I Built a Quiz Funnel, an Email System, a Coaching Program, and a Workshop. Then Threw It All in the Trash.

It was the right call

I woke up this morning with a familiar feeling: “What the f--- am I doing?”

That’s not unusual. I feel some version of that most mornings.

The triplet demons of self-doubt, second-guessing, and imposter syndrome whisper in my ear, telling me that whatever I’m doing isn’t enough or the right thing.

Then I sat down for a session with someone I’m helping become an AI-enabled operator.

Two and a half hours later, the demons were quiet. Not because I’d figured everything out.

Because I was in flow, helping someone do a real thing she’s excited about. At one point, she said, “Mind blown. That’s so crazy.”

She’s already using what we’ve built together to match consultants to projects, and her stakeholders are telling her the output is thorough and useful. That’s not theoretical. That’s someone’s actual business getting better.

That kind of session is a reminder: the doubts get loud when I’m sitting still. They go silent when I’m in motion, actually helping somebody directly.

And it reminded me that the new direction I’ve chosen is the right one.

Which means that what I spent six months building before that?

It was the right call to walk away from it. Even though it wasn’t really thrown away.

The Résumé of Things I Threw Away

In July 2025, I launched this publication: The Unscaled Solopreneur.

The premise: help solopreneurs build calm, profitable businesses without the grind. I also realigned my tactical AI newsletter, How I AI, on a similar vein, keeping it on a weekly cadence focused on practical ways to use AI to create emails and content for the same audience.

By September, I was all in:

• I started sending daily emails on September 30.

• Built a quiz funnel called the “Unscale Me Quiz” to diagnose what was keeping solopreneurs stuck.

• Ran a workshop called Email Alchemy for $27, teaching people how to mine coaching calls for content using AI.

• Launched a coaching program called the Unscaled Engine.

• Published here on Substack weekly, sometimes more. Posted daily Substack Notes.

• I wrote 149 daily emails.

I showed up every single day, even from the road, even when the emails weren’t brilliant. I put real effort into every piece.

The triplet demons followed me the whole way, but I kept building.

There was traction. A coaching client signed up. People took the quiz. The workshop happened. I got replies and kind messages.

It wasn’t nothing.

But the Numbers Don’t Lie

By January, my other newsletter had more unsubscribes than new subscribers. The daily emails had built some connection, but I couldn’t point to real momentum.

My coaching client got her money’s worth in terms of direction, clarity and un-bottlenecking a few things that had kept her stuck for years.

But she didn’t recover her investment in the way I wanted her to. That gap between “she got value” and “I wish the results were bigger” ate at me.

I wrote in my journal on February 6: “Everything so far this year feels like it’s reinforcing the self-image, or the reality, of a person who tries and fails no matter what.”

I stopped sending daily emails on February 10. The last one was, ironically, about authenticity.

The Thing I Couldn’t Say Out Loud

Here’s what was really going on: I was trying to make money online by teaching other people how to make money online, and I just didn’t feel good about it.

I was teaching people how to build unscaled solopreneur businesses. But I hadn’t fully built one myself. I knew the pieces. I’d done all of them in different ways for different clients over the years.

But I hadn’t been able to put it together for myself.

That’s not a business. That’s imposter syndrome with a Substack.

I’d told myself the quiz, the workshop, the emails, the coaching program would prove the model. Instead, they proved something else: the direction was off.

Then One Session Changed the Equation

About six weeks ago, I started working with someone one-on-one to help her become an AI-enabled solopreneur (the same person from today’s call).

Biweekly calls teaching her how to use AI to save time, get more done, and make her business run better.

The promise isn’t “how to make money.” The promise is to help her become an AI-enabled CEO.

And that just feels more aligned with what I can teach right now, what I want to teach, and who I can help in a way that doesn’t add stress to my life.

I don’t feel guilty about her results the way I did with my first coaching client. Because the value is immediate. She’s learning a practical skill she uses that week. Not chasing a revenue number I can’t guarantee.

This morning reaffirmed that. I woke up doing the usual “what the f--- am I doing” routine.

Had the session. Got into flow. And for two and a half hours, the demons shut up. Because I was doing the thing, not thinking about the thing.

That’s what all the stuff I built before was really about. It wasn’t bad.

It was just part of getting the parked car moving.

You Don’t Get Anywhere in a Parked Car

I don’t regret building any of it.

I built a quiz funnel. I’d been wanting to do one for years, and I finally did it. The daily emails and Substack Notes showed me I could show up consistently. The workshop showed me I could do a paid workshop. I didn’t get as many paid sign-ups as I wanted, but I did it. The coaching client showed me the gap between what I was selling and what I could deliver with confidence.

And this publication didn’t get thrown away. Neither did my tactical AI newsletter. I just refocused both of them on a slightly different angle. You’re reading the refocused version right now.

If I’d felt confident in the direction, the things I created were good enough. I could have doubled down, made them better, stuck with it. But putting them out into the world is what showed me it didn’t feel right.

I couldn’t have learned that from a whiteboard or from prompterbating with ChatGPT.

You don’t get anywhere in a parked car. Sometimes you have to drive in the wrong direction to figure out where you’re actually going.

I’m rebuilding now.

My new direction: helping solopreneurs and small business owners become AI-enabled operators who do better work in less time.

I’ve got a new low-ticket product in progress called The AI Operator Quickstart. And yes, I’m taking too long on it because the triplet demons are still here. But I’m building.

Even after walking away from six months of work, the doubts still show up every morning.

But they get washed away the moment I do the thing.

Here’s What I’d Tell You

If you’ve built something and it’s not working, or it’s working but it doesn’t feel right, that’s not failure. That’s data.

The only real failure is staying parked.

Build the thing. Ship it. See how it feels and how other people respond. Then decide if it’s yours.

What’s one thing you’ve been sitting on because you’re not sure it’s the right direction?

Build it anyway. The clarity is on the other side of the doing, not the thinking.