Still in the Trenches: Why I Write From Experience, Not Expertise

I want to be honest about something. I’m three and a half years into this journey from school employee to education entrepreneur, and I still don’t have it all figured out. I’m not writing this newsletter from some mountaintop where everything has clicked into place, and I’m not looking back on the struggle from a comfortable distance. I’m still in it. Still building, still learning, still making mistakes and adjusting course. I think that’s worth saying out loud.

The Expert Problem

There’s a certain kind of content out there that I’ve never been comfortable creating. The kind where someone positions themselves as the person who’s cracked the code, who has the system, who’s moved past the uncertainty into some state of complete clarity. That’s not me. And honestly, I’m skeptical of anyone who claims it is.

The transition from school life to entrepreneurship isn’t a problem you solve once. It’s an ongoing process of figuring things out, recalibrating, and figuring them out again. Anyone who tells you otherwise is either unusually lucky or leaving out significant parts of their story.

What I Can Offer Instead

Here’s how I think about what I’m doing with this newsletter: I’m just a little bit ahead of you. Not miles ahead. Not at the finish line waving you forward. Just a few steps further down a path we’re both walking.

That means I can tell you what I’ve encountered recently, what worked, what didn’t, and what I wish I’d known six months ago. I can share those lessons while they’re still fresh, not filtered through years of hindsight that smooths out the rough edges. I think there’s real value in that. Real-time honesty rather than polished expertise.

A Lesson I’m Still Learning

If you want an example, here’s one I’m living right now: I expected this to move faster. When I started, I had timelines in my head. Milestones I thought I’d hit by certain points. Revenue targets, client numbers, all of it. And almost none of it happened on the schedule I imagined.

That’s not a failure. It’s just the reality of building something. But I spent a lot of energy in the early days feeling like I was behind, like something was wrong, because my expectations were completely out of sync with how this actually works. I’m still recalibrating those expectations. Still practicing patience. Still reminding myself that the timeline I invented in my head was never real to begin with. If I were writing from “expertise,” I might package that as a lesson I’ve fully absorbed. But the truth is I’m still in the middle of learning it, and some days are easier than others.

Why This Matters for You

If you’re reading this newsletter because you’re considering the leap, or because you’ve already made it and want some company on the journey, I want you to know what you’re getting. You’re not getting someone who has all the answers. You’re getting someone who’s actively searching for them and willing to share what he finds along the way.

You’re not getting a highlight reel. You’re getting an honest account of what this transition actually looks like, including the parts that are slow and uncertain and unglamorous. And you’re getting the lessons as I learn them, not years later when they’ve been polished into tidy principles that sound good but lose the texture of real experience.

Still in the Trenches

I chose the name “Unschooled” for this newsletter because it captures something true about where I am. I’m unlearning a lot of what I thought I knew. I’m figuring out a new way of working that doesn’t come with a syllabus or a clear grading rubric. Three and a half years in, I’m more confident than I was at the start, but I’m not done. Not even close!

So that’s what you can expect from me. Not expertise from a distance, just experience from the middle of it. I hope that’s useful. I think it’s more honest than the alternative.