One Lesson Ahead

Music gave me a superpower. AI is the next one, and you don't need permission to pick it up.

I used to teach guitar lessons while I was touring full time. It was side money. But every time a new student sat down across from me, the same thought showed up: who am I to teach this?

I had a friend who taught music for a living. I told him about the fear. He said two things I never forgot. The first: as long as you’re one lesson ahead of the student, you’re still the teacher. The second: people want to learn from you because you actually do this. You’re not reading it out of a book. You’re living it.

That was it. The fear didn’t disappear, but it got small enough to work around.

Here’s the part I didn’t understand until later. I wasn’t just teaching people chords. I was handing them a superpower. Music is the most universal language on earth. I’ve walked into rooms all over the world where I had no business fitting in, and by the end of the night I was family. Not because of anything I said. Because I played someone’s favorite song, or I poured my heart out and earned their trust. Music got me in the door and music made me human in front of strangers.

Somebody gave me that superpower. A lot of somebodies, actually. Teachers, mentors, people who were one lesson ahead of me. So when a kid or a grown adult sat down and learned to play a song they loved, I knew exactly what I was giving them. The same thing that was given to me.

That’s the parallel I can’t stop thinking about. AI is a superpower too. We can do more today than we ever could. And it makes us more human, not less, for the same reason music does. It takes the busywork off your plate so you can get back to the part that’s actually you.

I’m forty seven now. I put the guitar down at thirty five to be a dad. Two kids, out of state tuition, health insurance, the whole thing. I traded the dream for stability and I’d make the same trade again. Corporate America gave me thirteen years at places like Microsoft and Salesforce, sitting in rooms solving million and billion dollar problems for some of the biggest brands on the planet. It was a blessing. It was also a lot.

Both my kids are in college now. I’m technically an empty nester. And for the first time in a long time, I have room. So I’m running it back. Not the exact same way. Something new. I’m taking thirteen years of enterprise experience and the musician who never really left, and I’m building something in the middle. That’s what this is. AI on your own terms.

Here’s what got me here. Every business I ever sold to spent millions to do what I’m about to describe. Could I do a version of it myself, for almost nothing? Turns out, yes. I started leaning into the tools. Wispr Flow, Claude, Fireflies, Obsidian, a dozen others. I built my own systems. I stumbled plenty.

My biggest stumble wasn’t a dumb mistake, it was decision fatigue. Too many tools, too many options, sitting there frozen trying to pick the perfect one instead of just starting. If you’ve felt that, you already understand the hardest part. It’s not the tech. It’s the anxiety. The overthinking. The paralysis before the first step.

In sales they used to tell me, fail fast. It was the whole philosophy. Try it, miss, learn, go again. Here’s what’s different now. With AI you can fail faster than ever, and it costs you almost nothing to do it. A missed rep used to cost time and money. Now it costs a few minutes. That’s the part nobody talks about. The price of trying went to almost zero.

I’m writing this to the parent reading on a Saturday. The one doing what they have to do to get by and stay sane in a strange economy. I don’t know what the job market looks like when my kids graduate. I don’t know what work looks like in fifteen years. Nobody does. But I know sitting it out is the riskiest move on the board. I missed the housing boom. I missed the tech boom. Not this one.

So here’s your one small step, and it’s the one that changed the most for me. Try talking instead of typing. Download Wispr Flow. Speak an email, a note, a message, anything. Let it write while you talk. That’s it. That’s the whole assignment.

I’m one lesson ahead of you. Not miles. Just one. That’s enough to be your teacher, and it’s close enough that you’ll catch up fast.

The mistakes are the reps. Come make some with me.

🤘🏽

Disclosure: the Wispr Flow link above is an affiliate link. If you download through it, I may earn a small commission at no extra cost to you. I only point you to tools I actually use every day.