80 Years of Financial Hindsight

Hey guys!

Got an interesting note from a reader of this blog who sent the following in the subject line: “A middle of the night thought.”

Of course I had to open it up to see what it was about :)

“Wondered if you would like a little article written by an old fart (80) about his thoughts and concerns and what he would have done differently economically? Thought it might be interesting to jump ahead approx 45 years for a different perspective.”

“Oh man, would I!!!” I responded. And below is exactly that – a mash up of what he ended up sending over, with the first half focusing on his life/career/choices over the years, and the second half getting into the numbers: his current income and expenses (broken down into “essentials” and “discretionary”), values of his current assets, and then his main financial concern now at his age.

At the end he shares a summary of all the things he considers important now with his perfect hindsight ;)

It might be a bit choppy in places when I moved things around, but hopefully you enjoy it and get some good nuggets… I was glued from the second paragraph!


My Background

I’m a retired dentist, spoiled only child, have had two divorces, and have three kids.

My father was a pharmacist who opened his own old-fashioned drug store with a phone booth, fountain with stools and all that good stuff. He worked seven days a week. Was about to go an all-around-the-world trip with my mom, when she had a massive stroke and died one week before their departure – at age 48.

I graduated from dental school at age 23 and opened my own practice. I think most people’s perception is that great wealth is given on a silver platter as a dentist. No wonder why we have the second highest suicide rate!

The gross receipts for my first month in July, 1960 were $54. I was an excellent dentist, but never charged appropriately for my services. After a year or so I moved into a brand new office with lots of expensive equipment, and was married with two kids by then.

Then I got drafted. It was a total economic disaster, but I did spend three years in Hawaii.

I liked the people I met from California there, so I took the California board exams and went directly to Buena Park without even thinking about returning to Michigan. Bought a practice from a shyster, and ended up with a bankruptcy and then a divorce. She got the house, I kept the practice and moved it to a new location.

Things were going pretty well so I made a decision – perhaps based on what happened to my parents – that I was only going to work four days a week now, M – Th. That allowed me to play over a three day weekend every week.

Then I married a girl I met over a root canal – been with her 42 years now.

I have no desire to leave a legacy – I want my last check to go to the undertaker and have it bounce. (More on this later)

My Lifestyle

We vacationed in the Caribbean for several weeks each year for maybe 12 years, first on Barefoot Windjammer and then on charters with friends. I taught one day a week at USC and lectured around the country giving private seminars. This allowed us to travel quite a bit with Uncle Sam paying a large portion via tax deductions.

A mentor explained that the difference between tax avoidance and tax evasion was about ten years in prison so we were very careful.

We ran away from Southern California after almost 40 years due to traffic and congestion. Took a job offer in central Maine which only lasted about two years, then moved to a house we built as a rental in Central Florida.

I’m one of the oldest to have taken the Florida Dental Boards. Associated for a while, and then bought a practice and kept it for five years.

I used to do something a friend called ‘plantrolling.’ The staff and I would get together and plan how many days we were going to work in any given year.

With that in mind, we knew every day where we were in relation to the economic goal we established. My staff received the normal hourly pay for their position, but if we reached the monthly goal, there was a substantial bonus. We took the gross receipts up 500% over the previous owner in five years.

Then we decided we had enough money put away and it was time to retire.

I had no specific goals or “bucket lists” at that time. Looking back, I think I should have pursued “Economic Independence or Freedom” – not having to go to work economically. I think this is something all you “youngsters” should look at very carefully.

We managed our own investments for the most part, and being very “progressive”, lost our asses in the Dot-com Bubble around 2000. Our gains from Cisco bought one of our houses in full though, but then it went down 86%!!

I became a realtor (buyer’s agent) after retiring, and quickly learned that you could invest your retirement plan into real estate. Sounded great to me – real estate was going up and off the charts – better get a piece of that action! Think it was late 2007 when we invested $350,000 in a waterfront property with Gulf of Mexico access in the Florida Panhandle. The current assessed value? $3,500!! That’s not a typo, and we still own it.

We recovered from the first of those disasters because we were young enough for the market to recover. I don’t think I will live long enough to recover on the real estate fiasco. Wouldn’t an additional $350,000 be nice to have right now?

Our Current Finances

We live off Social Security and what we have stashed away over the years – just under $665,000. This is in one big IRA, one smaller IRA, and one annuity.

At age 70 1/2 you are required to withdraw some of your assets that have been sitting there attaining tax-free growth and pay Uncle Sam. Based on mortality tables he’ll calculate your Minimum Required Draw. You can take more than that, but not less.

Then there is that fund that we paid into for years and years called Social Security. My wife worked in the dental practice and to maximize current income, we contributed the minimal amount to Social Security.

My wife managed our investments for many years, but recently got tired of trying to keep up with the markets so we turned the assets over to Fidelity. We have a balanced portfolio – basically 50% stocks and 50% bonds. We would like to be more aggressive, but at our age we might not have time to recoup the loss of a market downturn.

Here is our current income:

  • Social Security – Me $1,536/mo (or $18,342/year)
  • Social Security – Her $712/mo (or $8,544/year)
  • Minimum Required Draw from Big IRA – $1,975/mo (or $23,700/year)
  • Additional Draw from Smaller IRA – $326/mo (or $3,912/year)
  • Annuity – $439/mo (or $5,268/year)
  • Total – $4, 988/mo (or $59,766/year)

That is a pretty meager income in today’s world, IMO.  But considering we still have $665,000 in assets – which we have basically been living off of for approximately 16 years – we’re not doing too badly.

Up until now our portfolio growth has been sufficient to cover our draw and management fees, BUT, it’s almost become a daily frustration of having all that money and not being able to spend it. We want to buy a new TV and furniture but don’t know how many years our money has to last for? We are both in good health, but that could change at any moment and there is nobody to take care of us if we run out too soon.

We don’t want to leave a legacy, so we need to figure out how to best spend every last cent without running out. How do you do that?

Our Current Expenses

I have only been keeping detailed records for the last six months, so I will give you those averages. It is pretty hard to define what is “essential” and what is “discretionary,” but I will make an attempt.

Essential – those expenses that occur every month and are somewhat basic to day to day living.
Discretionary – those where you have a choice like dining out and travel.

Our essentials per month:

  • Mortgage and HOA dues ($1,023)
  • Car payment ($387)
  • Electric and water ($266)
  • Medicare supplement ($520)
  • Long Term care ($289)
  • Lawn care ($70)
  • Phone/TV/Internet ($324) <— Woahhh!!! – J$
  • Groceries ($618)
  • TOTAL: $3,497

We live in a Del Webb over 55 gated community with many, many amenities – it is golf course property but neither of us golf. We have a brand new 2017 Subaru Forester.

Doing the math, $4,988$3,497 = $1,491/mo left for all our frivolity like dining out, travel, clothing, medications, haircuts, etc…

Speaking of travel – we spent 10 days in February in Playa del Carmen, Mexico, 20 days in September in the Pacific Northwest and will be spending about two weeks in Mexico City and Oaxaca in February.

Yes, we like to travel. We would do considerably more if we could afford it – oh wait, we have over a half mil in savings! Why aren’t we spending more of it?

My Recommendations Based off 80 Years of Living


#1. Become familiar with the ‘future value of a dollar.’ Based on that, start funding your path to Economic Freedom to the maximum – NOW. Plan on kids education and start funding that – NOW. That may cut into your discretionary spending, so you may need some sort of side hustle but it WILL be worth it.

#2. Look at all the pros and cons before deciding where you want to live – utopia does not exist. I know, I looked for it in Southern California, in Maine, in North Carolina, in Texas, in South Carolina, and in Florida. Built a house in each of those locations, and currently in my fifth or sixth house in central Florida. I cannot believe the money I wasted spent moving around the country. It was fun living in the different areas, but very costly.

Work is becoming less geographically dependent. Find a place where you can live with the trade offs – rent for a while and make sure you love it and then settle there. Consider living outside the US – you can live in Mexico with a better lifestyle for about 50% of what it costs here. If I were 20-25 years younger, I would learn fluent Spanish and be living in Mexico.

#3. Try to find a job you really enjoy doing. Do side hustles if necessary to supplement your income, but make your primary occupation something you like to do.

#4. Figure out what you are going to do for the next 40 years if you achieve “Economic Independence” early! I read a lot about “giving up Starbucks and retiring at age 35 with the money you save” type of stuff. But let’s say you are able financially to retire at age 40. What are you going to do with your life for the next 40 years?

I would highly suggest that you live a bit as you strive for economic independence. How about – “Yea, I don’t have to go to work anymore BUT I WANT TO.” That way you continue to do something you love, but also make money without the stress.

#5. Seriously prepare for the future, but also LIVE each day. Want the thrill of driving a NASCAR race car, DO IT! I did!! Want to fly in an antique biplane – DO IT! It was fun being the Red Baron.

#6. Develop some type of passive income. Real estate, e-books or something that does not require your constant involvement. One can make decent living professionally, but most occupations require that you be there. In my case, if I was not there, there was no income but all the expenses continued.

Develop some type of passive income whether it is real estate like Paula from AffordAnything.com has done so admirably, or some other source of income. This will do two things: give you some inflation adjusted income, and take some of the pressure off the “required performance” of your assets.

#7. When you are young, you can be much more aggressive in your investments because you have time to recoup any losses from a downturn. Stay in the market during a downturn, you really lose out when it recovers if you are sitting on the sidelines.

#8. Become familiar with the “Plantrolling” concept of planning – it was used on the Manhattan Project and is a great tool. Basically, if you want $1,000 dollars saved at the end of one year, you need 1/12 of that or $83.33 at the end of the first month, $500 at the end of six months, etc. This allows you to see where you are and make mid-course corrections if necessary. Consider it goal setting with a time line.


Thanks Larry!

A couple things I took away from all this myself:

  1. Life changes sooooo much over the years! For the good AND bad!
  2. You never have to be stuck doing *one thing*. Larry got up and changed whenever he got bored or found something better, and it’s important we all know that no matter what our current stage
  3. It’s good to know when you have “enough!” So you don’t continue working forever! (unless it’s the “retired-type” of work that comes with financial freedom ;) Not unlike a blog or passion project.)
  4. Apparently you can retire even though you have a house AND car payment!  Haha… Perhaps one or both of those things came *after* retiring?
  5. And lastly, you should figure out what you want to leave behind (or not) when it’s your time to pass. I hear a lot about “wanting the last check to bounce,” but it has its set of pros and cons. As much as I personally would have a BLAST doing that, I’d rather leave my small fortune to my kids and/or their kids and/or THEIR kids. But maybe I’ll change my mind as I get older?

Anyways, hope you liked reading this as much as I did :) I’m gonna try and feature more “this is my life” type stories here because I find them absolutely fascinating. We all lead such different lives, and I think it helps to form our OWN decisions better too as we continue to live out our own…

But remember the most important takeaway of all here: WE ARE ALWAYS IN CHARGE!! It’s up to US to do the things we feel is best for us no matter what’s going on around us or what others are saying… It’s not always easy, but it’s incredibly important unless you like living with regrets.

Have a safe and wonderful weekend, everyone :)

[This post was previously published in 2016, but stumbled across it again and thought it was worth re-sharing :) Big shout to Larry again for always sending in his thoughts!]

UPDATE: Here’s an update from Larry on how his money’s currently now looking, 3 years later :) Thanks for coming back, brother!

The market’s performed pretty well overall since the original post (except for last year), so our total is still a rather comfortable $604k.

We discussed things with our financial advisor and decided to kick up our monthly draw from the IRAs to a total of $4,400/mo now. We also took 3 years RMD out of the managed account and put it in a high yield money market – about the same as a CD right now. The thought being that we would never have to sell in a down market (for the next three years) to meet the RMD.

Part of the rationale for this was we actually lost money last year. Our risk/reward profile was about 50/50 stocks and bonds in order to have some downside protection. Well, that sucked last year because bonds did poorly and we did not have enough in stocks (or the right ones) to get the increase. So we’ve since opted for the relative safety of a good money market for a portion to help improve our comfort levels.

We set a “benchmark” of keeping $400k in the managed account. Anytime there is a substantial increase, we could take some of that off the table as well (about +$7K this morning). If it goes below the $400k, we don’t touch it.

We also increased the draw so we have more to spend on travel while we still can do it comfortably. We are off to a couple of weeks in Portugal in May. I will be 83 in September so really don’t know how much longer I will be able to travel.

So, we seem to be “holding our own” in making it last as long as we do!!

Total of all accounts now = $604k: $194K in the money market (the 3 year RMD mentioned + some), $407k in the managed account, and $3K just sitting there in an old account.

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  1. Jon @ Be Net Worthy December 22, 2016 at 6:50 AM

    That was a fun read! It’s interesting to hear the perspective from the “other side” of retirement. And what a life! Lots of moving around – a couple of different careers – you never know what life has in store for you.

    Best of luck to Larry!

  2. Go Finance Yourself! December 22, 2016 at 7:44 AM

    Some excellent lessons in this story. This should be a must read for everyone just starting out and even those several years into working. I could not agree more with focusing on attaining economic independence.

    I think the biggest lesson here is that you need to take smart risks. Larry seems to be fairly impulsive and jumps into the latest thing (real estate bubble, moving frequently and buying numerous dental practices). When you’re young, you can take more risk in your investments, but that doesn’t mean putting half your portfolio into one stock or one property. Use the history of the market to your advantage, diversify and save as much as possible.

    Good luck Larry and thanks for sharing your story! Very insightful!

    1. J. Money December 22, 2016 at 10:01 AM

      Great point about impulsiveness :) I def. did more of that before I become a dad, haha…

  3. Paul @ ABL December 22, 2016 at 8:09 AM

    Nice story Larry. Great insights, like there isn’t a “perfect” place to live from someone with a bunch of data points.

    Did I miss a marriage and a divorce? I only count two marriages and one divorce, but the headline says two divorces. Perhaps a word with your editor is in order :-)

    Definitely vote for this to be the beginning of a series. Thanks J$!

    1. J. Money December 22, 2016 at 10:04 AM

      Haha… Maybe it was one worth forgetting about? :)

    2. Marty March 18, 2019 at 5:05 PM

      Yes, I liked the story from someone who is living in retirement and not a millionaire. Would like to see more of these and how they are coping in retirement. Maybe some with traditional retirements/SSA and living paycheck to paycheck. How they get from day to day. Keep it up J$

      1. J. Money March 18, 2019 at 5:36 PM

        Noted! :)

  4. Miss Mazuma December 22, 2016 at 8:19 AM

    Larry is awesome!! There are no lessons greater in the world than the ones that come from our elders. Wisdom from experience can not be bought! It sounds like Larry has mixed many lives within this one. So many great lessons and takeaways here…

    I, too, search for utopia – sometimes you find it but its brief and others you miss it completely…which means he may be right. It doesn’t exist (remember the movie The Beach?)?! :( But that doesn’t stop us from trying. Also, value of the future dollar is one I struggle with despite knowing inflation rates. FI has a lot of factors to consider beyond my current yearly expenses. I think about this a lot but plan to work after FI so hopefully it will all shake out in the end. :)

    Now I want to go interview my 93 year old Nana on money!! Strangely enough, she work in the dentistry field as well but as a receptionist. ;)

    1. J. Money December 22, 2016 at 10:07 AM

      OOOOH Do it!!!

      That’s the one part I never understood with society and how the elderly are treated. They’re always overlooked as if they were kids again, when they contain SO MUCH MORE information than any of us do?! And they have the experience to back it up vs all of us who spout out theories and ideas yet haven’t lived long enough to prove them haha…

      I know this isn’t the problem with everyone everywhere, but def. seems at least that the younger generations don’t appreciate them as much.

  5. Aaron December 22, 2016 at 8:25 AM

    These posts from our elders are my favorite. Such a wealth of information / insights. I always want to learn from others who have gone before me if I can as they’ve been through it all (and prefer not to make the same mistakes). Thanks Larry and God bless.

  6. Kalie @ Pretend to Be Poor December 22, 2016 at 8:40 AM

    Really fascinating story, J! It helps to see that life often doesn’t follow the neat little plan we imagine, and having a “good” career or income doesn’t guarantee huge wealth in retirement. I appreciate his honestly about both the fun and cost about moving across the country. It’s great to hear from an older generation about this stuff because bloggers are usually young.

  7. Brian @ debt discipline December 22, 2016 at 8:57 AM

    Thanks for sharing Larry. Great wisdom.

    “I want my last check to go to the undertaker and have it bounce.” How do your kids feel about this? :)

    I also wonder how Larry’s kids have benefited from his lessons?

    1. Larry December 22, 2016 at 10:05 AM

      We have five kids between us – only one of them is speaking to us and that is pretty minimal. Four are in California and one in Chicago so we have been geographically separated for a long time. Won’t go into all the detail but there is certainly no being taken care of by our children in our future – they basically want absolutely nothing to do with us so we are on our own for the Golden years. They are all making a good living so they don’t need any money. We sorta feel that if they have totally ignored us, we can reciprocate by totally ignoring them upon our demise.

      1. J. Money December 22, 2016 at 10:08 AM

        This freaks me out as a father :(

        1. Avery Breyer December 22, 2016 at 1:26 PM

          Yeah, no kidding, hey? Same here, as a mother :(

      2. Brian @ debt discipline December 29, 2016 at 2:38 PM

        Sorry to hear Larry. I wish you luck with the family matters.

      3. Bryan March 15, 2019 at 1:00 PM

        Let me preface by saying my wife and I do not have children. They just don’t interest us. Now when I hear someone say aren’t you afraid of being alone/dying alone/who will take care of you, etc. I say, is that the reason you had children? Did you have children out of fear? Fear of being alone? Shouldn’t you have children as an expression of love? To build a loving family and set them out in the world to make the world a better place? What makes you think you just produced two caretakers for yourself when you can’t use the bathroom anymore? It’s wonderful if they want to help you, but you’re kidding yourself if you think they are under some contractual obligation to do so. They, like you, are free to live their life to the fullest. Don’t let fear rule you. Perhaps a paid caretaker might be wiping my behind at 90, but at least I know I lived on my terms.

        1. J. Money March 15, 2019 at 3:11 PM

          Not sure who/what you’re referring to here, but my fear I alluded to above wasn’t about being alone or being taken care of or anything like that, but the idea that my kids wouldn’t be talking to me for some reason down the line :( Something really horrible would had to have happened for that to occur and it would just break my heart not having a loving relationship with them!

          1. Bryan March 15, 2019 at 9:27 PM

            Exactly right! My apologies. No, no, no, not talking about you or anyone here at all. I would never do that. I was just venting about real life people in my life who have “child shamed” us for not having children but gave the aforementioned reasons. Again, no disrespect intended sir. Sometimes things don’t come across right on the internet.

            1. J. Money March 18, 2019 at 3:19 PM

              All good! And don’t mind a lively debate anyways even if you were wanting to chat about anything :) Just wanted to make sure we were talking about *the same thing* as that makes it even more complicated conversing online! Haha…

  8. Primal Prosperity December 22, 2016 at 9:27 AM

    Hey Larry… you rock!

    I love #5, to LIVE every day. I definitely am a proponent of this. I have also flown in an open cock-pit bi-plane and I actually have my pilot’s license in gliders. I get restless very easily, so I like to try new things. Things like flying can get pricey, but I’ve never regretted it for one day.

    I like your suggestion of part time work. I left a six figure income, just before my 40th birthday, because my husband and I had accumulated enough rental income to cover basic expenses, but now, 3 years later, I’ve gone back to work, but in a capacity with far less stress, and only 2-3 days per week, and I can take extended time off between projects for slow travel. It keeps my skills and network up and brings in income for traveling. Best of both worlds in my opinion. I think the corporate world needs much more of these kinds of flexible work schedules. :)

    1. J. Money December 22, 2016 at 10:08 AM


  9. Amanda December 22, 2016 at 9:30 AM

    This was a very interesting read! I definitely would like to see more posts like this!

  10. Dividend Diplomats December 22, 2016 at 9:33 AM

    J –

    Thanks for sharing this without a doubt. Just read the article to the girlfriend, to get her more on board with investing, saving, etc.. as at some point we will have combined accounts/shared assets. Definitely a motivating article. Hope all has been well J!


    1. J. Money December 22, 2016 at 10:09 AM

      Now tell me the trick of how to get your girlfriend to listen???

      My wife’s eyes glaze over the second I mention anything with money (unless it’s about US getting more :))

      1. Gwen @ Fiery Millennials December 22, 2016 at 2:35 PM

        Hey now! There are lots of wonderful, money smart ladies out there.

        *smooths down front of dress*

      2. Dividend Diplomats December 22, 2016 at 5:37 PM

        J –

        Haha, too funny. I tried to say – “Hey don’t you want to own enough shares of Target that it pays you to shop there?” or… “Wouldn’t you like to drop everything and be able to travel off of other income streams built from our savings, such as a Euro trip?” . You know how hard it is.

        Definitely making progress with her though haha, we even sat down to write out her first time ever – goals for the year and there are about 4 built in $ goals (upped her 401k, HSA Maxed, IRA maxed and a goal of $X for investments in taxable accounts). Little by little there are small victories. Keep it up J, you guys are rockstars.


        1. J. Money December 26, 2016 at 7:10 AM


          (And I see you over there Gwen :)))

  11. Lisa Van Gemert December 22, 2016 at 9:38 AM

    I loved this. I love advice from people who have actually lived. The advice on where to live is spot-on, and I think it applies to colleges as well.

    I loved the idea of plantrolling, and it’s helped me do some of my planning for next year. Your website continues to be a source of effective, useful, actionable information.
    Thanks for this!

    1. J. Money December 22, 2016 at 10:48 AM

      “I love advice from people who have actually lived.”

      Haha yes!!

  12. Lindsay @ Notorious D.E.B.T. December 22, 2016 at 9:40 AM

    Awesome story! This is why i always try to think of what future me will say to current me when making decisions. It’s basically the reason I opened a Roth IRA for myself a year ago – future me is already pissed at current me for not starting it sooner. :)

    1. Larry December 22, 2016 at 10:45 AM

      future you will be happy you did it when you did, maybe just not AS happy!!

    2. J. Money December 22, 2016 at 10:49 AM

      Agreed. Can’t screw over future YOU! :)

  13. Rachel @ Adulting By Design December 22, 2016 at 9:41 AM

    Thanks for sharing Larry’s story, J$!

    I really enjoyed this – getting to learn from those who have lived and experienced personal finance mistakes and successes for a lot longer than I’ve even been alive. Reading PF blogs all the time can get repetitive, but hearing about what others have done keeps it fresh and in perspective!

    I’d love to read more of these types of posts in the future!

  14. Lisa O December 22, 2016 at 9:53 AM

    That was a good read! Lessons to learn and a great take away. Looking forward to more post like this. It is amazing to think ….. you need to spend your money :)

    Merry Christmas!

  15. Freedom 40 Guy December 22, 2016 at 10:09 AM

    What a great post and great perspective from someone who has years more experience than most of us. it makes me want to get on the phone to my parents and pick their brains a little bit about their own experiences with money.

    #3 and #4 resonate with me in particular.

    #3. Try to find a job you really enjoy doing. — unfortunately I can’t say I much enjoy my job anymore. I’ve been thinking about moving on to something else for at least a year, but now I’m getting closer to actually doing it. I think 2017 may just be when it finally happens!

    #4. Figure out what you are going to do for the next 40 years if you achieve “Economic Independence” early! — I’m very close to achieving this goal. Technically I could probably do it now, but I want to be safe. Plus – this is a great point as while I know what I’m retiring from, I’m still not sure I know exactly what I’m retiring to…

    1. J. Money December 22, 2016 at 10:50 AM

      Sounds like you’re on a damn good path over there :)

      (Now call your parents!)

  16. Nathan Bieck December 22, 2016 at 10:26 AM

    Thanks for another wonderful article J. Money. The hardest thing when it comes to money in my family is the talking about money and creating that initial budget. After almost 10 years of marriage, I guess one of my biggest learning is that when it comes to $$ and possessions…and to live a happy, healthy life and hopefully financially independent life you absolutely have to learn to give up things…lots of things. Bye bye Big 10 sports package ($90 a year savings). Bye bye subscription to Google play and Pandora ($95.76 a year in savings). Not taking a vacation every other year and putting towards a credit card or savings account (Last year we saved $3810 by not taking a vacation and believe or not…it was awesome). Thanks for listening. Wishing you all the happiest of holidays.

    1. J. Money December 26, 2016 at 7:12 AM

      Nice work!! $3,800 is no joke!

  17. Fiscally Free December 22, 2016 at 10:36 AM

    Cool story. I think the lessons at the end are all very good too.
    I’ve recently been thinking a lot about lesson #4. I have a pretty good idea of what I will do after “retiring.” I’m an engineer and a builder, so give me a workshop and I will tinker forever. However, I feel like most people have no idea what they would do with themselves if they retired at 30, and that might be a big reason more people don’t strive to do so. If they had something they were looking forward to doing, they would probably put a lot more effort into saving now.

  18. Band of Savers December 22, 2016 at 10:37 AM

    I love hearing stories and advice like this. One of my favorite quotes says, “A wise man learns from his mistakes, a Super wise man learns from the mistakes of others.” For this reason I love hearing the advice of someone that has gone before me like this. It’s so helpful to gain the perspective and what to expect as we proceed down this perilous trek we call life.

    Thank you for helping to make us a little more super wise.

  19. Mrs. Picky Pincher December 22, 2016 at 11:20 AM

    Woah, this is such a neat perspective! Thanks for sharing! I think it’s extremely important to have conversations with people who are older than us.

    My dad asked a retiring coworker what he would do differently in his life. He said, “Well, first of all, I’d take better care of my teeth. Once they’re gone, they’re gone. And second, I’d go to Hawaii when I was young. Now I’m old and I don’t look good in a swimsuit.”

    Ahh, words of wisdom. But I did take the teeth thing to heart; I take damn good care of my chompers!

    It’s good to have an outside perspective from someone who’s already been through the ups and downs of life.

    1. J. Money December 26, 2016 at 7:16 AM

      Hahahhaha… I like the swimsuit one.

  20. Todd December 22, 2016 at 11:55 AM

    And THIS post is WHY we ought to spend a bit more time listening to those who came before us!

    Thank you, Larry for pointing our the “Wins & Losses” you’ve experienced, and the true benefit of having experience (mentor-figure) not just youth and Google-Fu.

  21. Erith December 22, 2016 at 11:56 AM

    I’m 61, and 5 years retired

    Mrs Picky Pincher, I can concur with the comment ‘look after your teeth! I didn’t, as my dentist will agree (while charging me quite a lot of money)

    My hindsight lessons.
    1) save more, sooner. I left it all a bit late. Yes, I did all right in the end, but a bit more focus earlier would have improved my position considerably.
    2) Don’t put all your eggs in one basket. I had the vast majority of my savings in Bank shares in 2008. They finished up at 5% of their value a few years before.
    3) take care of your health, you will enjoy retirement so much more, if you have the health to make the most of it
    4) I concur with Larry – take time to do things on the journey

    And my lesson from my 94 year old mother who died 2 years ago, was
    – Look after your own life, be it money, health etc. Educate yourself on how to do it. Don’t rely on someone else’s judgement. Take control of your own decisions.

    1. Todd December 24, 2016 at 12:30 PM

      Thank you, Erith, for your wisdom.

  22. Avery Breyer December 22, 2016 at 1:31 PM

    A lot of good tips in there! And I like that you mentioned the living in Mexico thing – there are soooo many people who have pensions, retirement income, location independent work etc. who could have a higher standard of living from whatever money they have if they lived somewhere with a lower cost of living (and therefore didn’t need to work as hard or as many hours as they would have back home, or if retirement income their money would stretch a lot further). And as much as “living in a developing country” sounds intimidating, in my experience of traveling full-time with my family through many of them over the past 2.5 years, they have far more advanced infrastructure than many people imagine and one can have a very nice life there on what would be considered a very modest income by U.S. standards.

    1. J. Money December 30, 2016 at 11:10 AM

      Fascinating!!! The only reason I wouldn’t move overseas, at least right now, is just to be closer to family as my kids grow up… I can see it happening later though once they’re all moved out and WE’RE the older ones left in our family, haha….

  23. fbgcai December 22, 2016 at 1:49 PM

    Great story! Thanks Larry for sharing and a happy long retirement.

    I’m a bit mystified by the “plantrolling” concept – google finds only this post :)

    Could someone expand on how it works? or is it as simple as taking the BIG long(er) term goal and dividing in smaller (more easily achieved) near term goals? Positive reinforcement? easier tracking?


    1. Larry December 23, 2016 at 9:59 AM

      plantrolling is basically a goal with a time line e.g. if I want to save $1000 in a year, I need $500 at the six month point. This allows you to see where you are and enables mid-course correction.And yes, smaller incremental goals, $83/mo is not as intimidating as $1000. And yes, there is positive reinforcement and easier tracking. It was used in the Manhattan Project for development of the atomic bomb in the 1940s so the concept has been around for a while – almost as long as me………………

  24. Ty December 22, 2016 at 2:22 PM

    Hey Larry, if you’re reading this, I really enjoyed your story. Thanks for taking the time to share it with us.

    1. Larry December 22, 2016 at 4:01 PM

      Ty, you are most welcome – thanks for commenting.

  25. Syed December 22, 2016 at 3:10 PM

    Ton of great lessons here. My main takeaway from this case study is that life has lots of ups and downs but if you keep a steady savings habit, you’ll be fine. Going gung ho and paying off your mortgage in a year just so you can say you did is nice, but it is not sustainable and your quality of life will suffer. Make the best decisions for your finances over the long term and stick to it.

  26. Laura December 22, 2016 at 5:22 PM

    I would reverse mortgage the house. Use the proceeds to pay off the car, travel and enjoy life. No payments required, so Poof! No mortgage payments and no car payments. Heirs have one year after the death of the owners to sell, refinance, or pay off the balance. If they fail to do so, the property goes back to the bank. Since leaving an inheritance is not a concern, no sense building equity. Take those funds now, when they can do the most good.

    1. Larry December 22, 2016 at 6:04 PM

      thanks, Laura – will check out the reverse mortgage scenario in the AM!

  27. Nigel Burke December 22, 2016 at 7:48 PM

    Interesting to compare the author’s ‘pretty meager’ income to average US family income of $51,759 and median net worth of $81,000

    1. Larry December 23, 2016 at 10:10 AM

      Nigel, IMO, comparing the results of someone with 6 years of college and 40 years of working to the average US family income is comparing apples to cumquats – just sayin!

    2. Elle December 24, 2016 at 2:13 AM

      He lost me there too. Even if not “average” based on schooling and years of experience, it’s far higher than me and many others I know see each month. I can’t relate to feeling that over $5k a month is meager.

  28. Vanessa @ Achieving Freedom December 23, 2016 at 3:04 AM

    A great read at this point in my life, you never know where life will take you and making sure you are able to do what you want in the future is just as important as being happy with where you’re at now.

  29. Roadrunner December 23, 2016 at 7:40 AM

    The article is choppy? Come on, this is one of the most interesting and useful stuff I read this year! It’s so extremely good to read stuff from someone with a real life experience. Thank you so much for sharing it!
    Happy holidays everyone!

    1. J. Money December 30, 2016 at 11:11 AM

      Haha… means I did my job right then :) I mushed together a handful of emails and thoughts from our main man here.

  30. Joe December 23, 2016 at 11:21 AM

    Oh man, that’s rough with the investments. When you’re older, it’s more about capital preservation. I don’t want to lose the retirement fund I’ve worked my whole life for.
    We don’t plan to leave a legacy either. We’ll just help the kid with his education and he can find his own way. If there is any money left, then good. If not, it won’t be a big deal either.
    Thanks for sharing. You never know how life is going turn out.

    1. Joe March 15, 2019 at 9:50 AM

      Still an amazing read. I wonder how the author is doing now.
      How about a follow-up?

      1. J. Money March 18, 2019 at 3:19 PM

        I got an update I’ll be adding to this shortly :)

        UPDATE: Now added to the end of the post!

  31. Dividend Diplomats December 23, 2016 at 2:36 PM

    My takeaways are pretty in line with yours J Money. This was an amazing read by the way. To me, this screams “nothing is permanent” and things can change. Be ready to adapt when life hands you a different circumstances and enjoy the ride along the way. Each person is different, each life situation is different. Sure, my wife and I don’t have kids now and I can guarantee you our life priorities are going to change as soon as our first child is born. Embrace the change and figure out how to make it work once life hands you a new set up lemons.

    He makes a great point, we are young. Time is on our side. If he can survive buying a condo in 2007 and still live the retirement life he wants, then we will be able to survive the next recession. Maybe I need to just suck it up and stop complaining when my car needs to be repaired and I have to spend a little money on repairs or we decide to go out to dinner. Stop sweating the small things.

    Much like the email you received, I am starting to ramble and am just throwing thoughts left and right here. Take care and happy holidays.


    1. J. Money December 30, 2016 at 11:13 AM

      “Maybe I need to just suck it up and stop complaining when my car needs to be repaired and I have to spend a little money on repairs or we decide to go out to dinner. Stop sweating the small things.”

      As much as I agree that we ALL should be better about this, human nature is human nature and we’ll continue to bitch and moan for eternity ;) But hopefully we do *less of it* and we also keep it to ourselves vs adding more nonsense to the world – hah.

  32. Latoya | Femme Frugality December 23, 2016 at 4:59 PM

    This was very interesting to read, indeed. I think it’s interesting that he mentions living outside of the country ,especially the given costs for the same quality of living. It’s definitely something to ponder…

  33. Larry December 24, 2016 at 10:50 AM

    Thanks everyone – really appreciate the positive feedback. Hope some of the thoughts are useful.

    Have a very Merry Christmas and a Happy (and prosperous) New Year!

  34. Jakub @ Hanke.io December 25, 2016 at 5:17 AM

    I love the part – think about your future but live…

    I worked like crazy for two years to save up bit of money for my business. There was not much living in these two years. I still remember sometimes thinking “Hope I don’t get hit by bus before having time to enjoy life”

    Luckily no bus did the job and now I’m having pretty good time the past few years.

    1. J. Money December 30, 2016 at 11:14 AM

      Glad to hear that! :)

      If it weren’t for having kids I’d still be working 80 hour weeks and pretty proud of myself for it too. Took me a few years to realize there’s more to life than hustling.

  35. Kelly December 25, 2016 at 5:11 PM

    Great story, Larry! Your story is very informative with regard to handling finances. That’s really a great income each month. I think one thing you should be doing is to ponder on things you want to do and enjoy life.

  36. Michele Cooper December 26, 2016 at 8:08 AM

    Thanks for the great story you shared Larry..!!
    I agree with you on #3 to find a job that you really like doing. It’s very important to follow your heart and start something which you truly enjoy. You also need to figure out how to profit from your passion.

  37. Mr. Tako @ Mr. Tako Escapes December 27, 2016 at 3:25 AM

    Great story! Love this post!

    Thanks Larry and J$!

  38. Rena December 27, 2016 at 8:40 AM

    What is plantrolling…I have never heard of this before and can,t find anything on the web.

    1. J. Money December 30, 2016 at 11:15 AM

      Larry answered it above: “plantrolling is basically a goal with a time line e.g. if I want to save $1000 in a year, I need $500 at the six month point. This allows you to see where you are and enables mid-course correction.”

  39. Pete December 27, 2016 at 10:52 AM

    Great story and insight, and a little sad really. Maybe it’s the mustachian in me screaming but mother of God do they waste money. Also if you’re spending $1,000 on mortgage and HOA, what the hell is your HOA paying for? And J money is right, how do you even spend $300+ on TV/phone/internet? You can only watch 1 channel at a time, and most of them are awful. Honestly cut that crap out and enjoy what’s left of your life and travel. You’d have double the budget and enjoy your life 10x more.

    1. J. Money December 28, 2016 at 6:30 AM

      I agree the costs are a bit much (though some of it actually makes more sense now that he’s told me a little more about it on the side), but how do you know he doesn’t get joy out of watching TV? I feel like us cable cutters are always so black and white with it but if it’s something that makes others happy I don’t see a problem with it.

  40. ZJ Thorne January 1, 2017 at 5:45 PM

    I do love the idea of breaking down your yearly costs into monthly or weekly costs so they are more manageable and not as overwhelming.

  41. Pj January 20, 2017 at 10:36 PM

    This was so great. The bit about moving to Mexico sounds pretty good in light of the current political climate. ;)

  42. Laura October 31, 2017 at 8:35 AM

    K. So I’m the only one who read plantrolling as plant rolling and wondered exactly what kind of plant he was rolling? Lol

    1. J. Money November 1, 2017 at 1:32 PM

      Don’t worry, I think we all were wondering for a bit ;)

    2. Larry March 15, 2019 at 10:36 AM

      hmmm, plant rolling? Been there, done that. I think the plants were from Maui and/or Mexico way back when!! But quit a long time ago.

  43. 3P March 15, 2019 at 5:28 AM

    That’s a hell of ride Larry! But great advice and a fun read. I really liked his take on the future dollar. Save as much as you can now to get that Economic Freedom!

    1. J. Money March 15, 2019 at 7:06 AM

      You know it!

  44. Christine March 15, 2019 at 8:56 AM

    Thanks for reposting! I don’t think I saw this the first time and I love hearing advice from someone who has been there, done that!

    1. J. Money March 15, 2019 at 3:13 PM

      Glad you enjoyed!! And people would be glad to hear that Larry is doing just fine these three years later too! ;)

  45. Chris @ Mindful Explorer March 15, 2019 at 11:49 AM

    I bought an electric car and yes have a mortgage payment since reaching financial independence leaving work to only take odd side hustles now. Anyhow, thanks so much to Larry for writing to you and sharing his experiences. I really enjoyed how you presented it and was a great read to see how he has lived his life and to hear his thoughts.

    1. J. Money March 15, 2019 at 3:14 PM

      Thanks, Chris :) Always nice seeing your thoughts here!

  46. Paul March 15, 2019 at 9:06 PM

    Just read the article and I loved it. I gain much wisdom from people who have lived a full life and gained it. I hope you have more in the future. Since I read most of the FIRE blogs, I feel many of the people have great insights and plans but also that many of them have never had their theories put through a real life test…Yet. It’s good to hear the insights of one who has lived through real life tests. Thank you for sharing.

    1. J. Money March 18, 2019 at 3:14 PM

      That’s a great point, actually! Most people we do hear about here have even recently pulled the plug or are currently working on it.. Not too many have ha decades under their wing yet.

  47. Lbell March 15, 2019 at 11:11 PM

    I think he should take some additional distributions and pay off that mortgage and the car. Simplify life and get rid of assets that are not performing. I don’t know the amount of his mortgage debt but seems 600k will still be plenty to have security and more fun/travel time. Yes

  48. Dr. Cory S. Fawcett March 16, 2019 at 12:13 PM

    What a great read. That was one of my favorite stories in the last year. I wouldn’t have thought it possible to lose 99% on a real estate investment. Thanks for publishing it. I’m putting it on Fawcett’s Favorites next Monday.

    Dr. Cory S. Fawcett
    Prescription for Financial Success

    1. J. Money March 18, 2019 at 3:15 PM

      Saw it linked – thanks man! Appreciate you passing it along!

  49. Petra March 16, 2019 at 5:44 PM

    Larry, you are one lucky guy, please be aware of that.

    * You two have $660k in retirement accounts. With a withdrawal rate of 4% (very reasonable given your ages) that turns into an annual income of $26,400.
    * You two have social security income to the tune of $26,866 per year.
    * You also have an annuity for another $5,000/year.

    Total income $57k/year pretax. I can tell you that that is more than 60% of the households in the US earn. So you’re on the rich side, Larry. Good for you, but please be aware that you’re one of the lucky ones here.

  50. Smallbudgetretirement March 16, 2019 at 7:53 PM

    This was super interesting. Larry thank you for sharing your words of wisdom and everybody else for enriching the conversation.
    As I was reading I thought of many impulses I have had of moving precisely to California. I’m glad I didn’t do it. I was able to find happiness in the Midwest despite the weather.
    I also feel like I have been blessed with a great partner. I’m not exempt from what hasn’t happened yet but I can’t imagine a more devastating event financially than divorcing. Of course things sometimes don’t work and nobody marries thinking that it will be for some time; maybe celebrities.
    I always wonder though and I’m not judging; i have been in that situatin with relationships… when you’re not quite happy but you think that what you have is just like everybody has. A relationship that kind of works but when it doesn’t it is living hell and with the stressors of life it gets even worse. I have met people who have married 4 times and still it doesn’t work.
    I would love to hear Larry’s insight about love and relationships. Obviously he found the ONE soulmate and is happy. What may have made the difference?
    All this also made me think, is a prenuptial agreement recommended to avoid the pitfalls of love in the given case you have some wealth before getting married?

    1. Larry March 18, 2019 at 3:08 PM

      OK, I certainly don’t think I am qualified to give advice to the lovelorn but here are some comments.
      The first marriage lasted 12 years. It was to a high school sweetheart. We shortly learned what you call a couple that uses rhythm for birth control = parents! And then again and then again. She worked full time and came home to be a mother. There was no “wife” in sight. And no female companionship to speak of. I should never have had children; parenting was not in my DNA.
      The second was a lark and a “okay, why not?” in Mexico where I did not think it would be legal in the US. Lasted less than a year.
      And having revised my goals and values, I knew pretty much what I was looking for. I had a “list” of required attributes in my next romantic quest. And 45 years ago this week, she did NOT comply with anything on my list!!
      I can only offer a suggestion somewhat analogous to my house hunting suggestions. Know what is most important to you and conversely, those things that are not too important. Keep in mind that people do change but NOT VERY MUCH. Be sure that the “package” is what you want because core values do not change, IMO.

  51. omsivatri March 19, 2019 at 4:37 PM

    Thanks for sharing! YES, I would love to hear more personal money stories!
    I’m going to hold on to this gem -> WE ARE ALWAYS IN CHARGE!! It’s up to US to do the things we feel is best for us no matter what’s going on around us or what others are saying… It’s not always easy, but it’s incredibly important unless you like living with regrets.

  52. Stevo April 1, 2019 at 9:00 AM

    Thanks so much Larry for sharing your life story! (and the update!). Decades of knowledge summarized for us “younger” folks in invaluable.

    And Thanks J$ for posting it. Hope you keep reposting it every few years so new generations can keep learning! I think this in itself is a great mini-legacy whether Larry wants to leave one behind or not!

    1. J. Money April 1, 2019 at 9:45 AM

      Haha… That’s not a bad idea actually :)