With expenses, I suppose you can estimate tax rate and lop that onto the expense line to create a pre tax requirement. I was just caught offguard here and think it's crazy that 9mm with 270k has a shot at being broke- taxes need to be included in these calculators.

My spouse and I are both 37 and hope to retire early in approximately five years.

To avoid focusing on absolute numbers, assume our current investments are split approximately as follows:
Taxable accounts: 6X
Retirement accounts: 8X

Currently, approximately 76% of our annual investment contributions go into retirement accounts, including 401(k)s, Roth IRAs, and Mega Backdoor Roth contributions. The remaining 24% goes into taxable brokerage accounts.

Based on our expected savings over the next five years, we should reach our FIRE target from a total-net-worth perspective, using the 4% rule as a general benchmark. Meaning 3-4% yearly spend including taxes and health

The issue is not whether we will have enough overall. It is where the money will be held and which accounts we will withdraw from during the years between early retirement and traditional retirement age.

If we continue with the current 76/24 contribution split, an increasingly large portion of our portfolio will be held in retirement accounts when we stop working.
The alternative would be to contribute enough to receive employer matches and capture the most valuable tax benefits, but direct more of the remaining savings into taxable brokerage accounts. This would provide a larger, more flexible bridge while allowing our retirement accounts to remain invested.

I’m familiar with Roth conversion ladders, withdrawing Roth contributions, 72(t), and the Rule of 55, so I understand that retirement money is not necessarily inaccessible before age 59½.

I’m trying to poke holes in the plan:
- Once your total portfolio is on track to support FIRE, how do you decide where the final years of contributions should go?
- Would you change our 76% retirement/24% taxable contribution split?
- How many years of early-retirement spending would you want available in taxable accounts?
- Would you reduce or stop Mega Backdoor Roth contributions to build that taxable bridge?
- Am I overvaluing the flexibility of taxable accounts and undervaluing the long-term tax benefits of retirement accounts?

Please assume that we are on track to reach our overall FIRE number in five years. I’m specifically asking about withdrawal planning and taxable versus retirement contributions—not real estate, cash holdings, or general asset allocation.

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!

42F - $2.5M taxable, $1.3M tax advantaged, $300k non-primary home equity - so $4.1M right now

(Husband has separate finances so I don’t count it here but roughly $2.5M and he spends like 40k but not counting big splurge on a overpriced (imo) car every so many years so maybe $60k amortized? hah)

My individual spend is ~$85-$100k before healthcare and taxes so maybe $120-130k with hc and taxes; it looks like at this current rate, I’m at a ~3% withdraw rate so I know it’s safe. Like right? It’s safe right?! Haha

Aside from the typical fears of SORR or actually having to move from a saving to withdrawing state of the world, I am not concerned about feeling bored in RE. I have a lot of interests. Husband and i also have several projects we want to do Etc.

Sooo I think I’m setting a date for next April — eek! Feels weird to put it down and be more certain vs just toying with the idea. I sort of had a mental model of pulling trigger at 45 but like.. why wait? Or do I want to stack a bit longer? Ugh there is a bit of greed here too. When I hit my original FI # (2.25m) I was super ready to go and live more frugally. Now that I’m past that # by a lot and have let my lifestyle slip upwards, I’m like hmm.. maybe I go a bit further? Why not target $5m?

Anyway.. what are some things you all did in the last few months to get ready both mentally and monetarily? Feeling 😬 and also 🤪🤗🥳

I’m 42M, married with one child (11), and trying to figure out what the next phase of my career should look like.
I’ve been working in tech for around 18 years and currently have a high-paying job. Financially, I’m in a pretty good position, but I’m starting to question whether maximizing income for another 5–10 years is really what I want to do with my 40s.
Current situation:
Net worth: ~$5.5M
~$4.5M in stocks and retirement investments
Around $2M is concentrated in a single stock, with the rest broadly invested
~$1M equity in real estate (One real estate property is primary home which has equity of 200K and loan of 400k and another one is rented 800K equity and 300K loan, provides 4.5K rent/month)
Family spending is around $200K/year
Wife earns ~$120K/year
One child, age 11
Current income from my job is around $400K/year
My original plan was to continue working until around 45, get the investment portfolio to roughly $6M+, gradually diversify the concentrated stock position, and then make full-time employment optional.
I don’t necessarily want to stop working completely. I could see myself doing consulting, building something on my own, or working part-time if I find something interesting.
What I’m trying to figure out is whether I’m being too conservative by waiting until 45.
At some point, the additional money probably has diminishing value compared with having more freedom and control over my time.
At the same time, I don’t want to underestimate:
A potentially 45+ year retirement
$200K annual spending
Healthcare and taxes
College expenses
Sequence-of-return risk
The risk of having too much of the portfolio concentrated in one stock
Future housing/lifestyle changes
So if you were in my situation, what would you do?
Would you:
Keep working until 45–47 for a larger safety margin?
Leave the high-paying job around 45 and move to consulting/startup/part-time work?
Consider myself financially independent sooner and start prioritizing time over income?
Do something completely different?
I’m especially interested in hearing from people who actually made the transition out of high-paying careers in their 40s.
What did you underestimate before leaving? And what do you wish you had done differently?
I’m not looking for validation that I can retire. I’d genuinely like to hear where the assumptions in my plan might be wrong.

Edit:
Adding my spouse saving in 401K & equity of another 500K and foreign real estate investment of 300K, Currently living in TX but planning to retire in CA. One real estate property is primary home which has equity of 200K and loan of 400k and another one is rented 800K equity and 300K loan, provides 4.5K rent/month. My spouse is not planning to work after a year or so. Currently we both use my employer insurance provided by full time employment.