39 year old HWNI contemplating retirement

Read the book "How to Retire Happy, Wild, and Free" and be sure to perform its Get-a-Life Tree exercise. It's an easy read and recommended elsewhere in this community.
 
One of the reasons for success is outworking others. In a hyper-competitive business like financial management, those "others" are brilliant, experienced, driven folks. Congratulations on doing that and on living below your means, so that you have already accumulated enough that you could retire and certainly in the two year window you give yourself, your finances should be set.

So I suggest talking to your wife about the stress that your work is putting on her. Your financial future is excellent, don't mess up the more important parts of life - your marriage and your involvement in your child's life by chasing the next dollar.

Together you may find the right path. Maybe it is continuing to work for a specific goal or maybe you decide to work and give large sums to charity or maybe it's time to relax and focus on living your best life while you are still young.
 
If you will be traveling internationally, particularly in Mexico, take out ransom insurance for your family. Don't ever hint you are wealthy.

I know this sounds over the top but it happened in my nephew's family in Mexico and the victim was just a dentist. The perps overestimated the family's resources so he was killed.
 
Look up Fed Chair Jay Powell’s bio. Lots of good things are possible after one gets free from a lucrative job.
 
A couple of thoughts from someone who also left the buy side, albeit at a more jr level...

On the finances side, you can probably answer most of your questions better than anyone else. You’re certainly in a place financially where you will be fine, whatever happens.

On the identity piece, it is a shift, especially if you have young children. I didn’t realize until I left how much of my identity was tied to my job. And it comes up a lot in conversation, in particular with school related stuff. As a female, it’s easier for me to manage, but I still feel that competitive twinge when I’m in a group who is still ‘in the game.’ If we had stayed in the Bay Area, I think the social aspect would have been much harder to manage. You need to have an answer that you feel good about when someone asks what you do.

It took about 6 months for me to let it go and since then I haven’t looked back. Fitness, spending time with the kids and pursuing all of the interests/hobbies I never had time for have taken over my life and it’s wonderful. So is waking up at 6-7AM! I initially assumed I would take on a board position or two, but I just have zero interest right now.

I really wish there were more opportunities in the business to take a sabbatical. There is just never any extended time to recharge. One thing to keep in mind is that leaving doesn’t have to be a forever thing. I’m a year out and still get calls from recruiters all the time. One or two have been very tempting, but then I realize I have zero desire to return to that lifestyle. My advice, taken from others on the board, is to spend 6-12mo doing ‘nothing’ and then decide where you want to spend your valuable time and energy. It will likely be a very different decision than the one you might make right away.

You might also post this on the Reddit fatfire forum, where there may be more people in the industry/your NW bracket.
 
OP, If I were you I would have done the same thing as you have planned. In your situation, time is definitely more valuable than $ after a couple more years. Making up for the lost fun in your previous years should be satisfying. I experienced some of that, and it was worth it for me. Cheers.
 
Can you start building up a team, spreading responsibilities to junior, up and comers?


I was not in your industry or at your level of success; but, I was very fulfilled by my efforts at enhancing and launching careers of my deserving (hard working and talented) reports and their reports. In retrospect, that was one of the most rewarding times in my career.


Spreading my work, knowledge, and responsibilities was appreciated by both those advancing their careers and my employer (both for reducing key man risk and as transition planning since most knew I was retiring in the relatively near future).


I have been retired for almost three years now and still miss parts of the job and some of the people terribly. But, I also value my free time even more than I had expected.


Good luck with whatever path you choose. Whatever you do, try not to spend too much time looking back, thinking "what-if", etc.
 
man, everyone is a psychologist here

we have spent around $500k each of the last 4 years and it's just where our spending settles out. it's not some number i "get off" on. if i got off on spending big, i wouldn't be saving 85-90% of my after tax income each year.

it is harder to leave a job that pays better, but that doesn't mean it's about ego. almost nobody outside of my office knows i exist. i shun the limelight. i hate golfing.

we COULD spend less.. but $500k is the level where we can live how we want to, without "thinking" about expenses... and if I can guarantee that level of income in 2 more years of work (at which point i will be 41), why not just do the 2 more years and lock in a lifestyle that we prefer?

would it be rational to tell my wife "let's just do it NOW, and have 75% of the lifestyle we want, because i'm not willing to work 2 more years to get us to that 100% level?"

COULD we cut back to $400k? sure. but we would either have to slash charitable giving, or fly economy class to europe, or stop collecting wine, or downsize our house.

that's why i'm saying this has nothing to do with ego. it's about the math of sustainable financial independence. we aren't quite there yet, unless we want to cut corners.

how do we spend $500k?
- 50 property tax and yard maintenance
- 30 home renovations and repairs (some years the slate roof has to be replaced, sometimes the exterior needs to be repainted, some years it doesn't... and in expensive neighborhoods home repairs cost more)
- 120 regular weekly expenses (including wine collection, which is a hobby)
- 30 cars (2 luxury cars ... we prefer to lease)
- 100 vacation and travel (business class to europe
isn't cheap for a family... and we go overseas often )
- 30 tuition (this will rise)
- 100 charitable giving
- 40 passion investments (art, rare coins, etc!
 
man, everyone is a psychologist here

we have spent around $500k each of the last 4 years and it's just where our spending settles out. it's not some number i "get off" on. if i got off on spending big, i wouldn't be saving 85-90% of my after tax income each year.

it is harder to leave a job that pays better, but that doesn't mean it's about ego. almost nobody outside of my office knows i exist. i shun the limelight. i hate golfing.

we COULD spend less.. but $500k is the level where we can live how we want to, without "thinking" about expenses... and if I can guarantee that level of income in 2 more years of work (at which point i will be 41), why not just do the 2 more years and lock in a lifestyle that we prefer?

would it be rational to tell my wife "let's just do it NOW, and have 75% of the lifestyle we want, because i'm not willing to work 2 more years to get us to that 100% level?"

COULD we cut back to $400k? sure. but we would either have to slash charitable giving, or fly economy class to europe, or stop collecting wine, or downsize our house.

that's why i'm saying this has nothing to do with ego. it's about the math of sustainable financial independence. we aren't quite there yet, unless we want to cut corners.

how do we spend $500k?
- 50 property tax and yard maintenance
- 30 home renovations and repairs (some years the slate roof has to be replaced, sometimes the exterior needs to be repainted, some years it doesn't... and in expensive neighborhoods home repairs cost more)
- 120 regular weekly expenses (including wine collection, which is a hobby)
- 30 cars (2 luxury cars ... we prefer to lease)
- 100 vacation and travel (business class to europe
isn't cheap for a family... and we go overseas often )
- 30 tuition (this will rise)
- 100 charitable giving
- 40 passion investments (art, rare coins, etc!

Ha!

You should head over to Bogleheads' forums... :)

Your spending is no big deal for your income level...and if it takes another couple of years to get where you want to be to sustain that level, why not?

You'll still beat the majority of early retirees by years...after age 50 for most.
 
man, everyone is a psychologist here



we have spent around $500k each of the last 4 years and it's just where our spending settles out. it's not some number i "get off" on. if i got off on spending big, i wouldn't be saving 85-90% of my after tax income each year.



it is harder to leave a job that pays better, but that doesn't mean it's about ego. almost nobody outside of my office knows i exist. i shun the limelight. i hate golfing.



we COULD spend less.. but $500k is the level where we can live how we want to, without "thinking" about expenses... and if I can guarantee that level of income in 2 more years of work (at which point i will be 41), why not just do the 2 more years and lock in a lifestyle that we prefer?



would it be rational to tell my wife "let's just do it NOW, and have 75% of the lifestyle we want, because i'm not willing to work 2 more years to get us to that 100% level?"



COULD we cut back to $400k? sure. but we would either have to slash charitable giving, or fly economy class to europe, or stop collecting wine, or downsize our house.



that's why i'm saying this has nothing to do with ego. it's about the math of sustainable financial independence. we aren't quite there yet, unless we want to cut corners.



how do we spend $500k?

- 50 property tax and yard maintenance

- 30 home renovations and repairs (some years the slate roof has to be replaced, sometimes the exterior needs to be repainted, some years it doesn't... and in expensive neighborhoods home repairs cost more)

- 120 regular weekly expenses (including wine collection, which is a hobby)

- 30 cars (2 luxury cars ... we prefer to lease)

- 100 vacation and travel (business class to europe

isn't cheap for a family... and we go overseas often )

- 30 tuition (this will rise)

- 100 charitable giving

- 40 passion investments (art, rare coins, etc!



No Psychologist here but if working 2 more years gives you the required comfort, just do it ( based on your responses, this is where you are headed). Not sure what else you’re expecting from here. Good luck!
 
Ha!

You should head over to Bogleheads' forums... :)

Your spending is no big deal for your income level...and if it takes another couple of years to get where you want to be to sustain that level, why not?

You'll still beat the majority of early retirees by years...after age 50 for most.

I was going to say something similar. I was never told so much about myself until I posted a question on an internet forum. I was simultaneously evil and wonderful, stupid and absolutely correct, etc...
 
man, everyone is a psychologist here
This is an interesting point. Your questions are not financial, they are psychological.

Maybe consider talking to a psychologist or a life coach or something. But someone capable of providing advice at your socioeconomic level.

Not saying you have problems, you just need help sorting out your plan. You need to answer your own questions.

For my part, I am bringing in a fee-based financial advisor to help me plan my tax strategy for when I retire in ~10 years. Just like my accountant, my book keeper and my cleaning lady, I bring in specialists to help me. Proud of it.

On an un-related note. At a couple years older than you and a net worth of 1/10th yours, I do appreciate having HNWI on this forum who is willing to talk.
 
Welcome!

I dare say a few folks are thrown off due # of digits in your net worth, # of properties and $ size of annual income and burn. Furthermore, claiming to be (1) a stock picker, (2) preferring stocks with growth AND dividends, and (3)arching/beating the market likely lost a few more.

While I’m not quite at your values, I am retired with a 2% WD rate, 2 houses, and 2 grade school kids.

My only advice is to (1) ensure you know how you want to spend your time when it’s in your control and (2) think through limitations a grade school child may put on that. We choose public schools so that will keep us grounded for a while and is a pace setter.
 
I like the idea of 2-3 years. Define it as a glide path. Cut the engine off and head for the landing strip. My brother uses the metaphor of surfing (he was Cupertino), take the next wave all the way to the beach, drop the board, start walking. Your exit strategy has milestones, but the project plan is somewhat flexible in timing and execution, depending on speed of the wave and obstacles encountered.

Back up from the resignation letter. Do you anoint the chosen follower? What does a proper exit look like? I trained my successor in engineering and published several documents to capture what I had learned about design for manufacturability in gels with design team and others. What must you do for a best possible exit?

I do think ego and psych are at play, but so what? If you do your best to transition and exit, that door can re-open if you decide to revisit the decision.

What is the best time of the year to announce? A particular event maybe? Consider a personal road trip to sell yourself and your decision to your peers. They may be your peers again one day.

Make your best exit! It is the best way to cement references for a possible return, and it minimizes regret and opportunity cost/sunk cost fallacies.
 
Agree with others - work the 2 years and join a large non-denominational church. Join a small group within the church and you can address your charitable, (hopefully fulfilling) desires - while still working!

$500k doesn't go that far if you have a house in the tri-state area and a home in the Hamptons or a home in Northern CA. (Let alone offshore properties)

Similar position financially (albeit, not quite as large) but enjoy waterfront living and large boats.

We miss/loved our small group and look forward to starting another in our new home and location when the Covid-19 situation changes.
 
Before you make your decision on whether to leave your job or not, spend time really developing a plan for what you want to do with your life once you leave the workforce. Develop this plan with specifics. It's fine to say you want to travel, but where do you want to go and what do you want to do on those trips? What hobbies or volunteer activities would you want to pursue? It's really a matter of figuring out what you are retiring TO rather than retiring FROM. When I decided to retire from a career I loved and 38+ years at the same company, I worried how I would adapt to my new found freedom. Once I figured out my plan and settled on a timeline for leaving the job (1 year in my case), I started the mental shift to retirement that made the ultimate departure much easier. Make sure your wife helps you develop your post-retirement plan. It was an adjustment for my spouse when I was finally home full time (he was already retired). Planning this next stage of our life together was fun. Of course, COVID has put some of our travel plans on hold but we have the freedom now to start that up again as soon as it is safe to do so. Since you are so hands on in managing your portfolio, don't forget to include a plan for what your wife will do if you predecease her. Sounds like you should use the next two years to reach your financial goals and have time to plan the rest. Best of luck and congrats on your financial success.
 
man, everyone is a psychologist here

we have spent around $500k each of the last 4 years and it's just where our spending settles out....

Nothing wrong with spending that and planning for it. Heck, you are still stepping out very early. We worked longer (57/56), at lower paid jobs (md/jd) to ensure that we could spend far more after tax in retirement than when we were working. Still "only" a bit more than 1/2 your target, but we only own one house with less than 2k property tax. Majority of spending is travel--and like you, DW won't be going across an ocean in coach. Of course, if portfolio tanks, I might be in coach! :LOL:
 
Work is waaaay over rated, with your portfolio and money management skills, enjoy life with your family!!!
You only live once on this rock :)
 
Humblebrag. If a guy with that much money can't figure it out, what hope do us regular folk have?
 
Humblebrag. If a guy with that much money can't figure it out, what hope do us regular folk have?

Disagree. It just goes to show that all income levels have insecurities; need to plan and make adjustments to meet goals.
 
Congratulations on your success. You have won the game. If two years will get you to the comfort zone, 2 years it is. It will take some time to implement your exit strategy anyways.

I am married to an introvert. She is now a stay at home mom. I have found that more time and less stress has allowed her to become more social.

I am not sure if your plan is all or nothing. I am 6 years older. My plan has stages. At 50, go to 4 days a week. Either sell company or find a replacement to be done by 55.

You seem ready to go within the next few years. You've worked hard. Time to enjoy the rewards. Good luck!
 
Get examples of what other people are doing to fulfill their time. Also, what they feel they should be doing.

For example, these are things I'm doing every day in retirement:
Take a one-hour walk every day, with stretching before and after. Great for your body.
Work on the garden and yard. Plant lots of flowers.
Be a teacher for the kids. Especially appropriate with the schools being shut down.
Play on eBay and with email.
Keep your cars in good condition and add new things to them.

Should be doing:
Become more serious about your faith.
Volunteer to teach kids how to read or do math.
Teach people, young and old, how to drive. Obviously, many don't know how!
Learn how to fly a small plane, and use it for family trips.
Restore an old car and drive it every day!
 
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You seem to have figured out the finances, so I won’t comment there. Having changed course several times...Air Force officer to SAHM, then law, then retired, then life coaching (more a hobby)....I can say that when your self worth and value is tied to the kind of work you do or the prestige of the position, leaving can be a quite difficult. But we all leave sooner or later. So if you can find a way to reorient your thinking about what your job means about you as a human and be ok without the prestige, you can enjoy a lot of adventures with your family for many years to come.
But let’s be real...with a portfolio like yours, you’ll still enjoy a certain level of prestige...😎

Go have fun.
 
It's obvious that you can manage your money, and if you need 2 more years to lock in your current lifestyle, get back in the traces and pull--for two years. It's both easier (and harder) to work, once you know your exit; I found the last 3 months the hardest.

In my case, I told DW 2 years ahead that we could retire early; since we wanted to relocate from Houston to the West Coast near our two sons, it took almost that long to sell the house (and cabin), decide on where to move, etc, etc. (I taught part-time online for 5 years, so it wasn't cold turkey; in your case, this is really hard to turn off overnight.) You're staying in place, which simplifies things a bit, but you can use the time to plan/investigate what you want to do with yourself. I was lucky in that the University allowed me to teach online half-time for half the salary; I had spent 40 years in a University environment, so this really helped in redefining the sense of identity. We spend a lot of time volunteering with an non-profit outdoor organization--and I have more time to read!


I'm also an introvert but was lucky to have a fraternal twin who was an extrovert, so I appreciate the other side and those behaviors can be learned, and under your control.

Is your wife onboard?
 
man, everyone is a psychologist here

we have spent around $500k each of the last 4 years and it's just where our spending settles out. it's not some number i "get off" on. if i got off on spending big, i wouldn't be saving 85-90% of my after tax income each year.

it is harder to leave a job that pays better, but that doesn't mean it's about ego. almost nobody outside of my office knows i exist. i shun the limelight. i hate golfing.

we COULD spend less.. but $500k is the level where we can live how we want to, without "thinking" about expenses... and if I can guarantee that level of income in 2 more years of work (at which point i will be 41), why not just do the 2 more years and lock in a lifestyle that we prefer?

would it be rational to tell my wife "let's just do it NOW, and have 75% of the lifestyle we want, because i'm not willing to work 2 more years to get us to that 100% level?"

COULD we cut back to $400k? sure. but we would either have to slash charitable giving, or fly economy class to europe, or stop collecting wine, or downsize our house.

that's why i'm saying this has nothing to do with ego. it's about the math of sustainable financial independence. we aren't quite there yet, unless we want to cut corners.

how do we spend $500k?
- 50 property tax and yard maintenance
- 30 home renovations and repairs (some years the slate roof has to be replaced, sometimes the exterior needs to be repainted, some years it doesn't... and in expensive neighborhoods home repairs cost more)
- 120 regular weekly expenses (including wine collection, which is a hobby)
- 30 cars (2 luxury cars ... we prefer to lease)
- 100 vacation and travel (business class to europe
isn't cheap for a family... and we go overseas often )
- 30 tuition (this will rise)
- 100 charitable giving
- 40 passion investments (art, rare coins, etc!

Burgundy collector here. DRC specifically. Believe me, I get it. Good luck!
 
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