Most of the people I know who can earn enough to support a family and homeschool at the same time were already earning a lot of money before they started homeschooling. So they took a pay cut to work from home and but they’re still making pretty good money.

That’s actually what I’m doing. But it’s something that takes a tons of focus and planning before you start homeschooling, so whatever, this is not an option to most of the people reading this blog.

So you are going to have to sell something – either a product or a service. Here are some guidelines to help you think of an idea that will be successful:

Sell services. The easiest thing to do is to sell your services by the hour. If you have skills that are worth a lot, you can charge a lot. If you have skills that are general and entry-level then your hourly fee is lower. But in either case, the success of this business depends on your sales skills. Because it’s much easier to do the work than it is to convince someone to hire you to do the work. So when you think about selling services, think not so much about what services you can do but what services you can sell.

Look for people with money. So often people pitch me products for kids or recent grads or nonprofits. All these ideas have the same problem: they are aimed at people with no money. When you try to think of a company idea, think about who has money and solve a very very specific problem for those people. An example of a company that does this is Invoicehome because of course if you are sending an invoice then you have money. And this is straightforward solution to a straightforward problem, which is that places that make it easy to send an invoice (PayPal, for example) brand themselves instead of the sender.

Don’t sell to homeschoolers. Think about the problems you have outside of homeschooling and how you can solve them. Really. Most homeschoolers don’t have a lot of money, and besides that, things that they would be interested in (curriculum or parenting tools) are well addressed by Silicon Valley entrepreneurs – twenty something year old guys who don’t eat or sleep and just write code nonstop – and you don’t want to be competing with them. Instead think of a product that someone in Silicon Valley would never dream of — like Cybele for innovative undergarments or Piper & Leaf for the best loose tea I’ve ever had.

Don’t sell to schools. Selling to schools and government is very specialized. The process of selling is long, full of red tape, and a maze of connections and politics. Companies that have products to sell to schools are absolute masters of the education channel. For example Blue Label Power sells only to schools. They are great at what they do because they simplify the red tape around school purchases. Do you know how to do this? Don’t create a product for schools unless you want to spend hundreds of thousands of dollars to hire an education sales specialist to sell the product for you.

Make stuff and sell it. This is probably an Etsy business, and the products that sell best on Etsy are common products with a handmade differentiator – like tights with Emily Dickinson poems. The biggest hurdle for people who sell what they make is that there’s usually one thing that sells well and the rest doesn’t sell. People who are makers don’t want to make the same thing over and over again, but that’s how you make money. Some people resist this, and making money is difficult. Emily Free Wilson is an example of an artist who embraced the art her fans loved on Etsy and she created her own business based on just one, single design she created among hundreds of dishes she sold.

Consider the cost of your time. If you homeschool, it’s way better if one person takes charge of the family and one takes charge of the money. When you start thinking about a side business, add up how much time and energy it will take you to get the business off the ground. Businesses can take years to become profitable. And you might find that by the point you’re making enough money from a side business to justify the time it takes that your kids are old enough that you can just go work 9-5 at someone else’s company.

Make your goals easier to attain. When you started homeschooling, did you have some vision of yourself managing every lesson, teaching every idea, etc? It’s impossible and unpleasant and not really how homeschooling works, right? The same is true of creating and running a business. You can’t do everything, you can’t create everything you think of, because do everything is impossible and unpleasant and not really how a side business works. It’s about doing just enough so that you meet your goals.

So many people tell me they want to homeschool and make money while they do it. It’s hard enough to homeschool, so it’s not easy, but it can be done. And anyway, the truth is that the same principles that gave you the insight and gumption to homeschool will give you insight and gumption to run a side business. And both start with this motto: Do the least you can, not the most.

26 replies
  1. jen
    jen says:

    I enjoy the blog but this is not good advice. Half your career was giving speeches and being a coach. You didn’t just start it up one day. Most people can’t make a living just talking on the phone unless it’s x rated. Most people can’t afford to hire tutors all day as you do so they can work from home. You’re kind of doing the lean in routine but for the affluent not the filthy rich

    • Penelope Trunk
      Penelope Trunk says:

      Right. I say at the beginning that you can’t have what I have because I worked 80-hour weeks for most of my adult life, and that laid a foundation for a career that enabled me to scale back and homeschool. I have written about how the long hours I worked while I had small kids was an insane way to live. Here’s a post about that:

      http://blog.penelopetrunk.com/2013/03/10/i-had-to-take-a-xanax-to-read-time-magazine-this-week/

      So the ideas here assume you did not work 80-hour weeks. These ideas are what you can do in small steps, without spending any money, while you are dealing with kids all day. You can do this stuff when your partner is home. You can do this stuff when the kids are asleep.

      And I’m not saying it’s a good life. It isn’t. At the end of the post I warn that it’s probably cheaper to not work than work when the kids are young. For everyone. Not just homeschoolers. But there are lot of people who tell me they HAVE to earn money. They don’t have a choice. It’s really really hard, but it’s possible, and these are ideas how.

      Penelope

    • YesMyKidsAreSocialized
      YesMyKidsAreSocialized says:

      I don’t know any affluent etsy shop owners. I know some very successful ones who just scrape by.

      • Penelope Trunk
        Penelope Trunk says:

        I agree. I like that you guys are piping in here, because I’ve been saying forever that it’s too hard to make money and homeschool.

        But there are two types of people I talk with a lot:
        1. Single moms who homeschool.
        2. Women who are breadwinners and thought their husband would be the one who would homeschool but it doesn’t work. (For obvious reasons – very few marriages work with the woman as the breadwinner the entire time. There is so much data about that that I’m not linking to it. Google it.)

        These people have to figure out how to earn money while they are at home until they can leave the kids at home.

        But.. thinking out loud here… I was able to live in poverty when they kids were really young (public assistance, losing our electricity, etc) and the kids don’t notice, and that probably worked better than anything else I could have thought of. It gave me a way to be the breadwinner and work from home even if I wasn’t really earning enough money. So maybe that’s the best answer.

        Also, now I’m just rambling, I spent my (paltry) retirement account, I sold jewelry, I did everything I could possibly think of to be able to stay at home and figure out how to earn money. And I went into debt for babysitters. I told myself that I would have a chance later to make more money when I could figure out how. And I was right. If you can just get yourself to when the kids are about ten years old, the kids are way, way more self-sufficient, and the parents have way more options for making money.

        Penelope

        • jessica
          jessica says:

          I mean, Europe has figured this out for the most part. Mothers get paid time off, childcare vouchers, year round school, basically a lot of support for the mom married or not if the income is low enough (middle class or lower). Chilcare is gov regulated and can cost as low as 3 pounds an hour. My sister in law lived this. The difference is it is so engrained as an automatic entitlement to everyone that moms don’t earn as much because (my theory) it’s taken for granted. That is solely my theory, but maybe contradicted in later years if one persues a corporate career (shared resources as typical structure). To me, they don’t see the burden that they Would have in the US under the same circumstances. The main difference is the view of public assistance.

          I thought the kids had two nannies when they were younger? Was the low income time brief?

          • Penelope Trunk
            Penelope Trunk says:

            When my first son was born I didn’t realize I would want to stay home. I just couldn’t imagine going back to an office 9-5 and leaving him. But I had not been writing long and I was making $1200/mo and my husband was unemployed. It took me three years to earn above the poverty line in NYC. It was really scary and stressful. When I really had no idea how I was going to make things work, I got a six-figure book deal things turned around.

            Penelope

          • YesMyKidsAreSocialized
            YesMyKidsAreSocialized says:

            I know many families where the woman outearns the man, they are in healthy, happy, successful relationships and the women I know aren’t at all mad at their husband’s.

            One woman is older, and their daughter is in high school. The husband was a stay at home dad for a decade and he and his daughter would act in community theater together. The dad just went back to work and does temp jobs and still does theater. These people make me wish I was as happy as they were. The exude joyfulness, happiness, and contentment.

            My middle class family, granted the kids are younger, but male cousins are men, and they have zero ambition or desire to go corporate. They work for themselves in a trade, and similar to a start up there are periods of no work, and periods with lots of work. Their wives are the breadwinners, they are solidly middle class. Nobody is complaining about working.

            I think what you may attract to this blog are people who agree with you. They are upset at their husband’s and since you don’t hear from happy female breadwinners, because they perhaps don’t have time to come here like the rest of us do, or they don’t relate or for whatever reason…you are only getting one side of the coin.

            I don’t disagree that families who are struggling want their spouse to make more money. Or a parent who hates working and wants to stay home grows resentful over the situation. I believe that you are correct in those cases, but I don’t see the trend going that way, like back to 1950’s??? I see it going the opposite. Also, your son may want to be with a partner who is a breadwinner so that he can do his passion ;)

  2. YesMyKidsAreSocialized
    YesMyKidsAreSocialized says:

    Another option is to have a good support system outside of the two parent system mentioned here. Karelys has the support of her mom and friends, and is able to work full-time. I think that is a more likely option for people to start homeschooling. Of course, it’s so much easier homeschooling older kids because they are largely self-directed and don’t need constant supervision (at least mine don’t). That gives the working parent more flexibility. Generally speaking, a retired grandparent who is healthy would be the greatest asset when starting to homeschool.

    • Adrianne
      Adrianne says:

      Chiming in here, even though I don’t home school. An extended support system is extremely helpful – even if it’s not via the provision of childcare. Having extremely supportive family members from my side of the family who had their sh** together made transitioning to parenthood and working (and the current easing over to a form of entrepreneurship) feel significantly more manageable. My support network was able to help me with all kinds of parental-administrative stuff I was too busy to do – car-seat shopping, ordering new toys, arranging travel transport tickets, etc. If you have a good extended support network, it will go a long way to helping a homeschooling arrangement.

      • jessica
        jessica says:

        I agree with this. Through this child raising method the alleviated practical cost of available support, and the alleviated cost of stress and time burden to a couple is priceless and would be extremely expensive otherwise. Relatives nearby with their shit together and priorities in place makes a big difference. It takes a village, or buy one- especially with little ones.

  3. Satya
    Satya says:

    Totally agree with selling a service but I think it’s better to charge by the project, not the hour, based on the value that service provides. And the more your service helps other people make money (either through making people money directly or making their lives significantly easier so they can focus on doing it themselves) the better.

  4. Bos
    Bos says:

    It’s a good idea for PT not to cite imaginary data. The last time she made up statistics about working women, she was confronted with actual facts far different from her imagined ones. Made up statistics about homeschooling men would be more difficult to disprove, though, because not much is available.

    “Few marriages work with the woman as the primary breadwinner?” Nah, that’s just more made up stats and poorly-understood pop journalism, only possible to substantiate in a very small sample of sad-sacks, and easily disproved.

    The statistics on the prevalence of female breadwinners are changing so fast that it’s hard to get a bead on them. This isn’t the fifties anymore, and society is changing faster than some people imagine. According to “Breadwinning Mothers are Increasingly the U.S. Norm”, from the Center for American Progress, women are primary breadwinners in 24 percent of marriages today, and 42 percent of families overall. Only 13 percent of women live in families in which the husband is the sole earner. But according to the BLS, in 38 percent of marriages – and 29 percent of marriages where both partners are in paid work – the woman makes more.

    One could talk about a higher risk of unhappiness or divorce, as shown in the Chicago Booth study “Gender Identity and Relative Income Within Households,” but it’s only six percentage points higher (p. 602). What that means is the exact opposite of what PT imagines – only very few marriages fail because the woman is the primary breadwinner. For those (like pop journalists) whose grasp of statistics is poor, this indicates that the woman being the primary breadwinner doesn’t lead to divorce in 94% of families.

    Boston College wrote a good study called The New Dad: Right at Home. According to that study, dads are still the minority of stay-at-home parents, but numbers are rising, up to 3.4% in 2011 (which is to say, more than the overall percentage of parents who homeschool). Also, the majority of dads who stay at home do it by choice, and most men are or would be just fine with their wives being the primary breadwinner.

    There are probably more dads who stay at home and homeschool their kids than there are single divorcées who support themselves by giving career and relationship advice over the telephone, so if a woman wanted to make plans for homeschooling, the former would be a far, far better idea than the latter.

    • YesMyKidsAreSocialized
      YesMyKidsAreSocialized says:

      Most of my cousin’s married women who are the breadwinners. They are happily working as tradesmen, and taking care of kids with amazing lives where their hobbies define them, not their jobs. Their wives pay the bills. They are not affluent, but are solidly middle class.

      • Bos
        Bos says:

        Only a very few, very sheltered people will think it’s at all unusual for a wife to make more than her husband by the time our children are grown.

        • Penelope Trunk
          Penelope Trunk says:

          I disagree. I think it will be less common. Because I have never met a woman who is a breadwinner who has middle-scool-aged kids or older and is happy woth her choice to be the breadwinner.

          A big problem is that there is no public forum to say this, because its so undermining to their husband. So women keep it to themselves.

          Penelope

          • jessica
            jessica says:

            Whoa, really? Not happy?

            That is extremely subjective. If they are smart enough to be the breadwinner, are these people you’re speaking to or know not able to figure out a life rhythm that doesn’t leave them miserable with children? That seems to be a far fewer sample size of ladies than general pop.

            Personally, our family knows several families where the woman is the breadwinner. And we are talking women that negotiate government contracts for major road projects, design firms, bankers etc
            They are filthy rich or well off, under 50, with stay at home spouses. Unhappy? They are getting it done, and taking care of their families and spending weekends at holiday homes.

            The key I’ve seen in families that make it work and are not miserable seems to be choice. The husband or wife or wife and wife, can switch positions IF they wanted to – I.e. They both have family skills, they both have career skills.

            To be fair, I think the way incomes are going, right now, that this is going to be difficult to maintain besides the upper echelon of classes, unless the government provides childcare and time off for all women. That’s just the reality. It’s going that way anyway. But again we know a lot of stay at home or part time dads. Maybe it’s a city thing?

          • Penelope Trunk
            Penelope Trunk says:

            The idea that they could switch jobs is absurd. That’s why I specified that the kids are in middle school. Because by then the man has stayed home long enough to lose his earning power and the woman is stuck. The divorce rate is very high.

            On top of that, when dating, all things being equal, the vast majority of women prefer to marry someone who makes more than they do, even women who make a ton of money.

            And I can also tell you that this blog has a huge readership of female breadwinners – because I am one – and none of them is piping up here to say they are so happy they are the sole breadwinner.

            Penelope

    • MBL
      MBL says:

      “There are probably more dads who stay at home and homeschool their kids than there are single divorcées who support themselves by giving career and relationship advice over the telephone, so if a woman wanted to make plans for homeschooling, the former would be a far, far better idea than the latter.”

      Wow! Ad hominem isn’t usually your style. Not only did she not say that her path is a blueprint, but in the second paragraph she stated that her path “is not an option to most of the people reading this blog.” And then reiterated that in the comments before your post.

      Not sure what is going on, but I was really surprised by that deviation from your typical demeanor and I hope everything is going okay.

      • Bos
        Bos says:

        Sorry, MBL, I try to be nice and sometimes I fail. This is manifestly a case of someone who lives in a glass house throwing stones willy-nilly. I apologize for winging one back in.

        PT has outright made up statistics before here, and been called on it, but she hasn’t learned from the experience and continues to do so. The only recourse she has now is an appeal to secret knowledge, because statistics from the real world contradict her assertions on this matter.

        The technical term for this argument is argumentum ad verecundiam, because PT is a poor source of information or advice about relationships or marriages, and has no sources to back up her assertions, but wants us to accept her unfounded pronouncements based solely on our reverence for her knowledge about workplaces and careers.

        It’s sad when this blog loses touch with outside reality and just starts projecting the failures of the diarist as if they are generalizable to the population at large. I’ve had bad relationships too, in my earlier life. I can see how if I had not noticed their failure sooner, and persisted with them, they might have colored my entire perception of society. But I didn’t; instead, I married the right person and we have made a wonderful life together and we both see things clearly. Ours is similar to millions of other families – roughly a third of the families in America – in that the wife makes more than the husband, and we are both perfectly happy with that.

        In our children’s generation, very few, very sheltered people will see this situation as at all unusual. All the trends point in that direction now, and it would require a reversal for unexplained reasons to predict otherwise.

    • Mark W.
      Mark W. says:

      I have to agree with MBL here. When I started reading down through the comments and saw this ( 2. Women who are breadwinners and thought their husband would be the one who would homeschool but it doesn’t work. (For obvious reasons – very few marriages work with the woman as the breadwinner the entire time. There is so much data about that that I’m not linking to it. Google it.) from Penelope, I thought Bos will definitely have something to say about this.
      But I’m disappointed that the last paragraph was added. It really wasn’t necessary. Bos makes a lot of insightful and thoughtful comments on this blog. And he was the first to comment a few months ago that he was glad to see Penelope blogging again as I imagine we all were. I don’t believe Penelope’s comment was directed at Bos in any way. I don’t know what results I’d get from Google on this subject but it really doesn’t matter to me. What I do like though and haven’t seen in a long time is Penelope in the comments section. I hope to see more of that.

      • Jess
        Jess says:

        I really appreciate your considerate comments! Thanks for chiming in with some kindness.

  5. Wendy
    Wendy says:

    I bet you could make an entire course around what you wrote in the “Make stuff and sell it” section, if you haven’t already. (If you have, you should link it!)

    Do you know the artist Dan Tague? https://www.dantaguestudio.com/currency-portraits He made it big on his Currency Portraits series, which he’s been doing for years. The thing is, word on the gallery grapevine is that he gets kind of sick of doing these – but, they are so popular and such a great, concise, catchy product that people love. So he keeps doing them. Bills gotta be paid, after all.

    I thought of Tague as I was reading this post. Most, if not all, really succesful artists, illustrators, and craftsperson develop a very narrow aesthetic that becomes their brand/product. I’m sure this ties into what you’ve written before, that if you’re riding on talent to carry you in a career, you should do one thing really, really well. Artists and craftspeople who never narrow down their aesthetic/brand seem to struggle a lot to make a sustainable career out of their work.

    • jessica
      jessica says:

      This is a good comment. The over-arching theme of posts related to mom/dad jobs advice around child-raising is good and probably really helpful to those that need solutions.

    • Caro
      Caro says:

      I remember going to one of those art studio open houses and being surprised at how commercial most of the work was. Like Group of Seven imitation landscapes, that open window to the ocean with billowing curtains scene and motel art type things. But obviously it’s about making enough money.

  6. SM
    SM says:

    Just to mention, I agree with PT, but I managed to find some success in doing both, although it is NOT easy and I have been incredibly fortunate.
    I got my real estate license a year before my first son was born. I married knowing I did not want to pawn off my kids to anyone else, including schools, to raise. I tucked my baby under my arm and got to work. My husband would watch him in the evenings when it was better. I’ve done that for 17 years and eight children. I out-earned my husband many years but we invested our time and money in investment property–he does most of the work here. Now he’s left his job in education (the irony) and I’ve picked up more property management jobs that I can do at home on the phone. I have catered to high end investors who value my trust worthiness over services that compete with other managers and they buy property in other areas but still hire me to manage them.
    As PT mentions, my husband was supportive but did not provide primary support for homeschooling. I hired house cleaners as I could afford, used co-op homeschool classes as available, and hired private tutors (often other mothers or older homeschool students). My husband and I work too much, but so do our kids, and they like it most of the time because they feel successful or more competent that their peers. I spend most of my time at home in my pajamas now and really only leave when a former client or referral pulls me out for a big purchase.

  7. Lauren
    Lauren says:

    Hi,
    I like your pointers on how to go about coming up with a suitable business. Your personal example of homeschooling, teaching you independence and the importance of perseverance is quite apt. Learning at home is certainly more challenging than going to an institute. It teaches you to learn from your own mistakes and serves you a great lesson in autonomy. Something that’s necessary to kindle an entrepreneurial spirit in anyone. Having said that homeschooling isn’t for everyone and neither is running a business.

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