My youngest son loves a good shopping trip. Clothes. That’s his sweet spot. Shoes in a pinch. So when I’m at a loss as to how we will spend all the extra time we have in between cello lessons, I think, well, we can shop.

You might think that spending money is a messed-up way to kill time. Why don’t we go to the bookstore and cuddle in a corner and read a book, right? Well, the thing is, he doesn’t really like books. And anyway, I think it’s okay to have alternative approaches to money. My son loves clothes so it’s okay to spend mother-son time shopping together.

If you don’t like that logic, you’re not going to like any of the rest of this post. Because I’ve been looking at money in alternative ways for a long time—ever since I realized that most startup founders risk their family’s financial security to launch their company, over and over again. I realized there are no hard and fast rules for the best way to manage money.

One thing I do see clearly is that the financial advice you are used to reading is for kids who go to public school. And it’s aimed at families that can’t see past the mainstream. And the most common financial advice revolves around the geometric growth from a savings plan that starts early.

That advice works fine for the 1950s. In the 1950s you went to school and learned how to do what you’re told. Then you went to work and in exchange for doing what you’re told you had a job for life. But the old financial advice doesn’t work for a world that celebrates self-directed learners and life-long learners.

Here’s the advice homeschoolers should get:

1. Don’t save for retirement.
If you love the work you do, and you love the life you have, then you don’t need to save for some day in the future when you will get to do what you want. Retirement is an outdated idea for people who don’t understand how to find engaging work right now.

Create a life you love each day, and the next day, if you want to change it, you can. But real life is about making each day full of engagement and growth opportunities. What a sad life you would have if you woke up each day feeling that you didn’t deserve to have a good life until you stop working.

It’s a long time away, and sad to wait. But also, few people define work so narrowly as to say work is only stuff you don’t like. If you define work as the stuff that makes you feel valued in the community, then you never need to retire, you just need to adjust your work as you age.

2. Waste a lot of money in your 20s.
Taking risks in one’s 20s is a lot less riskier than taking those same risks later in life. There’s no mortgage. There are no kids on the verge of starvation. There’s just a twenty-something kid who ran out of money, which happens all the time. Go watch the first season of Girls: running out of rent money is totally standard for that demographic. (And also, seriously, Lena Dunham uses sex as a literary device better than anyone I’ve ever read—even DH Lawrence. How can you not watch that show?)

The other side of spending money willy nilly in one’s 20s is that the benefits are higher if you spend in your 20s than if you spend later in life. The faster you try things and quit them, the faster you learn about yourself.

The kids who do best in their 30s are usually lost in their 20s, because having no idea what you’re doing is a way to figure out what you’re doing. Pretending to have direction is a dead end in the realm of personal development. Being lost takes cash. Spending your last dollar to buy the right clothes for something that turns out to be wrong. Quitting a job without having another lined up. These are good decisions that blow through cash.

3. Raise money instead of earning money.
Y Combinator gives tens of thousands of dollars in startup funding to kids with no work experience. Kickstarter rewards kids who are good at making promotional videos for projects that may or may not be a good idea. Some investment sites allow people to invest in individuals instead of companies. Do you have a brain full of ideas but no track record? Sell shares of yourself to investors.

Just because you teach your kids to break financial rules, doesn’t mean you teach your kids to take crazy risks. In fact, the most successful risk takers are great at mitigating their risk. Teaching kids to take smart risks is the best thing you can do when it comes to financial literacy.

We live in a world where self-directed learning and lifelong learning is the gold standard for successful careers. Teach your kids to use financial tools to get that type of life. And, if they run into trouble, credit repair service should be part of any respectable curriculum, because people often learn the most when they’re making a lot of mistakes.


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33 replies
  1. Rachel C.
    Rachel C. says:

    #1 is terrible advice.

    Retirement savings for my generation (gen Y) and beyond isn’t about getting to do what you want when you retire, it’s about being able to survive when I’m too old or sick to work. I look at my 85 year old grandparents, who are in failing health, and who wants to work at a time like that? Even if you do get to do what you love.

  2. Rachel C.
    Rachel C. says:

    *i completely agree with not waiting until “someday” to do what you love, but still don’t think it should translate financially to not saving for retirement

  3. Gretchen
    Gretchen says:

    #1 sounds nice, however it’s not always about not WANTING to work later in life, it’s about not being ABLE to work later in life. Saving for retirement…actually just SAVING period, so one has a cushion, should something go wrong, is very important. That’s hard for many to do while also homeschooling, so, of course, the angle here is going to be to downplay that.

    What Penelope doesn’t understand is that she is extraordinary. Most people aren’t, so they need to do the boring, day-to-day grind crap and boring stuff like having savings.

    • Rachel
      Rachel says:

      And even extraordinary people age. Pitching investors when you are 60 or 70 is not as compelling as when you are younger and appear to have tons of energy to throw into your next startup.
      This is essentially planning that your kids will support you once you are no longer able to work. Don’t shoulder your kids with that burden!

  4. Jenn
    Jenn says:

    I havent read this yet but wanted to let u know that I started to have withdrawal symptoms! Pls do continue to write, you! have a powerful God given gift and “voice”

  5. Mark W.
    Mark W. says:

    What I’m not aware of or have read about is curriculum in public schools that would prepare students for an entrepreneurial career or a braided career. The offering of finance, risk management, and other types of courses that would be applicable. I can easily understand why these courses weren’t offered when I went to school many years ago. It seems to me as though schools are changing at a snails pace relative to the landscape of the reality of today’s economy. Even in large companies today, an employee is rewarded for an entrepreneurial mindset even though they are not an entrepreneur.

    • barchbo
      barchbo says:

      I taught public school for years and I am so frustrated by the lack of personal finance curriculum. Even as an English teacher, I advocate for much less Romeo and Juliet and much more personal finance, entrepreneurship, and career counseling.

      • redrock
        redrock says:

        I disagree – it is useful to learn about finance, and investing etc. but not at the cost of english literature, or science. Simply because we humans need also things which are exciting and ignite our passions not just stuff which promotes a career. Or you will end up with everything to manage your career but nothing to have a career about. Even an entrepreneur needs an idea to invest in and not just the ability to juggle the money.

        • Cay
          Cay says:

          I’m not entirely convinced re: English literature. Nice books are like tasty snacks, people tend to seek them out for themselves whether they are in school or not.

          Personal finance, however, tends to be more tedious to learn and practice for most, like eating raw vegetables. I’ve tried to help one of my friends with personal finance, she moans about being bad with money but she basically refuses to learn about it, too. It’s very worrisome.

          Almost everyone seems to be reading something, but almost no one seems to be on a stable financial track these days.

      • Jennifa
        Jennifa says:

        Probably personal finance is not taught because this is considered something parents should teach.

        Someone should make a list; this is what society thinks schools should teach/this is what parents should teach. It might make it simpler for schools, who increasingly are responible for teaching kids EVERYTHING….without stepping on the beliefs of the parents. (Fairly impossible!)

        It might also make it easier for parents of schoolers, who may not even be aware that they are still responsible for teaching their children something while they are in school.

  6. Kimberly
    Kimberly says:

    I agree with other commenters that saving for retirement is a great goal:
    #1. I want to get to a point one day where I don’t have to earn money if I don’t feel like it
    #2. I might want or need long term care better than what’s available to people with no financial resources
    #3. The best way to save a ton is to start early and take advantage of decades of compound growth.

    That said, retirement savings should not trump willingness to take risks and enjoy experiences in the moment.

    The very last sentence is what’s most disturbing to me here. Credit repair services can’t and don’t do anything that we can’t do ourselves for free. A MUCH more valuable lesson is how to maintain your own credit!!! Learn what goes into your credit file and credit score. Repairing poor credit means learning how to handle finances more responsibly, over time, and that’s a much better lesson than how to pay someone to negotiate on your behalf.

    • Jay Cross
      Jay Cross says:

      “Credit repair services can’t and don’t do anything that we can’t do ourselves for free.”

      Yes, people technically “can” do what credit repair agencies do for free…but will they?

      Apparently not, or else the credit repair services would immediately go out of business.

      My guess is the credit repair services turn all the scattered, tedious, pain-in-the-ass steps a person “could” take into a straightforward, clearly spelled out plan that’s mindless and easy to follow.

      I think people who use those services are being honest with themselves. They aren’t going to figure all that crap out on their own, and they know it. But they want the benefits, so they pay someone to make it easy for them.

  7. Jennifa
    Jennifa says:

    Often on this site I am astonished at the similarities between how very low-class people live and the recommendations of this blog. This is one of them. As I read I was nodding, yep, yep, yep, know folks who do all three of those.

    I tell you it is not pretty. Particularly when you reach your 50’s and have no money, no health insurance, and have burned every bridge you have. An amazing number of people do this, and what bails them out is called social security disability.

    So what is the differentiator here? Follow this if you have wealthy parents to fall back on? Or follow this if you have some extreme talent or skill to fall back on?

    So interesting to me.

    • Penelope Trunk
      Penelope Trunk says:

      There are plenty of people who follow all the rules of what they are supposed to do. They work their whole lives and put money away for retirement and they buy a house and pay it off.

      But then at age 50 they lose their job, stocks crash and the housing market blows up and they have no money.

      So I guess what I’m saying is that baby boomers pretty well proved to us that almost everyone does not have money for retirement, no matter how careful they were.


      • Gretchen
        Gretchen says:

        I strongly disagree. Financial literacy would teach that you don’t keep your investments in riskier places when you’re close to needing them. People close to retirement shouldn’t have had all their retirement in the stock market at that point. I was only in my late 30s at that time and it’s bounced back. As far as real estate, again, you buy less home than you can afford and you stay away from ARMs and you’re fine. You have two adults working in a home—that’s another buffer. Yes, there is bad luck, but I don’t think enough to inspire me to throw up my hands and say it’s not worth trying.

  8. Hannah
    Hannah says:

    While I reject your financial advice, I won’t discredit it.

    I would call your method of financial advice thinking like a Billionaire after he’s already a Billionaire.

    Most millionaires have to work hard and sacrifice to become millionaires (Millionaire next door, your husband, etc.), but most people could achieve that status by 35 with conventional-ish advice.

    Billionaires on the other hand, seem to think as if the initial money is no object, but the only thing to consider is the ROI. The difference is that the Billionaire has earned the right to think like that, whereas you have simply decided to start thinking like a Billionaire with one important caveat: You do not differentiate at all between investment and consumption.

    Good luck with your approach. If I had to guess, you will probably die rich; not that it matters.

  9. Isabelle
    Isabelle says:

    I’m honestly don’t know if some or all of this is good advice, but I seriously appreciate hearing someone think outside the box a bit with regard to retirement planning/risk taking for Millenials and Gen Z. I don’t know what the right financial planning is for me and my family, but I have a strong intuition that the smartest plan ISN’T the “conventional wisdom.” I’m a big long-term thinker, but even I have a hard time seeing past the next 30 years of my career (I’m 30 now.)

  10. YesMyKidsAreSocialized
    YesMyKidsAreSocialized says:

    I love that your son is totally into fashion. Does he give you tips on what to wear/not wear? I just keep thinking how cool it is to have a personal stylist living with you all the time!

  11. Kevin
    Kevin says:

    I agree that we all need to be saving money for when we can no longer work, but my takeaway from the first part of this post is that we need to rethink the concept of retirement. My generation (I am 40) was pounded with the message that you go to college, find a job, work for 30 or more years, and then retire and do the things you love. It was a message many took to heart and are now regretting. The other day friends were visiting. The couple had just returned from a trip. My friend (about 70) looked at my seven year-old daughter and said, “Some day when you’re our age, you can do things like that.” What a sad message to give a seven year-old. “Create a life you love each day. . . What a sad life you would have if you woke up each day feeling that you didn’t deserve to have a good life until you stop working.” That’s the message from this post that I want my kids to take to heart some day.

  12. Brad
    Brad says:

    Implied though not stated here: Since most people won’t save enough money to retire, you might as well save NO money and depend on public assistance in your old age.

    Though that sounds awful, pragmatically it is not without merit. You may have to live simply, but our society lets no one actually starve. At least not yet.

  13. Anna M
    Anna M says:

    As much as I have loved reading this blog, and P’s unconventional way of thinking, I hate reading her opinion on money and it makes me question reading Her blog in general. Two things, she always talks about how many companies she had founded, but it seems like she didn’t make any money from these ( tax problems, credit problems). A successful company makes money. Also, my husband started a software company 7 years ago, and although he got people to loan him money, he couldn’t get people to invest for equity. You have to get acquired for that to pay off for the investors since their isn’t an ipo market for small to midsize software companies. So he took the loans and bootstrapped the rest- paid his loans off and now has a successful company. My point is it isn’t easy to get funded! That can’t be your only trick up your sleeve. Learn to live on a small income and throw the rest of your money into a company. Than it is yours free and clear.

  14. Brynn
    Brynn says:

    I would add that homeschoolers need to learn about how to raise capital. That does not necessarily mean by having a job. Much like the Kickstarter campaigns and such, kids can raise capital in a number of ways. My ten year old has three weeks till his last pitch for non-profit status with a major player. He has already been awarded grants for his non-profit venture and has a stack of mentors who all work pro-bono. Large scale grant writing begins at the start of the year as well as a Kickstarter when he and his videography mentor really get the footage just so. He is working is butt off to learn how to raise capital from nothing based on how you present yourself and what you can leverage through charisma.

    If we did not homeschool, there is no way we would be able to pull it off. A large part of my life right now is being his PA and secretary (I’m an INTJ). A large part of his life right now is harnessing his ENFP into quantifiable results. It is the best financial curriculum I could possibly think of.

    • YesMyKidsAreSocialized
      YesMyKidsAreSocialized says:

      I really like your comment Brynn! I personally enjoyed PT’s post and think it’s great advice for homeschoolers/unschoolers who accept the advice. Not everyone will accept it, not everyone will agree with it, but I still think it’s good advice and I like how you and your son demonstrate it so perfectly. I would probably add 2 or 3 more to the list, but it served its purpose.

        • YesMyKidsAreSocialized
          YesMyKidsAreSocialized says:

          I think the 95% number is a stretch, don’t you? I mean, 95% of the population doesn’t even work right now, it’s closer to 60%.

        • YesMyKidsAreSocialized
          YesMyKidsAreSocialized says:

          Her advice was geared for homeschoolers, which is about 5-9% of the population, who already are doing things differently. Anyway, I feel PT prefaced the whole post as advice for homeschoolers, and I assumed it was for kids being homeschooled… she didn’t say it was for people in the mainstream who do what they are told and work regular jobs. Right?

          • redrock
            redrock says:

            Don’t get me wrong – I am all for trying out different things including crowd sourcing, entrepreneurship, having a company etc. But many of those solutions do not work if they are the only thing people should do with their lives. They only can be sustained if there are people who work the “normal” jobs, the engineers, the carpenters, nurses etc. those are still the backbone of a society – providing the basic services and production for things we need to live the way we do. There are always exceptions, and those not working are included in the exceptions. I also disagree with the assessment that all those working normal jobs are somewhat to be despised and addressed universally as something “less worthy” and “just following what one should do”, and homeschooling automatically sets you on a path of being someone who plays solely to one’s own tune – which begs the question whether this is always a good thing anyway.

        • YesMyKidsAreSocialized
          YesMyKidsAreSocialized says:

          But no one is arguing against that red… this post was for our kids that we’re homeschooling, not for mainstream thinking. Is it disparaging to say that someone takes a job that tells them what to do? Or is it just stating a fact?

          • Commenter
            Commenter says:

            PT’s basic argument on this blog is that homeschooling should be mainstream.

            The argument that homeschoolers should all be financial risk-takers presupposes them not being mainstream. You can’t swim against the current if there isn’t a current.

            Thinking everybody should act like entrepreneurs is a fascinating piece of ultra-American philosophy, but it’s internally contradictory.

            As for “a job that tells you what to do,” there’s a big difference between working at McDonald’s and having a professional position at a corporation. The former is the most common job in America, and therefore the main thing for which our public schools are preparing children. Like the majority of jobs in America, you will closely follow a script written by someone else. Thirteen years spent at meaningless busywork, driven by the sound of bells, prepares you well for that. How could you stand it otherwise?

            If you come into the latter expecting people will tell you what to do, you won’t even get the job, let alone succeed at it or move up the ladder. You need to invent constantly what you’re doing and what you should be doing to meet the current and projected needs of the organization. Homeschooling prepares you well for that.

          • YesMyKidsAreSocialized
            YesMyKidsAreSocialized says:


            I think homeschooling can prepare you for anything as well. There isn’t really anything a homeschooler can’t do that a traditional schooled student can. But there is more time to focus on your interests as a homeschooler than if you were a kid in traditional school, which if you are an entrepreneur, artist, athlete or inventor is excellent.

            But you made the point which is being conditioned into traditionally schooled children all the way until age 17-18. In order to succeed the kids need to do what they are told and do the task exactly as they say to do it or you will fail. It’s starting to pervade into their family lives now. Ok, so then suddenly they are “free” from school and have no clue what to do except take a service job because they were never set up to make independent decisions. And so instead of pre-adolescence ending at 18 it now extends into ones late twenties!

            I’m thinking that a majority of service jobs don’t need you to reinvent yourself. Call centers, government workers etc, I wasn’t even talking about McDonald’s entry level workers at all. If you are a homeschooler in this sort of employment, then this financial advice doesn’t apply, right?

            As for mainstream, homeschooling is gaining in the mainstream, unschooling is not mainstream thinking… not yet anyway. And what would I do if it ever becomes mainstream…. go back to traditional school? lol.

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