39 year old HWNI contemplating retirement

[FundManager81]

Hi everyone -

I don't know how unique my situation is, but I have not found many others in a similar spot, so I figured I'd post on this forum and see what comes of it!

I am 39 years olds, and manage a $5-10B mutual fund on the west coast. Though my job is interesting and very lucrative, I am getting burnt out, and my job does not lend itself to "sabbaticals"... so, essentially, you're on the treadmill until you're out of the game. The thing that the job does provide is status, financial means, and constant intellectual challenge. The thing that the job does NOT provide is two-fold: (1) a break; and (2) a sense of fulfillment re: "helping other people and making the world better."

I'm trying to figure out whether to get out of the game and "retire" in my early 40's (which, realistically, means taking at least a year or two off, and then re-assessing). This would give me a chance to travel with my family (perhaps live abroad), and it would give me a chance to simply do something new that energizes me in ways my current job does not.

The biggest question marks in my mind are:

1) Will I regret leaving a job to which so much of my identity is tied? Though I'm happy enough, this nagging feeling of un-fulfillment + greener pastures has gradually grown over the last 5 years.

2) How likely is it for me to successfully fill my time with endeavors (projects, jobs) that are genuinely emotionally fulfilling? Going from a high profile job where I'm my own boss + am surrounded by the best and the brightest, to a less visible and more ordinary job that "helps other people," can sound appealing and altruistic on paper, but am I just tricking myself into thinking that the grass is always greener?

3) How much of a "buffer" should I give myself, financially, to recognize the fact that I still have half of my life to live. Things change. People get sick, life events happen, laws and regulations change. For example, if Biden's tax plan were implemented, the after-tax yield of my passive income would be greatly reduced.


Here are a few specific statistics about me:

- Household net worth is rougly $25 million, of which $15 million is liquid assets, and $10 million is tied up in personal real estate around the world.

- Annual income is in the $5-10 million range (not a typo), before passive income such as dividends and stock appreciation.

- I have a wife and a young son. We will not have more children. He has not yet started grade school

- We live off of roughly $500k after-tax income per year. Some years less, some years more. It's an upper-class lifestyle, but not an ultra upper-class lifestyle.

- My wife is currently a stay-at-home mom, and for now, has no ambitions to return to the work-force. She could be happy travelling the world for the rest of her life (has been to 60 countries, and has lived in several).

My current thinking is to work for 2 more years, to get my liquid assets close to $25 million, and then retire around the time my son begins 1st grade. I'd force myself to take a year or two off, to give myself time to figure out where I really want to re-orient myself. We would split our time between Europe and the US (we are building a new house on the west coast... and we already own property in Europe).

The reason $25 million is our "number" is because it would allow us to live off of $500k/year at a 3% drawdown rate (750k gross, minus taxes on any capital gains or dividends). In other words, it's a level where we could SUSTAIN our current lifestyle, while still being able to grow the portfoio over time. It's important for us to sustain our lifestyle. I'm confident in the ability to generate returns of >5% per annum (historically we have done a lot better than this), whcih would result in the portfolio growing at least in-line with inflation, net of withdrawals Also, if needed, we could liquidate some of our real-estate portfolio, to flip the mix from $25mm liquid / $10mm real estate... to something closer to $30mm liquid / $5mm real estate.

The biggest risks to sustaining our lifestyle are either catastrophic health problems, or major tax hikes on the rich (does not seem unlikely to me).

The biggest reason this would be a bad decision, is that I'd end up missing the job more than I expect to + have trouble finding a replacement that's as fulfilling as I hope to find.

I don't think the idea of being worth "$100million" vs "$25million" really motivates me at this point. Money is a means to an end, not an end unto itself. And, frankly, we will soon have more than enough.

Do any thoughts jump to mind?

We are vey lucky to be in the position that we are. It all came via hard work. My net worth was negative until I turned 30, because of student loans. All of our net worth has been accumulated over the last 9 years. I had to pay for a decent chunk of my college tuition, and I never had free years in my 20's to goof off and see the world. I regret not being able to do all of those fun things, and though it's not the same at age 40 as it is at age 22, in my mind, I'd rather "make up for this lost fun" while I'm still young, rather than working until 55-60 and having less endurance + energy + passion to explore the world.

Thanks for your thoughts and advice -

FM

 

[GTP2022]

Go live life.

 

[pjigar]

How would you withdraw from illiquid portfolio?
For your age, i would be comfortable using lower withdrawal rate like 2% because you may not get a second chance to go back to your current job that is so high profile.
Personal fulfillment is the hard one. Everyone is different. What make me tick would be vastly different than you and vice a versa. Do you have a bucket list? If not then start making one and then reassess in few years.

 

[FundManager81]

It's a liquid portfolio. Will be $25mm liquid by end of 2022.

The only illiquid portion is real estate, and that can be sold, as don't need all of the 5 properties we currently own.

 

[Dtail]

I would go for it. I had a lucrative job on Wall Street with 72 reports. I don't miss the job one bit and have been retired for 3 years and have no contacts from my old job.
However, I did retire at 57 y.o. Not sure I would feel the same in my early 40's, although definitely would have gone by 50 if I could have.
So one other question is if you miss work, would you be satisfied with a lesser job?

 

[FundManager81]

Thanks for the advice.

I don't see any need for a withdrawal rate as low as 2%. I agree it should be lower than for a 60 year old, given the length of time until reitrement. But there are two reasons I'm not going to insist upon a rate as low as 2%.

1) The weighted dividend yield on my portfolio is 2.5%... and the average dividend growth is 10%. So, a withdrawal rate of 2.5% would result in ZERO shares of any stock sold in a given year.

2) I am a stock picker, professionally. I have outperformed the market well more than 10 years in a row, with market-average risk, and favorable downside capture. I'd share the name of my fund, but I don't want to reveal msyelf. But bottom line is, I trust myself to at least not massively lag the market.

There are, believe it not, a handful of growth stocks, with high dividend yields, that are very very safe. I recently put $800,000 into a stock with a 6% dividend yield. Since then, the dividend was raised 10%, and the yield has fallen to 4.9%... so.. the stock is up 30% in three weeks. Dividend yields can fluctuate, but as long as you are careful in the companies you choose (avoid high payout ratios, avoid cyclicality, avoid secular chalelnges), the dividend dollars are monotonically increasing and reliably so.

My equity holdings will be over-indexed towards dividend growth stocks. so that I don't have to worry about where stock prices are each year...

I also won't increase the dollars I take out simply if the value of my portfolio rises. I'll have a budget, based on an initial withdrawal rate, basd on the initial portfolio value. And if the portfolio goes up dramatically in value, maybe I'll take out a bit more. But much more likely is that the drawdown rate will drift lower if the portfolio outperforms in the future.

 

[Brat]

Make an exit plan, just as you do for investments. Work the plan.

Assuming you will be stepping back it is important that you consider how you communicate that. "Spending more time with family" as the reason for leaving at your age has a certain smell in the industry. Start building your transition team so redirecting your attention isn't so evident. Have a good story, maybe directing your efforts to a non-profit or educational institution where there is a good fit for your skillset.

I sent you a pm.

 

[SnowballCamper]

1) Will I regret leaving a job to which so much of my identity is tied?

Only you can answer this. If you do leave the job, write a personal essay about why you're leaving and what you want to accomplish outside of work. Keep it, and refer to it as a way of preventing regret...

2) How likely is it for me to successfully fill my time with endeavors (projects, jobs) that are genuinely emotionally fulfilling?

If you're willing to consider non-profit board service, or an executive director position of a charity you love, then probably high. There are high cost hobbies, like flying or yacht ownership where considerable time can be spent learning the craft. Imagine being home with your kid during the covid induced home schooling, it is pretty nice for me.

3) How much of a "buffer" should I give myself, financially, to recognize the fact that I still have half of my life to live. Things change. People get sick, life events happen, laws and regulations change. For example, if Biden's tax plan were implemented, the after-tax yield of my passive income would be greatly reduced.

The standard 4% withdrawl rate (4%*25mil=1mil) gives you room for 50% taxes.

 

[Dtail]

The standard 4% withdrawl rate (4%*25mil=1mil) gives you room for 50% taxes.

The 4% WR is more for a 30 year retirement, not necessarily for a 50 year retirement.
Nevertheless, it sounds like there are discretionary expenses and it logically easier to cut from a 500k budget if necessary.

 

[FundManager81]

Good comments.

In terms of "how much will I miss it," the odd thing about this job is that it's actually very lonely. Being a fund manager, you certainly interact with other people. But it's not really in a social way. All of those CEOs and CFOs I know, it's professional, it's not golf and yacht buddies. You make your own decisions, you live with them, and you are "managed" by your numbers (aka we can see if he's doing a good job based on the output, not the qualitative touchy-feely stuff).

I am an introvert by nature, and so the role fits me. But it's almost too much introversion.

Having the ability to expand social circles is an important part of this. Not just people who have drive + intellectual horsepower, but people who share common non-professional interests.

Serving on a couple of non-profit boards could be a good way to pivot, but time management is the challenge. If you're doing your job the *right way* as a fund manager, you really *shouldn't* have a lot of time leftover during the week. Just the nature of the game.

I appreciate the advice. That bit about writing an essay to myself, I think it's a good one.

 

[socca]

I googled "boutique independent registered investment advisor" and got some interesting hits. Here is one of them: Alamar Capital Management.

If you would like to keep your hand in the game but be able to dial down the stress to a more reasonable level, you could open your own boutique independent RIA. Managing $100M for a select group of HNW families might be less stressful than managing billions. Owning and operating a successful small business will involve some aggravation from time-to-time, but your ability to provide your own seed capital for the business would be great.

You've got a couple of important stakeholders in whatever decision you make: your wife and son. I have a relative with a kid who has failed to launch properly - it's a real mess with no clear end in sight. You'll obviously want to think a great deal about what kind of environment will maximize the probability that your son launches OK (sadly, there are no guarantees of success no matter how hard you try ...)

Congrats on your financial success thus far. It sounds like you've got a good chance of becoming a non-financial success as well!

 

[RetireBy90]

I would suggest that being an introvert is something you can work to overcome. I am also and have to push myself into positions where I interact more on a personal level even though uncomfortable doing it. Sometimes I actually make a list of things to talk about if I were to leave a post without a plan to replace it I would have failed. 2 years into RE I have made changes to the plan and dropped out parts completely. It took about a year but I finally found a place to fit in working with charity couple times a week. I would suggest a schedule of some sort before you punch out. You can change it any time but start with some structure. Kids to the park Tuesday and Thursday afternoons, golf lessons Friday mornings. Then time each week to visit places you can find meaning to your efforts. A plan like I’m sure you do at work. Put the effort into finding a new routine and purpose and you will find it.

 

[FundManager81]

Thanks for the RIA idea. The reality is that managing a few hundred million is a similar burden as managing a few billion... that's why the economics of the asset management industry are so insane... someone can manage $50B with only 10% more effort than if they manage $10B! Just own more of each stock, right?

At some point down the road, I might consider the possibility of becoming a financial advisor. But, the current intent is to just "get out" of the asset management industry altogether. It's the whole concept of "being tied to the market" that is tiring. The market never sleeps for more than 3 days in a row. You can't have people rely on you, and say "by the way, I'm going camping in Patagonia for 3 weeks, and I'll be un-reachable."

I appreciate the thoughts and advice that are popping up on this forum so far...

 

[38Chevy454]

Financially and age-wise you are on a different scale than most, but the old saying "you may have a job to retire from, but what will you retire to?" still applies. I am sure you will do a fine job of managing your finances and the 3% withdrawal is likely quite sustainable for the rest of your life after retirement and working income stops.


I like the idea to make an exit plan. That will provide you with a defined end you can not only work toward, but also to know when you have reached that point. It will always be easy to keep working with the high income to get more. The question is if you have enough do you need to accumulate more?


Congratulations on the incredible success you have had so far. I have a lot of respect for those that have made it on their own. IMHO you have already hit a FI point if you just pare down expenses a little. From here on out you are just increasing discretionary spending allowance.

 

[bigcmagor]

I would suggest that being an introvert is something you can work to overcome.

I had to work (very hard) to overcome being an introvert in order to succeed in my career. I'm very much enjoying embracing this trait in retirement.

 

[Golden sunsets]

Hi everyone -

I don't know how unique my situation is, but I have not found many others in a similar spot, so I figured I'd post on this forum and see what comes of it!

I am 39 years olds, and manage a $5-10B mutual fund on the west coast. Though my job is interesting and very lucrative, I am getting burnt out, and my job does not lend itself to "sabbaticals"... so, essentially, you're on the treadmill until you're out of the game. The thing that the job does provide is status, financial means, and constant intellectual challenge. The thing that the job does NOT provide is two-fold: (1) a break; and (2) a sense of fulfillment re: "helping other people and making the world better."

I'm trying to figure out whether to get out of the game and "retire" in my early 40's (which, realistically, means taking at least a year or two off, and then re-assessing). This would give me a chance to travel with my family (perhaps live abroad), and it would give me a chance to simply do something new that energizes me in ways my current job does not.

The biggest question marks in my mind are:

1) Will I regret leaving a job to which so much of my identity is tied? Though I'm happy enough, this nagging feeling of un-fulfillment + greener pastures has gradually grown over the last 5 years.

2) How likely is it for me to successfully fill my time with endeavors (projects, jobs) that are genuinely emotionally fulfilling? Going from a high profile job where I'm my own boss + am surrounded by the best and the brightest, to a less visible and more ordinary job that "helps other people," can sound appealing and altruistic on paper, but am I just tricking myself into thinking that the grass is always greener?

3) How much of a "buffer" should I give myself, financially, to recognize the fact that I still have half of my life to live. Things change. People get sick, life events happen, laws and regulations change. For example, if Biden's tax plan were implemented, the after-tax yield of my passive income would be greatly reduced.


Here are a few specific statistics about me:

- Household net worth is rougly $25 million, of which $15 million is liquid assets, and $10 million is tied up in personal real estate around the world.

- Annual income is in the $5-10 million range (not a typo), before passive income such as dividends and stock appreciation.

- I have a wife and a young son. We will not have more children. He has not yet started grade school

- We live off of roughly $500k after-tax income per year. Some years less, some years more. It's an upper-class lifestyle, but not an ultra upper-class lifestyle.

- My wife is currently a stay-at-home mom, and for now, has no ambitions to return to the work-force. She could be happy travelling the world for the rest of her life (has been to 60 countries, and has lived in several).

My current thinking is to work for 2 more years, to get my liquid assets close to $25 million, and then retire around the time my son begins 1st grade. I'd force myself to take a year or two off, to give myself time to figure out where I really want to re-orient myself. We would split our time between Europe and the US (we are building a new house on the west coast... and we already own property in Europe).

The reason $25 million is our "number" is because it would allow us to live off of $500k/year at a 3% drawdown rate (750k gross, minus taxes on any capital gains or dividends). In other words, it's a level where we could SUSTAIN our current lifestyle, while still being able to grow the portfoio over time. It's important for us to sustain our lifestyle. I'm confident in the ability to generate returns of >5% per annum (historically we have done a lot better than this), whcih would result in the portfolio growing at least in-line with inflation, net of withdrawals Also, if needed, we could liquidate some of our real-estate portfolio, to flip the mix from $25mm liquid / $10mm real estate... to something closer to $30mm liquid / $5mm real estate.

The biggest risks to sustaining our lifestyle are either catastrophic health problems, or major tax hikes on the rich (does not seem unlikely to me).

The biggest reason this would be a bad decision, is that I'd end up missing the job more than I expect to + have trouble finding a replacement that's as fulfilling as I hope to find.

I don't think the idea of being worth "$100million" vs "$25million" really motivates me at this point. Money is a means to an end, not an end unto itself. And, frankly, we will soon have more than enough.

Do any thoughts jump to mind?

We are vey lucky to be in the position that we are. It all came via hard work. My net worth was negative until I turned 30, because of student loans. All of our net worth has been accumulated over the last 9 years. I had to pay for a decent chunk of my college tuition, and I never had free years in my 20's to goof off and see the world. I regret not being able to do all of those fun things, and though it's not the same at age 40 as it is at age 22, in my mind, I'd rather "make up for this lost fun" while I'm still young, rather than working until 55-60 and having less endurance + energy + passion to explore the world.

Thanks for your thoughts and advice -

FM

The fact that it's important to you and your DW that you maintain your lifestyle at an average of 500K/yr give or take, tells me that you aren't ready to recede into the background with a lower key philanthropic/giving back type of job. My sense is that you would miss the ego boost your current job gives you and any less than that status would take a toll on your sense of self worth. if I were in your position I'd stay where you are for another 2-3 years, and then "quit the rarified world that you exist in now, with a stash that is much greater. In that 2-3 years cultivate some Board positions on Corporate and Plilanthropic organizations and parachute into a world like you live in now, but without the current day to day.

 

[FundManager81]

ehh, ego really doesn't play a role here. the reason the spending is set at 500k/year is just because that's what we happen to spend now. your comments are a lot more judgmental and less helpful than others.

i said i'm not planning to retire for another 2 years anyway. so the wait 2-3 years advice is what i articulated to begin with.

 

[HawaiiShrimp]

Hi FM,
Congrats on your success! Amazing job!! I read the whole thing and here are my 2 cents.

1. Work 2-3 more years to increase liquid assets to $25-$30M.

2. Lower RE from $10M to $5M if you are okay to do so. This will lower your property tax, maintenance burden.

3. After 1 & 2, you should now have $30M liquid assets and $5M in real estate

4. With 3% withdrawal rate, you can safely draw $500k to spend annually and still growing your portfolio.

5. I don't think you will regret leaving a stressful job. If you ever need a job, get one that's NOT stressful, and give you joy along the way. Doing something you enjoy is hardly a job.

I hope it helps. If you can kindly DM me the growth stocks that yield high dividends, I'll highly appreciate that.

Thank you and welcome!!

-Shrimp

 

[Ready2Go]

Someone asked me this question recently...If you have enough money to comfortably last your lifetime plus a legacy, would you work at your current job for free? If not, it’s time to go because that’s basically what you are doing.

 

[Closet_Gamer]

ehh, ego really doesn't play a role here. the reason the spending is set at 500k/year is just because that's what we happen to spend now. your comments are a lot more judgmental and less helpful than others.

You may not enjoy the questions about ego gratification, but it strikes me as integral to your situation.

Can a family successfully retire on $25M?
I'm pretty sure you'll find a way to scrape by.

Set the money questions to the side. They're not relevant in this situation.

Something is driving you to believe that a $500k after-tax spending threshold is table stakes...and its not just inertia. And something is driving you to want to stop this train you're on. Those things need to be reconciled.

I think you should figure out what you want to do, get out ASAP and work on those things. Further preening the financial portfolio is something to do because you are clearly good at it and therefore its comfortable, but its not advancing you.

Front and center should be fulfillment, purpose, and contribution to society.

$50M won't make you any more fulfilled that $25M.

My $0.02. Good luck.

 

[BeachOrCity]

OP. your original post said all that is needed. The job is not fulfilling and you dont really enjoy it, it is just a means to an end.

So this is really about YOU and your taking responsibility for your post work life and fulfillment. If you were successful enough to get where you are you should be able to focus enough to find fulfillment post fund management career.

 

[RunningBum]

My current thinking is to work for 2 more years, to get my liquid assets close to $25 million, and then retire around the time my son begins 1st grade.

It seems to me that once your son is in school, it's a lot harder to take trips whenever and wherever you want, and bounce between homes in the US and Europe. Unless you plan to home school.

 

[Keim]

I'm only qualified to comment on #2. You shouldn't feel that going into an area where you are helping others doesn't also have some of the best and brightest. Many, many people sacrifice income for the other rewards their work offers.

I chose to start my own nonprofit, and coordinate a statewide coalition of similar efforts. In 5 years the Latah Recovery Center has become one of the best known nonprofits in our town, and with a shoestring budget we've gotten attention from the state govt and academia for our innovative approach. I am no slouch. But my work frequently brings me into touch with people better and brighter.

I echo others. In the year or two before you step back get involved in a nonprofit board or something similar. Start seeing where and how you can make a difference. Perhaps an advisory role on a foundation? That could be a decent bridge between what you do, and finding out about local charitable causes.

I know a gentleman of great means that also volunteers as a coach to newer executives...

My best wishes to you. I am certain your next chapter will be as fulfilling as you desire.

Hi everyone -

I don't know how unique my situation is, but I have not found many others in a similar spot, so I figured I'd post on this forum and see what comes of it!

I am 39 years olds, and manage a $5-10B mutual fund on the west coast. Though my job is interesting and very lucrative, I am getting burnt out, and my job does not lend itself to "sabbaticals"... so, essentially, you're on the treadmill until you're out of the game. The thing that the job does provide is status, financial means, and constant intellectual challenge. The thing that the job does NOT provide is two-fold: (1) a break; and (2) a sense of fulfillment re: "helping other people and making the world better."

I'm trying to figure out whether to get out of the game and "retire" in my early 40's (which, realistically, means taking at least a year or two off, and then re-assessing). This would give me a chance to travel with my family (perhaps live abroad), and it would give me a chance to simply do something new that energizes me in ways my current job does not.

The biggest question marks in my mind are:

1) Will I regret leaving a job to which so much of my identity is tied? Though I'm happy enough, this nagging feeling of un-fulfillment + greener pastures has gradually grown over the last 5 years.

2) How likely is it for me to successfully fill my time with endeavors (projects, jobs) that are genuinely emotionally fulfilling? Going from a high profile job where I'm my own boss + am surrounded by the best and the brightest, to a less visible and more ordinary job that "helps other people," can sound appealing and altruistic on paper, but am I just tricking myself into thinking that the grass is always greener?

3) How much of a "buffer" should I give myself, financially, to recognize the fact that I still have half of my life to live. Things change. People get sick, life events happen, laws and regulations change. For example, if Biden's tax plan were implemented, the after-tax yield of my passive income would be greatly reduced.


Here are a few specific statistics about me:

- Household net worth is rougly $25 million, of which $15 million is liquid assets, and $10 million is tied up in personal real estate around the world.

- Annual income is in the $5-10 million range (not a typo), before passive income such as dividends and stock appreciation.

- I have a wife and a young son. We will not have more children. He has not yet started grade school

- We live off of roughly $500k after-tax income per year. Some years less, some years more. It's an upper-class lifestyle, but not an ultra upper-class lifestyle.

- My wife is currently a stay-at-home mom, and for now, has no ambitions to return to the work-force. She could be happy travelling the world for the rest of her life (has been to 60 countries, and has lived in several).

My current thinking is to work for 2 more years, to get my liquid assets close to $25 million, and then retire around the time my son begins 1st grade. I'd force myself to take a year or two off, to give myself time to figure out where I really want to re-orient myself. We would split our time between Europe and the US (we are building a new house on the west coast... and we already own property in Europe).

The reason $25 million is our "number" is because it would allow us to live off of $500k/year at a 3% drawdown rate (750k gross, minus taxes on any capital gains or dividends). In other words, it's a level where we could SUSTAIN our current lifestyle, while still being able to grow the portfoio over time. It's important for us to sustain our lifestyle. I'm confident in the ability to generate returns of >5% per annum (historically we have done a lot better than this), whcih would result in the portfolio growing at least in-line with inflation, net of withdrawals Also, if needed, we could liquidate some of our real-estate portfolio, to flip the mix from $25mm liquid / $10mm real estate... to something closer to $30mm liquid / $5mm real estate.

The biggest risks to sustaining our lifestyle are either catastrophic health problems, or major tax hikes on the rich (does not seem unlikely to me).

The biggest reason this would be a bad decision, is that I'd end up missing the job more than I expect to + have trouble finding a replacement that's as fulfilling as I hope to find.

I don't think the idea of being worth "$100million" vs "$25million" really motivates me at this point. Money is a means to an end, not an end unto itself. And, frankly, we will soon have more than enough.

Do any thoughts jump to mind?

We are vey lucky to be in the position that we are. It all came via hard work. My net worth was negative until I turned 30, because of student loans. All of our net worth has been accumulated over the last 9 years. I had to pay for a decent chunk of my college tuition, and I never had free years in my 20's to goof off and see the world. I regret not being able to do all of those fun things, and though it's not the same at age 40 as it is at age 22, in my mind, I'd rather "make up for this lost fun" while I'm still young, rather than working until 55-60 and having less endurance + energy + passion to explore the world.

Thanks for your thoughts and advice -

FM

 

[anothercog]

At some point down the road, I might consider the possibility of becoming a financial advisor. But, the current intent is to just "get out" of the asset management industry altogether. It's the whole concept of "being tied to the market" that is tiring. The market never sleeps for more than 3 days in a row. You can't have people rely on you, and say "by the way, I'm going camping in Patagonia for 3 weeks, and I'll be un-reachable."

I appreciate the thoughts and advice that are popping up on this forum so far...

It can be done. I work in the fund industry too but not on the investment side. We had a star fund manager that wanted to go on a long, dangerous trek. We took out a massive insurance policy on him, gave him a sat phone and he was gone for at least 6 weeks. We kept it on the down low until he came back alive.

It sounds like you just need a good break and you may need to quit your job to get it. My guess if you tried to quit your job your employer would do everything in their power to keep you on including offering a 3 month sabbatical. In any event, if you have a good track record you won't have too much of a problem finding another gig. I would think being a CIO of a University or non-profit endowment could be a good change.

You are young enough that you can definitely re-build something if you want to take a few years off. It seems like we are always re-hiring people that left and offering them more money to come back.

My uncle was a fund manager for a real estate portfolio. He was constantly on the go and seemed to enjoy his job but a cancer diagnosis in his late 60s forced him to stay home and opened his eyes to what he had been missing. He finally retired at 69 and is trying to make the most of time with his family in his remaining time. I don't suggest you wait that long.

Taking time off to travel the world before your son starts first grade sounds like a good idea to me. Good luck!

 

[HarveyS]

Go for it!

1) Will I regret leaving a job to which so much of my identity is tied?
2) How likely is it for me to successfully fill my time with endeavors?
3) How much of a "buffer" should I give myself, financially?

The biggest risks to sustaining our lifestyle are either catastrophic health problems, or major tax hikes on the rich (does not seem unlikely to me).


FM

My thoughts and a request, please.

1) No. However I was surprised at how many people forget you. They are there now because of your position. Once you leave many will move on. It might bother you for a few months. Realize they were never friends anyway.
2) Very. You seem to have an active mind. There are many ways to channel that. Be careful not to over-commit to helping. So many people will reach out for your help on many various issues.
3) Working for 2 more years would be great, but your son is 4 yrs old only once. I think you have enough now based on your net worth, skill set to navigate changing markets, and real estate holdings.

If a catastrophic health issue comes up, you will likely not need the global real estate holdings and can liquidate them.

Many of us on the forum have trouble spending money. There is a separate "blow that dough" thread to help us see what others are doing with their hard earned stash. There is another thread on UHNW spending (which has so far been anecdotal). Can you please share your budget/expenses? How does the $500k/yr break out? That might help some of us approach spending differently.

Thanks and good luck. Come on in, the water is fine.