Why I Was Working But Making No Progress (and What Fixed It)

There was a time not too long ago I spent way more time than normal repeating myself. The problem wasn’t my inability to express my thoughts. It was that the people I was talking to couldn’t remember the stories and shared experiences I was talking about.

What started as a dropped memory or sequence of events occasionally, became progressive memory loss.

Tough days for sure. For my loved ones and for me. Too much time spent in hospitals, rehab centers, and – eventually – funeral homes. And too many lifelong happy memories now tainted by those last few years.

Working All Day but Not Making Progress

I wasn’t thinking about any of this when I sat down to work last week.

But it found me anyway.

There’s a specific kind of frustration that shows up when you’re working all day and still feel like nothing is moving.

For seven or eight days straight, I put in full days. Not casually working. Sitting down, doing the work, checking things off.

But the list kept growing faster than I could complete it.

Every step forward opened three more things that had to be figured out. The never-ending growth was overwhelming me.

Somewhere in the middle of the week, it became clear the problem wasn’t how hard I was working.

At the time, I was juggling three separate projects: AutomateOneThing (AOT), a website and brand for solo operators, AI, and automation; Finance Abridged, a brand new, highly-automated, faceless YouTube channel I had just started 12-week traction test with; and ReimaginedLiving, a website that focuses on general health and aging.

All three existed in some form. Barely started. None had meaningful traction.

The issue wasn’t effort.

It’s that most of my work didn’t make me feel like I was making progress.

For Finance Abridged, I was building and troubleshooting automations to get the test running properly. Workflows, integrations, and making sure everything would function without constant intervention.

For AutomateOneThing, I was stuck on something more basic. I didn’t have a clear sense of who I was building for. I could describe the audience in general terms, but every attempt to narrow it down opened more questions. It, and I, felt lost, disconnected.

Who exactly is the customer?

What problem do I solve first?

What would they actually pay for?

How do I position this in a crowded AI and automation space?

No clear answers. Just more branches. All with uncertain answers.

So the work expanded.

I stayed busy.

But I couldn’t point to anything and say, “this is working.”

Feeling Overwhelmed and Stuck Between Too Many Projects

All this coalesced in about a week. Maybe ten days.

During that time, it took over all my waking hours. It even invaded a few of my dreams.

The sense I wasn’t getting anywhere. Running on a treadmill. That question of how to change things…or to just struggle through them.

When I sat down to work, instead of pushing into the questions and trying to make progress, I started pulling away.

I didn’t stop working. But I stopped working on what I had told myself mattered most.

I’d open something else. Look at a different idea. Shift into something adjacent with a clearer path forward.

It was avoidance.

Not dramatic. But consistent.

The arguments piled up in my mind.

People are trying to use AI and automation to run their businesses. They have problems. They spend money. That means it’s a solid niche.

The Finance Abridged test was already running. It needed to continue.

ReimaginedLiving had a direction, even if it wasn’t fully formed. And it was subject I really liked.

In my logical mind, the decision was simple. I kept telling myself, “Stick with it. Don’t pivot again. You’ve already done that too many times. At some point you just have to commit and push through.”

It made sense.

It just didn’t change anything about how I felt.

The gap between what made sense and what I could actually bring myself to do kept widening.

Why I Wasn’t Making Progress (Even While Working All Day)

The turning point wasn’t planned.

It started as another form of avoidance.

I watched a video about nutrition and Alzheimer’s. It’s a topic that’s been on my mind for a while. A few years ago, both of my wife’s parents died from dementia-related illness. And before my mom passed last year, I wondered if her memory loss was normal or it there was something more to it.

So the video grabbed my attention. Because I want to protect myself and my wife from those horrible conditions.

Instead of working on the projects I ‘should’ have been working on, I opened Claude and started asking different questions.

Is there a gap in the nutrition and brain health space?

Is there something specific around Alzheimer’s and dementia prevention not being addressed well?

Is there a business opportunity there?

That was the entry point.

But because I had also been working on AOT and Finance Abridged inside Claude as well, it had context about me and my life I hadn’t connected yet. It knew what I was trying to build.

The conversation shifted.

It wasn’t just about the new idea. It became a comparison between what I was doing and what I was actually interested in.

As we worked through it, something quickly became clear.

I didn’t have a real customer in mind for AutomateOneThing.

I could describe the audience, but I couldn’t picture a specific person or feel the problem in a concrete way. That lack of clarity showed up in everything I was trying to get done.

At the same time, this health and dementia angle was different.

The customer wasn’t abstract.

It was me.

My wife.

People our age who have watched parents decline and are starting to think seriously about what it means for their own future.

That difference mattered and Claude brought it to my attention.

One direction required me to figure out who I was talking to. The other didn’t.

How I Decided Which Project to Focus On

Once that became clear, the next steps followed naturally.

I decided to stop building AutomateOneThing.

Not because the niche doesn’t exist. It does. But because I didn’t have a clear handle on the customer or the entry point. Everything depended on solving that first, and I wasn’t close.

Finance Abridged stayed as-is.

It’s in the middle of the test and it’s largely automated. It takes a few hours a week to maintain. The decision is simple: let it run and evaluate it when the data is in.

ReimaginedLiving was a tougher decision. It was similar to, but different from my new angle. Could it be used or should it be scrapped?

The broader “health and wellness” framing wasn’t specific enough. It didn’t have any clear, urgent problems a non-medical expert could claim. There was no specific audience I could target.

I wanted to reach people like me. People who have watched loved ones suffer one of the cruelest deaths imaginable. They know there are things they could do to greatly diminish the odds of suffering like their loved ones and they’re still young enough to do something about it.

That specific audience demographic demanded a name change as well as a change in approach.

ReimaginedLiving became UndauntedLiving. And instead of being website first, it’s going to be YouTube first.

I’ll use my story to connect with people like me, walking through some of the same things my family and I walked through. I’ll talk about how we can fight the cruel, insidious enemy years before it actually appears through practicing better nutrition, behavioral and social habits now.

What Happened When I Stopped Splitting My Focus

The immediate change in focus wasn’t excitement.

It was relief. And hope.

The constant expansion of the to-do list stopped. Not because there was nothing to do, but because the work is now tied to a smaller set of decisions with real clarity.

I’m not trying to build three different things at once, which makes it possible to focus on output instead of preparation.

Instead of setting up systems indefinitely, I can work on things that actually create progress. Content. Direction. A defined audience.

Not because any of the tasks got easier, but because the connection between my effort and the outcomes became clearer.

When to Stop a Project (And Why It’s Not Failure)

From the outside, this looks like changing direction again.

That’s not entirely wrong.

But what actually changed was stepping out of the things that made logical sense into something that makes logical sense and creates an excitement in me rather than a dread.

The new direction isn’t guaranteed to work any more than the original ones were. Breaking into health and nutrition is anything but simple or easy.

But it is clearer. More specific. Easier to act on.

And right now, that’s enough. Enough to honor what those years continue to teach me about life. And about myself.