Another aside that kind of relates to this topic:

Some may be familiar with the "Die Broke" philosophy (I read the book 25+ years ago). Essentially, the last check you write should bounce. Spend down your assets as you go. While I in no way align with this philosophy overall, there are some learnings from it that might be useful to some. Here's one:

I know someone well who has a belief that helping his grown kids out with house downpayment, car purchases, paying off credit cards, etc. is not right, and not good for them. I generally agree. However, he has significant real estate assets that he plans to provide as their inheritance. I'm talking hundreds of acres of producing timberland, residential lots in established communities, commercial land and buildings, and the like. He has 2 kids who will jointly receive the property. My point to him is several-fold: That's a lot of frictional cost and work for them when they do inherit it, not to mention potential disagreements on when and how to dispose of the properties, etc. I urged him to liquidate just a part of it and take them all on interesting trips and experiences while he's alive (they already do this and enjoy it, mostly dutch treat), and can enjoy time with his grandkids more. Would he really get more joy knowing they get a lot of property when he passes, or spending quality time with them when he's alive? Sure, it reduces the size of the inheritance, but he's already said he doesn't believe in bailing them out of their regular financial decisions, so why not enjoy the fruits of his thriftiness while he can? Also, as he ages, maybe start the move to more liquid negotiable instruments than real estate?

I'm not a financial advisor, and it's not really my place to give him this advice, but if any of you were in the same position, how would you handle it?

SF2004 said:

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Bob Knights Paper Hands said:

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One piece of advice I wish I would have been given when I was younger was to start saving in a 'pre-retirement' account. I've ended up with more than I'll need in retirement but not enough to stop working yet. The tax benefits are great, but I wish I would have started to do both earlier. I had buckets to save for house, my next car, emergency, etc., but no bucket for pre-retirement until I was well into my 40s.

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This... this this this

A lot of people go overboard on hiding from the tax man or they do nothing at all.

I wish someone would have explained that is you want to retire early then that gap has to come from pre-retirement savings.

Also, I feel people need to figure out when it is enough and not piss away their life working and calculating the Future Value of one vs two ply toilet paper.

Lastly using debt on somethings (like a swimming pool) provides a return on that interest paid in non-financial means. If paying some interests allows your children to enjoy a pool in their prime years then it might be worth it to some people. Be reasonable and thoughtful but waiting is always going to incur opportunity cost.

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This post needs to be read and re-read and read yet again!

Sounds like smart advice.
If nothing else, this person you speak of should clearly divide any real estate beforehand so there is no joint ownership after he passes.

YouBet said:

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That Time, Health, Money paradox is valid. We are 50 and 48. Can retire now if we want to, but I'm working my ass off at a startup. My hours have eased up since we finally hired a few people under me but it's been 55-70 hrs per week for close to two years now.

But I've been constantly thinking about the time box we have from 50ish to 70ish that you can physically do stuff. I haven't taken a PTO day that was real in a year. We are squandering our time on earth and I know this. It's time to fix that and we are now planning real time off this fall.

My next decision is going to be do I wait for the golden handcuffs to pay off or do I just walk away from it and forego the payoff. First world problems but I'm leaning more and more just walking.

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jja79 is right. Sometimes I feel useless not having a job. I still "work" a little and now trade stocks some but that is coming to a halt. I have an Aggie friend who went to work for Dell before most of the world had heard about Dell. He retired 20+ years ago. About 10 years ago I asked him at our tailgate if he ever gets board. He said "Never". His golf game was in great shape, he had a personal trainer who worked his ass off and they traveled. Now, he has more money than 99% of this board so he has advantages, but I have somewhat followed his path and have not been bored very much. But it is a big change.

And 70 is not the end of life. I am knocking on the door of 68 and in really good shape. I truly believe I have 8-10 good travel years in me. To me, early 50s would have been too young for me to retire, but every life has a different story.

SW AG80 said:

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YouBet said:

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That Time, Health, Money paradox is valid. We are 50 and 48. Can retire now if we want to, but I'm working my ass off at a startup. My hours have eased up since we finally hired a few people under me but it's been 55-70 hrs per week for close to two years now.

But I've been constantly thinking about the time box we have from 50ish to 70ish that you can physically do stuff. I haven't taken a PTO day that was real in a year. We are squandering our time on earth and I know this. It's time to fix that and we are now planning real time off this fall.

My next decision is going to be do I wait for the golden handcuffs to pay off or do I just walk away from it and forego the payoff. First world problems but I'm leaning more and more just walking.

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jja79 is right. Sometimes I feel useless not having a job. I still "work" a little and now trade stocks some but that is coming to a halt. I have an Aggie friend who went to work for Dell before most of the world had heard about Dell. He retired 20+ years ago. About 10 years ago I asked him at our tailgate if he ever gets board. He said "Never". His golf game was in great shape, he had a personal trainer who worked his ass off and they traveled. Now, he has more money than 99% of this board so he has advantages, but I have somewhat followed his path and have not been bored very much. But it is a big change.

And 70 is not the end of life. I am knocking on the door of 68 and in really good shape. I truly believe I have 8-10 good travel years in me. To me, early 50s would have been too young for me to retire, but every life has a different story.

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I have the unusual experience that I actually retired at 47 for two years. It's probably more accurate to call it an extended sabbatical in hindsight. I consulted for about 6 months of that and did not enjoy that. If I'm going to work, I want to work with a team.

I was perfectly happy being "retired" and could go right back to it and have zero worries about being bored. Now, was I super active when I I wasn't working? Not really because my wife was still working as an executive in F500 and I was managing our home and a family home at the time. So I was actually pretty busy just doing house stuff.

This time around there would be much more of a concerted effort to travel and do fun stuff, but I know me and I would have no issues about not having a job like many do. And I don't criticize that at all. People are wired differently. I'm wired that I work my ass off, but I'm also wired to focus on the here and now. I tend to not have regrets and don't worry about what could have been so once I made the decision to retire (I agonized over it up until the second I mentally made the decision), I happily walked away and didn't look back.

Only reason I'm working right now is because the opportunity that was presented to me was somewhat innovative and I wanted to see if I could pull it off. So far I have with several punches to the nuts along the way though. I gave myself 3 years for this gig and I'm about to hit 1 year left. Will need to stay 3 more to get all the financials though.

This time around there would be much more of a concerted effort to travel and do fun stuff, but I know me and I would have no issues about not having a job like many do. And I don't criticize that at all. People are wired differently. I'm wired that I work my ass off, but I'm also wired to focus on the here and now. I tend to not have regrets and don't worry about what could have been so once I made the decision to retire (I agonized over it up until the second I mentally made the decision), I happily walked away and didn't look back.

Only reason I'm working right now

Does not compute.

We are trying to save as much as we can for retirement and also diversify (buying rent houses). BUT we still travel. I only get one life, so I am going to travel 2-3 times a year, I'm going to eat at the restaurants and not cook every meal. (Who am I kidding, I never cook).

I definitely think it is a balancing act. Could I save another $5k a year by cooking meals at home? Absolutely. Could we save another $10-$15k/ a year by not traveling? Sure. But I would rather work an extra 1-2 years and enjoy all these things, then scrimp and save - and what happens if one of us gets sick, or worse dies?

The earliest I can retire is 55, but likely will be 57 or 58 due to the hit I would be taking by not working til I'm 60. BUT I do plan on stepping wayyy back as I near that number and not working in my current position. By 54-55, I hope I'm just doing some light administrative type work.

Planning to go at 55 (5 more to go) and look forward to more golf and making my health a bigger priority. Instead of having to make time for my workouts, I look forward to building the rest of my schedule around my workouts. I also look forward to having more time to cook healthy meals at home.

There are so many things I enjoy doing, but it always feels like I am working to find time to squeeze them in. I am so looking forward to when those things ARE my schedule.

The times I've stayed home for a week the past 5-10 years have proven to me that I'll have no trouble with boredom. Less cortisol. More fun.

I really agree with your last sentence. I too often wonder how I had time to work. I think that sentence epitomizes how much of life we missed while working.

Pacifico said:

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This time around there would be much more of a concerted effort to travel and do fun stuff, but I know me and I would have no issues about not having a job like many do. And I don't criticize that at all. People are wired differently. I'm wired that I work my ass off, but I'm also wired to focus on the here and now. I tend to not have regrets and don't worry about what could have been so once I made the decision to retire (I agonized over it up until the second I mentally made the decision), I happily walked away and didn't look back.

Only reason I'm working right now

Does not compute.

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Maybe it doesn't. I was trying to make the point that my day to day life is focused on the here and now. I've always been a long-term planner when it comes to finances but not much else so I'm trying to recognize that I want to align the reality of our finances and our age with the reality of our life.

Ive never really enjoyed working for large corporations in office, but have worked remotely for some cool smaller companies, where the work was fun, enjoyable, laid back, well paid, great coworkers/bosses. I used to travel overseas for vacations or around the US, and work remotely and take Zoom meetings while overlooking the beach. Something like that would be a perfect retirement job, and I would love to work a job like that in my 70's or until I croak lol.

Unfortunately, most corporate jobs aren't like the above and can often be soul sucking. I like to work and make money, its fun and makes me feel productive. I could see myself retiring from the corporate life in my early 50's and start a business or work part time. I dont care if its driving Uber, I just like feeling productive everyday.

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I honestly think it's harder to STOP working so hard when you still can and take the journey of self discovery and asking hard questions than it is to maintain status quo just because it's what you've always done.

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Absolutely. This is why I agonized over retiring from my corporate gig. It was all I knew for 20 years. It was just funny that literally the second I mentally got there it was a complete 180 and I never worried about it again. Just took a bit to get there.

JMac03 said:

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herewegoagain said:

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I'm honestly just so happy to see people having this conversation. Knowing the majority of this board is high capacity, successful, driven men makes it all the better. We just do not talk about this enough in our culture, and it's at our own life experience.

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Just know there are a lot of badass women here too. We aren't all men.

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I purposely said "majority of this board" because of women like you

jja79 said:

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If you polled truthful retirees they would tell you the first 2 or 3 weeks of retirement are boring as hell. When you've been on a schedule, had responsibility and the positive feedback of accomplishment waking up with nowhere to go hits hard. If it happens to you welcome to the club.

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I can't say for sure but I think it may be different for different people. That is where it may make a difference if you are an introvert vs extrovert. Some people want to be among other people all the time, and feel the difference when they have retired. Some others value their alone time and find things to do which don't require other people. I do a lot of reading, online and otherwise, learning new technologies (I am in tech), investing (I do a lot) and more recently have started focusing more on keeping fit. I also do gardening. None of these require people. I can expand to sports like tennis and golf (I don't know how to play but would love to learn).

I got laid off last year and spent 7 months looking for a new job until mid of this year. I spent a lot of time from home and frankly loved it. I did not feel like I was waking up with nowhere to go. I enjoyed not having a work schedule or deliverables and dumb meetings and stupid 1-1 meetings. I spent more time with my daughter in HS and drove her to sports and to school. I enjoyed our conversations in the car, she is 16. The caveat is I was still job hunting so I had this feeling that this phase would end soon. But when I retire, that would be permanent. Would it matter to me? Not sure.

So I think it is about knowing the type of person you are and planning accordingly.

A quote from my long time financial guru & radio host extraordinaire, Bob Brinker - "you don't want to be the richest person in the graveyard"

I was talking about the first 2 or 3 weeks you wake up without being in the game. I relocated 14 months before I retired and have a great friend group here but it still hits you right at first.

jja79 said:

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I was talking about the first 2 or 3 weeks you wake up without being in the game. I relocated 14 months before I retired and have a great friend group here but it still hits you right at first.

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Yes, I can see there being a 2-3 week shock. Also my situation may be different because I had an end date, but if you retire, it is permanent. I will know only when I jump in.

I definitely need to focus more on "bridge" investing to get us from an ideally early retirement to tax advantaged withdrawals.

How have y'all estimated what you need for that period? Or is it even worth the hassle? Just invest what we can and when we get close to that age figure out how it looks

I saw a recent news article that saddened me.
This guy was 59, a hyper successful tech businessman, after a successful academic career with a PhD in neural networks (a kind of AI). He never got to wind down and move to the next phase of life where you don't have responsibilities other than "where do we go for dinner?". Life has unexpected turns and limited. We should also learn to enjoy the wealth we create at some point.

British tech CEO Mike Lynch's 'devastated' family break silence after Bayesian yacht disaster
https://nypost.com/2024/08/23/world-news/mike-lynchs-devastated-family-break-silence-after-bayesian-yacht-disaster/

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The sale of Autonomy to Hewlett-Packard in 2011 led to accusations of fraud and resulted in civil litigation in the UK in 2019. The case was decided largely in favour of Hewlett-Packard. In 2023, Lynch was extradited to the United States to face criminal charges. He went on trial in San Francisco in March 2024 and in June was found not guilty on all counts. In August 2024, he celebrated his acquittal on his family's superyacht, Bayesian, which capsized and sank in a storm off the coast of Sicily on 19 August. Lynch, his teenage daughter and five other people died when the yacht sank.

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water turkey said:

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What do you guys that retired at 55, or earlier, do for health insurance? That to me seems to be the biggest issue to retiring early, unless you have a bunch of money in your retirement.

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I have asked some folks who insure through Obamacare they say it is about $15k a year.

That's how they tax your money and time.

water turkey said:

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What do you guys that retired at 55, or earlier, do for health insurance? That to me seems to be the biggest issue to retiring early, unless you have a bunch of money in your retirement.

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That's a legit issue. Your options are Obamacare or concierge.

If you can retire this early then you can likely afford concierge. If you can't, then you might not be ready to retire early.

infinity ag said:

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water turkey said:

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What do you guys that retired at 55, or earlier, do for health insurance? That to me seems to be the biggest issue to retiring early, unless you have a bunch of money in your retirement.

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I have asked some folks who insure through Obamacare they say it is about $15k a year.

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I can get on my wife's teacher retirement insurance for about $400 per month so that's a factor in me wanting to possibly retire a couple years early.

water turkey said:

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What do you guys that retired at 55, or earlier, do for health insurance? That to me seems to be the biggest issue to retiring early, unless you have a bunch of money in your retirement.

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You can still get a high deductible bcbs PPO policy with an LLC and your family being a small group. But it is expensive and goes up slightly every year.