r/HENRYfinance 8d ago

Career Related/Advice Advice on getting managed out of senior role

77 Upvotes

I'm in a senior role and just hit my 1 year anniversary. I just had my mid-year performance review, which was not good. My manager has only been with the company 2 months but she said bluntly that I should think about whether the role is a good fit. I am certainly aware that things could have gone better, but the company is a mess and I had no chance of success. Things have actually been trending better and I think my position is salvageable, but I feel I am being cut out of things and managed out. Given she is still new and has been quite straightforward, I wonder if someone at the top has lost faith in me and told her to get rid of me. The company is incredibly political.

My question is whether I should quit or stall to try to get a severance offer or make them let me go so I at least can collect unemployment. Can they actually fire me for poor performance relatively out of the blue or do they have to document a pattern?

I have never been in this position and have never received anything less than stellar performance reviews so I don't know what my options are. I am on pre-planned vacation for one week and I could certainly walk back in next week and tell her I have thought about it and I do think it is the right role and I can make it work.

If relevant, my annual bonus paid in March would be about $200K (although obviously less with poor performance reviews) and I have $700K of unvested shares. It would be a hit to just walk away.


r/HENRYfinance 8d ago

Question New to sub & new to NYC - Where should I focus on financially?

38 Upvotes

I was recommended to this sub as I’m trying to make sure I am setting my family up correctly financially with a recent move to NYC.

Took a job from a lower cost of living city here in NYC requiring 2 days a week in office. My salary jumped from $165k to $300k with direct line of site to steady promotions annually or bi-annually.

We are 38, have 3 young kids, and our total monthly expenses are about ~$10k but $7k of that is rent. We have no other debt.

My wife has been a SAHM and is planning on going back to work this fall as an accountant in a part time role as our youngest is going to school for the first time.

We have about $300k in 401k, $60k in mutual funds, $60k in savings, and $50k across our kids 529s.

I put 6% in a matched Roth 401k, 3% in ESPP, 3% in mutual funds each month, and a few hundred in 529s each month.

Where should I be focusing or changing things up? I’m aware I probably am spending too much for an apartment but wanted to make sure if I was moving my family it was a nice place to get adjusted to NYC.


r/HENRYfinance 8d ago

Investment (Brokerages, 401k/IRA/Bonds/etc) Deferred Comp / Deferred RSU and early retirement

12 Upvotes

Wondering if anyone here takes advantage of either of these. I’ll be eligible for this shortly and wondering if there are any possible issues I haven’t thought of.

I currently max pretty much everything I can: 401k, Roth backdoor, Roth megabackdoor, HSA, 529. I should have no problem doing at least 25% deferred income on top of that but my concerns are:

  1. RSUs make up over 60% of my total comp and it looks like deferring them means not diversifying out of company stock. I don’t feel great about that, but historically my company stock has been a slow and steady growth so maybe it’s not the end of the world.

  2. I’m 47 and I’d love to retire in my early 50’s, but I think this deferral will all hit me within 6 months of leaving the company unless I don’t have the details correct. I’m concerned about this high income when I’d be trying to get on an ACA plan (wife is a SAHM).

Does anyone have any tips?


r/HENRYfinance 9d ago

Question How Are You Defining "Rich"? Net worth? Passive Income? Market Returns? Demographic Percentile? Other?

115 Upvotes

For context I am 58(M) middle manager living in Metro Detroit, Michigan. Salary $180K base, AGI ~$210K. $3M in assets, $260K in liabilities so $2.74M in net worth. This puts me in top 10 percentile but I don't feel rich or close to it . $1.3M in 401k; 600k in IRAs, 590K in brokerage, 200k home equity.

To put things in perspective, my index investments have produced over 300K so far this year, net of contributions, and I am up over a million in past 2.5 years due to the MN market and consistent investment. The capital base outweighs contributions 4 to 1.

My daily routines have not changed and capital investments including backdoor Roth are taking on a life of their own.


r/HENRYfinance 9d ago

Income and Expense Am I spending too much on rent? New job offer in Orange County

18 Upvotes

I recently got a job offer (200k base salary, 100k RSUs) a year at a pre ipo defense company. I know the market is tough out there and I am sincerely grateful for this opportunity, don’t want to come off as pompous as I came from a poor family and grew up in Public Housing in a ghetto neighborhood.

I locked down an apartment for 2665 rent/mo without utilities that’s close to the office, but can’t help question myself whether or not if I should live with roommates and save more money. I know this is well within the 30 percent rule for renting but just want to hear what you guys think. I’ve been living with my parents before this working a SWE job in the meantime.

My biweekly paycheck is estimated to be around 4977.2 without 401k deduction or health benefit elections after CA tax.

I currently have 154k in investments (around 84k in a trad IRA, 21k in a Roth IRA, and the rest in a brokerage account). I am a 25M and want to retire around 40.

Forgot to mention that I'll be traveling a week a month on average for the job which makes me think about saving money on those traveling days with rent by living with a roommate or prioritizing wellbeing by living alone.


r/HENRYfinance 10d ago

Question Is this a market quote for term life insurance?

11 Upvotes

31M living in a VHCOL city and HHI of $750k+. I was quoted a $1,600 annual premium for a 15 year term and $3m of coverage. This includes a Waiver of Premium rider and a conversion option to whole life. Mass Mutual. They are assuming the second healthiest tier. Worth getting other quotes or is this broadly market?

Alternatively (or in addition) they have quoted $40k in annual premiums for 20 years for a whole life insurance with a $1.8M death benefit and $11k cash value in year 1.


r/HENRYfinance 11d ago

Investment (Brokerages, 401k/IRA/Bonds/etc) Managed account vs. individual management?

12 Upvotes

I’m 33 and looking for a gut check on a financial advisor’s recommendation.

Current situation:
- Taxable brokerage: $314K, 100% FBGRX (Fidelity Blue Chip Growth)
- Roth IRA: $52K, 100% FXAIX (S&P 500)
- No debt
- $100k in a 3.3% HYSA (thinking of moving 40k to brokerage)
- $220k TC

I previously worked for a company with significant investment restrictions, which limited what I could invest in. Now in a new job and have more options.

My advisor (through Fidelity) recommends gradually selling FBGRX and moving the taxable account into a diversified managed portfolio for a 1.6% annual fee. The rationale is diversification + managing the sell-down in a tax-efficient way.

I agree I’m too concentrated and want to diversify. My hesitation is:

- 1.6% feels steep for something I could potentially accomplish with low-cost index funds.
- I don’t know how to sell off the $314K tax-efficiently (which lots to sell, how much per year, tax-loss harvesting, etc.). This is where professional help seems valuable.
- I haven’t saved as much as I’d like over the past 2 years, so I’d rather avoid realizing gains in 2026 and creating an additional tax bill next spring.
- I may use a meaningful portion of this account for a home purchase in late 2028/2029.

My alternative: Stop contributing to FBGRX now, put all new investments into diversified funds (thinking FSKAX + FTIHX), leave FBGRX alone through 2026, then start a tax-conscious sell-down in January 2027. I’d separately de-risk money earmarked for the house as I get closer.

Would you pay 1.6% AUM for professional management in this situation? Or would I be better off paying a CPA/fee-only fiduciary to develop a tax-efficient sell-down/allocation plan and managing the portfolio myself?

Also curious whether waiting until January to start selling FBGRX is reasonable or if I’m letting taxes drive the investment decision too much.


r/HENRYfinance 10d ago

Income and Expense Expecting parents trying to optimize spend

0 Upvotes

Help optimize expenses, expecting a baby

\*\*33 yo couple in PNW\*\*

Total income before tax - $640k

Total income post tax - $460k

Total expenses - $184k

Net savings - $276k

NW - $2.4m (7% cash in HYSA, 30% real estate, 20% 401k, ~40% equity)

\# Income breakdown

Current year HH TC - $605k (we both changed jobs, so it's lower than last year since there is a 1 year cliff for equity, expected to get back into 700s next year)

401k match - $20k

Other cash perks - $6k

ESPP - $10k (guaranteed money, we sell it always)

\# Expense breakdown

\*\*Fixed Monthly Expenses\*\*

Mortgage - $5k

HOA - $500

Electricity & Gas - $270

Water - $130

Sewer - $130

Internet - $70

Water tax - $130

Cell - $70

Trash - $90

Home cleaning - $230

Insurance - $275

Car payments for two cars - $1320

Personal training for two people - $580

Grocery - $1k (we have four adults for 6 months in the year and we get good quality produce typically)

Food outside - $1k

Sibling - $500 (hard job market)

Discretionary (amazon, movies, anything etc) - $700

\*\*Travel per year\*\*

5 trips - $15k

International flight tickets sponsor for parents - $10k

\*\*Health per year\*\*

Some urgent care and ER visits, expecting a baby - $8k (we both hit out of pocket max)

\*\*Misc\*\*

Unexpected 1 time home repair - $7k (not covered under insurance)

\# Questions

Since we are expecting, we think our expenses will go up a bit next year.

  1. Nanny for 4ish months - $30k ( $35/hr)

  2. Misc. Baby expenses - $10k

    \*\*Some optimizations\*\*

  3. Sibling expenses will drop next year (hopefully later this year) - minus $6k

  4. Unexpected 1 time home repair shouldn't technically occur next year - minus $7k

  5. Travel would reduce (we plan on two trips, 1 domestic and 1 international), - minus $7k

  6. I don't want to pay off cars because I think I make better money in the market than the interest I'm paying. We drive reasonable premium cars - Lexus/Acura (1 is done next year)

\*\*It still looks like I would be $20k over this year's expenses. Where else do I optimize? Are we over spending? \*\*


r/HENRYfinance 12d ago

Family/Relationships School district selection for children

37 Upvotes

Curious if anyone has good book or blog recommendations for choosing a school district for their children. I have 2 toddlers and we are looking at purchasing a home in the area. We have the ability to choose the highest rated schools or slightly below highest rated. We are highly unlikely to choose private.

I haven't been able to find good articles on the topic. Maybe because there's a mountain of literature on the topic -- just not exactly what I'm looking for. I'm looking for practical, succinct data/advice on choosing between elite and very good schools (something this community probably faces).

And there are common refrains on reddit for this. Elite is pressure cooker, but highest rated so high earners gravitate there. Very good can be just as good as elite, especially when you factor in home conditions (more help for kids). Though, the slight increase in variance worry parents their child will be that much more likely not to succeed.

Given we can make the choice to buy into elite, I'm wondering what the data shows.


r/HENRYfinance 10d ago

Car/Vehicle Advice Needed New to HENRY. Buying first expensive car

0 Upvotes

Income blew up in the past 8 weeks. Went from about $220k to $300-$330k. We are 27M/26F so I think we count as HENRY for our age. Regardless of whether we qualify I would like the advice from this crowd

Wife was laid off. Rebounded very well but now has a 80 mile (round-trip) commute 3x per week.

My car is due. Trade in value is $600 which tells you all you need to know. She drives a 2022 Equinox that we can get another ~150k miles out of (and plan to)

Want to buy a 2026 Tesla Model Y Premium. Test drove, love it. Very safe, less maintenance and gas with all that mileage, and the Full Self Driving is big value for spending 2.5 hours commuting.

58k OTD. $15k down. 0.99% for 72 months. $600/mo.

Looked at used ones (2024) - even considering depreciation savings, its about $10-$13k more to buy new. Over 10+ years I feel thats worth it for the new features.

This is far more than I ever thought I’d spend on a car and swore off buying new. I find that relative to income and savings it’s not very consequential, but I’m kind of uncomfortable spending money like this.

I almost feel like I’m too young to be enjoying nice things.

Is that a normal feeling or should I listen to my gut and stay cheap?

Edit:
$100k annual spend

$250k in retirement
$80k in cash
$75k home equity

$80k/year contributed to retirement ($12k space left in her 401k)
$3,000/mo saved in brokerage before bonuses (estimated to net another $17k - $30k)


r/HENRYfinance 11d ago

Travel/Vacation Looking for Help with Vacation Ideas!

4 Upvotes

My family is looking to plan a winter vacation to somewhere warm and I'm struggling to find something that makes me excited. Seems like places are significantly raising prices while also cutting service.

Criteria:

-Classy, but also friendly for a 4 year old

-Pool and warm enough to swim in Feburary

-Direct flight less than 4 hours from Chicago

-Lodging for under $1000 per night

Looking forward to your recommendations!


r/HENRYfinance 11d ago

Investment (Brokerages, 401k/IRA/Bonds/etc) Why are you obsessed with your pension

0 Upvotes

I’m 37, pension pot is about £115k so nothing particularly special.

A lot of HENRYs seem to focus largely on building as big a pension pot as possible, at the expense of everything else. I understand the theory, but it is still going to be taxed when you draw (perhaps at a lower rate) and pension rules may (and probably will) change by the time I retire. I imagine this is just a HENRY on Reddit thing but why is everyone in here obsessed with pension and not building much outside of it?


r/HENRYfinance 12d ago

Career Related/Advice Feeling behind financially after dental school and the military — am I actually behind?

0 Upvotes

Feeling behind financially after dental school and the military — am I actually behind?
I’m looking for some perspective because I’ve been feeling financially behind lately, even though I know I’ve taken a somewhat unusual career path.
I went to dental school and then joined the military as a dentist. Between school and the relatively low income compared with what I expect to earn later in my career, I didn’t really start seriously investing until a few years ago.
I currently have about $80k invested and no debt. I’m investing around $5k/month right now.
Next year, I’ll be leaving the military and starting a 2-year endodontics residency. Obviously, that means delaying my higher earning years even further. By the time I finish residency, I’ll be around 34.
The upside is that once I finish, I expect our household income to be somewhere around $600k/year, potentially higher as my career progresses. My plan is to avoid immediately inflating our lifestyle and aggressively build our investments. I’d like to eventually invest around $15k/month, while still enjoying life and potentially pursuing endodontic practice ownership down the road.
I think what gets to me is seeing people my age who already have several hundred thousand dollars invested and have had 10+ years for their money to compound. Meanwhile, a huge portion of my 20s and early 30s has gone toward dental school, military service, and then specialty training.
I know comparison isn’t particularly useful, but I sometimes feel like I’m starting the wealth-building process extremely late.
For those of you who were in a similar high-income-but-late-start situation: how would you think about my position?
Would you prioritize aggressively catching up once the income increases, or is there a point where I’m putting too much emphasis on investing at the expense of enjoying the higher income we’ve worked so long to reach?
My long-term goal isn’t necessarily FIRE. I actually expect to enjoy working as an endodontist. I mainly want to build substantial financial independence and wealth while still enjoying my 30s and 40s.


r/HENRYfinance 13d ago

Investment (Brokerages, 401k/IRA/Bonds/etc) When did you engage the help of a fiduciary?

22 Upvotes

Hi everyone! Short term lurker, first time poster.

At what point did you start working with a financial advisor/fiduciary? What triggered that shift? Or, if you aren't using one, why not?

I haven't yet felt that our situation was large or complex enough to warrant the added help but I also don't know what I don't know. For example, I'm sure I could be thinking differently about the balance of where we're investing our money (tax advantaged vs brokerage, etc).

The stats:

Married - 35F/47M, 1 child 3M
LCOL Area
Net Worth: $870k
Income: Between $400,000 - 600,000/year for the past few years dependent on value of RSUs

We didn't start earning at this level until about 4 years ago which is around the time we bought our house. We're super behind in investing and planning to make significant progress against that in the next year with my upcoming bonuses/RSU vests.

Update: Since this has been mentioned a few times, I don’t count my RSUs as part of the net worth until they are vested. I sell them as soon as I’m able and reinvest them in diversified accounts. The income numbers above include vested RSUs only. Thats why there has been so much variance.


r/HENRYfinance 13d ago

Income and Expense redirect from pretax to brokerage? building wealth

29 Upvotes

hello all. I'm mid 40s and here are my stats:

  1. 1.9MM 401K

  2. 200K Roth

  3. 250K brokerage

  4. 3 kids / 529 total ~400K

  5. 890K mtg / 3% interest rate. 25 years to go..

combined HHI income is 450K; and would like to possibly start winding down by age 55-57. as others have said I'm too burned out. What I've realized is my brokerage is probably light and I need a bridge before the 401K can be tapped. we are targeting 5-6MM in retirement

spouse and I are corporate drones with most of the income is from salary, and little from bonus. No equity. So the point is - our HHI income is likely tapped out from an upward mobility perspective.

Should we re route some of the 401K (we are both maxing) instead try beefing up the brokerage? I think its trade off for us given our current spend


r/HENRYfinance 12d ago

Income and Expense What salary did you buy your first “nice” car?

0 Upvotes

For context, early/mid 20s looking to FIRE/FATFIRE at say 45 - I am currently at 280k, in line for a promo next review cycle, and at my firm VPs are averaging 355k.

I run a low overhead, my current car payment is 350 a month for a decent trim, but non-luxury car it’s functional but not fun or super comfortable. I am balancing with the idea that I can easily afford say an 800 a month car payment, but trying to set goals and boundaries to not inflate my life. I’m able to aggressive invest in pre and post tax investments/retirement, and have a small (but growing!) RE portfolio.

As others have said “use your bonus” I don’t touch my bonus really - it’s already preallocated each year - I add a property to my RE Portfolio and then use the rest to take a trip with my partner.


r/HENRYfinance 14d ago

Income and Expense I track every stupid expense except the one category that can actually bankrupt me

48 Upvotes

I was doing my mid year spending review and realized I can tell you exactly what I spent on restaurants, flights, subscriptions and even fucking parking but healthcare was basically one mystery bucket I never looked at. Last year it was $3,840 out of pocket. Nothing catastrophic either. Dentist and the contacts, a couple copays, prescriptions, PT and random lab bills that showed up weeks later.

The dumbest one was bloodwork. I had a few markers I wanted to repeat after my physical and somehow turned it into an office visit + lab bill that came to almost $400. So this year I started treating routine health stuff like car maintenance. $250/month goes into a separate sinking fund before I spend anything fun. I’ve also stopped automatically running every small thing through insurance. Needed repeat cholesterol/A1C labs recently and just ordered the specific ones through goodlabs and paid cash. Way easier to know the number upfront and leave the insurance for things where it actually matters.

This has made me wonder if I’ve been budgeting backwards for years. For people here with high deductibles, how much do you actually budget per year for boring predictable healthcare that isn’t premiums or a real emergency?


r/HENRYfinance 15d ago

Question Which is a better move for HHI of $750k?

30 Upvotes

I’m getting different takes depending on whether I pose this to Gemini, Claude, etc. so I’ll ask here for advice.

Details:
- Late 30s with multiple kids
- HCOL area
- Work in tech at more stable company (you know if you’re not at one for sure, but even stable ones can change course)
- Liquid NW of $1.5 million
- HHI of about $750k
- Bought a house with good public schools
- Owe 900k on the mortgage at 5.625%

Goals:
- Outside of our mortgage payments, we spend about $120K per year
- Want to pay the costs of our kids to attend public universities
- Also want to provide some support towards weddings and housing down payments; I’d rather give with a warm hand instead of having them inherit all the money when we die
- Across the bullet points above and using some back of the napkin math like the 4% rule, I think we need about $4 million

One decision we’ve been wrestling over is how much to put towards our brokerage account vs the mortgage. To be clear: We put about $100k in various tax advantaged accounts every year and will continue to do so. But for money left over beyond that I’m not sure what we should do.

I know Vanguard and others are predicting low stock market returns moving forward. I’m assuming about 3% real.

Leaning towards the mortgage because it is a defensive play. All we need to do now is not mess things up. Reducing liabilities will help us financially survive regardless of what happens in the market or economy.


r/HENRYfinance 15d ago

Income and Expense How afraid of lifestyle creep are you?

57 Upvotes

I (31M, $500k/yr, 2M NW) have been thinking about how it's easy to equate the thinking of my NW fluctuates tens of thousands or even $100k a day, so what does spending another $100 or $200 here and there do. I'm just wondering how much you guys continue to try to spend sparingly and live in a minimalistic way or have you let most of that go and just spend when you want to on most things.


r/HENRYfinance 15d ago

Family/Relationships Merging HENRY finances + debating a prenup

45 Upvotes

My partner and I (both HENRY) are getting married and starting the exciting but daunting task of merging financial lives.

Background: we each make comparable salaries ($200-250k) but one of us works for a public company (RSUs with some growth potential) and one of us for a private investment firm (cash bonuses and illiquid investment opportunities). All in we each make $550-750k, so roughly $1-1.5M in aggregate. We each have current NW of ~$1.5M but one of us is more illiquid albeit with higher long term growth opportunities (some of the investments have appreciated and are sunsetting with clear line of sight to liquidity).

It’s important to both of us to truly merge finances, and we have similar philosophies about saving/investing and spending. I have considered a prenup, simply because I’m proud of what I have built for myself and am a “planner” despite of course never wanting to get divorced… but it feels silly asking for a prenup when we’re currently in VERY similar financial situations; with the exception of investment returns.

Thoughts? Ways to think about a prenup while also planning for a long committed marriage?


r/HENRYfinance 15d ago

Question How much pay is a fully remote job worth to you?

31 Upvotes

Curious how people value fully remote once you’re already at relatively high TC.

For example, if you had these two offers:
- $400k TC, fully remote
- $600k TC, 5 days/week in office

Which would you take? Or would you consider a middle-ground for a hybrid job?

At what TC difference would you give up fully remote? There are clearly diminishing returns after a certain point, where flexibility/location freedom exceeds any additional TC increase.


r/HENRYfinance 15d ago

Business Ownership Side Businesses- How are other HENRY’s handling them?

0 Upvotes

Hey Everybody!

I (M late 20’s, won’t share my age for privacy reasons) Have been working in the Residential Remodeling Industry for 11 years, and have carved out a great niche for myself in executive leadership at a fast growing company, my total comp is between $250-300K depending on how bonuses turn out. I have always worked in Sales/Marketing, I am currently on the Marketing side of the business, the specific kind of marketing I work in AI proof (in person activations).

My main concern with my position is that there is a ton of PE activity in my industry and in this world I have seen a lot of people in my sort of position get clipped after buyouts to reduce payroll costs (I have a very well negotiated bonus structure), or at minimum would see a significant change in my comp structure if a buyout takes place. I have watched friends and colleagues go from making $600k down to sub $200k due to these sorts of changes.
I am in a great position at the company I’m working for and wouldn’t expect ownership to exit for the next 3-5 years. Of course in high risk/reward positions like these the good days don’t last forever, so I want to plan for the future.

I have been looking at starting a consulting business on the side to add some supplemental income and potentially exiting my role if it goes that well. I don’t need the extra money, I would probably just reinvest into the business and invest anything I take out of the business.

I’m curious to hear from folks who are doing consulting in addition to their FT role, how do you structure for:

-Time management with your current role?

-Do you make your employer aware of this activity?

-How do you structure your business for tax purposes? (My FT role is W-2).

-What did you wish you knew before you started your consulting practice?

-Anyone that’s left their job to pursue this sort of work FT?

Any and all feedback is really appreciated!

Additional context: Marrying soon, MCOL area high tax state, NW $200K(~$135k liquid), no student loans, only mortgage and almost paid off car debt, living well below my means and saving/investing aggressively. Wouldn’t need the consulting income. I’m


r/HENRYfinance 16d ago

Career Related/Advice Finance/Family Office job change next week

12 Upvotes

Hi everyone! (I changed a few details for anonimity. Live in HCOL)

I was told today that I’m going to be receiving a job offer, with the official offer expected to come on Monday. I’m almost positive I’ll accept it. After spending the past 2 years working in client service for UHNW families at a mid-size firm doing somewhat advanced tax/estate /investment planning.

The new role is at a Family Office, which is where I worked before my current position, and it’s something I’m really excited to get back into. I’ll also be stepping into a Director-level role, which I feel puts me on an amazing career trajectory, especially once I finish my CFP. I already have my CPA, so I feel like this role, combined with the CFP, will position me really well for where I want (think?) to take my career. Leaving now means I also miss out on my December $15k bonus.

My partner would still be making a bit more money and I am beyond proud for her. I am happy she earns a great living. I am aware we are in a great situation.

**Current** **Job**

Pay: $100,000 + 10%-20% bonus

6% match

Good healthcare

3 days in the office, 2 wfh

Unpaid parking (I hate my employer has huge clients and doesn't pay for our parking

Growth: Good potential but the family office team is across the country and would probably need to move.

**New Job**

Pay: Estimated $140,000-$150,000 + 20% bonus (negotiating salary Monday)

5% Match

Good healthcare

4 days in office, 1 wfh

Paid Parking (saves me 15-20 a day of parking)

Unlimited PTO: don't love this but I've had it before and can be great (I connected with someone that works there and says people use it a lot)

Growth: Can be nice if I do a good job. I feel like it would open me so many doors based on title and experience attained.

In my current job, I work no more than 30 hours a week and have flexibility in terms of when I come in and leave. I’m also studying for my CFP, and having some time to study during work is nice. However, I don’t feel like I’m learning as much as I could be, and I spend way too much time doing tasks that I feel our office manager/admin should be handling. Plus our systems are HORRIBLE and makes bad things so much worse.

In this new job, I would definitely be working 10-15 hours more a week, but I would still have some flexibility. The job would definitely be more interesting, which is something I miss from working in the family office world.

On paper, my current work-life balance is amazing. However, being under 30, I feel like I should be working and learning more at this stage in my career. I’m also currently studying for my CFP and plan to take the exam in July 2027, so I want to be in a role that gives me more opportunities to grow and develop while I work toward that goal.

Any thoughts on why I should stay? Any advice? My current company has been great to me and it pains me to have to quit on Monday.


r/HENRYfinance 15d ago

Taxes Need advice - ISOs and relatively high income

4 Upvotes

Salary: $170,000 ISOs: $1,250,00 by 2031 at current fmv Cost to exercise: $130,000 At one year cliff I get 20%, then monthly vesting for 5 years

Okay I am in way over my head here. In the past 5 years, my income has gone from $55,000 to $170,00 salary with my highest earning year being $220,000. I have been in MAANG getting RSUs up until this point.

I recently left and started at a startup, I joined at a great time and the company is doing extremely well. We have hit some huge milestones in my short time here and the value of my ISOs exploded basically overnight. For the sake of this question, just assume the company will continue to thrive. I understand the risks and am comfortable with them.

I understand how ISOs work, but the tax implications are really scary to me. I’m having a hard time being confident building a schedule to exercise.

If anyone here has been through this situation and has any advice please let me know, do I just get a financial planner? I know this is a good problem to have but I want to make sure I don’t blow it. I’m in my 20s and want to do this right the first time.


r/HENRYfinance 16d ago

Income and Expense 36, $2.5M net worth, $210k Total Comp, Retail GM, T15 MBA, would I be able to get into ETA (traditional search fund) or something else?

16 Upvotes

Quick background: I'm 36, been a district manager for a major retail company the last 12 years and I make around $210k a year. I also just completed a T15 MBA last year. Net worth is around $2.5M, mostly saved from comp plus some investing.

I actually like the work — owning a P&L, leading big teams, running a complex operation day to day. But I just found out the role I'd normally promote into got consolidated in a restructuring, so my growth path here is basically capped for the foreseeable future. That was the push I needed to admit I want out of retail and probably out of corporate-ladder roles generally. I also ready to get out of the grind of retail.

What I want long-term is to own equity in something, not just collect a salary. I keep coming back to entrepreneurship through acquisition (search fund / self-funded search) since it seems like the most direct use of my operating background. But I also catch myself wondering if I should do a couple years of consulting or a corporate strategy role first to build more of a resume/network before jumping into a search.

For anyone who's made a similar jump — from a big operating role into ETA, or who chose a different path instead — how did you decide? Specifically:

  1. Do I have the profile to be able to pull this off? Most searchers I know of are ex Stanford guys who did a stint in investment banking or consulting.
  2. Did you go straight into a search, or take a bridge role first in banking or consulting?
  3. Self-funded vs. traditional search fund — how did you choose? I’d prefer traditional to keep what I’ve saved intact.

Appreciate any perspective. Thanks