Career Insurance: The Guaranteed Way To Prevent Unemployment

The coronavirus pandemic really got me thinking about all of our children’s’ futures. The world was suboptimal for two years. But what will their world be like in this already brutally competitive place full of constant rejection? Let me share a guaranteed way to prevent unemployment: career insurance.

In big cities, expect to spend up to $1,000,000 providing for your child through college. In 18-hour cities, expect to pay at least $250,000. Either way you cut it, raising children is expensive. Now imagine spending all that time and money and not being able to find a job, let alone a fulfilling career? Terrible!

If extremely wealthy and famous people are willing to risk their reputations and their freedom and bribe their kids' way into well-ranked private universities for better employment opportunities, what hope do the rest of us have?

We need career insurance to help our children achieve upward mobility.

Career Insurance For Our Kids

As someone who has experienced unending rejection since childhood, I fear my children may experience this same level of hardship or worse.

The optimist believes perpetual hardship will make them grow stronger. But it's also possible that frequent rejection will break them into a thousand pieces.

There are some very angry, bitter people out there who wouldn't be so terrible if they had experienced more love and support growing up. Having a meaningful career and a loving partner makes a difference.

Therefore, I ask all of you how much insurance would you pay to ensure that your kids find meaningful jobs so they don't grow up extremely angry at the world?

My answer: Everything I have short of going bankrupt. There is simply nothing I wouldn't do to help my children live a meaningful life.

Let me share a couple stories that demonstrate why too much work or not enough work created unhappiness and hate.

Career Insurance As A Protection Against Unhappiness

When I talked to my softball buddy, Biff about his upbringing he said that his parents were never home when he got back from school. As a result, he hung out with some unmotivated kids who experimented with drugs and liked to skip class as much as possible. He was hardly ever happy.

When Biff was a Junior, the girl he had a secret crush on laughed at him when he presented her with a rose on Valentine's Day. As a result, he began to resent every pretty girl in school. His self-esteem got crushed and he began to gain a lot of weight.

He also stopped studying hard, not because he was stupid, but because he began losing hope about the future. His parents were never home to talk to him. Nor did they provide him with the immediate love and support that he needed. Sometimes, his father would disappear on business for weeks.

Solution To Combat Unhappiness

Have at least one parent be a stay at home parent to always be there when their child or children come home. By having a parent to always talk to and check in with, a child should feel more loved and get into less trouble. When a parent is never home, the tendency may be for kids to stray.

The cost to the parent is his or her career and income. The alternative sacrifice is finding a more flexible jobs that allow you to work from home or have more flexible office work hours. Hopefully the coronavirus pandemic will encourage more employers to have work from home options.

Related: Solving The Happiness Conundrum In 5 Moves Or Less

Career Insurance To Prevent Hate & Bitterness

I traded e-mails one day with a reader who hailed from Georgia. She had started leaving nasty comments so I reached out to try and understand her story. Let's call her Karen.

After a couple exchanges, she admitted she grew up in a racist household where both her parents used racist terms to describe all minorities. She became accustomed to using those terms because that was the environment she grew up in.

When I asked her why she thought using racist and hateful language was OK, she attributed her language to her father losing his job at a textile mill. Her father's former co-worker told him that three months later after he was let go, that his old employer had hired a Black person to do his job.

Ever since that incident, her father has been very belligerent towards any minority group. He believes the Black guy took away his dignity and ability to provide for his family. There was no looking inward by the father on how he could have been a better employee.

Karen blamed her rejection from the University of Georgia on its perceived lowered admissions standards for minorities. As a result, she also adopted her father's bitterness towards all minorities, including myself.

Solution To Combat Bitterness And Hate

As a parent, create your own business so you won't have to depend on an employer to provide for your family. You also won't stress about your kids not getting into college or getting into an expensive university and having to pay for it. Heck, you might even prevent your kid from growing up with racist tendencies because your livelihood is more secure.

In order to create your own successful business, you need to put in extra hours developing your business while working a full-time job. This is the safest route to travel. You could also spend time learning about a business before buying one. Or you can call all-in with the help of some seed funding. But I wouldn't recommend this path.

If you are currently unemployed, take advantage of the expanded unemployment benefits and use this time wisely to start building something for yourself.

What I've also found interesting is that if you want to become nicer, get richer! Richer people tend to be more self-confident and less envious of others because they already have financial stability.

How Much Insurance Would You Buy To Help Your Kids?

My main financial goal since I left work in 2012 is wealth preservation. If I wanted to still rapidly accumulate more money, I would have simply stayed at my miserable banking job instead of negotiate a severance. Every person looking to retire early or leave their job should learn how to negotiate a severance instead of quit.

My main parental goal is to provide a better life for our children. One way to preserve wealth is to sell Financial Samurai, lock in gains, and reinvest the proceeds conservatively.

Although I don't think it's wise to sell a high margin, cash flow positive business in an extremely low-interest rate environment, selling is definitely a possibility for the right price.

However, if I sell, I lose my career insurance policy that I would sacrifice all my wealth for. Therefore, logically, the only way I would sell Financial Samurai is if I could get more than my existing net worth.

A Difficult Childhood Might Be Inevitable

Despite being an optimist, I'm also a realist. I know with at least 70% certainty that my children:

  • Will get bullied in grade school
  • Will experience racist encounters
  • Will not get into a top 25 university due to a war on merit
  • Will not land a fulfilling job that keeps them mostly engaged for years
  • Will need to commute during horrible rush hour traffic
  • Will need to put up with office politics
  • Will get backstabbed by colleagues
  • Will one day get laid off
  • Will get passed over for a raise and/or promotion
  • Will get rejected from dozens of job applications
  • Will waste a lot of time finding the right job opportunity
  • Will graduate in or near a recession
  • Will experience an existential crisis
  • Artificial intelligence will eliminate jobs in the future

I'm pretty sure many children will experience similar types of difficulties as well. By keeping Financial Samurai, I could mitigate some of these negatives.

Yes, part of growing up is getting to experience all these things above. However, I'm not sure all that time and stress is worth it. Do you?

If we have the ability to save our children time, heartache, and suffering, we probably should. But not everybody can accumulate generational wealth to minimize all of these difficulties. We’re talking having a net worth of $10+ million.

Creating A Small Business Will Help

Therefore, creating a family-owned small business that can be managed from home or anywhere there is internet access is a no-brainer. It is one of the best insurance policies against a suboptimal life for our children. And if you already have a family-owned small business, keep it going until your kids decide they don't want to have anything to do with it.

As my children grow older, I will implement all the things I wished were incorporated in work or all the positives that made work fulfilling:

  • A constant correlation with effort and reward
  • The ability to transfer to different departments once a skill is mastered or boredom sets in
  • The ability to take charge and grow a business unit
  • The ability to help people solve important problems
  • The ability to develop new positive relationships with clients
  • The ability to work from home and have better work life balance
  • The ability to make a positive difference to people

Let's just hope the stepped-up basis doesn't get abolished. Otherwise, there will be big tax consequences for parents who want to follow my career insurance path.

Do Whatever You Can For Your Kids

Yes, I know all this may sound crazy. But nobody thinks it's weird to buy life insurance to insure our lives, flood insurance to protect our homes from big storms, or auto insurance to fix our cars after an accident. So why is creating a career insurance policy any different?

Creating an environment to earn and learn is a much better path than just giving your children money. Otherwise, we may raise unmotivated, entitled brats who still depend on their parents well into adulthood.

Having insurance helps protect against terrible unforeseen events. But in this case, we know what these unforeseen events are.

It is clear life is getting more difficult because of globalization, hyper-competition, stagnant wages, outrageous healthcare and tuition costs, and a rigged system for the ultra rich. Therefore, creating a career insurance policy makes logical sense.

If my children want to go their own way, they are more than welcome. I plan to keep the insurance policy going just in case.

How much would you pay to insure your kids have meaningful careers so they can be more happy and fulfilled?

View Results

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Investing in Artificial Intelligence For My Kids

One of the worries I have is that artificial intelligence will eliminate jobs and make it difficult for my kids to find fulfilling careers. As a result, I plan to invest in private and public artificial intelligence companies. This way, in 20 years, if AI is really detrimental to the labor market, I'll have a lot more money to take care of my kids.

Check out the Innovation Fund, which invests in the following five sectors:

  • Artificial Intelligence & Machine Learning
  • Modern Data Infrastructure
  • Development Operations (DevOps)
  • Financial Technology (FinTech)
  • Real Estate & Property Technology (PropTech)

Roughly 35% of the Innovation Fund is invested in artificial intelligence, which is a big deal. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI! They are only 4 and 6 years old.

The investment minimum is also only $10. Most venture capital funds have a $250,000+ minimum. You can see what the Innovation Fund is holding before deciding to invest and how much. Traditional venture capital funds require capital commitment first and then hope the general partners will find great investments.

Investing in AI companies today is like investing in career insurance for my young kids.

Reader Questions And Recommendations

Readers, how much in career insurance are you willing to pay for your children to have a good life? What are some of the things you're doing now to insure that your children don't have an unnecessarily difficult life? If you have the ability to help your children in their careers, should you? What are some things you shouldn't help with?

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67 thoughts on “Career Insurance: The Guaranteed Way To Prevent Unemployment”

  1. Manas Jagadev

    The best that you gift to your kids is knowledge not wealth.
    The second best that you can gift your kids is health not wealth.
    The worst that you can gift your kids is wealth, and all negative elements will find attracted to the kids.
    So my way, just be role model in how you value your health and minimalistic life to keep this earth habitable
    and teach how “not to pursue to get those luxuries”, which are only negative.

  2. Creating a business for your kids to have meaningful careers is a great idea, however, it could create resentment. You mention you would let them find their own way if they weren’t interested, which is great, but how would you feel if they wanted to do something else? Would you resent the time and effort you spent on a business that they didn’t want to have anything to do with?

    What about the kids’ perspective? They may feel pressured and resentful that they are expected to take over a business they are not interested in.

    1. I would feel happy for them if they wanted to do something else. Because that would mean they don’t need the career insurance and found something even better to do, which is great.

      Career insurance is just a side benefit of running a small business. I write because I enjoy the process. Career insurance also helps keep me motivated after almost 15 years so far.

      Over the years, I’ll try to reach as much as I can to my children about business, communications, finance, branding, and marketing. That’s a great benefit itself, to teach practical knowledge.

      I’m excited whatever happens. And insurance feels comforting as a parent. In general, you don’t want to use your insurance policy.

  3. Great article Sam!

    With our children being young (5 and 3) my wife and I have been working towards building a financial portfolio that will enable our daughters to be financially independent when they reach their early 20s. That way they will have the freedom and time to pursue their business and/or academic goals without having to deal with the work culture of an organization out of fear of needing their paycheck.

  4. In some of your articles, you mention that very wealthy people can be very unhappy. Money can alleviate some immediate pressures, and it can buy a quick thrill, but it doesn’t create permanent joy or satisfaction in life. It also doesn’t buy you more life. You can argue the difference between someone living to be 76.8 or 77.3 years of age but we are not talking about a big difference here, and certainly not immortality. Money has many limits.

    I would also advance the idea that children of the wealthy who inherit wealth turn out to be spoiled or otherwise self-destructive through drug use or other activities too often for comfort. They often feel empty or bored. A question I have for you is if you sincerely want the best life for your children, do you believe that the solution lies in giving them more money?

    The human spirit is restless, and we were meant to work. We were also meant to be looking for something that is beyond the limits of this physical world. I would ask you if you have ever given consideration to spiritual matters, and how your faith, if you have this, plays a part in your relationship with money.

  5. Frugal Bazooka

    No, no insurance policies for life, career or other random variables that make up our existence. The reason we have car insurance is not because we need it all the time but because we actually statistically never need it. Theres nothing wrong with planning for life but dont turn your existence into some kind of mathematical equation that creates certainty. What a bore that would be. Live life and let it unfold in all its glory. I wouldnt trade all the crappy twists and turns of my wretched life for a guaranteed job or guaranteed anything. I worked hard and put up with a lot of bullshit like we all do…and I won. Would you deny your kids the chance to feel a level of success and self actualization that few ever get to experience? Living life without guarantees does not create hate or anger or crime, it creates better humans who learn how to solve problems and get paid lots of money for those skills.

  6. You had 18 years to develop a new human being to be an adult. You have failed your children if they are not able to develop them to be self-reliant. The biggest lessons I’ve learned was when I was out of my parent’s house. The 18 years of being sheltered under my parent’s financial protection made me clueless about the value of money. Life is about failing foward. Let them fall or they will suffer 2nd or 3rd effects from your inability to let them.

    1. If you have children, can you tell us where your children attended university and what they do for a living?

      Given you say your parents financial protection made you clueless about money, does this mean you are financially struggling or behind the average?

      I’d love to learn more about your viewpoints.


      1. My husband and I have one child, a daughter, who attended private schools from kindergarten through medical school. She attended a secular girls’ school from grades 6 through 12, U PENN for college and medical school, and completed her residency at the Hospital of the University of Pennsylvania. Her practice is focus on obesity medicine.

  7. Commenter Paper Tiger’s list of what a parent can do for their kids is pretty spot on.

    I think you may be over worrying and overestimating how much control you have.
    Starting a business just so your kids can fall back or continue the family business doesn’t make sense. Most likely they will want to do something else and you wasted years building a legacy fo nothing. Business owners often have less time for their kids. Their company is their baby.

    Also it seems that you think one parent staying home is the only way to raise confident and motivated kids. I think it is certainly easier to be involved but many kids turn out great with two working parents. Girls especially need a role model.

    I assume you would pay for your kid’s college and maybe grad school. Would this be contingent on choosing a practical major? If your child end up staying at home after a short time in the workforce, do you think that you wasted money paying for his or her education?

    1. Couple things.

      1) FS was started eight years before my eldest was born. So if referring to me, it’s more of a motivation to keep on going.

      2) Insurance is to be used just in case something bad happens. Ideally, it is never used.

      How are you planning on insuring your children don’t fall through the cracks? How old are your kids?


      1. My kids are eight. I am not rich enough to insure they don’t fall through the cracks. Upper middle class and the rich can easily outspend my family in terms of extracurricular activities, enrichment camps, etc..I can only do my best to instill values that are important to me and hope they can fend for themselves.

        We do save/ invest for retirement and own a house. Maybe we could help a little with tuition but not much. We want to be stable enough to always be a home base for them if they fall on hard times.

  8. Most of the negatives you put in that list are the unfortunate parts of life in the developed world. I have heard friends say they would never have children because of these reasons. Ultimately, life is a struggle, always has been. There is no guarantee that having a small business will give them a good work ethic and make them happy working in the family business. In a way, one can argue is that they will be depending on you their whole life if they go into it.

    I do like your list of positive things to do to keep them engaged growing up, though. Being present in their lives and having your own self-confidence is huge.

  9. My kids are 2 and 5. If I put $100k for each kids on vtsax for 30 years, then they have $1.3 mil each. Is it good insurance for them

  10. Paper Tiger

    My wife and I have one daughter who is 21 and will be a senior in college this fall. The best insurance I could give her was a solid foundation while we had her at home. I can break out into 2 categories what we did and what we intend to do:

    What We Did

    – Presented a loving, secure home setting
    – Were involved parents in her life and her activities
    – Demonstrated a strong work ethic as an example for her to follow
    – Stressed the importance of doing her best, learning from her mistakes and moving on from her failures
    – Taught her to respect others and treat people like she wanted to be treated. Be nice to everyone even if they may not deserve it. Stand up for yourself when you have to but pick and choose your battles. Always being right can become a lonely place to be
    – Surround yourself with people who are the type of people you want to become. You are who you hang around with
    – Told her that if she wanted friends she had to first be a friend
    – Encouraged her to believe that she could accomplish almost anything she put her mind to as long as she was willing to put in the effort and not give up
    – Helped her understand that you get what you give. If you give good effort you get good results and poor effort typically returns poor results
    – Frequently told her how much we loved her and how proud of her we are

    What I want to do

    – Teach her about saving and investing. Get her started on the right foot and help her to stay focused on her financial goals
    – Encourage her to go for things that she may not believe she can do. Take on stretch assignments. Never let anyone convince you that you can’t do something you really want to try. Unfortunately, a lot of people will go out of their way to hold you back
    – Have her finish school debt-free and pay for graduate school if she goes that route
    – Take our own financial planning and create a generational plan that leaves her a strong foundation as our legacy to her and her future children. Who knows what kind of world they will live in. I think my generation (baby boomer) had many advantages that her generation most likely will not. And, her generation and those that follow are going to be left with a mountain of debt to deal with that my generation continues to pile up

    These are some of the things we have tried to do to “insure” our daughter has every advantage to deal with whatever life has to offer her in the coming years.

    1. Very cool. Are you nervous that the “moment of truth” is fast approaching regarding whether she will be able to find a job she enjoys in 2021?

      I can see this time as perhaps one of the most nervous times for a parent since we will have spent 21-23 years nurturing our children to go off into the world on their own. If they end up not finding something or not getting accepted by someone or an institution, I feel I’m going to be even more hurt and disappointed inside than them!

      Maybe it’s b/c for the past 10 years, I’ve been surrounded by post college graduate men who have lived with their parents and could not launch. They work jobs that are totally unrelated to their majors and they seem sad and lost. I donno. Maybe I’m just overthinking things. But I would feel terrible if I hadn’t launched by 25-28.

      1. Paper Tiger

        Fortunately, her degree is in Nursing which should afford her many job prospects and flexibility, even under these challenging times. I helped start a small healthcare company 5 years ago that employs homecare nurses so she potentially has this as a fallback option but we certainly prefer for her to find and pursue her own path. I guess this answers the question of whether or not we would be willing to help with her career pursuits ;)

        She hopes to work 2-3 years and then go back to graduate school to become either a Nurse Practitioner or a Nurse Anesthetist. She has identified a program in our state that will allow her to earn both Masters and Doctorate degrees in 3 years. There is just enough money leftover in her 529 to cover the cost of this program such that she will be able to complete her schooling debt-free.

        Like you Sam, we will do whatever it takes to help our daughter get started with her career on the right foot. We never know what kind of world she will have to live in and just hope and pray she finds something that allows her to realize all of her God-given talent and potential in a way that encourages her and helps others.

  11. Hi! I’ve been reading a lot on your site, really appreciate your writing. I’m reading lots of books, and although it might sound funny, I think you would appreciate reading a book called “The Millionaire Next Door”. Don’t let the name mislead you, a great part of it is about how circumstances shape one’s destiny. They repeatedly point to the tendency that the less things come easy in life, the better one seem to be able to take care of oneself. From reading your articles, I get the impression this applies also to you. They also point to how things point the other way – the more one is taken care of, the less turns out to be able to take care of oneself (within certain limits of course)

  12. Shrihari Chiwarkar

    What if the small business is no longer profitable as it used to be. What if the small business fails miserably after a few years. There is no permanent thing in this world. Still can you give an example of sustainable small business which will last for say 70 years guaranteed.

    1. For sure, even life insurance companies fail. But I think it’s worth trying at least. Even if you don’t have a small business as career insurance, you can still be a good parent who makes time to spend more time with theur children.

      This is one of the takeaways from the coronavirus pandemic I hope more parents will discover.

      Do you have children?

      1. No I am working in a multinational firm from three years, not even married. Found your blogs via one of the CNBC post that you had written. They are so much relatable even in India and the experience is the same. I also want to start a small side business or have assets /net worth that make me financially independent by the way.

      2. No I have been working in a multinational firm from three years, not even married. I found your blogs via a CNBC article that you had written. The blogs are so much relatable even in India and the experience is the same as you have mentioned above. I also desire to start a small side business and invest in a manner that will make me financially independent.

      3. I gotta say the first time I read your blog it was pretty unrelatable because you had no kids. I do have children older than yours by a few years, and glad you see the light now. Given the current times, well done with your ever-changing view and siding with our greatest asset the health and wealth of our children.

  13. Long time reader but don’t comment much. Love your website and appreciate your insight. Long time resident of Georgia and I can only tell you that Georgia has changed for the better in my lifetime (I am 46), so please don’t judge us by a bad apple. The vast majority of people here are kind, in my experience, regardless of race.

  14. Ensuring your kids future sounds great but I worry that it will always come with “strings” attached and it could end up hurting your long-term relationships with them, restricting their independence, and limiting their ability to achieve great things on their own. I’ll bet that once you see your kids as teenagers, your views will change. Great post, thanks for sharing. I have two teenage daughters and believe that being a great parent is one of the most important jobs we will ever have.

    1. Can you share more why my views will change once my kids are teenagers. In what ways? I’m truly curious. I decided to coach boys HS tennis to get a glimpse of the teenager life. I know from speaking with parents, a lot of their kids didn’t want to have anything to do with them for a while.

      But the kids were as expected overall. Maybe it’s because I was a pretty uncontrollable teenager that I felt the kids were quite mild in comparison.

      1. Thanks Sam. I too was an uncontrollable teenager but turned out alright as well. As your kids get older, they start going in their own directions, making their own mistakes, and having different interests than you. At first, it was difficult but I kept reminding myself that it was the same way with my parents, and I’m sure with my grandparents as well. Freedom to make mistakes and face adversity is actually a great thing. And, when you follow your own arrow like you did, i.e. retiring early, makes the accomplishment that much more special.

  15. There are too many variables to answer this question. First, do any of your kids have special needs? How severe are those special needs? What is the employment situation when they graduate? How able are you to support your child/ren and still responsibly take care of yourself? I mean by responsibly — who will pay for your care when you are old, disabled, need assisted living, need memory care, etc. etc. I believe it is my responsibility to NOT be a financial burden to my children. That frees them to support themselves without worrying about me. If you think educating a kid is expensive — look at how much a good (and I mean good) senior community costs – independent living, assisted living, memory care, skilled nursing, and/or hospice care.
    I say; love them, teach them how to be good parents, teach them good work habits, teach them responsible money management and, if possible support their education. Then, if no special needs, push them out of the nest. Go on to fund your own life, whatever that requires, until death. If you have some money left over….that is another question. Sorry for the wordy answer. It’s a difficult subject.

    1. “I believe it is my responsibility to NOT be a financial burden to my children. That frees them to support themselves without worrying about me. ”

      I agree with this. What a blessing to have parents who are financially independent, healthy, and sane. I don’t take this for granted.

  16. Don’t have kids now but if/when I do, I would not want to support them beyond age 18.

    My parents did not support me financially beyond age 17, and I am grateful for that now. I went to mid-level HS in a developing country but managed to get full scholarships at great schools for MS (UC Berkeley) and PhD (NYU, pursuing), and also founded and sold a startup in between. I think not having the safety net of wealth from my parents has definitely made me more ambitious and self-reliant.

    The other side of the coin I have observed is that parents can also have more control over their children’s career trajectory when they support them financially beyond a point. I believe the parent’s responsibility is to inculcate good values in their kids, help them grow wings, and provide just enough wind beneath it to help them soar on their own.

    1. Great answer ! I moved out on my 19th birthday and would never be where I am with out that valuable life lesson. I do wish my parents guided me more but they frankly didn’t know any better and I was the oldest of 5 kids so all the mistakes were made on me. (Immigrant’s with 5 kids, poor, had a bad relationship so it wasn’t a great environment to grow up in)

    2. I thought the same way. Then I experienced even more hardship, met more people online who’ve been through hardship, had kids, then decided Career Insurance is a no brainer.

      Insurance is best not used, b/c then something would have gone wrong.

  17. The concept of earning and learning is great. Especially if they are learning skills that can translate into the real world such as writing, marketing, growing a team, etc. These skills are in demand no matter what field you are in, and the sooner they are learned the better.

    I worked for my dad’s company every summer from high school until I was a junior in college. I was in a factory, and didn’t learn many marketable skills outside of how to interact with people who were older than me. Much better to be in a family business setting if you are learning valuable skills IMO.

    I am newly engaged, and we are definitely talking about having kids. To answer your question, I think teaching kids skills that can help them in their career is crucial. Handing them a job/money won’t teach them anything (like you said), but giving them meaningful responsibility, helping them explore various careers/opportunities while they are in high school or college and teaching them how businesses work are all wins in my book.

    Hope your kids enjoy Financial Samurai as much as you do one day. They have a good role model.

    1. “I worked for my dad’s company every summer from high school until I was a junior in college. I was in a factory, and didn’t learn many marketable skills outside of how to interact with people who were older than me. Much better to be in a family business setting if you are learning valuable skills IMO.”

      Very cool. Yeah, I expect my kids to not really care about what I do as middle schoolers and teenagers. But with the off chance that they do, I will be excited to teach them everything about writing, communication, sales, business development, PR, optimization, finances, etc.

      It’s my insurance for them and my motivation to keep on going.

  18. Hey Sam,

    20 years ago, when our children were in grade school I bought a small little e-commerce website in a medical-related niche.

    As they children grew, each one of them took on different tasks related to running the business.

    Operations, Customer Service, Production, Finance, Inventory Management, Sales/Marketing, Vendor Management and assorted Web-related tasks.

    With them all off to college and beyond now, they still talk about the lessons that they learned and the fun that they had “running a business”.



  19. Great thought provoking post. I have always had a belief that once they are done with college the fiscal support stops. Our kids will graduate with zero debt from a undergraduate degree, and if they can get any scholarships or grants during undergrad they can use that money towards a graduate degree. After graduating from college I never asked for any financial support from my parents. My parents have given to me great job advice, and talked me several times off the ledge from quiting my job. Love and support from you and your spouse is the most valuable thing you can give your kids! Your kids will fail at something, but if they know they have love and support from you failure will make them better and stronger people.

  20. The question was: How much would you pay to insure your kids have meaningful careers so they can be more happy and fulfilled?

    I’m in the minority saying 61%- 90% of net worth. Hell yeah, isn’t ensuring that your kids have meaningful careers what it is all about? Or do you just care about yourselves? Apparently, the latter for most of you.

    That said, I’ve instilled work ethic and provided good examples of both what to do and what not to do for all three of my boys. I’ve emphasized athletics and academics, and all three are excelling in both. My goal was to keep them busy, while letting them have fun. I have rules, but they’re allowed to do what they want as long as they get the job done.

    Results have so far been three very talented athletes all getting straight A’s. My oldest didn’t get into our city’s “good” public high school (in spite of him being Salutatorian at his middle school – he got one A- all through middle school to miss out on tying for Valedictorian). So we sent him to a top notch private school where he’s rocking a 4.0 GPA late in his Junior year. Straight A’s for the others as well.My younger two are on track to get into the top public HS.

    That said, I want the best for my kiddos, and hell yeah, if I could just spend some $$$$ I’d do it. But the reality is is that you’ve got to raise them right. Spend time with them. Teach them values and priorities.

    Covid-19 note, relating to kids: I’m really bummed they’re missing out on their sports seasons. My middle kid was supposed to be on 3 baseball teams right now, playing basically every day. Instead, I pitch to him as often as possible, and he shoots free throws in the driveway. Sucks. But it will pass.

    Keep working with your kids. Be a good role model. Teach them what you know, and if you don’t know it, heck, learn it with them. Learning is a lifelong process and is the key to success.


    1. The lack of sports is a bummer. I was looking forward to helping my high schoolers defend their Northern Cal conference tennis championship! It would have been a 3-peat!

  21. Long time reader, first time commenter. Just wanted to say that I love checking in to see your creative posts. Your posts either give me something to think about or something to think deeper about. Your sincerity and strive come through (although I think you have to be a long time reader to see that better).

    I have two kids, one in MS and one in elementary. Although we do have the money to put them through college, we are raising our kids to believe both we and they are responsible for their college costs. We don’t put pressure on them, but we do talk about ways they can start saving for college, and what we are doing so that we can help them pay for college. We talk about all kinds of scholarships that are out there, the kinds of summer jobs that are available, and even ways to grow their savings through investments. But these conversations are not frequent nor intentional, but rather, they come up naturally when on topic. Since we’ve been having such conversation since they were in about 3rd grade, it’s rarely heavy and requires little effort to keep up. And that is intentional because we don’t want their thinking and spirit to be boxed in by pressure.

    I like your list for making work more fulfilling. Took a snapshot of that for reference. I am trying to accomplish something similar through our approach to their school education.

    I chose “Nothing” because that’s how my parents raised me. But I always had the comfort of knowing I would never go hungry because my parents had my back. That was enough insurance for me to go out there and carve my future.

    Thank you!

    1. Hi Lucy – Good stuff talking to them early and constantly talking to them about these issues.

      Perhaps the insurance of having stable and loving parents is all the insurance kids really need.


  22. My kids are 1, 2, and 8. My PhD is in Biomedical Engineering and now I work in the pharmaceutical / medical device R&D.

    I’m not sure if my 8 year old has the diligence/smarts I did, but we are working on it. We have put plenty into their 529s (but maybe not enough based on your comment to me on that article).

  23. Nothing because it is about learning skills to always be in demand. I too was rejected a lot. A whole lot. And I volunteered, learned communication skills, got a PhD, learned how to get things done, had some good work accomplishments that help people’s health and now have no shortage of recruiters calling me for remote opportunities. I started a new job about 7 months ago that pays more, has a boss that really believes in me, and is lower workload, more remote, that I don’t know what to do with myself.

  24. Nothing once he’s done with college. Life isn’t fair, deal with it. Most kids don’t even get support for college. Kids need to go through some adversity. If life is too easy, they won’t make it when the zombie apocalypse hits. Do you think Jared Kushner will survive the zombies? Hell no.
    I might help out occasionally, but not a huge amount.

    1. Here’s the thing though. If that’s the case, are you donating 100% of the $2,900 in stimulus checks you received from the government? You guys don’t need it, yet are getting assistance as multi-millionaires. I’m not judging. I’m just saying that in order to not help your son at all after college, you have to also be consistent with refusing help from the government as an adult with financial means.

      1. spaceassassin

        I hope they keep the stimulus payment–it clearly defines his point, “life isn’t fair.”

        Same reason we are taking the extra $600 in unemployment per week despite it providing a 400% increase in my wife’s weekly pay.

        And also like Joe, I don’t intend to offer much financial assistance beyond college. My parents financially supported everything growing up and through college, i.e. school, car, gas, food, etc., but that (almost entirely) stopped at graduation. The most important support didn’t stop, emotional and mental support, i.e. holding the net.

        The absolute best thing they did was constantly hold a large enough safety net below us. No matter what, they were both always there, through the successes and failures/troubles (and there were some serious troubles) of us 3 children, always knowing they would be there to catch us really gave us the strength to leap off the ledge. (There were severe consequences and/or praises and lessons taught after they caught us in the net, but the catching us was the important part.)

        That safety net gave me the courage to pull out of a PhD program at 24 years-old, move back to our hometown, find a new job, and do something new and completely unrelated, which has paid off considerably. The world isn’t fair and it doesn’t care if you have a net below you or not, sometimes it will push you off the cliff regardless, but if your spouse, parents, or friends can hold that safety net for you through life, I’m not sure much financial support is required beyond the basic necessities of getting kids through high school (and college, if necessary or makes sense).

        1. This is spot on. We’ll provide a good safety net for our son. He can take chances and find the life he enjoys. Of course, we’ll help out occasionally if he needs it. But don’t expect a trust fund from us. There might be some left when we’re gone, but there might not.
          As for government assistance, I’d encourage our son to take it if he can. That’s a different story. It’s like the 401k matching. If you don’t take it, someone else will get it. Oh, we’ll spend about half our stimulus check and save the other half in case our tenants need help. I’ll donate a small amount.

    2. Jared is the perfect example of his parents having Career Insurance.

      His family business helped him get into Harvard, marry into Trump family, and be a Senior adviser with zero relevant experience.

  25. Christian R Mena

    Hey Sam,
    Great post buddy. As of right now my Wife and I do not have kids. However the way myself and my wife were raised we will not be spending money on our kids after they are 18. Our mindset may change once kids come in to play. However I have been looking at a 529 plan. My wife and I both enlisted into the Marine Corps at the age of 18 and have our schooling pay for. We were thinking of potentially serving additional years so we can pass our GI Bill to our kids once they are born.

    This goes back to us thinking “what if” they get everything they want and just don’t learn to work for themselves like we did. They may simply just choose not to go to college meaning us serving 4 more years to transfer our benefits may have been for nothing. Which is why a 529 plan maybe the best option. Do you ever wonder about passing your wealth to your kids? What impact it can have on their lives?

    I do believe they would be grateful but i also believe it would create a more “entitle” generation.

    1. Hi Christian,

      A 529 plan is a no brainer IMO since parents will want to save and invest for their children’s college education anyway. Way not do so in a tax-advantageous way.

      But I promise you this: Your feelings about wanting to help your children will absolutely change once you have children. It is part of our DNA!

      I think about passing down wealth all the time, hence why this post is about earning and learning, not just giving them money.

      Related: Stealth Wealth With Children And Real Estate

  26. “Hopefully the coronavirus pandemic will encourage more employees to have work from home options.”

    As I’m finding out, it’s equally difficult to be home and have to ignore my child’s desire for attention. I’d rather work when I’m at work and be home when I’m home.

    1. I work from home. It’s about getting into a routine and being realistic. If you have a standard 40 hour W2 job, you cannot use it as a way to avoid childcare. My kids are our of the house when I am working and I have a dedicated office. When i am in there, I am at work. I still get more kid time. Spending what could be 2+ (unpaid) hours a day commuting in LA traffic is not a good use of anyone’s time.

    2. spaceassassin

      Having never worked from home before, the past 4 weeks have been a huge experiment for our office of 15 people. Some people are struggling and keep finding their way back to the office in order to be productive or to even print something. I think its really about finding a location and schedule that works in your own home and with/for the family.

      Personally, I am significantly more efficient and productive at home. I set up a desk in the garage, and my young sons (6 & 2) understand that “Dad is at work” while in the garage. The lack of interruptions I am used to in the office setting is significant and I am accomplishing a greater amount of work. Having specific projects that sometimes need 100 hours of CAD work, might take 4 weeks in the office with all the interruptions, meetings, etc. Not the case at home, 100 hours of work can be done in 2 weeks, no question. It’s significantly easier to manage “my” work time without all the office noise.

      But the best part? I take 45-minute walks with my family in the morning, I have had lunch with my older son for 30 consecutive days (the younger one naps through lunch), and every so often they pop out in the garage to say hi, bring me a snack or ask a question. I am extremely fortunate to be able not only keep working through the pandemic, but excel and likely find a new way of working into the future within our company.

      And I know there are a lot of people figuring out the same. Being in construction, I know some large developers/architects are already flipping gears about office space design/development and exploring alternative uses to projects already under development. Things are going to change in the work space–they already are on the Design/Developer side.

    3. That is true. So true.

      I try to get most of my writing done by 8 am – 8:30 am to spend time with my kids, and then after 9 pm. But it’s hard and it takes a lot of endurance and discipline.

      BUT, it gets easier with more practice. I’ve done it for 3 years now and I feel it is easier. Like a routine.

      1. Instilling good values and modeling those are important in raising kids. You want them to develop a strong work ethic, and your primary job is to get them safely to adulthood and have them then be independent and resilient enough to deal with life’s inevitable pitfalls in a positive way. Hopefully, they also learn the importance of empathy, kindness, sacrifice, contribution to the larger world, fun, love, joy—all in balance. Providing everything for them you might have wanted as a kid and making all their life choices for them won’t accomplish that. And even if “raised well,”most people will want to march to their own drum as they reach adulthood, a drum which may sound very different than you hoped. Sadly, people also do go off the rails regardless of upbringing and ruin their lives through addiction, criminal behavior, and pursuing wealth at all costs.

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