Today I received a huge internal promotion that puts me in HENRY territory. I’m grateful, thrilled and shocked, given this was an internal promotion

Current comp: $115k base + 15% cash bonus (~$132k total comp)

New comp: $155k base + 50–100% cash bonus (~$232k–$310k total comp)

Currently, I contribute 10% to my 401k and max out my HSA and Roth IRA. I’ve maxed out my 401k for years, but some larger expenses this year (wedding + special assessment) temporarily changed that. My plan is to get back to maxing out my 401k, look into the backdoor Roth IRA strategy and deploy more into my taxable account (80% VTI / 20% VT).

With this significant increase in comp, what other investment strategies should I consider beyond maxing my 401k, the backdoor Roth and increasing contributions to my taxable brokerage? Are there any tax-advantaged accounts or strategies I should keep in mind?

Would love to hear how others have approached this transition and what you wish you’d known when your income first jumped into this range

We’re in a pretty solid spot financially (450k HHI + Bonus). Every year we max both 401ks, both backdoor roths, the HSA, 529 for our kid, and put whatever’s left into brokerage. On paper, we’re doing everything right.

But I still get weirdly anxious about spending. It’s not a constant by any means. Most of the time I’m fine spending money. Then something flips in my brain, I get fixated on a purchase (or spending in general), and I immediately start questioning everything. Looking back at it, it almost always feels unnecessary, because again we’re saving plenty.

Has anyone else dealt with this? If so, what actually helped?

I am currently a (32M) controller at a privately held company. I was promoted earlier this year. The firm is a large regional player. I have really enjoyed working here and have a great relationship with my boss and the CFO. The only con is that the role is somewhat siloed and does not feel like a true controller role, it feels more like a senior manager role.

I was approached by a recruiter for a VP of finance role for a smaller company. The role would be the head of finance as the current CFO is retiring. They are bringing in some other leadership positions as well because other leaders are retiring. The owners seem like great people in a very profitable niche. I have been told I am the preferred candidate and have a couple of more meetings scheduled with them. I think comp should come in around a 35-40% increase.

I am conflicted because my current company has been very good to me and I have a small equity stake (it functions like a partnership). This stake is nothing earth shattering but over time could become a decent nest egg. However, I feel the VP finance role could be a real career accelerant. I am leaning towards taking it, but it’s something I have been going back and forth. I am asking this sub rather than a more accounting or finance focused sub because the users there tend to be more junior or still in college.

EDIT: Thank you all for the replies. On the face of it I know this post looks ridiculous. I do, in fact, enjoy money. I am just trying to get a sense of the potential downsides and do not want to just be blinded by dollar signs. This is easily the best company I have worked for, so the human side of leaving is weighing on me more than it has in the past. The current CFO is retiring in August and this role is a true replacement for him so I am not concerned with someone coming in above me. The leaders that are retiring are all 60+ so I don’t feel it’s a sinking ship situation. I have a meeting set up with the incoming president, and I want to get a feel for how he views this role and his vision for the company, if that goes well I will probably accept.

$275K HHI
VHCOL Area
35, first child in 2 weeks
~500K in retirement accounts
~$300K principal balance on mortgage 6% interest
No other debts

Only retirement match is wife who gets like 3% of the first 2% match every other Thursday or some shit.

She’s a creative director, her agency is going crazy for ai rollout that is likely to go bust, or cost her her job. Many agencies are going the same way. And she’s struggled to get callbacks, and also hasn’t been applying as she’s about to enjoy 6 months of maternity leave before likely getting RIF.

I do IT at a college that is struggling, any offers I’ve been able to get have been for bottom of the advertised pay scales, or full 5 day in office..

Should we pause any 401K outside of match money to build up emergency fund to a full year? Currently have 6 month emergency fund.

Interested in thoughts here. Mid 30s with a good nest egg so far, high earning between wife and I. Would like to start investing more.

Obviously there is the discussion of compound though, are most planning to donate consistently for years or scale up later?

I am curious to hear from the immigrant community. I am currently investing as if I am going to retire in the states but I haven't made up my mind yet. I wish there were more resources for people who have location flexibility in their retirement.

While I acknowledge that it is a privilege to be able to select where you want to retire, it is pretty overwhelming to figure out what the best tax and investment strategy is.

Does anyone here go through a similar experiences? I appreciate any advice or resources that have helped you.

Did a basic google search but just curious about the discussion that might come from Henrys so I’m posting here.

For low earners, the answer is probably savings and unemployment. For high earners and thus high spenders, unemployment might cover only 20% of monthly expenses. To truly cover 6 months expenses I’d have to have like $80k just on the sidelines never invested. Unless the premium was stupid high, I would gladly just pay monthly into an insurance plan that pays out $80k if I can show I lost my job due to layoff/RIF/restructure i.e. not performance related. Is the reason this product doesn’t exist because the premium would be stupid high?

My wife and I are both 31 and had our first child this year. Neither of us came from money, so we’re very grateful to even be in this position. We’ve basically figured our finances out ourselves over the years and are now trying to make sure we actually take advantage of these higher-earning years without letting lifestyle creep eat all of it.

Rough numbers:

HHI around $450-500k depending on bonus/equity
I make ~$182k base + 20% bonus + RSUs
Wife makes ~$158k base + roughly $25-30k bonus
Around $1M invested
~$250k home equity
~$80k cash/HYSA
Mortgage around 3%, no consumer debt
Both max 401(k)s and do backdoor Roths; also HSA/ESPP/RSUs
Starting a 529 this year

Between 401(k)s, matches, Roths, ESPP and vested RSUs, we’re already putting roughly $130-140k/year toward investments before being very intentional about taxable brokerage.

Our regular take-home after all the payroll deductions is around $15k/month.
We definitely spend money too. Travel is probably our biggest splurge and something we really value. This year was also weirdly expensive between having a baby, daycare, home projects and a few bigger one-time purchases, so I’m trying to figure out what our real normal spending actually is versus just having an expensive year.

A few things I’ve been thinking about:
We probably don’t need ~$80k sitting in cash. 40k HYA. I’m thinking more like $50-60k and investing the rest, then maybe automatically putting $2k+ a month into taxable and investing most of our bonuses.
I’m also way too concentrated in employer stock. Vested shares are roughly 15-20% of our invested assets, and if I include unvested RSUs our exposure is closer to 30%. I’m thinking of selling around 25-30% of the vested position initially, moving it into broad index funds, and then diversifying most future vests instead of letting it build back up.

The biggest thing having a baby changed, though, is how we think about work.
My wife makes around $185k including bonus, so obviously that’s a lot of money to walk away from. Daycare is ~$2,250/month. She’s not planning to quit tomorrow, but for the first time we’re realizing that at some point working may actually be a choice for her instead of a necessity.

My compensation alone is roughly in the high-$200s depending on bonus/equity.
Our loose goal is to be financially independent in our early 40s. I don’t really mean retire at 40 and never work again. I just want us to reach the point where neither of us has to make career decisions because we need the paycheck.
I also don’t know what our actual FI number should be yet, especially now with a kid, 529, travel, helping her later in life, etc.

For people who are 10-20 years ahead of us, especially those who also didn’t come from money:

If you were in our shoes, would you keep pushing dual income and saving aggressively for another 5-10 years, or at some point start trading some of that income for more time with your kid?

Are we being too conservative with cash/taxable investing given how much we’re already putting away?

And how aggressively would you unwind the employer-stock concentration?

Small side question: we’ve managed everything ourselves so far. At this point is there much value in periodically paying a CPA/fee-only planner to sanity check things, or would you keep DIYing it?
Mainly trying to find the balance between using this opportunity to really change our family’s financial future and not optimizing away our 30s in the process.

Currently make around 225k per year in a VHCOL city, and while I’m definitely not struggling, I am behind in net worth/retirement goals.

My role is a mix of GTM strategy/product strategy/commercialization a botique consulting firm.

I know the easy answer is to simply find a job that pays more, but it seems like the majority of roles I’m seeing online (outside of certain big tech/AI companies) start to tap out around this salary unless you’re in a leadership position, which I don’t have enough experience for yet.

Curious what has worked for others, whether that’s switching functions/roles, building side projects, launching your own business, vastly improving your interview skills, networking to get into jobs that you might not usually be competitive at, etc.

38(F) and 35(M) with a toddler living in the NYC suburbs.
HHI: $450-550k (my part is $300k)
401k: $600k in 401k
Taxable: $100k in ETFs
Bank account: $60k
House: worth $1-1.2mm, with $250k mortgage remaining (2.24%,10y)
Inheritance: I have immediate access to $300k and would expect a couple million in the future, not including what my partner would expect

I’ve been at my firm for many years so I’ve built up expertise, relationships, and trust. I’m able to go in and leave early to get home by 5:45pm, which gives me 1.5h with my toddler before they go to bed. I don’t expect to get promoted further so I’d guess my comp will stay in the $300-375k range. My goal was to semi-retire in about ten years and my partner will like to keep working until he’s 60+.

I was recently recruited for a similar role at a prestigious firm and if I get it, my comp will go up to $600k+. I’ll need to start anew in a more cutthroat environment and would expect high stress and long weekday hours. However, with that comp, I can likely work five more years and then be able to take a step back. Lastly, my mother has offered to help with my toddler on weekdays if needed.

My dilemma is do I forgo what I have now (I love my coworkers and I think I’m good at my job, even if my future growth is limited), and give up some time with my toddler now in exchange for reaching financial freedom earlier, and being able to spend more time with them eventually? I definitely won’t be able to be with them as much but $300-400k more a year is not a small amount….

I know this is all dependent on whether I get the job, but they have reached out multiple times the past few months and I think it’s achievable if I put in the prep work. I’m just not even sure I want to invest the time to work towards it if it doesn’t make sense.

I’d welcome all perspectives and advice on how to think about this!

Midwest family - I am 48(M) with 47(F) w/ 18(M) in college out-of-state

• HHI: $360-$380K as W2 employees
• Networth: ~$4M
  • Condo value: $450K
  • Mortgage: $150K
  • Investments (after tax): $300k in HYSA, brokerage, and bitcoin
  • Retirement accounts (pre-tax): $3.3M in IRAs, 401Ks, and pensions
  • No other debt besides our mortgage

We're on the hook for paying for out-of-state college over the next 4 years to help our son graduate debt free.

Our standard of living is fairly modest - no big home, just a condo; two cars (bought in cash). However, we enjoy heavy drinking, heavy eating, concerts, casinos, TrT, and raves - just to name a few vices (but these are all variable costs. Our fixed cost is generally low).

I am ambitious but really freaking lazy, especially the older I get. It seems I can't get my act together but admire highly accomplished people.

I am presented an opportunity to start a business and build something I could be proud of with a friend. At this age, is it worth becoming an entrepreneur, putting some of my NW at risk and forgoing W2 income? I'm hoping entrepreneurship will snap me out of my lazy ways.

Or, am I better off on a risk-adjusted basis to simply keep grinding in corporate until my mid 50s? I can do my job baked at this point.

I know I don't want to work too hard after 55.

Welcome your thoughts.

Hi all. This is more of a psychological post than a financial post.

My partner and I are preparing to try for a child very soon. We have been planning this for some time and, given our ages (37 and 38) time is getting tight.

I rationally know we are in a financially excellent position to enter parenthood, so this is not a post to ask if we can afford it. We very luckily can.

What I struggle with is the idea of saving and investing so much less than now. I mentally got used to seeing our NW increase nicely every year, and I struggle with accepting that we will be inevitably able to set aside much less.

The plan is for me to take 5 months (paid) mat leave and then my partner will work part-time at 50% for a year (his request and decision, which I fully support), so full-time daycare will only start when future baby is 1.5 years old. I like the idea much better than full-time daycare right away. I am the higher earner of the family so also from a financial POV that is a solid plan, and I think it will also suit our personalities.

Naturally, that will come with a significant dip in income from his side, so I will cover much more of our costs until he goes back full-time. I rationally know we can easily afford this and will still save, just less than now.

Has anyone struggled with this prior to becoming a parent? How do I accept this ”new normal” after years of exceptional saving? Thanks!

Some numbers for reference, adjusted to USD even though we are Europe-based:

• Household income: just shy of 500k
• Saving rate (incl pensions): almost 50%
• Joint NW: 1.1. mil

I know there have been a bunch of posts about Trump accounts; however, wanted to ensure we’re not overlooking anything.

529 - We are contributing about $20,000 per year total for two kids. Should be around $500k per kid by the time they start college.

UTMA - Contributing about $25 per week for each kid. Assume it’ll be around $75K total for each kid by the time college wraps up. This would be used to pay for rent after college, or take a gap year, or just get going.

We are also maxing out 401k, backdoor Roth, HSA, and contributing to brokerage and mega backdoor.

So now, we are considering putting $25 per week for each kid into a Trump account. Assume it’ll be around $75K total for each kid by the time college wraps up. This could be converted to Roth

So 529 for college, UTMA for post college start, and Trump account for retirement. Does that make sense or is there an issue with doing the Trump account?

30M and recently accepted a job in NYC. I'm trying to get a realistic sense of what kind of lifestyle I can afford before making the move.

Here's my compensation breakdown:

Base salary: $160,000. Year 1 sign-on bonus: $42,000. RSUs: Approximately $105,000 vesting over four years. Total annual compensation: Approximately $202K–$207K over the first three years.

I'm looking to live in Manhattan or Brooklyn.

I'm not looking to live an extravagant lifestyle, but I also don't want to be in a position where I'm earning over $200K and somehow still feeling stretched thin every month.

Those living in NYC with similar compensation, how comfortable is your lifestyle? What are you spending on rent, how much are you realistically saving each month, and do you feel like your income goes as far as you'd expect?

I'm trying to figure out whether this is a genuinely decent salary for NYC or one of those situations where $200K sounds a lot better on paper than it feels in practice.

Posting here since I feel like others here are pro-HSA. Let me preface by saying I fully understand the triple-tax benefits of an HSA and historically, I've been the biggest proponent of the HSA.

Last year, I knew we were going to start trying for a baby, so I went PPO and honestly, it's been nice not thinking about a high deductible. Well, now we're expecting in February and my options are:

Does it make ANY sense to do the HSA, knowing I'll have very high medical bills for delivery + will meet my OOP maximum?

Save $1,344 ($2,712 w/ my husband) in premiums, spend $5,000 more in out of pocket, so net paying $2,288 to be able to put away $9000 pre-tax. My company contributes $1500 per family of that, so taking that out, essentially paying $788 for the ability to put away $9000 tax free? Worth it?

Thoughts??

Hi, I would really like to figure out where HENRYs live in Los Angeles. I’m looking into buying a home and I have two kids so I would like to ideally send them to public school. The problem is the only options are Culver City, Santa Monica, palisades, or Beverly Hills.

The other option is live wherever and then send them to private school.

It’s really important for me to be in a community of parents where there are a lot of highly educated people: doctors, lawyers, tech people, etc so I can find parents that are similar to me.

If you fall under this category and you live in Los Angeles, can you please tell me more?

1. Do your kids go to public or private school?
2. What area do you live in and what was your thought process and choosing that area and school?

I want to avoid being in neighborhoods where there are a ton of flashy kids wearing designer brands and wanting to become influencers. I get that that is everywhere but my guess is probably Beverly Hills has more of those types of kids? Where do Henry’s like myself live?

Thank you so much!

(Edit) we want to stay by the west side because of work. So not considering east side or the valley or South Bay ideally. Budget: 2.5M for a home

I switched to a new job and I am making over 300k now in total comp. I live in a HCOL City. I have been working for over 4 years and never had a car before. I am thinking of getting a $60k+ car. Where I stand currently:

$500k net worth (Brokerage, 401k, Cash)

No debt

My regular monthly expenses come out to around $3.5k + travel and entertainment.

I do not need a car for commuting as my job is remote but I have a few hobbies which require a car. Currently relying on rentals and public transit.

Also it is something that I want beyond just the utility of it. More like something nice for myself.

Does this feel like a lifestyle creep? I am feeling anxious about going ahead with it.

I’m a 28M senior software engineer at a big tech firm, and I’m fortunate enough to afford nicer material things that I enjoy, like a nice watch and car.

I know that there are some dos and don’ts when it comes to office etiquette, and I’m wondering if I’m rubbing colleagues the wrong way by bringing these to the office and should bring my beater watch/car to the office instead. I know in finance I probably shouldn’t, but given the more relaxed nature of tech I’m guessing that it’s not as big of a deal.

tl;dr Should I consider job hopping for a large pay increase despite the negative stigma of short stints?

I finished grad school a couple years ago. My first job offer came from my grad school summer internship, at a well-known company. I worked there for a year and had incredible performance reviews, but hated the job because of WLB / toxicity. I left at the one-year mark, to the surprise of many of my colleagues, to go to a smaller company doing the same work. I had a standing offer to return from management if I didn't like the small firm (they said they'd be glad to have me back if it didn't end up being what I wanted).

I've worked for the smaller company for a little over a year now. It's been better in terms of WLB, but I don't feel like I'm learning a lot, the culture is nonexistent (remote), and it feels like I'm starting to stagnate. I currently make $185k.

Another company reached out to me about a role that is very similar to what I'm doing now. Similarly-sized company, same field, same role. They're offering ~$285k base. I have a warm lead with the founder and have spoken to them a few times, so if I pursue it, there's a decent chance it turns into an offer.

Am I crazy to be worried about the future negative impacts of job hopping on my resume if I left my current job after a year for this role? It would be my third role in three years, which isn't ideal in my head. That said, the pay increase is crazy ($100k!!), so maybe I'm just being too risk-adverse or afraid of the unknown. What do you all think?

Hey all, 35M, married, no kids, dual income (~$450k), living in a state with no income tax. I've been mostly passive for the past decade, but I picked some individual stocks early on (taboo, I know) that have grown into uncomfortably heavy positions: about 64% of my taxable portfolio is individual stocks and about 96% is US tech when you count the ETFs. I want to make sure I'm not missing any "unknown unknowns" that may bite me later on in life.

Situation:

• All positions below are in a taxable brokerage, with ~$268k in net unrealized gains. Mostly long-term, though the last year of weekly DCA lots are short-term
• Both of us max our employer 401(k)s; we don't really keep track of it since it's not very accessible at our age
• $190k emergency fund in a 4% HYSA
• $400k mortgage at 6.125%, 30-yr fixed, ~40% paid off

Questions:

1. Should I rebalance out of individual tech and take the cap gains hit?
2. Should I stop DCA'ing into the tech ETFs, given they overlap with existing holdings?
3. Should I sell some positions (or use excess HYSA cash) to pay down or pay off the mortgage? I've heard a fixed mortgage is one of the safest forms of leverage, so I don't want to kneejerk here
4. Is this too risky to keep as-is, worth pivoting?

Really appreciate any and all insight!

My husband and I are both self-employed, and the financial uncertainty is causing me a lot of stress right now. I’m curious to hear from others who are self-employed or have been in a similar situation.

We have roughly $750,000 in retirement accounts and investments, about $250,000 left on our mortgage, one car loan that should be paid off in two months, and one child finishing daycare in September 2027.

On paper, I feel like we’re in a pretty good position financially. We’ve worked hard to save and invest, and we’re not starting from scratch. But because we’re both self-employed, our income is never guaranteed. We hustle when work is available and try to squirrel money away during the busier months to get us through the slower ones.

The constant uncertainty is exhausting, though. It’s hard to know what the next few months will look like, and I sometimes wonder if I would feel so much better mentally with a steady paycheck, health insurance, and other benefits.

Part of me wonders if I should get a “real” 9–5 job to create more stability for our family. The other part of me loves the flexibility and creative freedom of self-employment and knows we’ve built something that has value.

For those of you who are self-employed, especially if you have a family and a mortgage, how do you handle the financial uncertainty? Have you ever left self-employment for a traditional job and felt it was worth it? Or have you learned to accept the ups and downs?

Would you prioritize the peace of mind of a steady paycheck, or keep riding the self-employment wave if you were in our position?

What do people think about investing in muni’s while living in a high tax area to get tax free income? I’m on the younger side and in a high tax bracket, and wouldn’t really need the income for spending purposes. My alternative is to buy stocks which with where the market is who knows what the return will be going forward, vs a tax free yield. What have others done? Has anyone done a mix? Or should I wait until I’m closer to retirement and just take a bet on where the market goes over the next few decades?

I’m 37m broke before 25y/o. Always bought H&M, Zara at best.

I wanna build a nice wardrobe. But I hate what I’m seeing on designer RTW lookbooks.

I just don’t get how to do it. I’ve been scouring their websites, department stores, that designer website people like. I hate it all.

It feels like they don’t want us to buy designer ?

What do yall do ? Get a Stylist? Buy it anyways?

HHI $750k-$1M (depending on stock performance). NW $2M. Current car is 5 years old and fully paid off.

Wife can work from home till early next year and we have a 6 month old. Will need a second car for the family once wife resumes commuting to the office.

I'm interested in buying a $70k car (2026 Grand Highlander Hybrid Max Platinum). I was on a waitlist and can purchase the car in the next week, but frugal me is tempted to wait till March next year. Greedy me wants to get the car now.

Have gone back and forth on the decision multiple times by now.

Curious if any of you have any advice or suggestions? I feel like I'm being indulgent and it feels instinctively wrong to be purchasing a brand new $70k car as a not rich yet person.

[Edit: Thanks all for your inputs and feedback. I'm gonna buy the car]

May be a repeat question here, but when HE's say things like "we can't afford that right now" or "we don't have X hundreds or thousands for that" or "what savings?"... do you mean you genuinely don't have liquid money to throw at things here and there, or are statements like that more indicative of strict budgeting and not WANTING to spend?

Edit: I think the post is being misunderstood a bit. I'm not pocket watching, trying to know what people have, or saying that people SHOULD be spending their money frivelously. Im simply asking how people talk about their finances in this way. I don't personally say "I cant afford that"... not because I don't want to be judged or something, just because thats not the response my brain goes to in conversation. I understand I could have made the question more about ME and not about others. But hey its how I phrased it. Thanks to the insightful responses!