I’m homeschooling my 12-year-old again this fall, and I still don’t know if I’m doing it right.
I don’t think that ever fully goes away. I work. I homeschool. My house and my schedule don’t stop needing things just because we chose this. I can find plenty of advice about which curriculum to use or how to structure a day. What I actually want — what I can’t find enough of — is perspective from people who are on the other side of this. The ones who can look back after 5, 10, 20 years and tell me what actually mattered, and what turned out not to be the catastrophe it felt like at 2 a.m. on a Tuesday.
So I built it. Because that’s what I do.
Who I Am to Say Any of This
It’s easy to look like an expert right now. Buy some followers, fast-track visibility with Meta ads, ride a viral niche with content that’s good enough, and within a year you have a digital footprint that reads as authority. Most of us are too busy surviving our own lives to check whether there’s anything underneath it.
I’ve spent almost 30 years doing the underneath part.
The first community I ever moderated was a listserv in 1997. I watched Steve Jobs unveil the iPhone at MacWorld in 2007. I piloted a brand MySpace platform in 2006, moved communities off message boards and onto Facebook groups in 2012, livestreamed press conferences on Periscope, and got dragged through more than one online crisis I’d rather not relive. During the pandemic, I ran virtual conferences for organizations that had built their whole model around gathering in person and suddenly couldn’t, while coaching entrepreneurs trying to build expert businesses from scratch, in real time, online. There was one week in 2022 when I moderated 17 two-hour live events in 10 days.
And after all of that? My Facebook group has fewer than 1,000 members. My podcast gets about 200 downloads a month. My social following across every platform combined is under 10,000.
I say that not to be modest. I say it because it’s the actual point: the people who know where all the bodies are buried in an industry are usually too busy doing the work to build a following around it. That’s true in my industry. It’s just as true in homeschooling.
Last year, at Mary Williams’ CEO Summer Rebellion, a room full of us — people who’ve been at this grind for decades — sat on something called the Dino Club Panel, comparing notes on how our success for other businesses came at the expense of our visibility. That’s where this started.
My own 12-year-old, Abbie, put it more bluntly than I would have: “Mom… you never talk about homeschooling online; you’re gonna mess up your algo.” She’s not wrong. And I don’t care.
Before You Take Homeschool Advice, Ask One Question
How old are their kids?
You can’t tell me what got a family through a resistant 12-year-old if your oldest is 8. You can’t tell me which elementary-school worries turned out to matter if you haven’t reached high school yet. You can’t tell me what homeschooling did for a child’s future if yours all still live at home.
That doesn’t make newer homeschoolers wrong, or their ideas worthless. It means experience has a timeline, and a lot of the loudest voices in this space right now haven’t reached the chapters they’re giving advice about. When I’m scared I’m getting something wrong, I want to hear from someone who’s already lived the part I haven’t gotten to.
I found my way into this world years ago through Jen MacKinnon, founder of Practical by Default and the Working Homeschool Mom Club — a community with more than 30,000 members. Jen’s the reason I believed working full time and homeschooling weren’t mutually exclusive. My girls eventually went back to traditional school, but this spring I’m homeschooling the youngest again, and I went straight back to the people I trusted the first time — including Dachelle McVey, whose language arts curriculum is one of the most effective and engaging I’ve ever seen (especially for my reluctant reader).
Introducing Been There, Homeschooled That
Together with Jen and Dachelle, I designed a homeschool summit with one non-negotiable rule: Every speaker has to have actually launched at least one homeschooled child into adulthood.
And it turns out, we aren’t the only ones hungry for this sort of event. We have 18 speakers participating in a mix of themed live and recorded sessions with a few panel discussions thrown in for variety:
- Sept. 1 — The Practical Side addresses the logistics nobody warns you about. You know, curriculum that doesn’t fit, schedules that fall apart, and the systems veteran homeschoolers actually use to keep the wheels on the proverbial bus.
- Sept. 2 — The Human Side covers the identity shift, the isolation, the guilt, and the relationships that change when you wear the hats of teacher, parent, spouse and individual.
- Sept. 3 — The Long Game addresses what actually matters by the time you’re standing at graduation — transcripts, college, trades, and the choices that turned out to count for more than you thought at the time.
You don’t need to attend all of it. Seriously. If you’re already homeschooling, feeding people, keeping up with laundry, working, and trying to remember what you meant to order three days ago, the last thing I want to hand you is 20 more things you “should” be doing. Pick the conversations that solve your actual problem this week. Skip the rest. Recordings stay up through Sept. 8, so you don’t have to rearrange your life around three specific days.
Homeschool Planet is our presenting sponsor, and everyone who registers gets a full 30-day free trial, no credit/debit card required. It’s the kind of tool that keeps your home, school, and work calendars in one place and lets you drop in lesson plans from popular curriculum companies instead of building your own from scratch. Start with the planner itself, or jump to whatever solves your current headache.
You don’t need a homeschooler in your house right now for any of this to be useful. If you’ve ever had to figure out who to trust when everyone sounds equally confident, that’s really what Been There, Homeschooled That is all about.






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