Sadly Giving Up On Retirement And Going Back To Work

After doing a deep dive on the different ways to pay for college and how to get good financial aid, I realized the best thing for my family is for me to go back to work. Coming up with $1,500,000 for two kids' college experience in 12-15 years is daunting.

Going back to work feels like giving up since I helped kickstart the FIRE movement in 2009. But the reality is, times are always changing.

Sitting idly on my hands, hoping my investments will miraculously cover such an expensive nut in the future feels uncomfortable. I want to take action while I still can!

When I retired in 2012, my wife and I had planned to live a simple life on Oahu with less than $100,000 a year. We would help take care of my grandfather's fruit farm, sell some mangos and papayas to the local supermarkets, and feed ourselves with what was left over.

After trying for so long, we thought kids would not be in our destiny. But our son was finally born in 2017 and then our daughter in 2019. Suddenly, our whole world had changed and so had our expenses.

Going Back To Work Isn't A Total Failure

In 2017, I made a promise that I would be a stay-at-home-dad for five years. After five years, my son would be able to go to kindergarten full-time.

I fulfilled my promise plus an additional year because of our daughter. I wanted to give her the same amount of time as I had given my son.

But after being a stay-at-home dad to my daughter for three-and-a-half years, I decided I couldn't stay any longer. Daddy had to go back to work because of the 2022 bear market.

A ~20% decline in the S&P 500 hit our net worth by ~7% in 2022. Both my kids' 529 plans also got hit almost equally as bad because bonds performed terribly in 2022 as well. The funds are in index target date funds.

Real estate has been a relative bright spot with all our rental properties fully occupied for years. My investments in private real estate across the heartland have also performed well during the pandemic, especially in 2021.

However, the Fed needs to pivot by the end of the year to prevent a 10%+ nationwide decline in real estate prices. And I'm not sure the Fed really cares given it hiked rates by another 0.25% after the bank runs.

Going back to work will replenish the bank account and provide a buffer for a potential decline in passive income. If a recession returns, then everything from dividend payout ratios to occupancy rates will be at risk.

Going Back To Work Is A Compromise

I do feel guilty about not spending as much time with my daughter as I did with my son. However, she still received a lot of love for the three years before she started preschool.

We started her off going two days a week at the beginning of 2023. Come summer, she will be attending three days a week. And if she really loves school, we'll bump attendance to five days a week at year-end. Learning how to socialize with other little ones and learning Mandarin is good for her.

With my wife always at home, I am clearly my daughter's second love. I've experienced many hurtful rejections that have made me question the point of being a stay-at-home father for so long.

Going back to work protects my heart, while also optimizing my purpose. I've spoken to many dads on paternity leave who can't help but feel restless after the third month. If they were the breadwinners before, they felt an immense draw to go back to work to earn.

Having two stay-at-home parents is great for the first year of a child's life. There's so much that needs to be done to take proper care of a baby. The second year of life is pretty wonderful given most toddlers will begin walking and playing by then.

However, after the second year, I think it's more efficient for one parent to go back to work. It's better for financial security, peace of mind, and work/life balance.

House Is Getting Small Again

No matter how much you love someone, it can sometimes be hard to be around them 24/7. You might scare the bejeezus out of them when you silently get something in the kitchen. Or maybe you might get annoyed by the mess they leave behind in the living room.

Whatever the case may be, having some separation is healthy for any relationship. There's a reason why best friends sometimes no longer are best friends after a long roadtrip.

I've done my best to get out of the house every day by playing sports. However, my body can no longer play for longer than two hours before my back, heels, hips and right shoulder start hurting! As a result, my outings don't last as long as they have in the past. Further, I usually rest the entire next day, which means staying at home.

My wife enjoys being at home more than I do. She definitely doesn't want to go back to work either. As a result, it is up to me to adapt. I don't mind because I enjoy meeting new people. Luckily, life is more or less back to normal.

Not Buying A Mansion For Relief

Buying a larger house in 2020 gave us three years of extra comfort so far. However, as our kids grow bigger and accumulate more stuff, our house seems to grow smaller.

I strongly considered buying an even larger house. However, my wife doesn't want to move. Further, I'm hesitant to concentrate even more of our wealth on San Francisco real estate. Our total annual property tax bill is already too high for comfort.

Instead, I want to continue diversifying more into heartland real estate. Working from home and the spreading out of America to lower-cost areas are here to stay. Check out Fundrise if you're interested in investing in this long-term trend as well.

Going back to work now that both our children are in school gives us space.

Work Seems Easier Today

Early retirement is becoming obsolete thanks to the pandemic. The amount of flexibility people have at work today is incredible compared to the past.

If I had the freedom some workers have today, I would have worked for at least five more years. Back then, I had to sneak away to take a 15-minute nap in my car! Today, you can play pickleball for 1.5 hours during the weekday and then take a half-an-hour nap after if you want.

As an efficient person, I'm sure I can get eight hours of work done in four hours or less. So long as I'm not encumbered with meetings, I have no doubt work will be more manageable.

I'm also pleased that companies seem to be less focused on face time and more focused on production. So long as you get your work done, that's mostly what matters.

Hard To Pay The Bills As A Writer

They say “follow your passion and the money will come.” Good luck with that occupation strategy! Instead, it's better to do something that pays and then pursue your passion on the side.

Despite writing Buy This, Not That, a WSJ bestseller, I still have not earned enough from the book to support my family. To do so, I need to be raising my national profile regularly. But I'm disinterested in the spotlight.

Despite having a 60,000-subscriber newsletter, I feel bad moving to a subscription model where I could probably make at least $200,000 a year. The goal of my newsletter is to help anyone and everyone interested in building more wealth while also staying on top of the most important financial topics.

Given the difficulty of being a professional writer, the logical solution is for me to get a day job again. I'll still write, just not as often. Or maybe I’ll leverage AI to write my content for me.

For all you creatives out there, don’t lose hope! I had a really good run for 11 years, but all good things must come to an end. It’s still better to try than never try at all.

More Active Income And Good Benefits

The ideal income composition doesn't consist of 100% passive income. Instead, it's better to have at least 10% of your total income coming from active day job income. This way, you feel like you're doing something productive in society.

One of the biggest negatives of early retirement is feeling lost. Without a day job bringing you purpose, it's easy to fall into despair as you question what is the point of life. The longer you work, the more you will have your identity wrapped up in work.

Giving Up On Retirement And Going Back To Work
Working hard in Istanbul

Having a day job, no matter how mundane, helps provide structure and purpose in our lives. With school teachers now taking care of educating our children, a large part of my purpose as a stay-at-home dad is gone.

I'll certainly continue to provide supplemental education after school and during the weekends. Being the family driver will always be my duty. But I'm now left with a void that needs to be filled.

It'll be nice to earn a steady paycheck and receive subsidized healthcare benefits again. I'm also looking forward to getting a 401(k) match or profit sharing once more.

Even though I’m going back to work, at least I won't have any regrets trying to make it as a professional writer. I don't have regrets leaving banking before making Managing Director because I at least tried for one year.

Trapped By The School Schedule

So long as your children are attending grade school in person, parents are trapped by the school schedule. Therefore, parents might as well make some money as we wait for spring, summer, and winter breaks.

Homeschooling is in the cards given that's what we did from March 2020 to August 2021. Kids learn so much quicker than regular schooling. However, given our children are still young, they won't appreciate their travels just yet.

Going back to work helps kill time as we wait for our children to grow older. When they're both at least eight, we can then slow travel the world.

Having a goal of saving up for years of world travel makes going back to work more meaningful.

My New Job Thanks To A Return To Normalcy

So what will I be doing?

Well, I love basketball so I've decided to apply for a job as the video coordinator for the Golden State Warriors. Although the job only pays $40,000 a year, I get to be around the coaching staff and the players. Fingers crossed!

I feel like I've got good analytical insights to share with the team. Matchups intrigue me and so does the ability to build winning teams. Besides, the NBA needs more Asian diversity!

When I coached high school tennis, we won back-to-back Northern California Sectional championships partially due to lineup strategies. Before then, the school had never won an NCS championship.

There you have it. Starting this October 2023, I hope to be busy working through April or May 2024. The season will be hectic and I may have to do some traveling.

But it'll be fun! Barista FIRE for the win. And at least I'll still get five or six months off a year, depending if we get to the playoffs.

In A Different Life, Perhaps

OK, I was joking about landing a job with the Warriors. I’m still waiting to hear back from them. But everything I've written in this post is true.

I need to find a way to get out of the house more often. For six years, so much of my life has evolved around raising young kids. Once both kids are both in school full-time, I need a new purpose to help fill the void.

Last year, I was invited to a players and coaches event with the Warriors and it was exhilarating. It felt wonderful to be a part of a team, especially one that has won for so long. I miss the camaraderie.

In the meantime, I've got some other ideas on how to fill the void:

  • Host a book signing event for up to 100 attendees in San Francisco at the Sports Basement at Stonestown Mall. Anybody want to come?
  • Become a pickleball product ambassador or affiliate partner. I met a guy who is one for a pickleball energy drink. Maybe I can use my platform to meet new people, attend events, and play in tournaments.
  • Join an author group and write my next personal finance book.
  • Become a school teacher in Hawaii where I’d like my kids to go. One of the benefits will be a discounted tuition and easier entrance. I’ll also get to see them more often during the day.

So Old And Tired To Work As Hard As Before

Despite some serious upcoming expenses in the future, it's difficult for me to get a regular day job again. I'm too old and too unmotivated to grind as I once did. There needs to be a job that provides better balance and more fun. I'll figure the money out as I always have.

In addition, I realized if I send my kids to community college, I won't have to come up with $1.5 million to pay for two private college tuitions in the future. Hence, there pressure to make a lot of money at work won't be as high.

If you are under 45, please don't waste your energy! It will eventually fade. When it does, you had better have a pile of money saved or invested. Otherwise, you may feel trapped in an increasing state of misery.

I hope this post has provided some insights into some of the complexities of life. The more you have (time, children, money, etc), the more decisions you will need to make.

Don't think that just because you reached your target net worth, got that promotion, or finally gave birth to a girl after two boys, you'll be forever happy. You'll be elated for a bit, and then it's back to your steady state of being.

Life takes work! Maybe that's the job we should really be focusing on all along.

Reader Questions And Suggestions

Readers, what are some fun jobs you'd love to take if you had the opportunity? How has your life changed after retirement?

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If you're looking to generate more passive income, take a look at Fundrise, my favorite private real estate platform. Fundrise began in 2012 and now manages over $3.5 billion in assets. The firm predominantly invests in Sunbelt residential properties, where valuations are lower and yields are higher.

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160 thoughts on “Sadly Giving Up On Retirement And Going Back To Work”

  1. I wish you nothing but the best in this decision and this new chapter, Sam. I hope you are able to reach a point where you can let go and take comfort in knowing everything will work out as it’s meant to, rather than trying to account for every worst case financial scenario. You are a good man. You have set your family and your kids up for a very successful start to their own journeys. Having read your blog for as long as I can remember, I’ve watched you grow in innumerable ways.

    Obviously we each have our own individual journey and perspective. And you are absolutely entitled to yours and at the end of the day, you must make the decisions you feel are best for yourself.

    My only offering here is to make sure you‘re also letting your family, your kids, and even yourself learn that there are times when “enough” is enough. There will always be a perceived need for more and more money. There will always be another worst case scenario that is worse than the last one. Millions of children never even live to see college age.

    I’m not saying going back to work is the wrong decision for you. Only you can know that. Just be careful of what you may be inadvertently conveying to your children along the way.

    1. I appreciate it Mike! Hopefully, my kids will appreciate the 4-5 years I spent staying at home with them before going off to Pre-K 4 and kindergarten.

      What was it like with your kids? Did you also retire early as well and spend the first 4-5 years of their lives as a stay-at-home dad? It’s always good to meet other stay-at-home dads and hear from their perspectives. Hopefully, the worst case scenario you mention didn’t happen.

  2. Yes, homeschool your children. You can meet the state requirements the way you think best. You know them better than any teacher will and can adjust to their learning style. You are in charge of their socialization. My wife homeschooled our three — two are college professors and one is an attorney and all are debt free except for their houses. She/we have no regrets and neither do they.

  3. Why not write articles for fortune as your next gig? You can publish articles without talking to the subject or even reading through their full post. Seems like you’ve gotten a ton of attention, so can’t wait to hear what’s in store for next year

    1. It’s a possibility, but another solitary job. I’d rather be in the mix and interacting with people in real life.

      I’d rather get a job that is totally different from my writing in the comfort of my own home. Getting out of the house is the goal.

  4. Paul Taylor

    “Coming up with $1,500,000 for two kids’ college experience in 12-15 years is daunting.”

    One thing I’ll never understand is the feeling that you need to pay for you kids’ college in the US; why would anyone put this kind of pressure on themselves is truly mind boggling.

    I grew up in a lower middle-class family in the UK and moved to the US in 98. I immediately saw that college was expensive and inferior in quality of education. So, I moved back to the UK alone, separated from my family and took out student loans to pay for my entire college degree and living expenses. During college I worked a part time job to help with expenses, lived frugally and made sacrifices when I graduated to pay down my loans quickly and move on with my life.

    As other comments have highlighted in this thread, paying for your kids’ college does not help them, they become entitled, don’t learn the value of money and screw around instead of focusing. This sounds more like an issue with your need for purpose and “feeling useful” than anything else.

    To be honest I’m a bit confused with your overall messaging on this blog and through the book. One minute you’re preaching financial freedom and the next going back to a job just to pay for lifestyle inflation/college tuition :/

    1. Do you think the low cost of college in the UK when you went compared to the high cost of college today and 15 years in the future has something to do with the differing views? It’s a 35-40-year spread.

      I hope my kids will be smart enough to get scholarships and work minimum wage jobs like I did. If they do, I’ll have $750,000 leftover for each 15 years from now to spend at will. But if they are not smart or financially savvy enough, there is a backup. I’m not going to work a miserable job. I plan to do something fun and new.

      What did you do after college and how are you doing in your career and financially now? Getting this back on would be helpful. Also, how do you plan to pay for college for your children? Thx

  5. William Mapouka

    Hubby and I are both tenured professors, which is theoretically one of the most secure professional situations one can have. However in reality nothing is 100% secure, because right-wing politicians are doing their best to dismantle public universities. So our goal is to secure our “financial freedom” so that we can continue working without spending even one millisecond worrying about what nefarious plan our Republican state legislature is going to cook up next. For us our target number is US$2 million, which we are hoping to reach by Jan 1, 2026.

    We make around $250K a year and save 60% of it. Once we have that $2M in secure, guaranteed investments (I’m loving the current high interest environment for that reason!) we can rest easy knowing we will likely be OK. The plan is for hubby to retire in 2028 at age 60 (since his role is way more physically demanding than mine), following which he can be on my insurance plan until he reaches Medicare eligibility.

    I want to work till I turn 62 in 2035, when he will be 69. We then want to move to a small historic town Portugal (hubby is an EU citizen so we can move there legally) where the cost of living is 1/7th that of the US. We both plan to claim SS at 62, so we can get back some of the money the government took from us while there are still some pennies in the SS pot.

    1. Hope you’re able to move to Portugal even sooner than 2035, William! We’ll be glad to be rid of you here in the US!

    2. Charles Dart

      “However in reality nothing is 100% secure, because right-wing politicians are doing their best to dismantle public universities.”


      “We both plan to claim SS at 62, so we can get back some of the money the government took from us while there are still some pennies in the SS pot.”

      Lol funny. You like it when the government taxes other people to fund your nice secure public uni jobs. You don’t like it when the government taxes you for your own retirement.

  6. Why not just sell your blog and/or move to a cheaper location? As a father of 4 teenagers, life will only get busier.

    1. Hard to sell your baby. I’d like to use this site as a way to teach my kids about writing, speaking, storytelling, interacting, marketing, and business. Practical knowledge on how to make money in the real world is valuable.

      We may relocate to Honolulu, which is about 20% cheaper due to lower cost of housing.

  7. I am a long time follower of your blog and on my own journey – half way to FIRE!

    I don’t fully understand the reasoning to return to work. My understanding is that you forecast passive income already of $380k for 2023. Why give up all that time and go back to work for $40k per year.

    Surely you can find a way to boost your passive income by $40k per year? Is relocating also not a better option – I know you have been considering this long term anyhow.

    1. Nice to hear from you Michael. Money is only one component of going back to work, but a big one, especially if I can get subsidized, Healthcare and Retirement matching.

      After three years of the pandemic, and six years of being a stay at home dad, I long for the purpose, excitement, and camaraderie of work.

      And if I can work in a new industry that I love, such as the NBA, I think it would provide, for a lot of fulfilling challenges and new experiences.

      What would your dream job be if a big focus wasn’t on the money?

      Another thing to understand is that the more you have, the more you lose during a bear market. And with interest rates coming down, passive income could come down as well.

      1. Thanks so much for replying Sam. Actually been thinking a lot about this since I read it – you have had me thinking!

        I actually thought since posting my comment that perhaps this was a late April Fool’s article, I just wasn’t certain.

        If work is what you crave, then go and do it for sure. I have been working hard over the last 18 months growing our FIRE nest-egg, but after buying two investment properties in 2022, we have now made the decision for me to start working towards semi-retirement – working part time on work I enjoy.

        You have mentioned in the past that Barista FIRE is likely the best version – and certainly anything around the “Semi FI” movement seems to be a great balance. Your story certainly highlights this.

        I personally think you will struggle returning to work. Being told what to do is never fun! I struggle with this myself on a daily basis. Could remaining self-employed be better than taking a job? Could you get the camaraderie from volunteering your time? I have done some neat stuff with volunteering, such as setting up sports club, coaching kids in sport, setting up native tree planting organisations etc. These tasks give fulfillment without being stuck to the 9-5.

        I think there are other ways for you to save for your kids education without needing to return to work. Even living in Europe / other parts of the US for a year where you would likely need way less than $100k to live for the year would do it – while your passive income can be invested in the background. Keep in mind, your numbers are HUGE living in San Fran – even in an expensive city like Dublin, you would find your expenses be reducing dramatically. We spent around $50k USD last year living in Ireland as a family of 5.

        I also challenge the notion of $1.5 million for your kids education. They may decide not to go to college. The rest of the world is able to educate themselves for far less than this amount and no doubt other families in the US are able to get college degrees for a lot less. Is you going back to work for the next decade or so to help pay for this the best thing? Your kids are still young, mine are a bit older, but I have realised that that time from 3pm – 6pm is the most important every day after school. Try be there for that time, as its the most stressful part of the day, but also the best opportunity to spend time with your kids. The time goes fast!

        1. That’s the great thing in life. It’s full of mysteries!

          I’m not sure folks are doing the math regarding college expenses in the future. It sounds nuts, but that’s what they will likely be in 15 years or so for all four years. If my kids go the cheaper route, then we’ll have money left over to start life.

          Finding that fulfilling job will be the challenge. But challenges are what make life fun! If 3pm – 6pm is all one needs to spend time with their kids, that’s pretty easy to do. I’ve been spending 8 am – 8 pm with them, with breaks in-between, for the past six years.

  8. Hi Sam,

    It gets worse once you are past 55. The kids are grown and no one wants to hire you for anything. All the while your peers who remained employed are still enjoying the accolades and accomplishments of a career. FIRE gets old.

  9. I estimate that I started reading the financial samurai blog about 7 years ago and although don’t read it constantly, do enoy keeping up with you from time to time. Imagine my surprise when I read (in Yahoo finance of all places) that you were going back to work. I’m sure some people will offer some advice like a cheaper college, lower cost area, etc. but I think it’s good that you found something that you want to do and will earn a little bit of money. One thing that I don’t understand is $40K in exchange for your time and energy (~$32K after tax)? Don’t sell yourself short Sam.

  10. Do you really think energy levels drop off that much at 45? Could it be that you have young children that consume a lot of energy?

      1. 46 year old checking in here Sam. Energy does seem to start dropping a bit in the 40’s. I’ve always felt like the 30’s surprised me as still feeling young and 40’s surprised me starting to feel old. Best is advice is the standard eat healthy, get good sleep and work out.

  11. Sam,

    With respect my brother if you are going back to work it is simply and only because you want to.

  12. Kevin Kanter

    Very interesting post emphasizing that you need to keep your mind engaged . That said. It seems that 10-11 years each of two careers is your standard for depth of interest in a career. The video gig seems more like a vanity project.
    Having read your blog & some contributions to others I really think this title of going back to work for the money is disingenuous. Given your holdings I think maybe you are missing your true net worth — you can easily afford education for your children. The main driver him your blog has always been continued hyperaccumulation, so that should be acknowledged.

      1. Michael Merrill

        Why wouldn’t you consider that? Why is an expensive college the way to go and is that what you want to teach your kids? I don’t say that with judgement, but because it is something we are reflecting on. I went to Jr. College and then a Cal State college (aka, lower price). I had to fund my own college as my parents weren’t in the picture and then still went on to have an envious career. Right now I’m in my own “mini-retirement” at 43 and charting my next chapter.

        Education is changing and by the time they even get to college YouTube and other forms of self-education, on top of AI tools may change the paradigm of college anyhow. The ROI on college is often questionable and most skills are actually picked up on the job. There are some exceptions, like if they want to get into to medical, but why not remake education as part of the Fire movement?

        I recently read a story about a dad who goes on a 3 week trip with his kid when they turn 16 to teach them about the world, and then when they return they start a business for two years and then sell it and go on a mission. Then they return with all of those skills and confidence. I love that. That’s an amazing eduction! Something their dad can do as an owner of multiple businesses.

        Heck, if you are going to work and earn 1.5 million…imagine instead setting your kids up with real estate, house hacks and other ways that have them earning 100k a year from that money by the time they are 25!

        First time write but it struck a cord to think that someone doing as well as you and who has been about financial freedom might be modeling a different approach vs. what I think might actually better set you, your kids and followers up for success!

        Of course, nobody really knows. Good luck!

        1. Definitely an option, as I went to public school and public college and felt the experience was great.

          I’m just planning for a worst-case cost scenario. If my kids decide to go with a cheaper route, then there will be money left over for the next generation, or help them launch.

          To me, the $1.5 million is an exciting challenge to amass over the next 15 years.

          I love the idea of the kids starting their own businesses.

          Related posts:

          1. Both of us went to community college and earn 6 figures before we both retired in our 60’s. All our children went to community college and transferred to state universities total college costs for 5 children $180,000 no grants no scholarships nothing. They paid their own way. They all earn over 6 figures and one son and his wife earn 7 figures. Relocate and live responsibly instead of high rolling nonsense. Texas and Oklahoma have low property taxes. We only pay $1500 a year in Oklahoma in our retirement home. In Texas we paid $6500 on a home we didn’t need after the kids had their own families. So what if your kids have Debt it will motivate them to work smarter not harder. 2 of the 5 children had their debt paid off in 2 years $46,000. The other 3 took 4 years. It takes not buying the newest cell phone or taking naps. They didn’t buy new cars until they could pay in cash. I realize your post was for April Fools but mine is not.

            1. Wonderful! I will strive to send my kids to community college as well then. Let’s see what they say when the time comes.

              And when they graduate, they will have ~$1.5 million each to launch their lives given I still plan to save and invest for their future.

              Sounds like most kids who graduate from community college make six figures from your example, so you may be onto something. It’s worth spreading the message!


  13. The great thing about FIRE really is the ability to do cool work you enjoy with money not as the primary purpose.

    So much of what you have written is true, regarding camaraderie, having a purpose, and filling the void once your kids are in school.

    I did a lot of part-time work with the parks and recreation department once my kids went back to school. Keeping busy and involved in society provides life more meaning.

    Hope you get the Warriors job!

  14. Great points about increasing cash flow to invest in a down market and getting out of the house. Re college costs, several years ago I did unretire to return to a high paying soul crushing career to fund high-cost, top tier college experiences for my two kids. They both could have gone to state college on a full ride , but they wanted to follow their dreams in creative arts and Daddy couldn’t say no. Now, three and five years after graduating they are no closer to achieving their dreams because they lack the internal drive to succeed. I learned a couple very expensive lesson, which is that your kids will manipulate and disappoint you like everyone else when it comes to money. And your children will be who they are regardless of what you have taught them and given them. (Big believer in nature over nurture here.) If I had to do it over again, I would have paid for them to dig deep with a career counselor to pick a career that suits their strengths and then only paid for them to go to a state school to major in that discipline. They would be better off right now in jobs they enjoy a bit working towards FIRE, rather than working service jobs while pursuing their dreams. I hope you end up with better results than I did with my “investments” in my kids.

    1. Mark! Thank you for sharing your situation. I have to give you huge props for returning to that soul sucking job to pay for your children’s college education because you LOVE them! And as a good father, you did what you could to help them.

      Imagine a scenario where you didn’t go back to work, and they ended up going to colleges they didn’t want to go to. Maybe they would have dropped out. Maybe they would have ended up working the same service jobs as well. Then you might have always wondered, what if you had return to work, and they went to those nicer colleges. But now, you will not regret having tried.

      Fight on! I admire what you have done.

    2. Mark – I feel great empathy with you. I hope your experience helps others faced with a similar dilemma of deciding what level of a child’s “dream” to fund when you feel that their motivation may be an issue. Try not to regret your decision – it is done and you cannot fix it now. You did what you felt you had to do and you can be proud of the sacrifice you made.

    3. Mark

      Thank you for the sincerity of your post!

      I do not have children but most of my colleagues have had your unfortunate experience versus the experiences Champ has had.

      It seems to me that children who are encouraged to succeed with minimal help from their parents are the ones who develop the skills, discipline and self motivation required to excel in life.

      I grew up in an environment where 90% of the 16-17 year old boys had their own cars to drive to school while I was required to say out loud “Free Lunch” to the cafeteria cashier in order to eat.

      I remember that most of the kids were talking about getting paid up to $50.00 for an A on their quarterly report cards.

      A’s came easy for me except in the classes where I didn’t like my teachers, So naively I suggested to my mother that she should also pay me for getting A’s like the other kids!

      Her Response:

      Get an F! It’s your future not mine!

      Because of the bureaucracies of subsidized housing programs I had to move out on my own as a 17 year old senior in high school, work 40 hours a week and pay rent to a friends mother for a place on the floor next to his bed to sleep in order to graduate and enter the Marine Corps.

      Education itself is actually just a joke!

      Every level of education has its own set of requirements and standard textbooks! So no school is any better than another, it is upon the individual to read and decipher the information and develop a solid understanding of it and then establish the ability to apply it in a practical manner.

      I finally got my online Bachelor’s degree from ERAU in my early 40’s and had already attained my current 6 figure salaried job before attaining that.

      I am certain I am the unexpected Millionaire by all of the postings I have read over the years!

      Slow and steady with integrity will get you there eventually!

      My mothers only guidance was to not lie, cheat or steal!

      Sadly a man with Integrity who speaks with brutal honesty with a storied past of personal sacrifice for justice is not easily liked so I have but a few friends and rarely communicate with them or my immediate family.

      So you might want to teach your children how to lie cheat and steal so they can get high paying jobs through Nepotism and Cronyism.


      1. Chris,

        Thank you for your service. I am a history teacher and one of my major themes I teach is gratitude for those who protect our freedoms.

        I do take issue with your view on education. A democracy depends on public education and an educated citizenship. It is second only too fair and safe elections.

        You have a limited view of education. There are all kinds of essential trade schools, licensing degrees, literacy programs, and scientific research which will save this country. (Not to mention history majors who fiercely believe that to forget injustice means to be doomed to repeat it.)

  15. I’m sorry to hear you find it necessary to go back to work. It doesn’t sound like you’re making a pity party out of it. Maybe more of a strategic move.

    I’m kind of moving in the opposite direction. Between my state pension, rental income from mortgage free properties, and the job I’ve taken in retirement, I got absolutely murdered by income tax for 2022. In three years I can begin taking social security if it’s still there. Then I’ll have to retire. I own the house I live in outright as well. The expenses just aren’t there.

    Could things change for me? Absolutely. Before the eviction moratorium, I felt untouchable. Now I know 100% safety this side of heaven just isn’t possible

    1. Congrats! Enjoy the remaining 3 years from 59-62. Life goes quick, doesn’t it?

      Make sure you come up with a game plan on what to do once work doesn’t fill your day. You may feel this hole of emptiness if you don’t have a regular activity to do from M-F.

      Best of luck!

  16. Hi Sam,

    I’ve been a long-time reader of FS and wanted to thank you for your years of thoughtful posts and have definitely helped me inform my own personal approach to personal finance. It’s bittersweet to hear that you are returning to work after so many years, but I’m really happy for you.

    With the recent sticker shock of Ivy college cost of attendance skyrocketing to $90K per year, I recently performed a 10-year ROI analysis based on the income after taxes and student loan payments between attending an Ivy vs. state school as an in-state resident. For families making $91K in household income (the US median for a family of 4), the ROI is ~8X largely attributed to the generous financial aid package to reduce the cost of attendance by 84%! However, for families making $189K (the median Ivy league student demographic), the ROI is only ~1.8X as there is significantly less financial aid offered and it actually pays more to go to an in-state school unless your child can graduate and make an extremely high six digit starting salary. I can’t imagine in 15 years when the cost of attendance is $750K per child!

    If you or your readers are interested in my analysis, please feel free to check it out here:

    Please keep posting as FS has had a tremendous impact on my financial journey.



    1. Thanks Harvey. Yes, it is a little bit bitter sweet, but life is a journey! And I look forward to seeing what else is in store, even if I can’t get a job with the Warriors

      I’ll check out your analysis! Earning less than $100,000 per kid is definitely a sweet spot for getting the financial aid for college.

  17. Hi Sam

    Best move we ever made was giving our kids who were two years apart $7,500 each and telling them before high school:

    You can go to any college/university you want but how much debt you accumulate will be on you;

    You must apply for scholarships and work the whole time through and in the summers.

    Both kids graduated debt free and never gave me grief about seeming cheap.

    Meanwhile, many of their “friends” flunked out as they had no skin in the game and the parents were footing the bill.

    Both are doing very well in their professions and are 24 and 26 here in Phoenix.

    Just sayin’!

    God Bless and thanks,


    1. charles vaughn jr

      Good job.It does not require $750k to send kids to college. Not to a public u. Like Sam attended and he did quite well. There is nothing wrong with going to an inexpensive community college for the first year to complete the basics. Very inexpensive, the best kept secret in America.

      1. There is nothing wrong with going to public college, indeed! This has been my message forever. Of course, I’m biased. But I just don’t want people to send the kids to college they cannot afford. There’s a reason why we have this big student loan problem.

  18. Greg Gibson

    Ha! That’s awesome!! Well played, Sam…

    I was going to suggest becoming a pilot. We’re hiring an extra and if you can do all you’ve done, you can easily handle this! Pull back, the houses get smaller… push forward, the houses get bigger! Buy the first round at the bar that night and you’re the hero! Doesn’t get any simpler than that…

    Enjoy the kids while they’re small… first wedding for mine next week! THAT will really make you reassess your finances when you’re writing checks for 200 of your “closest” friends and relatives… (“You know, Sweetheart, if you invest that… awww, never mind… open bar sounds like a GREAT idea…”)


  19. You are not retired Sam – you are self employed and an investor. You are employed and working. Whether you can make more in traditional corporate finance is the question. Who cares anyway; what’s more money for really when you have enough… It might be fun to go back for a year or two for kicks though. BTW I find no one has energy anymore; not even the young – everyone is burnt out!

  20. Wow – you really got me! I’d love to attend your book signing at Stonestown and bring my two kiddos (3 and almost 5) to meet you. My eldest can read and tells me that he wants to read Financial Samurai’s book (because he sees me reading it) for nighttime routine. :)

    1. Great to hear about your son! It’s so true our children observe everything we do. So, good job setting a good example.

      When it comes to reading, I always think about this image that shows the frustrated parent with a kid always on a phone or a tablet, while the parent themselves are on their phone. And then next to the picture is a parent, reading, a book, and the kid is also reading a book.

      What I found really interesting is that once I wrote Buy This, Not That, my appreciation for books, skyrocketed! Because it took me two years of writing, and editing and marketing, and all that stuff, I really appreciate all the effort authors and editors put in to making a book.

      And now that I’ve read so many books over the past several years, I feel reading Books is like a “secret” weapon for knowledge, wisdom, and success!

      If I ever do a meet up, I’ll let newsletter subscribers now. Thanks!

  21. When I read the part about you accepting a job at the Warriors, I had a hunch that it was an April fools type of joke.

    If I could take on any job and not worry about money, I would be a tea sommelier or open a boba shop.

    Would love to attend your book singing at Stonestown sports basement if you have one!

    1. Maybe just first try working at a boba shop part-time first. Could be fun for a week or a month. But not sure for how much longer after!

      I still have hope for landing the job! Résumé is in the system.

      Keep the dream alive!

  22. Ms. Conviviality

    I can’t believe I was fooled AGAIN!!! this year!

    I occasionally have the lovely thought of working for a prominent florist in a major city, where they get all the extravagant event bookings by the super rich. How fun it would be to put together magnificent flower arrangements.

  23. Hey Sam, interesting to see the latest turn in your life journey. I look forward to see more of your writing, and would appreciate getting the same kind of insight into the workplace that you’ve given about retirement planning.

    I was wondering about your thoughts on the Fundrise IPO, and what you think is the best thing to do with that. I’ve invested in it based on your strong recommendation, but not really sure what the IPO would mean for small investors like myself.

    Best wishes to you and your family!

    1. Thanks. in general, I am not for Angel Investing, or investing in private companies because we have no edge. If you want to invest in private companies, I would invest in a fund that invests in private companies. The general partners are much more plugged in and they often get some of the first looks at some of the best companies.

      Fundrise, founded in 2012, is a great company with a CEO who focuses on the long term. I’ve talked to Ben Miller many times before and I really like his management style and his more cautious outlook instead of the “growth at any price” type of hype outlook.

      If you invest in a private company, don’t expect to get any liquidity for 5 to 10 years.

      Here are some relevant articles to read:

  24. I recently experienced rejection from my daughter as well. Initially I was thrown off by this but upon further research discovered that it is a simple developmental milestone. It’s a small measure of autonomy that they can claim. It also demonstrates that she knows she is loved by yourself and doesn’t need to actively seek it.

  25. Is this the first April Fools joke you’ve pulled off, or is the a compilation book in the works?

    You had me for a minute, and I was so disappointed…

  26. Haha this one had me going for a minute. Really appreciated the April Fools Day switch. With that said, you bring up great points regarding active income v. passive, a changing market, and how to view your priorities as your life and finances change. If you were to tell me you went back to work, I would completely understand. We all have to be adaptable. However, I think I have read enough of your work at this point to know you are more creative than that! I have no doubts you wont find a new opportunity that occupies your time and challenges you mentally while still affording you the lifestyle you currently have at home. As I continue to write and practice medicine full time, I often catch myself day-dreaming about a time where passive income from The Motivated M.D. supports me so I work part-time, or not at all. However, as my father continues to struggle with Alzheimer’s dementia in his retirement, I see that balancing the avoidance of idle hands with time can be a tricky one. Anyways… I digress…

    I look forward to you writing about your new endeavors. Cheers my friend!

    The Motivated M.D.

    1. Thanks. Keep daydreaming, as the dreams may eventually come true! That would be a great balance, to practice medicine on the side while your site continues to generate a healthy amount of income.

      I would like that side job actually. When I did consulting for several start ups in 2013 to 2015 it was good to be part of something growing. Camaraderie is great!

  27. Good Morning Sam,

    My 3 yo daughter recently attended a Daddy Daughter Dance where they gave a book out to all the Dads, Strong Fathers Strong Daughters by Meg Meeker.
    The book is phenomenal, I intend to gift a copy whenever the opportunity presents itself. I got a lot of value out of it, as a Father of a little girl yourself I think you would appreciate it as well. Maybe it will inspire a future post.

  28. Sympathies-having kids will do that to you!
    Perhaps because I was a large animal veterinarian where reproduction is the primus inter pares ie generate as many offspring as possible we had our 3 kids starting at 25 and finished at 29
    I remember my wife being called an elderly prima gravida with her first child at 25!
    How times have changed
    It was the right move -if you want kids-but circumstances alter cases
    It works out but it’s just harder

    1. I would have liked to have had children three years sooner. You folks are blessed to have the courage to have them so young! From 25-29, we were still struggling to save and invest enough to feel like we were going the right direction. Then at 31, the financial crisis occurred, knocking my net worth back 35% in six months.

      But as older parents, I’ve found there are a lot of benefits too. We just need to live long enough!

  29. I can’t believe I read till the end you got us for sure!
    I’m really looking forward to fake retiring in order to work in some form of conservation work. My childhood dream was marine mammal research. I also love bees and in Malaysia the authorities in urban areas still set fire to hives if anyone complains about it. So maybe a mix of education and research.

    1. Save the bees! Go for it sooner, rather than later. You’ll never feel like there’s the right time to take a leap of faith.

      Might be kinda like getting married or having children.

  30. Happy to host a meet in the sunset at Footprint, corner of 27th and Taraval. Can’t fit 100 but can fit 30-40 people. I host a young men’s financial workshop and they would love to gather n chat.

  31. Congrats on landing such a cool gig with GSW. Do you mind writing about how you got to land that job? I’m planning to retire early and would love to find a gig in sports after grinding the career ladder in technology.

    1. I thought you were talking about Goldman Sachs initially. I got a post for that!

      Just gotta apply. Once you’re on their radar, you can be flexible.

      The reality is, I have a connection at GSW b/c he’s been reading FS for the past five years. Over this time period, we’ve built a relationship.

      So creating stuff, helping others, and being out there is helpful.

  32. Not to get into your business but how is $3000+ per month extra minus taxes owed on that going to effect your lifestyle when you passive income is already 25 k per month. As far as needing 1.5 million for college seems excessive. You can move out of San Francisco to a much cheaper state, send your kids to a state college and live like a king. Aren’t all the people with bucks leaving California. I wish you well as always.

    1. Hi Steven, what’s the $3,000+/month coming from?

      College is excessive. Best to have low expectations by expecting the worst, than expect the best and not have money.

      Lots of irrational high schoolers insist on going to an expensive private university over a better-ranked public university. What are your kids doing?

  33. I agree with the post that in order to maximize happiness and minimize regret retire at ~age 40. However, I decided to stay until age 50 (even though I’ve been in a soul crushing finance job), so that I don’t need to do a low paying “Act 2” for a long time. Since Covid I’ve been working from home 3-5 days a week. It’s a game changer and has extended my working. I’ll be 55 next year and will be retiring feeling very financially secure.
    Ps. No need to spend $$$$ to get a great college education.

    1. That’s great WFH has helped you extend your work. Although, I don’t like to hear how you find your job to still be soul crushing. Financial security is a big win. Just be careful not to neglect the soul inspiring work as well.

  34. Pickleball really seems to be taking off; so much more accessible than tennis and very conducive to inviting friends out with varying levels of athleticism.

    Developers are building up a recreational area near me with pickleball courts, outdoor patio and bar, overlooking the lake and just half a mile from the trail system. I think if you really lean into the pickleball thing, you may find opportunities far and wide, even in the midwest.

    1. I think you’re right. It just takes a while to get to know people well. I’ve gotten to know plenty of people, but the whole process takes time.

      I’ve actually leaned back toward tennis b/c of the friendships. I’ve come to realize the camaraderie is now 65% – 70% of the reason why I plan as my body ages.

      I hope you try the game!

  35. LOL aw I was actually really excited for you getting that job with the Warriors! You totally could, maybe part-time? I agree it’s great that people have flexibility but personally, I hate WFH as a rule (only in favor of it one day/week at the moment) because it seems people have gotten so lazy and entitled. I also think it’s lonely and isolating. We have deadlines and training isn’t really getting done at my job. Also, people who only come in once a year for an hour max are *still* complaining about the commute! They should get fully remote jobs instead of complaining non-stop about a commute they don’t even take. Some people are never happy.

    Anyways, I also agree it’s healthy for people to have a purpose and make friends outside of their relationship, etc. I am very grateful to work at the company I do to be honest. Good luck to you Sam! You will have fun with the Warriors if that’s what you end up doing.

  36. The only person Sam is fooling is himself! If he thinks 45 is low energy, wait until he’s 75.
    Here’s a better written article using GPT4.0 in the voice and style of a true financial samurai!

    Title: Unmasking Early Retirement: A Financial Samurai’s Take on the Hidden Drawbacks

    As devoted readers of Financial Samurai, we’ve navigated the treacherous waters of personal finance together, always striving for a brighter and more secure future. Early retirement might seem like the ultimate prize for our efforts, but it’s essential to unsheathe our swords and cut through the illusion before making a hasty decision. Although the prospect of limitless free time is alluring, the reality of early retirement often fails to meet our lofty expectations. Bidding farewell to a steady income can lead to financial instability and require us to scale back the lifestyle we’ve worked so hard to achieve.

    Remember, my fellow finance warriors, there is honor in staying the course and embracing our careers. Persisting in the workforce brings a sense of purpose, cultivates our professional identities, and offers continuous opportunities for learning and growth. For many of us, the thrill of overcoming professional challenges and celebrating our victories brings unparalleled satisfaction. It’s important to recognize the camaraderie we’ve built with our colleagues as well, for they’ve been our allies in the quest for financial success. Prematurely retiring from the battlefield may leave us feeling isolated and disconnected from these valuable relationships.

    By postponing retirement, we not only preserve our social bonds but also strengthen our financial fortifications. This delay allows us to enjoy a more comfortable and worry-free retirement when the moment is right. As steadfast followers of the Financial Samurai way, we must carefully assess the advantages and disadvantages of early retirement, ensuring that we remain on the path to true financial independence. Ultimately, it is often through continued engagement in the workforce that we can secure the most fulfilling and prosperous future.

    1. Incredible AI post! Insightful, personal, and full of wisdom. More reason to go back to work.

      How do you keep up your energy at 75 to do the same things as you did when you were 45 or younger?

      1. By what stat are you saying 335k for 4 years? Is that for a specific college e.g. U Penn plus living expenses all in? That number is certainly not the average you’ll find for current costs using any Google search results. Your tuition inflation rate might be on, but you are painting a doom scenario that might not be realistic for the mean costs.

          1. Greg Gibson

            Very accurate numbers…. I have kids at both those schools (funny those are the ones you chose!). Hurts to see numbers like that in writing… much easier to just complain about the tuition bills every semester! (“That doesn’t seem right… can that be right? That’s robbery! I see what they do there!!”)


            1. That is funny! I guess I know my audience well. So far, do you think it’s been worth it for your children to attend the schools? Do you feel less anxiety now that they are in college? Or do you still worry about what they will do after college? I am trying to understand when parents will mentally let go. Thx!

  37. 1,500,000 for college? Perhaps you are projecting forward 15 years? Even then, that seems rich. My wife and I are about to start paying that bill; we’re anticipating 200k for 4 years for one child. Public school, mind you, but a very solid one. I suppose if you’re planning on sending your kids to the Ivy League without any scholarship support, it could be possible to spend that much on them.

    1. I am projecting for the cost in 12-15 years. $335,000 for four years of college today. 5% compound growth rate for 12 years = $700,000. For 15 years = $800,000. Got two kids.

      Fingers crossed they get grants or go to a great public school like Cal or William & Mary.

  38. Regarding “House Is Getting Small Again”.
    There is a saying for this: “How can I miss you if you won’t go away?”

  39. Hmm: how much can one possibly consume on this earth..,. Oh forgot @ it’s for the family”. I’m single and happy and retired

  40. Vdeo coordinator for one of the best teams in sports history? You had me all the way with this one. How do I keep falling for your April Fool’s jokes?

    Anywho. Yeah, if you retire for more than a few years, you’ll never want to go back. My dream retirement job is being an online professor (been doing this for several years now), and I’m getting to the point where I don’t even want to do that anymore. LOL!

  41. Already have post retirement planned. Trouble with retiring is I love what I do (airline pilot), and am being forced due mandatory age limit. So, going to scratch the itch in the summer with some Alaska flying, maybe a small corporate fill in flying, etc. Continue my tennis journey, work on my guitar chops, through a dart at Europe and spend the month of September there.

      1. A beautiful sabbatical while launching your entrepreneurial gig?

        You’re doing great and I enjoy reading your posts. However, you are definitely not FIRE or retired.

  42. Hi Sam, this is unrelated but I noticed a discrepancy in your asset allocation recommendations and was wondering if you could clear it up. We are just turning 40 and it seems like it’s time to add some bonds. I’m one your FSAA charts you list starting to have 10% bonds at age 40, but an older one says 20% bonds at age 35. Why the change? Also, could you share shat bonds to add? Thanks!

  43. Paula A Borman

    I didn’t figure it out until you said work provides needed structure.

    People who work hard enough to achieve FIRE are never those strange people who can’t entertain themselves without a day job!

    1. Well… not all of us can figure out how to entertain ourselves without a job.

      When you’re Locked down with kids in school, there’s not a lot of adventure you can take in under 8 hours. Someone has to pick them up!

  44. Dunning freaking kruger

    And oh ya – I sniffed out the Tom foolery of April fools with your title. Did not buy it for a second. The GS Warrior job was icing on the cake.

  45. Dunning freaking kruger

    Readers, what are some fun jobs you’d love to take if you had the opportunity? How has your life changed after retirement?

    After reading this site for years as well as finance and personal finance books, decided to study for the series 65. It had been a goal after I retired to help educate people looking for help. I Passed first time out. Accepted a formal part time job offer with bonus, RSU etc.

    The best part, I’m still working full time at my primary job. I set my own hours on my days off including nights and weekends. I can work from home. That’s flexibility. Part time monies are assigned to pay off mortgage and dump into 529s.

    Once I retire the plan is to segue into advisory job full time. Cash flow kids undergrad without touching 529s. 529s will be rolled into their custodial ROTH IRAs and/ or used for graduate school or our (hopeful) grandkids.

    While not retirement it is a second career undertaken for a purpose. Not sure if I will ever retire if I enjoy what I’m doing.

    A lot of the inspiration for this undertaking has been this site. Thank you.

      1. Dunning freaking kruger

        I bought it a week after it came out. Consumed it in two days. I’ve loaned it out. Quite a few people have been introduced to FS because of moi. I regularly email and text your articles.

        It’s cool to get free advice from an MBA with 13 years of investment banking experience.

        Do you think you mom or dad would ever do a guest article about raising a hellion?

        Be water my friend!

        1. You rock!

          I’ve asked my dad, who edits 70% of my posts, to do a guest post in the past. He’s always said no. But, I’ll ask him again! Maybe even get him on a podcast! Yes, that would be a good idea.

  46. Because you didn’t send this on the first, i read this thinking it was real and it was one of the more depressing things i’ve read in a while. if you can’t do it then how can the rest of us!?!?

    1. Agreed. I read 3/4th of the article during my lunch break. Made me depressed and sad for Sam. I had to stop reading. Thought about it all day long until I decided to finish the tough read after putting the kids to bed this evening. Almost bought a second copy of Buy This, Not That just to help him out. I wasted a lot of emotional energy on his April fool’s joke, hahaha. I total deserved it for getting duped. Good one Sam!

  47. I read this today (4/3) so my April Fools day radar was dormant. I was thinking though: what a fun job to have despite the pay…

  48. As I started to read I thought “well, this is sure off-brand for Sam”. Then I got to the Warriors and the yuuuuuge $40k salary and I thought, we’ll that’s not really going back to work, that’s just a way to get out of the house.

    I’ve often thought about “retiring” to be a $30k/year park ranger and I thought this was where you were headed. I was glad you were not pinched by a measly 7% drop in net worth.

    Nice one Sam.

  49. “If you are under 45, please don’t waste your energy! It will eventually fade. When it does, you had better have a pile of money saved or invested. Otherwise, you may feel trapped in an increasing state of misery.”

    This is me. Over 45, not enough saved/invested to stop working, and losing interest & energy every day. The only thing that keeps me going is my 3-year old and wanting to provide her a great future.

    1. No greater POWER SOURCE to work hard than a small child. We’ll all jump through a burning building to save and provide for our children.

      Congrats on your little one, fellow older dad!

  50. I’ll miss your posts! I share many of your views on finance and life, and very much enjoy reading your newsletter — your wisdom, insights and knowledge on finance are very educational.

    I left my day job in 2020. After spending the past three years in an international move and settling down in a new country, I feel a bit lost now and am contemplating to look for a job. I agree with you that a day job gives one purpose and structure no matter how mundane it is. I hope you’ll find your dream job soon and thank you for spending the time in writing these fun to read posts.

    1. Paula A Borman

      he was doing an april fool’s joke. He’s not going back to work. He got me til the end as well.

  51. I was wondering what happened to your April 1 post. Sounds like you and Jeremy got together to collaborate on how to spin April Fools Day. ;)
    I definitely feel you on the “Too old, too tired” paragraph; and I don’t even have children. :)
    I sometimes wonder what happened to the old me and the hustle I had but then I realized, hustle can have a season. When I mentioned my upcoming retirement a few years ago (at 49) people (that didn’t know me very well) kept asking, “How will you fill your time?” but really, that’s the point, I don’t have to fill my time anymore. It’s wonderful.
    A (nationally highly rated) local radio talk show host passed away unexpectedly recently at age 61. He regularly talked about how he got to his level of success in broadcasting by “outhustling” everyone else and I believe that. But his hustle included getting only 3-6 hours of sleep a night for 20+ years as he prepared for each weekday’s show, looking for the latest breaking news on our local officials and news around the world. Now, just as his daughters were starting their adult lives, he’s gone. Get busy livin’ or get busy dyin’.

  52. Sam,

    I actually appreciate your honesty in this story. I always read financial stories and ask myself what am I doing wrong and we all know everyone has regrets with their financial moves. So along that thread, would you be willing to do a letter on your own personal 5 biggest blunders/learnings by failure in investing?

    I do hope your portfolio recovers quickly. Getting ready for my own kids departure to college and even through I prepared, I know it will be woefully under funded and with plenty of surprises.



  53. I enjoy reading your articles & seem to hang on every word. ** I also enjoyed your book!** I’m a post career naval officer, 29 years, with 2 small children 6 & 9. After 2 years of teaching H.S., I’m going full-time dad next year thanks to the nuggets of wisdom you have uncovered and share. I may not be able to give my kids everything……..but they are well on a path I could only have dreamed of. OBTW, I’m an ODU grad….William & Marry is a GREAT school!!

    1. Wonderful! Thank you for your support. You did my semi-dream job of being a HS teacher. I was a HS tennis coach for 3 years and it was a good experience.

      Go ODU and W&M! Good luck on your next chapter.

  54. I can agree to so much of what you’ve said. I stayed home with the kids on and off throughout the years. Its a delicate balance between career and family life. Kids are expensive but worth it! Parenting has a way of making us a better version of ourselves because of the discipline and patience learned in the process. Best wishes in your new endeavors, my husband and I enjoy reading your posts!

  55. Sam- I am in my late 50s and I can say, you can never know what you did not know at the time. The Last 20 years I was forecasting where I worked. The owners retired and the firm closed. A lot of excellent points in the article, but unless you are an Olympic athlete and have good genes, you will have less energy every year after age 40. Best to you and your family. I am trying my best not to go back to work, but as you said, there are more options now- work has changed.

    1. “unless you are an Olympic athlete and have good genes, you will have less energy every year after age 40.”

      I’m pretty sure Olympic athletes get tired over time as well! Have you seen some of the ex-pro athletes 10-20 years after they’ve retired. Oh gosh, time sometimes is not kind.

      Maybe the more fit you were in your 20s and 30s, it’s actually easier to let oneself go.

  56. Nice one. You got me. Still, this sentence you wrote is important, “When I retired in 2012, my wife and I had planned to live a simple life on Oahu with less than $100,000 a year.”

    The whole time I was reading I was thinking, “yeah, $100K in 2012 felt like a lot, but it’s not the same now”. The older I get, the more I feel that famous retiree complaint, “I’m on a fixed income!”

    On a totally unrelated note, after over a decade of Mandarin lessons (outside of school) for our own kid, we’re killing them next year as he moves into 10th grade. 10th-11th grade are no joke (and there, he takes French) and he needs every hour back that he can get. Ditto piano.

    1. Yeah, and not $100,000, but LESS THAN $100,000. Maybe even just $60,000. Hawaii produce is expensive. So is gas.

      Hope your kids Mandarin is pretty good after 10 years? I plan to take them to Taiwan when they are older for the hot summers.

  57. Loved your post. It’s been a rough day. Needed that laugh! Some of us could use more of your wisdom and experience with finances then just a newsletter! Would you consider being a financial advisor or something like that? You could work part time from home?

    1. Always happy to hear I made a reader laugh :) But this is a serious subject! I need out! haha.

      I’m actually advising a reader this morning. But I don’t advertise this consulting service b/c the demand is high and it takes up a lot of time. You’ll have to Google it!

  58. When’s the Stonestown signing? Also, we have an office space in FiDi if you need a private location.

  59. Great post! I was in your situation 23 years ago. I took my winnings from the first dot-com bubble and went back to school and then got a great entry level job at 41 years old. Ditch the mid level manager stiff, be a direct contributor doing something enjoyable, be a role model to your children and start enjoying your third career.

    1. Hi Doug, Can you share what entry level job / career that you pursued after your dotcom winnings? I am in a similar situation. I just turned 42 and after a 20 year career on wall street and some well timed investments, I am no longer motivated by the wall street pay check. I am looking for a less stressful and more rewarding career. I have been contemplating the value of being a role model for my children by having a higher purpose than earning a large year end bonus. Thank you in advance for your reply.

      1. Sorry to interrupt, but I reset my career at age 47 (15 years ago) by becoming a Registered Investment Advisor. I only suggest this because of your background, meaning you could likely jump right in. YOU can control your workload, income, etc. as an independent advisor AND you can make a huge difference in the lives of individuals and families. In your case (as was mine), you don’t have to take on wealthy clients to make a living. They tend to be the pain in your arse anyway LOL. Good luck!

        1. Thank you for the suggestion and taking the time to reply! Becoming an advisor has been on my short list of ideas for what’s next.

  60. Ah you got me until the very end. That video coordinator gig sure sounds like quite the dream job, although it probably does exist in reality.

    Your ending sentence really resonates with me, “Life takes work! Maybe that’s the job we should really be focusing on all along.” Too often we get so overwhelmed with focusing on our work jobs that we forget to prioritize work-life balance and “working” on our overall lives.

    Which reminds me, now that we’re in Q2 it’s a good time for all of us to go back and revisit all the goals we set at the beginning of the year. I certainly can’t remember all the goals I set. So, it’s time for me to go review my list and get back to “work” on things!

    1. You are consistently one of the most thoughtful commenters on the site – thanks Untemplater!

      Agree, a quartet has flown by and a good time for a checkpoint. One strange thing is that YTD numbers look pretty good…

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