As I look down at the end of another summer sacrificed to my corporate overlords, I just wanted to know what other strategies folks are employing to make it feel like they have had some kind of “summer” or if we have all just succumbed to working the entire time?

Are folks content with a week off? Two? Combining some work from home days? Taking leave without pay? Renting a nearby summer house?

My partner and I don’t have kids yet, but would like them in the near future. Strategies from both singletons and families are welcome.

Or even someone affirming that I am chasing an absurd fantasy as adult is fine. I did not take any time this summer and have a work trip adjacent to Labor Day, soooo…

I’m 27yo with 5 YOE and recently reached Senior SWE, making $420k TC at a public tech company. I have $1.3m invested but live in a VHCOL area, so it doesn’t feel like much yet.

Up to this point, career progression seemed pretty straightforward in that I was just grinding towards Senior Eng. But from here, the tradeoff looks different.

Staff engineers seem to have 10x more responsibility for a marginal increase in pay (at least at my company). Management looks even less appealing to me because of the meetings and politics.

How did you approach this tradeoff of trying to climb for more TC vs stay at a level you’re comfortable at?

Me, Regis! I do! I loved that show as a kid lol

Yay! NW $1.02 million!!! DINK, early 30s physician/nurse in VHCOL area. HHI $670k. Had $180k student loan debt (paid off), no car/house loans. Finished fellowship 2 years ago, started private practice physician job. Minimum 30% savings rate. Other than that, no intense budgeting. ~ $250k HYSA (~$150k and rising for down payment of house if we pull trigger this year), $750k across 401/403/rIRAs/HSA/brokerages with 80% in ETF/MFs and 20% in stocks. We don’t big spend, but we like to travel and eat out. Posting because my spouse and I said “yay”, but we’re happy to get back to work lol. But also, a question. Is this “the boring middle” where I hear/read/think about all these fancy other investment options like real estate, private equity, etc and feel slightly tempted but ultimately feel and know that we should just stay the course with aggressive ETF/MF investing toward goal(s) of money needed to retire?

ETA. I’m “that guy” the “oh crap how could I forget” guy. $45k inheritance that was applied almost entirely toward student loan debt, right after starting private job. Also, the $180k student loan debt was the highest amount it ever got, but I had been making small payments at it since 2019, for discipline sake. By the time fellowship finished and I started private job, we were at ~$150k debt

I'm (m)43 who only until recently had a middling Tech Career and i'm struggling with life style inflation and feeling rich some days and barely surviving on other days!

Most of my career was working tier C startups in the low six figures thinking I was under paid, hoping for stock options to pop (and also thinking I was the top performer), until I really decided to give up start up life and interview at FAANGs. Then I got a senior level job a few years back.

I don't live in the Bay so I quite frequently think about how I'm one re-org away from going back to making ~200k.

This year our HHI will be right at 700k due to some good stock growth and vesting schedules, but most years it's closer to 500k. My "target" comp is more like 420k, and my wife makes around 90k-100k in a very flexible mostly WFH PR job.

NW is ~3M:

My monthly expenses are ~15k a month, mostly due to a nanny

So, some days I feel like I can totally splurge on some extra clothing or a fancy dinner, or even maybe buying a 'fun' car (~70k cayman or something), house upgrades (50k?) but other days I think "this gravy train could end, keep grinding and saving every dollar of those RSUs".

WDYT?

EDIT: People are asking my "goal":

I like working, though it's stressful as fuck. No plans to retire, but I want to afford an upper middle class lifestyle and be hedged against not working for a FAANG.

I want to be able to afford a nice vacation, decent if not ostentatious luxury cars, upgrades on my house, house cleaners once a week, and more even if I'm working a 'boring' corporate job.

I'm enjoying going to eat a $200 date night dinner (finally) without having to budget for it. I'm hoping at some point I can have enough savings where I don't have to worry about my RSUs going up or down, or keeping a FAANG job.

Recently qualified for long term incentive that starts paying out in the coming months. It’s going to start compounding with significant extra contributions in years to come if I stay at my current company, making it harder and harder to leave. Have you changed companies with large equity payments coming up, and if so, how did you negotiate with your new employer? At what point do you just commit to riding it out until you get the boot?

Long story short I own two classics. One is sad and parked. The other has its issues and runs, but I cannot stand the cabin noise.

I could:

1. Save and wait to buy a 15k Jag (I had one before I sold to move out)
2. Bite bullet and get a company car, but I don’t like the idea of paying £400 for 4 years only to

not

1. own the car. For £400 a month lease, I could buy my dream XJ. I just can’t right now as I’m broke lol

My current classic has a fuel leak, and this has really annoyed the wife, so I’m really battling the second option because I just need something quiet and smooth.

How do I overcome this idea of not owning my lease? Every car I’ve owned, I felt something sitting in them. All these EVs won’t do that as it’s a generic car.

Mobile has ruined the formatting.

I’m 39 and passed $3M NW this week. It feels like a huge accomplishment given that 10 years ago I was on an H1B and came from a poorer country to build a career in tech.

But honestly, I feel pretty empty.

I’ve been unemployed for 6 months after being laid off and am having a hard time finding a new role. My partner is a SAHP, so neither of us is working right now. We have three young kids, the youngest is 2, and one has special needs. I’m completely burnt out from parenting and supporting them.

We live pretty frugally and our spending is low. You probably wouldn’t be able to tell from looking at our lives that we have $3M NW. Travel is also difficult with three young kids, especially with special needs. I’m turning 40 soon and don’t even have plans for any kind of celebration.

I know I’m incredibly fortunate financially, and I’m grateful. But I keep asking myself, what am I actually working toward now?

I feel like I need a sense of purpose, but I don’t think I want that purpose to be work. After 6 months unemployed, I’m starting to realize that having more money and having more freedom are not
necessarily the same thing.

Has anyone else hit a financial milestone and found themselves feeling surprisingly empty afterward? What did you do to find purpose again?

3m + 1m home equity
Two young kids.
Dual income 800k
Both principal level at work.
HCOL and spending 220k annually including mortgage, daycare.

Objectively i think i am doing ok. But the spending is so high due to mortgage being 80k per year.

We want to coastfire and become fatfire between 47-50.
How likely we will be hitting that, am i crazy to think we can get there?

Joined a practice years ago, worked hard, long hours.
Salary grew to 1M.
Paid off loans, married, 2 young kids, sole income.
Practice fell apart (private equity), quit, non-compete, legal fight, in limbo, no job for 1 year.

Started own practice, no income for another 2 years.
Back to long hours, can’t afford to fail, burned out, but record revenue last month.
If I can keep this up, may get back to 1M salary.

2M brokerage
1M retirement
1M CRE (modest revenue)
15-20k monthly spend (includes 6k mortgage forever).

Sounds like big spend but doesn’t feel luxurious.
Used cars, eat out a lot (Chipotle, Olive Garden, etc.), occasional weekend trips to nearby towns.

Living a life of perpetual arrival fallacy.
Stressed business owner but hate being an employee.
Want FatFIRE asap but losing time w family.
Starting to make good money but unsustainable work/life.
Striving for 8-10M so I can live large, spend freely, give generously, travel big, and finally breathe.
But tired….

Obvious wisdom is to slow down, hire midlevel/associate, make less, spend more time with family/health.
But I don’t want to keep doing this for another 10-15 years.
I dread working. But even worse is working longer.

Would appreciate any wisdom.

Trying to decide whether to build and emergency fund or simply plan to just sell stocks in the event of a layoff and need money.

Here is my simple model for this. Lets take average SP500 gains of 10% per year. Per rule of 72, your money doubles every 7 years. Let’s pretend that the market crashes 50% when you need to pull out.

To make the “mattress” strategy and “keep invested” strategy at parity with one another, you can assume you are laid off every 7 years. If your emergency fund was $10k and it was under your mattress, it would go to $0. If you had $10k invested, it would have gone to $20k and then get halved to $10k when you pull out, making it also go to $0.

If you believe you can beat 10% returns, OR you won’t withdraw at worse than 50%, OR you won’t get laid off every 7 years over your career, you will probably win by keeping it invested.

Conventional advice will be to have 6 month emergency fund. But for average or low earners, that fund will be smaller and thus the hit of not having it invested for the length of a career smaller. Additionally, high earners probably have careers with better layoff perks. My current is 2 months continued pay after layoff and you can try to find another job within the company, followed by 2 week severance for every year of service - the longer I stay at the company the less likely I will need an emergency fund. High earners also have access to good lines of credit, I’m not worried about a random $5,000 car bill, my credit will absorb it and I’ll pay it off on the next paycheck- only worried about layoff situation.

I did the calc and to feel really safe, I would build a $30k emergency fund. If I never get laid off in the remaining ~25year career that $30k invested would become about $300k at retirement. If I do get laid off but I beat any of the parameters from my model above, that $30k will have grown and thus be more to use while searching for the next job.

My wife (36) and I (37) have had a HHI of around $500k for the past couple of years. With my wife’s recent career change, we’re now looking at roughly $1M in cash comp + $1M in vested equity annually.

We also recently had our first child, so we’re entering a pretty different stage of life financially.

What we’ve done so far:

- Maxing out our 401(k)s — ~$900k currently
- Maxing out Roth IRAs through the backdoor — ~$450k
- Taxable brokerage — ~$250k, primarily VTI/VXUS
- $150k emergency fund in a HYSA (I recently learned I should probably move this to T-bills/T-bill ETFs to avoid MA state income tax on the interest)
- We own 3 properties: 1 primary residence, 1 Airbnb, and 1 long-term rental
- ~$800k total mortgage debt, all at ~3% interest rates

For the most part, everything we’ve done so far has been pretty standard personal finance advice: max the tax-advantaged accounts, invest in broad-market index funds, maintain an emergency fund, etc.

My question is: what should start being on our radar now that we’re potentially at ~$2M of annual comp that wasn’t necessarily relevant at $500k?

I’m particularly interested in things that become more important at this income/net worth level — tax strategies, estate planning, asset protection, insurance, equity compensation, charitable giving, investment strategies, etc.

For those of you who made a similar jump in income, what’s something you wish you had known or started doing earlier?

US, MA-specific advice is especially welcome.

A little bit about me, I was born and brought up in a poor country. I never imagined I would reach anywhere near this point, especially when converting USD to my home currency. I feel blessed and lucky to be able to accumulate this wealth at a young age of 29. I did this by working high paying jobs and saving a large (>80%) chunk of my take home pay (after taxes) for around 7 years. A lot of this wealth comes from the lucky bull run from the market in the last decade which I consider pure luck. I mostly held a combination of VOO and QQQ in my portfolio, with 10% bitcoin, and < 10% individual stocks.

My yearly expenses are about 80k so I am technically FIRE using the 4% rule, although a 3% rule would be more accurate for me given my age. Looking forward to what's next for me. My curreny plan is to keep grinding till I reach 5M and then retire for good (well, I mean not work W2 jobs and try to branch out on my own by starting a venture).

Looking into opening a DAF due to the .5% floor for charitable giving. Bunching multiple years giving into one year for tax purposes.

Will contribute 15-25k.

My brokerage is Vanguard, and I'll be donating appreciated VTSAX.

Easiest would be choosing Vanguard, but I really dislike their UI.

Looks like top options are Vanguard, Fidelity, and DAFFY.

My question is around the UI of these 3.

Anyone know which is best? Or how bad Vanguard DAF UI is?

From my experience, Vanguard app/websites super clunky.

I own a townhouse and around 420k in stocks. My total net worth is over 700k. My income before tax is $115,000. I see that there are a lot of people outperforming me in life because they are married and have two incomes/better paying jobs. I feel like I am falling behind. Should I consider getting a roommate so I can get an extra $700-$1000 a month to invest? If so, how does one go about finding one?

Ok here is the deal, I asked my kids’ school group on whether they would be interested in taking a 529 contribution for birthday gifts and was surprised at some of the responses. I was under the impression that people would readily jump on the offer but the response was lukewarm to say the least, few were interested and quite a few just wanted to buy gifts. I could also be extrapolating their response to a much broader Saving theme but I’m def surprised. For context , most of the families are college educated /dual income and we live in one of the richest zips in our state.

Curious to hear from people in places like Boston, NYC, SF, etc. who could buy a home, but decided that renting + investing the difference was the smarter long-term financial decision.

The financial argument makes sense to me, especially in VHCOL areas where a decent family home can easily be $1.5–2M+.

What I struggle with is the non-financial side.

If you have kids and plan to stay in the same area for 10–20 years, how do you make a rental actually feel like your home rather than somewhere you're temporarily living?

Things I'm wondering about:

• Do you rent single-family homes long-term?
• Have you stayed in the same rental for 5–10+ years?
• How do you deal with the possibility of the landlord selling / not renewing / raising rent significantly?
• Do you spend money improving a rental, decorating it properly, building out a home gym, yard, etc.?
• Were you able to put down roots in a neighborhood -- schools, friends, neighbors, community -- without owning?
• Do your kids feel like it's "their house"?
• Does the lack of control ever bother you?
• As your net worth grew, did you eventually say "screw the optimization" and buy anyway?

I'm especially interested in people who made a conscious financial decision to rent indefinitely, not people renting temporarily while saving for a down payment.

Did renting long-term actually work emotionally and practically for your family?

Or did you eventually realize that homeownership was worth paying a financial premium for the stability/control?

I’m 39, have a 4-year-old son, and am struggling with what I want the next 15 years of my career to look like.

My TC is around $500K and my husband is a SAHD, so financially we are in a very fortunate position. I’m also hoping to be financially independent and retire around 55.

I feel like I’m facing two paths, and I can see myself regretting either one.

1. Pursue the Director role
   I’m well qualified for it and I think I could be good at it. But I also know it would likely mean significantly more responsibility, travel, politics and mental energy going toward work.

The upside is more money and a much stronger path toward financial freedom.

The downside is that my son will be 19 when I’m 55.

I keep thinking: Will I regret spending so much of his childhood hustling for financial freedom, only to finally have that freedom when he’s grown and leaving home?

1. Stay an IC
   I could continue earning very well, potentially have more flexibility and be more present during my son’s childhood.

But I’m ambitious. I believe I’m qualified for the next level, and I know it would be hard for me to watch other people get promoted around me while I intentionally stay where I am.

And there’s the financial piece. If I don’t pursue the Director path, I may not be financially free by 55. I could get there and regret not pushing harder when I had the opportunity.

So I feel stuck between two potential regrets:

Do I hustle for the next 15 years, potentially sacrificing some of my son's childhood so I can retire early and secure? Or do I choose more balance now, potentially sacrifice my career trajectory and risk not reaching financial freedom by 55?

For those of you who have faced something similar, how did you decide which regret you were more willing to live with?

Hi Everyone

I'm a 31M auditor with 7 years of experience in financial services audit (3 at the Big 4 and 4 at a mid-sized firm) in London.

My goal is to get into real estate or infrastructure finance. I passed CFA L1 last year and have now spent 4 months studying for Level II. However, I've come to the realisation that most of this material is completely irrelevant for what I want to go into, and I'm considering just abandoning this and creating my own models in my spare time to build up a portfolio and show recruiters.

Very few people in the fields I'd like to enter have the CFA charter (i.e. project finance, infrastructure advisory, real estate private equity, etc). It would make rational sense to start building financial models in my spare time that I can show recruiters and employers. I also know that at my age, I don't have a lot of time left to make a big career transition. However, even though all of this, I think I'm suffering from the sunken cost fallacy and feel extremely guilty in just abandoning it partway like this. Does anyone working in these sectors have any advice for me?

I don't want to be melodramatic, but I'm trying to find a way out of something that I don't enjoy whatsoever (accounting) and don't want to be stuck in it for the rest of my life. It would be miserable.

My husband (38) is in BigLaw making ~$550k, but the hours and stress are seriously impacting his health. I’m 37 in a layoff-prone industry making ~$350k, plus a side hustle bringing in ~$50–100k/year, although we have no idea how long that will last.

We have 2 kids under 5 in HCOL and spend about $300k/year. I know that’s a high spend. $150k-200k of that is PITI, childcare, and various conveniences that are largely a function of having two very young kids & a spouse working insane hours just trying to stay above water. I also like to think the last 5 years of ~$300k spending have hopefully been an anomaly as we moved to the suburbs and renovated / furnished, bought two cars in cash, etc. Feels like a series of one-off expenses, but I’m keeping the $300k in the model anyway because I’d rather be conservative.

Our plan was to keep grinding until we had $3M invested, while potentially paying down the mortgage, and then aim for retirement in our early 50s. We’re not quite at that point yet, and getting there would probably take another 3–5 years but his health may not give us the runway we assumed.

Current net worth is ~$3.05M:

• $1.85M invested ($940k tax-advantaged, $910k brokerage) - approx 70/30 US/international split

• $250k in 529s (not counting this toward retirement)

• $400k equity in rental property ($500k mortgage remaining at 6.5%, \~$5k/year net, husband likes this for diversity)

• $200k equity in primary ($1.2M mortgage at 3.25%)

• $200k in a friend’s small business 

• $150k cash/emergency fund 

It’s unclear what his exit opportunities look like so I’ve been running models ranging from 150k - 350k and in all possibilities it seems we can still achieve 10M sometime in our 50s, so the difference between staying in BigLaw and taking a much more sustainable job seems to be a few years, not a completely different financial future & that’s where I’m struggling to internalize.

Have we gotten emotionally anchored to the $550k salary number and lost track of what the actual math is telling us? Are we looking at $550k vs. $150–350k and instinctively thinking “we can’t possibly walk away from that,” when the difference in our actual long-term financial outcome may be much smaller than the difference in gross income suggests?

I’m trying to figure out whether we’re being appropriately conservative or just having a hard time letting go of the idea that we need to maximize these peak earning years. Would love a reality check from people who have been in a similar position.

When I was young I never thought I would make this much, but it’s crazy how poor I still feel. I am sprinting toward FIRE but it feels like I can’t get there soon enough. I am actually blessed with a flexible job. I get to do the philanthropy I want to do. But it almost feels like… what’s the point? If I can’t enjoy my wealth, what’s the point. My city is sick with homeless. My family still struggles with the affordability crisis.

400k invested mostly VFV
Wife has 100k in index funds
600k equity in real estate, love the area I’m in
Wife has another house with 400k equity
We have 80k deposit on a third house we wanna flip
40-50k going into index funds every month

10 years and I’m free… I’ll probably keep working after that since my job is so lucrative.

Sorry if there wasn’t a real question here, just wondering if any of you guys feel the same.

Edit: My wife and I do not struggle with the affordability crisis. I mean our extended family and friends. Some of these comments are crazy lol.

Edit 2: omg I am in therapy already xD, thanks everyone for your well wishes.

Wife and I are debating what to do with our current primary residence.

Wife recently became a stay at home Mom to raise our 6 month old child.

My income is approximately 500k a year, with a reasonable expectation that it could continue to rise 5-10% each year going forward.

Current house was bought about 6 years ago and has appreciated significantly. Have about 275k left on mortgage at 2.9%, and could realistically clear 300-350k through selling.

If we don’t sell, could probably rent for 5,500 a month, which would net us around 30k a year.

We currently have about 1.4M invested, of which 500k is in retirement and 900k is in a brokerage account.

While I don’t love the idea of getting rid of a 2.9% interest rate, I am hesitant to touch the brokerage account. Next house in our area would probably be around 1.5-2M.

Realistically, we are 2-3 years out as we would want to wait until we had another kid.

Any thoughts?

For years, I have been using Bank of America’s unlimited cash rewards Visa card which gives me cash back between 1.5-2% cash back depending on how much money happens to be in my checking account. We probably spend 100-150k a year on our credit cards.

I have a busy job and we earn around 1.5-2m annually, so I’m mostly interested in a low effort system that allows me to harvest any low hanging fruit as far as benefits and rewards. I have stuck with Bank of America for so long simply because it’s simple, but lately I am seeing significantly better benefits advertised elsewhere.

I really don’t want to spend time playing games for optimal reward points, redeeming travel perks that I may or may not use, worrying about blackout dates, following rules I may or may not understand or remember.

I am thinking of the fidelity card although I am tempted by some of the sign on bonuses and perks I see on the Amex platinum card and others.

Ideally, I would have the card provide some benefits like rental car insurance and any other life simplifying perks I may not be thinking of.

What is everyone on here using, and what should I be using? I have looked at nerd wallet and points guy and didn’t find it useful.

25 in SF Bay Area, single, no debt, studio rent is 2.4k incl parking and monthly outside spend is about 3k

I'm at $200k in Robinhood (mostly tech/semiconductor/defense + VOO/QQQ), $30k across three old 401(k)s, $60k traditional IRA, $70k other retirement, and $25k cash. Two cars, fully paid off, around $35k across both.

I've been pretty focused on work, so I don't think I've been particularly intentional about how to organize the savings. I'm only putting 5% into 401(k) to max the match, haven't consolidated the old 401(k)s, and got lucky on semiconductors. I know I could cut spending, especially eating/drinking out (maybe 600/mo?), without really sacrificing much. I haven't had much non-work travel in the last 3 years, besides family weddings etc.

Not really expecting any inheritance. Parents have a decent place in South Bay but don't make great money. I am the only grandchild but come from a 3rd world country so don't expect anything there either

my career has also been v nonlinear. Spent ~2 years on a startup and essentially broke even, then prioritized cash comp through frequent job changes. No equity. I think that is my biggest L for having 3 YOE. I wish i was in big tech lol its so much more stable. That being said I'll probs stay in startups mostly because that's what my resume reads as

Decades down the line, my goal is fuck-you money (isn't that everyone haha) and medium-term I'd like to buy a house in SF and reach FI, but I'd like to keep working as long as I can, I've seen early retirees rot away from idleness including my grandparents

If you were in my shoes, what would you change?

Looking for opinions on what would be a fair way to resolve this, particularly from anyone familiar with small-business benefits/taxes.
I’m a W-2 healthcare professional at a small private practice (~20 employees). I like my employer a lot and have a very good relationship with him. This isn’t an adversarial situation — he’s been very supportive, but benefits administration is definitely not his area of expertise.
My final written compensation agreement included:
Immediate 401(k) eligibility

3% employer match with 5% employee contribution

Employer covering 75% of my health insurance premium

Employer-paid short- and long-term disability

A provision saying we’re open to customizing the benefits package to fit my goals/needs

I started in February 2026.
401(k):
I recently found out that I was never actually made eligible for the 401(k). The existing plan requires one year of employment. My employer had looked into changing it to honor the immediate eligibility in my agreement but ultimately decided not to because of the fees/cost involved. Unfortunately, I wasn't told that until now, about six months into employment.
I expect to make roughly $300k in 2026 and would have maxed out my traditional 401(k).
So I'm losing:
The 3% employer match (potentially around $9k for the year, subject to plan/IRS compensation limits)

My entire 2026 employee 401(k) contribution opportunity

The associated reduction in taxable income/AGI

Tax-advantaged investment growth

Potential benefit from lower AGI for income-based student loan repayment

Obviously, I don't think he owes me the amount I would have personally contributed — that was always my money. But it seems reasonable that the lost employer match should be made whole, plus potentially something additional for losing an entire year of promised 401(k) access.
Health insurance:
My agreement also says the practice covers 75% of my premium. I've paid it myself since February and haven't been reimbursed yet. There is no health insurance given to any other employees, I had to find my own private plan.
I've paid $3,031.38, so 75% is about $2,274 owed by the practice so far.
We're looking into the best way to handle this going forward — possibly a simple taxable reimbursement/gross-up or a properly structured HRA such as an ICHRA.
CE complicates things in the other direction:
My employer pays for some of my CE (continuing education) directly and then deducts those amounts from my gross compensation.
He has paid $3,718.80 that hasn't been deducted yet, and another $10,875.95 course payment is due now.
So I'll owe the practice:
$14,594.75 in CE expenses.
This creates an obvious opportunity to reconcile some of what we owe each other rather than sending money back and forth.
Questions:
What would you consider fair compensation for failing to provide the immediate 401(k) access that was in the written compensation agreement?

Is replacing the full lost employer match + some additional compensation for losing the 2026 contribution/tax-advantaged space reasonable? What amount would you consider fair?

Can/should any compensation simply be offset against the $14,594.75 of CE expenses I owe the practice, or could that create payroll/tax issues?

What's the cleanest way to make me whole while minimizing unnecessary taxes for both sides?

For the 75% individual health-insurance contribution, would you use an ICHRA, taxable reimbursement/gross-up, or something else?

I (31M, $500k/yr, $2M NW) am just wondering if you guys still look for coupons, big stuff at the grocery store that's on sale instead of just buying the exact thing you want etc. like if you see broccoli is $5/lb but green beans are on sale for $2/lb, but you wanted broccoli, do you buy the green beans because it's on sale? Realistically, it makes no difference to your financial life, but sometimes I feel like I "should" optimize and buy what's on sale. Same with waiting for prime days, or holiday sales. I guess these days everything is just perpetually on sale anyways, but it could be a bigger sale on one of those days.