A while back a specific fantasy started circulating in the solopreneur / bootstrapped product / maker communities:

You are an authority. Teach everything you know. You’re already an expert at something, and all you have to do in order to start a great business is start teaching what you know.

I bought it hook, line, and sinker.

Fast forward, and I’ve written 4 books, 2 courses, and more articles than I can count.

And honestly, all that stuff about “anyone can be a teacher” is a load of bullshit.

After all of those efforts to teach, I’m still not that good at it. In fact, I’m pretty bad.

A while back, my wife Rachel wanted to learn to play guitar. I have played guitar on and off for 20 years. I’m not as good at guitar as that makes me sound, but I know a little. So naturally, I volunteered to give her a few lessons.

But after the first lesson, she refused to keep learning from me. She almost quit learning guitar altogether because I was stressing her out. I pressured her to play guitar my way: for the sake of artistic and personal expression rather than just as a fun hobby of learning songs and singing along. In the first lesson. I was a bad teacher and I was unintentionally discouraging her from doing something awesome.

Later when I was writing my first design course, I brought in some early access students and realized my shortcomings as a teacher—I put way too much pressure on students, just like I had with my wife’s guitar lesson. So, I worked with professional educators to polish up the courses and make them less intimidating and easier to use.

Pretty much every company, blogger, product maker, etc is doing content marketing right now. Practically everyone on the internet is masquerading as a teacher.

And in this time where everyone is trying to be a teacher, be careful about who you listen to.

Teaching is extremely difficult. It takes an incredible amount of patience, empathy, and skill to be a teacher. Teaching isn’t something you can master overnight just because it sounds like a good way to run your marketing.

All those people and companies trying to be teachers are doing it for business purposes. They teach to sell. They don’t necessarily teach to teach. And that means some of them are bad teachers. I was one myself , and I’ve certainly found my fair share of bad teachers.

In high school I had a physics teacher who inspired me to learn about science, and that inspiration persists to this day (thanks Mr. Roble!). I also had a history teacher who forced us to memorize facts and dates, which gave me a bad impression of history that also persists—I still avoid the history channel, historical fiction, and any kind of history if I can. And that’s kind of a shame.

A good or bad teacher can make all the difference.

And when everyone is pretending to be a teacher, there’s a good chance you’re getting inaccurate bad impressions or that someone is steering you wrong somewhere. Not because they’re trying to do harm, but just because they don’t realize it.

Being an expert in something doesn’t mean you can teach it. In fact, instructional designers and professional educators—who are trained in working alongside experts to create courses and training—call people like me “subject matter experts”. Through working alongside these experienced teachers, I learned that experts are often the worst teachers because we don’t remember what it’s like to be a beginner, we’re more concerned with advanced subjects and techniques, and the basics are boring to us.

(Maybe this is why it’s almost impossible to find a decent book about design fundamentals, but there are like 400 books on design systems. But I digress.)

So all those experts out there might not really be the best people to teach you. And all those businesses out there trying to teach have ulterior motives.

Everyone can be a teacher, but not everyone should be. Honestly, with so many people writing books, courses, articles, etc, it’s a total disaster and I don’t even.

I’m not writing this to you to act like I’m the only teacher worth listening to. Please be careful about which advice you listen to—including anything I send you.

As for me, I’m trying to be a lot more careful about how I approach the role of teaching. It’s a huge responsibility, and I am immensely humbled that you read what I write. And I’m done with the bullshit marketing technique of writing lessons for the sake of making sales, because it makes for bad teaching. Instead of preaching at you all the time, I’m just going to share what I’m learning—because if it’s valuable to me, it’s probably valuable to you too.

If you’re trying to be a teacher yourself, my honest advice is: don’t. Teaching is hard, and it is a huge rabbit hole to fall into. It took up years of my career. But if you decide to teach, take it seriously. Don’t just teach because someone says it’s easy marketing. If you’re going to teach, put in the hard work to become a good teacher.

Anyway, as a reader, what can you do about all the potentially bad teachers out there? Check everything, and make your teachers earn your trust first. Remember that a successful person is not necessarily a good teacher. Pay attention to how they treat you before you listen to what they say.

Remember that all the free content comes with strings attached. Everyone has a reason for teaching you that goes deeper than just trying to help you learn.

We all feel pressure to tune into all the free content out there. It’s part of keeping your skills up to date, FOMO, yada yada. But, don’t be afraid to stop listening if you don’t like what you’re hearing.


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