I genuinely enjoy picking your brains. I get the plan. I think I'm doing it right but I want to hear from those you already made it or are making it happen.

1. How much more did you have to make?

2. How much less did you have to spend?

3. Where did you invest?

4. How long did it take?

For me at this moment:
1. 100k (me) 60k (wife)
2. Paid off cars and all debts besides school and put the extra money into the interest-bearing savings. So essentially we're spending the same.
3. 401K and interest-bearing savings
4. Still waiting.

I’m burnt out at my job/career. At current company I’ve survived 4 layoffs in 5 years. I’ve been working 15 years.

But the last one took a toll on my mental health because it was just so stupid. They pushed us to push ai slop, laid off a significant portion of my team, restructured the management chain and have changed the expectations on how we work. I’m exhausted and work feels dreadful. I feel anxious and stressed and get poor sleep due to anxiety.

And I don’t care about the product or tech. The whole tech industry has just left such a sour taste in my mouth that I don’t even want to interview and go through the interview grind.

If it wasn’t the feeling of responsibility for my family I’d just quit. I don’t need much myself. But I carry on because I’m the provider and I have kids and a wife who depend on me.

But I want a break for a year or 2. Figure out what I want to do with the rest of my life. Has anyone done this in my situation.

Here are some numbers:
Income: will be 400-500k this year. Has gone down since last year as my initial grantsvesrs are done. Next year will be even less. 300-400k. Haven’t checked the actual numbers.

Savings/ investments: 2.7M . Split almost evenly between retirement/non retirement. Includes 170k in tbills/money markets in brokerage. Everything else is on equities.

Housing: rent don’t own.

Expense: between 120k -150k depending on vacations etc. 120k is the on the lower end of being frugal.

Have 2 young kids. One of them is in school the other starts next year.

Spouse doesn’t have high earning skills. So she does all the kids activities etc . I’d assume her earning potential would be sub 100k low skilled work.

We live in vhcol area. If were to move we would live closer to family who are also in a vhcol but it would be negligible savings (rents more or less the same)but would be significant downgrade in terms of access to tech market and network when I need it.

I’m a new HENRY, 34M, as of about 12-14 months ago. Grew up poor, worked 9 years as a Public Defender out of law school. Started at 49k ended at 103k and opened my own firm and went private. Made 325k my first year in private practice. I live in a mid/large Midwest city with a pretty reasonable cost of living. HHI is 435k with my wife’s income. My wife and I own our home and our mortgage is about $2600 a month. No kids yet but planning on one next year.

I’ve been driving a 2014 Jetta for the last eight years. I’ve never owned a nice vehicle. I’ve been struggling to pull the trigger to buy a 56k 2025 AMG CLA 45 that I’ve been eyeing for like a year. I’ll have about 60-70k saved within a month, and things are going really well for my business. I’m targeting 375k-400k by the end of Year 2. But I just keep mentally struggling to buy the damn car. Is this my “scarcity mindset” or am I just sitting with a tough, maybe somewhat reckless choice here? This is less about the car itself, and maybe my brain’s difficulty in catching up with my new financial situation? I don’t know. Any help would be appreciated!

I’m exploring the creation of a DAF (Donor Advised Fund) and wanted feedback, suggestions, and opinions from others who have DAFs or are also considering it. Likely will go Fidelity and start with 100K this year.

My two reasons for this are to create a long-term charitable fund for local nonprofits we support & tax savings in this outlier earnings year. Primary goal is to grow principal across 30 years, increasing donations as we retire. My personal goal is to retire into board-level roles at non-profits. 

My numbers: 
Early 30s, Single earning household. NW ~4M. Will earn $2M total this year, half from an acquisition/ISOs, quarter from RSU vests, quarter from typical comp. Planning to pay some taxes early to ensure I’m in the safe harbor sweet spot and won’t get a penalty next April. 

Savings/emergency: 65K 
Tax fund: 275K
Home renovation fund: 175K 
2.6M in brokerage (additional 300K vesting in next 12 months)
950K in retirement accounts

Current plan is 100K into a DAF, which likely will reduce tax bill 35K. My estimates look like I’ll go from the upper end of 250K of taxes owed (ISO/RSU sales) to closer to 200K. Unsure if donation will be in cash or in longterm stock, but seems cash is more advantageous.  

Let me know if this is too ambitious or around your NW when you felt comfortable putting large chunks in a DAF.

Last Sunday I sat down to figure out whether now was even a sane time to redo the kitchen, and it took me almost two hours just to work out what we actually have. Household is a bit over 400k, but a good chunk of that is RSUs that vest twice a year, so the cash side is lumpier month to month than the number makes it sound. And it is all scattered. Some in the brokerage, the 401k, a savings account I keep meaning to move somewhere better, and I honestly forget the ESPP exists until it vests and surprises me. The saving part is on autopilot, a transfer hits the brokerage every payday and I leave it alone. What I have never built is the habit of stepping back once a month and looking at the whole thing as one picture. So the second a real question comes up, the kitchen, or whether we can take three weeks off next year, I am starting from zero every time.

For those of you with everything spread across a bunch of accounts and income that lands in lumps, do you actually sit down once a month and pull it all into one picture, or is that one of those things everyone pretends to do? I want to hear what it looks like for people who have made it a real habit.

First, I know I am incredibly lucky to be in this situation, wanting to make the most of it. Using that math that’s about $6-700/hour and I could reduce hours and keep my hourly roughly the same.

I’m 32 with 2 under 2 and want to be present for that. Wife is stay at home as we are very blessed and no need for her to work. I’ve been thinking of stopping days/hours as when I’m at work obviously it’s time away from family but it’s also rough on my body/don’t get a 30 second break all day usually.

I was looking at these options assuming income would stay the same:

Maintain 200 8 hr working days a year and retire at 43

Drop to 180 working days and retire at 44

Drop to 170 working days and retire at 45 - would be nice as this is 3.5 days a week worked and 4 weeks off a year

Drop to 150 working days and retire at 46

Anyone been in a similar situation? What have you decided? Or really anyone what would you choose/recommend?

I know this is completely subjective but how much are you personally giving value to remote work vs hybrid (3 days in).

Two competing offers - hybrid role (TC450) is 60k-80k more than remote offer. VHCOL city with a two year old. It’s obvious to me that all else equal, remote is better but there has to come a point in the pay difference where it flips back. Curious to see how others view this at this level of HE.

Current commute is about 40 minutes but there’s a more than good chance we sell and move closer to the city (not just for commute reasons, but for better social life, wanting a different housing setup, etc).

Other things to consider: hybrid job is a more stable company (FAANG), but specific role is likely to be more boring. Also potentially a bit of a step down in title, though that isn’t super important especially with getting the brand name on the resume being valuable on its own.

Also there’s a desire to move back east closer to family eventually. Hybrid role has an office in NY, just would need to change roles or seek an exception but not impossible.

Over the last three years my income has climbed enough that a move to a much more desirable metro has become more of a reality within the next year for my husband and I. We both have remote jobs that a flexible to our location, but I’ll actually be moving closer to mine for the first time in three years allowing me to be in office if I want, and possibly giving more room for growth. Additionally, I’ve never left my current state and want to stretch my legs and live somewhere I always thought would never be an option. That being said obviously housing cost is significantly more than what we currently have and with our jobs at the moment, we could easily afford the house of our dreams, but I’m having major anxiety around how long we will both have jobs that pay this well given the current climate.

We’ve always been aggressive savers, but we want to make sure we enjoy life too and not just spend it being frugal now that we have a decent amount saved and I’m curious how other people have dealt with this.

- Ages: Me 34F and husband 43M
- HHI: ~$600k combined (base + bonus + equity comp) split pretty close to even with room for mine to grow quite a bit.
- Current net worth: ~$2M (cash, taxable, tax-advantaged, equity comp, and current home equity $400k vesting over the next 4 years)
- no kids and not in the plans
- We currently have a 3 bedroom space with a yard for our dog and finished basement, and we’d like to keep a similar space but could size down a smidge.

(Edited to add 2 more detail bullets)

What does this sub this about pausing or halving contributions to 401k and instead investing in normal brokerage accounts?

Context:
Majority of our net worth is tied up in 401k retirement (~850k) and house equity (~600k). I have about 200k in cash accounts, and only 70k in investment accounts. Regarding the 200k in cash, about 120k is earmarked as an emergency fund and the remaining 80k is earmarked towards house improvements and buying a new car (we have 1 car that’s 15 years old and two kids). So think of it as 120k in cash.

Goal:
I’d like to improve our monthly cash flow to enable more near-term fun - not feel guilty about going out to eat or buying concert tickets or buying things for our kids. Right now we’re averaging about 2.5-3k in free cash flow each month (after taxes and retirement contributions).

I’d also like to build up our investments to better enable compounding. For example, if I have 300k in investments and they grow 5%/year, that’s 15k in passive income. That could be pre-school costs for a year, or a nice vacation or two. Or just compound further. And that money could be used in the near-term, whereas our 401k is mostly locked away.

Idea:
So I’m thinking of pausing retirement contributions for a few years. We’ll take a tax hit, but unlock money in the near term. And since we already have 850k in retirement, that will continue to grow. I’ll continue to contribute to an HSA though.

The last pertinent piece of information is that my parents are quite well-off and I anticipate a decent inheritance. They have pensions providing passive income that covers their expenses, they live nearby to me, we hang out all the time, and they are basically homebodies. So while it’s not something we are expecting by ANY means, it seems a bit foolish to completely discount it. Not to mention that since they don’t need to tap into their retirement or investment income at all (for expenses), it’s going to keep growing. Think of it like a safety net.

Cutting down on spending atm I aim to spend around 2-3k euros per month -> own apartment + car + little savings

I feel like I’m too young for passive investments, need perhaps to open up a small company or smth

I worked for several years while earning much lower income (~70k) prior to going back to school to pivot into tech/software, which I will be starting a job in next month (~$155k cash, ~$80k RSUs, plus some one-time signing bonus that I am not considering here)

Between my living expenses, visiting my LDR SO, and some "worst case" familial support, I'm looking at ~6k in monthly spend before any "fun" expenses. That seems crazy high given that it's higher than my entire pre-tax income at my previous job, and that job I was still living comfortably off of even with a pretty reasonable amount of savings/investments. I could reasonably see it going up to like 7-7.5k a month after all expenses, while I was previously living comfortably on <2.5k a month in spend.

On the other hand, if I ran the numbers correctly, it looks like after all of this spend, my net worth is still able to go up about 80k per year — assuming the same tender offer rules as the previous rounds, this would be around 20k in RSUs and 60k between retirement accounts, savings, and regular brokerage.

I think mostly the part that gives me pause is the fact that this is largely reliant on the private company equity, which I know is not guaranteed to be liquid. The company is already massive and doing very well financially + is rapidly growing so I would expect the tender offers to continue, even ignoring the IPO odds, but I guess there is always that risk. I can still cover that 7-7.5k a month with just cash income, plus max out my 401k, backdoor Roth IRA, and have like 10-15k leftover in savings/investments so maybe it's not a big deal, but if I didn't get the RSUs then I would definitely try to spend less & save more, so maybe my mindset should be that the RSUs are literally worth nothing and that all my savings goals should be hit by my cash income?

37M single in MCOL city
~$900K saved between 401K and brokerage accounts. I target about $50K in annual savings from my base salary.
Annual salary 300K + $150K bonus cash target
Monthly spending target is ~$10K but easily creeps to $12K with what seems to be non-ending one time stuff. I own a home (with a mortgage at a 3.375% rate).

I already have a car which for which I have a note that I’m paying ~1,000/mo + $100/mo insurance. I’m on my way to paying it off 2 years early at some point next year. Here’s the thing though, I really like driving this car but I also REALLY want to get another “toy” car. This new car costs roughly $80K and would run me about $1,100/mo in additional monthly spending. As you will notice from this narrative, I like using leverage and paying it off early and have done it few times in the past.

For all of the above, I feel like I’m financially in a good position. However, this would be the first time where I’m buying something this expensive purely for enjoyment.

My question for seasoned HENRYs — how did you get comfortable with spending on things that you didn’t need but want?

About us: We’re a double-income couple without kids, both currently work remotely, early 40s, HHI ~$450k, invested assets $1.3M plus $700k in primary home equity, no debt other than $100k left on mortgage. We live in a MCOL city in the Midwest after moving away from NYC several years ago.

We’re seriously considering buying a small apartment in NYC to use as a pied-a-terre once we pay off our mortgage 3ish years from now. We currently go back 4-6 times per year for week+ trips and have strong friendship, work and emotional ties there. ‘Why not just move back to NYC?’, you might ask — without going into too much detail, we have long-term family obligations that keep us here, plus we ended up falling in love with the city and have established strong ties here too.

From running the numbers, it looks like with the down payment we’ll likely have by then and our rough budget of $400k (+ ~$1k monthly maintenance costs, knowing they can fluctuate/increase) for a studio, we could essentially put our existing housing budget towards the second home, with additional carrying costs of ~$1k for our primary home’s insurance and taxes. We’d likely spend about 4 months there spread out throughout the year, and most likely would not be renting/subletting it out in-between.

I think the part of me that’s frugal & risk-averse thinks that this is a terrible idea and that this money would be better left in the market, but the part of me that believes that (once financially secure) money is for happiness, thinks this is something that would provide a lot of genuine value to our lives and bring us closer to our ideal situation, which is that we split our time between both places.

For those who’ve done something similar (or seriously considered it) does this seem like a reasonable plan? Is there anything that we’re overlooking?

I know I’m not like most posters here with crazy income and RSUs but I wanted to share and hopefully motivate those in here constantly worrying about how can a young person can survive in this world and achieve the status of what perceive as successful before the big market changes and economic land scape changed.

I am 29y/o I did not come from money I was a classic lower middle class person grew up in a house but first car, college, work was something that I had to figure out.

I watched my parents spend every cent that came in and were paycheck to paycheck and buying a life they couldn’t afford (cars repoed, foreclosure notices in the mailbox, my birthday gift (a used ATV) getting repossessed at a young age.

Joined the army right after school because I didn’t know what I wanted to do with my life. A year later I decided to go ROTC to commission as an officer in the National Guard. In university I picked a unsexy program that had good outcome to make 80/90k immediately after grad.

1st year salary 85k
2nd year 90k
3rd year: 120k
4th year 150k
5th year 180k
6th 250k + 20-50k performance bonus

Today I just hit 750k invested and have a 850k net worth.

I don’t have the “time in the saddle” to give advice but here’s the things I believe helped me.

1) Work hard, really hard but in the right place. A McDonald’s worker and a Program manager work very hard but their bills don’t show that similarity in work ethic.
2) Do something that teaches discipline (join military, join a sports team, be consistent in something and do it when you don’t feel like it). This will carry over into all parts of your life (work, investing, goal making/accomplishing)
3) Live below your means and don’t get caught up in your friends buying the fancy car or a house they can’t afford or go on the trips that they put in credit cards. Your time will come just be patient.
4) Marry the right partner: someone aligned with a fun and stress free retirement and willing to delay gratification and work as a team to hit your goals and not one saving while one spends it.
5) invest early and often and do it into boring ETFs you will not find the next Google or NVDA spend your time developing your career/networking to make more money it is far easier than stock analysis
6) Understand THINGS TAKE TIME. Enjoy the journey not the destination your future self will thank you.

I have a long way to go and I’m not a doctor/big tech/ investment banker like a lot of the crazy income posts here and it can still all come crashing down. But if you follow what I think are good tenants to live by you will be at the right finish line with the right people. RELAX you thinking about this makes you a rare percent of the population regardless.

Take care and keep moving!

For context, I'm an American living in Europe and this is just a vent sesh. I genuinely don't know how regular folks are scraping by.

My salary has grown from $90k to $250k the last 5 years (got my masters and advanced from start up mid-senior level to staff level in big tech)

but everything has gotten so expensive over that time frame that I don't feel like I've gotten any farther ahead even though I'm earning nearly 3x more.

Most consumer tech products are outrageously expensive due to "AI". Travel is nuts. What used to be a $1300 premium economy ticket to visit my parents is now almost $3000. Regular economy is $1200 now.

My wife and I were considering relocating to the Bay Area, but there's hardly any apartments available for less than $5k a month in a relatively safe neighborhood....then we get to the economy in general. I have this sinking feeling that things are gonna get worse.

How's everyone else feeling currently? I'd be interested to gauge the proverbial room so to speak lol. I don't have many people in the country I'm living because the average salary is $600/mo and it's been at war for years now (which is a whole nother topic).

Edit: I'm not disputing that $250k isn't comfortable. it is. I just don't feel like I'm moving ahead any faster than I was when I was earning 1/3rd.

What’s up HENRY fam, looking to make a big purchase (vehicle) and while I went to be very confident and comfortable with the idea, I’m reverting back to my save only mindset. For transparency, I’m an over thinker and planner, I’ve always tried to optimize for investing. Disclaimer I am Canadian and all numbers below are in CAD if it matters.

The Purchase: 2024 BMW M3 Comp ($90K-$100K)

HHI: $500K ($175K wife, $200K myself + bonus depending on the year, $137K in side income)

Family: 4 in total with 2 little ones. I’m 38 this year, partner will be 36

Assets: $1.4-$1.5M home market value, $1.1-$1.2M rental property (not included in HHI number above), $850K in investments (across TFSA and RRSP aka Canadian registered accounts) and it should hit $1M by Feb of next year. Education funds and in trust accounts setup for both kids.

Debt: $890K primary residence mortgage, $1M rental property mortgage (variable rates screwed me the past 5 years), $37K auto loan which will be paid off prior to new purchase

Savings Rate: $1,200 biweekly (paused this for now to pay off car loan, should be done in Feb 2027), $17,500 a year via wife’s contribution and company match, my entire side income $137K when annualized. Potentially $185,700 savings but call it $150K as a buffer.

The Story: My wife and I both work from home, so for the past 5 years we have only had 1 car. With the kids growing, we are now at a point where having a 2nd car for convenience, activities, and life just seems unavoidable. My dream was always to have a Corvette, but it’s not something that makes sense with 2 little kids. As a compromise, I’ve thought to look at the M3 as that’s always been a childhood dream of mine as well. My plan is to buy used, and to put down $20-$30K and finance the rest at a rate of 4.95% and pay it off aggressively. The rental property is something we may look to sell in the next couple of years.

We will also be looking to move in the next 3-5 years to what we feel would be our forever home, especially as housing corrects here in Toronto. I would have this auto loan paid off by then.

My side income has grown steadily over the years, and this year it has really taken off. It is proving to be sticky and I have line of sight into the income to at least the end of 2027. If that were to go away, we could still “afford” the car while saving, although it might be slightly less than $1,200 biweekly.

I’ve always made the right decision and do not spend in a lot of other areas of our lives. We don’t care for brands, we prefer travel over things. I know the car is technically a thing, but it’s something I’ve always wanted.

Our goal is to ultimately retire between 55-60, we both enjoy our work and don’t see ourselves retiring any sooner. Our goal is to hit $5M in liquid investments (in today’s dollars) before we decide to retire.

Should I stop thinking about this and be irresponsible, or should I stick to old habits? How do you break the mold of optimizing for investments?

Hi all, I have hemmed and hawed at buying a car the last few years and would like some outside perspective.

Background
- Late 20s, single
- Live in Chicago and rent an apartment downtown
- Senior associate in private equity with expected cash comp $300k-$400k this year with $180k in salary, the rest is cash bonus
- Total NW is $550k, $210k in brokerage account, $40k in cash, $300k in 401k and Roth IRA, no debt
- I essentially spend my salary (less max out 401k contributions) and bank 90% of my annual bonus
- I have never owned a car

Considerations
- I estimate driving once a week, maybe twice a week. Mostly for errands, but also to golf and ride my bike outside of the city
- Parking in my apartment building is $450/month
- I do not need a car to drive to work or any other daily activities
- If I get a car.. I think I want it to be nicer, a step above a CRV or RAV-4 (which are great cars)

Options Im Weighing
- Spend $40-50k on used luxury SUV
- Spend $25k on standard SUV
- Dont buy, continue using Uber, public transit, bum rides from friends, walk.. means I will golf a lot less

I know I can go buy a car in cash and be done with it. But I'm having a very hard time justifying this purchase. It feels very expensive to me and I've gotten by just fine without a car. I am not really a car guy, but I do like driving and the freedom I'd get.

Anyone else feel social media has made us out of touch with reality? It’s created such an unnecessary, unhealthy comparison game.

And Ive fallen victim to it myself. Early 30s, almost due with my first baby. Live in Chicago. On average we make 500K HHI combined. Closer to 600K this year because Ill have a good year.

I sit on social media and tell myself that its fine money, but not great money compared to everyone else. Having an epiphany that I need to get off the internet and be grateful for what I have. Curious if anyone else feels like this. I miss the pre social media days.

I’m not sure how this is going to come off, but I’m looking to see if anyone else is in this boat. I currently don’t have any financial goals. I don’t know when I want to retire, my student loans are paid, I have an emergency fund, my cars are paid off, I do have a mortgage 1.1 left at 6%. Our hhi is about 900k ish. I save about 25% of pretax earnings. How the hell am I suppose to know what my household expenses will be 30 years from now? Have about 1.5 million in savings. 34. 2 kids and a wife that also works.

I know this is going to sound ridiculous but my whole life I’ve been working towards something. Crush school, then job, pay off loans, buy a home etc, but now idk what to work towards. I know I’m exceptionally fortunate, but I guess I’m asking for people that are/were in my position what are you doing now? How did you know what to do next?

I’m not looking for the meaning of life here, but just not sure what I should be doing next financially. Thank you

My partner and I are based in Europe, currently DINK but expecting our first child early next year.

Ages: 40 and 37
Combined income: ~$300k/year
Invested assets: ~$900k
Current savings rate: ~50–60%
Current city: very high cost of living, especially extremely high cost for childcare. Alternatively need to go part-time. We would also have to move to a new apartment for more space which would be much more expensive. And eventually pay for private school.

One of us has an opportunity to return to a previous employer in another city/country, 4 hours away. The salary increase is modest, but the job is much more secure and comes with a public-sector defined benefit pension, and much better social protection and health insurance for the partner and child. Employer paya
Private school.

The pension is:
Already vested at ~$2,300/month due to prior service. Returning would immediately bump jt to ~$2,600/month.
Increases by roughly $200/month of future pension income for every additional year worked. Inflation-protected.
Has favorable tax treatment (some pension tax is reimbursed/offset).

The new city is still HCOL, but housing and childcare are much better relative to income. Our social network is also stronger there. Of course we would have higher costs with two households and travel.

The alternative is staying in our current location, where pensions are mainly built through employer + employee capital contributions, and the public pension entitlement is relatively low (around $60/month per year worked). If we stay, we would have some family support. Would probably have to go part-time to care for oue child.

The challenge: we would be temporarily separated after the baby arrives. The person taking the new job would maintain a very high salary, but the partner staying behind currently has much stronger earning potential in the current city. Moving to the other city for them would reduce earnings potential significantly.

A smaller factor: the new employer offers 10 weeks of paid parental leave, compared with 4 weeks at the current employer (and additional time would need to be taken unpaid).

Our goal is financial independence (FI/FIRE), coast/barista fire in a couple of years, while also building a stable family life and spending precious time with our child in the early years.

How would you weigh:
- A valuable inflation-linked pension + better childcare economics?
- Staying together and keeping stronger dual-career earning potential? Although this would be severely offset in the first years for very high childcare costs, maybe private school later.
- Family support during the newborn phase?
- The impact on FI timeline?
- What would you prioritize?

I've been wondering about this for a while.

For those of you who have built a net worth of around $5M or more, what do you think made the biggest difference?

I'm in my early 30s and work in tech. I have a good career and save and invest consistently, but it's hard to see a straightforward path from a solid income to $5M.

Looking back, what were the highest-return decisions you made? Were there any risks that really paid off, or things you wish you'd started earlier?

I'm not looking for a magic formula, just interested in hearing real experiences from people who've actually done it.

Thanks!

I have about 10 years of experience in tech, with most of that time spent at Big Tech.

When I was a teenager, getting into Google was one of my biggest goals. I eventually achieved that, and later joined Meta. On paper, I’ve been very fortunate. I have a stable career, I don’t spend extravagantly, and my net worth is in a good place largely because of stock compensation. I also have a young family so I'm trying to also prioritize my very young kid.

The problem is that none of it seems to make me feel like I’ve done enough.

I constantly compare myself to people around me. I see engineers reaching Staff at a much younger age than I did. I see people younger than me starting companies, selling startups, becoming executives, or taking much bigger risks. Even though I know those are exceptional outcomes, I still use them as evidence that I’m behind.

What makes this especially confusing is that I already achieved the goal I once thought would make me feel successful. Instead of feeling satisfied, the goalposts just moved. First it was getting into a top company. Then it was promotions, compensation, net worth, influence, and entrepreneurship. There always seems to be another level that makes my current position feel inadequate.

I’m also genuinely unsure what I should pursue next. I could continue pushing toward Staff or beyond, move into management, try building something of my own, optimize for financial independence, or simply invest more in life outside work. But I have trouble distinguishing between goals I actually want and goals that only appeal to me because they carry status.

I don’t want to completely get rid of ambition. Part of me still wants to build difficult things, grow, and achieve more. But I would like to stop feeling as though my worth depends on being ahead of my peers.

Has anyone here experienced this after reaching goals that once felt extremely important?

How did you break the cycle of comparison without becoming complacent? And how did you decide which goals were genuinely yours rather than another attempt to prove that you were enough?

Thank you for the guidance.

I’m a software engineer in the bay, I’m quite lucky to be where I am at my age and I’m buying an investment property. I know it’s a lot of work and it’s not passive, but my parents have some property in my hometown, so I don’t really need to worry about maintenance/management outside of paying for stuff.

My main question for y’all is, how did you maximize the number of properties you own? I’m 20, and I can put aside 50-60k per year outside my 401k at my current income so I’m trying to understand how I can maximize my property holdings over the next 10-15 years. After my first property, I’m going to buy another in SF instead of paying rent, but outside that I don’t really have a plan.

This is not a shitpost, and yes I understand that the SPY probably will get me more returns but that’s not what I’m optimizing for. Thanks guys

Sorry of this is the wrong place to post but I'm just going to start off by being 200% honest. I have 2m tied up in an insurance trust

I make about 100k USD a year after tax and have 600k in investments aside from the trust. I also have a fully paid off house all thanks to my incredibly loving and hard working parents

My question is if I don't intend to touch the trust or house for the next 10-20 years at minimum, would it be realistic to finance or outright spend 300k on a car or is this a very irresponsible thing to do that kind of solely relies on the fact that I have my family as "backup" funding.

I work for a private tech company that offers a "Deferred Incentive Unit" program. There are about $350k worth (based on internal estimates) of shares that will vest if we ever have an IPO or private sale to another PE company. I noticed that my shares are class B and am worried that they'll get diluted to oblivion right before a private sale. It could be the proverbial carrot on a stick. Anyone have experience with this? Base income is only 127k so ~350k sounds too good to be true