The course went live and nothing happened.

I checked again an hour later. Then again after lunch. By the end of the first day, nobody had enrolled. Nobody ever did.

I had spent nine months building that course. Portfolio design and development, priced at $500. It was for students applying to art schools, where a strong portfolio could mean thousands of dollars in scholarship money.

I had taught the material for years through an institution where students paid over $3,000 to take it. They had shown up, done the work, and gotten into schools. I assumed that demand would carry over to a course I offered independently, and that the course could become the foundation of a business of my own.

So I followed the playbook. Free workshops. Lead collection. Weeks of engagement and generous free content. People kept showing up, and I took that as encouragement to keep building.

By launch week I had already designed what came after. The next cohort. The community that would grow around the course. A whole second layer of work built on top of a result that hadn’t happened yet.

Nine months in, I was finally asking whether this audience would pay for what I had made.

The answer I didn’t expect

A few days later I started asking people who had attended the workshops and opened the emails.

The people I spoke with had come for free help. Paying for an online course was different.

Looking back, I can see how much I had asked their enthusiasm to tell me. I read the attendance and engagement with the free content as proof the plan was working, without testing whether it would translate to paying for what I offered.

The question (and embarrassment) that stayed with me was how I had built for so long on an assumption I had never checked.

Why the work felt like progress

Those months were not idle. I wrote curriculum, recorded videos, and integrated everything into the platform I was using. I drew on years of teaching to shape the material into something students could work through and finish with a strong, flexible, and effective system focused on sharing their work and creative potential.

That work made the course good. It was well designed, and building it taught me a great deal. But I hadn’t set out only to make a good course, or to keep offering help for free. I wanted a viable business, and none of that work touched the question of whether anyone would buy what I was making.

Within the plan, though, there was always a clear next task. Another lesson to record, another module to finish. Each completed piece gave me a sense of progress while the uncertainty underneath it became easier to overlook.

I felt as though I was reducing risk. My investment kept growing, and each layer made the underlying assumption more expensive to question. By month seven, asking whether anyone would pay would have felt like a threat to everything already built.

I can understand the appeal of staying with the next task. It was work I knew how to do, and completing it gave me something definite to show for the day. Asking someone to buy meant making room for an answer I couldn’t control.

What a smaller step could have shown

I could have offered a single paid workshop much earlier. It wouldn’t have settled whether people would buy a $500 course, but it would have shown me how they responded when I asked them to pay for a smaller piece of the work.

That response could have changed what I built next, while there was still less to change.

I could have run ten more free workshops and still left willingness to pay untested. A useful next step needs to touch the question we’re actually asking.

The learning also depends on returning to what happened. The free workshops were actions too, and I had their responses in front of me for months. What I needed was a closer look at what those responses showed and what they left unknown.

A place to begin

Think of something you’re planning or building. What are you counting on that you haven’t yet had a chance to check?

Choose an assumption that would change your next decision if it turned out to be wrong. Then consider a small action you could take this week to learn more about it.

Before you begin, decide what you’ll watch for. Afterwards, return to what happened and ask what it gives you reason to change, try, or investigate next.

The quiet of that launch day made one unanswered question impossible to overlook. What I’m still learning is how to make room for that kind of question sooner, while the answers can help shape the work.

Until next week, may your next small step tell you something you couldn’t have planned for.

Jeff