I hate being the person with hindsight

Hindsight is so sucky. It was so much more fun to write about homeschooling when I was the deer-in-headlights parent who was so scared of making mistakes. In hindsight, I should have hired more people to give me advice. It’s so absurd that I didn’t. I notice that with things I’m great at —  like managing my career, playing beach volleyball — I had no problem hiring lots of people to steer me. The idea of making even one wrong turn because of lack of guidance was so upsetting to me.

But as a homeschooler, I decided I could just read everything. I hired so few consultants. I think because I knew so little about it, I decided I could do it myself. This is a proven thing: we read more info about what we’re already good at. Like, if you are really good at productivity, then you read a lot about productivity. If you’re really good at nutrition, you read a lot about that. It’s not a chicken and egg thing, it’s an egg-chicken-egg-chicken-egg-chicken-egg thing. We just get stuck doing the stuff we’re good at and not doing stuff we’re not good at.

So it must also be proven — I’m proving it right now — that we hire consultants to help with what we’re good at. I think it’s because we can imagine what the help will be like. I understand what help with beach volleyball looks like. I can ask good questions and get good consultants. I was so lost with homeschooling that it was hard to even know who I could hire.

I see this with people who hire me for coaching. Everyone hires me for career coaching because they have had careers, and they understand how to ask career questions. But almost no one needs career coaching. (Right now I am about to kill my whole career coaching business, so if you were ever thinking of hiring me, go do that right now. Stop reading.)

Okay. So either you have a good career and people in your career are helping you, or you don’t have a good career and you should do something else. But it’s hard decide to not have a career, and it’s hard to know how to ask about that. So people just hire a career coach because that’s socially acceptable. This happens so often that I am shocked when someone genuinely needs career advice.

This is all to explain to you why I did not hire people to give me advice on how to homeschool. Well, I also didn’t want to hear the advice. Which, of course, is how people feel when I tell them they should just forget the whole career thing and focus on something else. We all hate realistic advice about an area where we are not high-achieving.

In hindsight, I should have hired a place that does college application consulting by starting really young and doing project-based learning with kids. But the projects are super-cool, memorable projects that go on college applications. Too often homeschoolers pat themselves on the back for project-based stupidity. We shouldn’t do that. Projects should have milestones and goals and hurdles, not just a fun way to pass time for parents. (Which is for another post, but really, so much of homeschooling is just so parents can do what they like. Myself included.)

Here are places that have great resources to hook your kids up with professors, professionals, experts who will help your kid become an expert and have something to show for it. And stop pretending you will learn right alongside your kid and become an expert. That’s not fair to your kid. Your kid should get to be with someone who knows more than you.


Go to that link and click on “Crimson Rise.” It will probably be really expensive. I’m sorry. I don’t know what to tell you. Homeschooling is expensive. But it’s not as expensive as private school. And it’s not as expensive as going to a mental institution from the drama of being in school-not-school, and on Zoom, and on not-Zoom, and teachers on strike, and not on strike etc.

Another place that has great resources for doing project-based learning:


I know it seems weird to turn homeschooling into all college applications, all the time. But it makes sense when you look at the cost of really meaningful project-based learning: of course parents will only foot the bill for this when it’s related to college. Otherwise, parents aren’t used to paying to make education a great experience.

So really, this is my message: all the good homeschooling resources are project-based, and all the best project-based opportunities are with the college application consultants. The really big places, with a national or international presence, have many levels of support for a kid who wants to have deep, meaningful experiences before they leave home. The opportunities for these projects are narrow: between age 11, when a kid can handle it, and age 15, when a kid needs to start focusing on SATs.

So in hindsight, I regret not leveraging the resources these consultants offer during that period between 11 and 15. But there’s something comforting about regret: you can only pinpoint the things you regret if you feel like you did most of the other stuff in acceptable ways.

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