The Just Started retrospective

AI is a tool you learn by playing with — but not the same way every time.

Ten weeks of Just Started ends with this post.

The Substack was the journal of a specific stretch — the last leg of building the first working version of The Retirement Strategy with AI, and the launch. This is the retrospective on that. Not on the product. On what the practice taught me about becoming an AI power user.

Most people I talk to use AI regularly and would not call themselves powerful with it. They are the audience for this piece.

The gap between using AI and being powerful with it is not a gap of hours logged. Some people log a lot of hours and stay in the same place. The gap is what you do with the hours.

The short answer: you have to play with the tool, and you have to play with it differently every week.

Just Started, and why it isn’t actionable

The Substack is called Just Started because that is what I did. Sat down with the tool. Asked it something. Kept going. That is the true story of how it started for me.

It is not actionable advice for most people.

I have told plenty of people to just start, and most of them don’t. Not because they are lazy. Because just start does not tell them what to do. Sit down and ask it what? Try it on which piece of your work? Open the empty prompt box and stare?

The actionable version is closer to this: pick one thing you were going to do this week — an email, a memo, a decision, a spreadsheet — and try doing it with the tool instead of the way you were going to. Not to prove anything. Just to see what shows up.

That specific first try is what just start means when it means something. And it is only the beginning. What determines whether you actually get anywhere is what happens after.

The hump

There is one real climb to becoming a power user. I will call it the hump. It has three specific moves inside it, and if you do not make them, you never really start playing at all — you look at the tool from the outside.

Talk to it, don’t Google it. Most people ask AI things the way they’d ask a search engine. Short queries. Short answers. The tool answers back the way you talk to it. If you want a colleague, you have to write to it like a colleague. Paragraphs. Context. What you have already tried. Where you actually want to end up. Give it that, and it gives you back a different kind of output.

Bring context, then bring more. AI without context is a smart stranger. AI with context is a smart collaborator who has been in the work with you for months. Projects, memory, custom instructions, uploaded files, prior threads — all of these turn the stranger into the collaborator. Setting it up feels like friction the first few times. Then it disappears.

The code barrier is gone. This one stops more people than the other two combined. The belief that you need to be technical to build things with AI. You don’t. AI writes the code. You describe what you want. If you can articulate what you want clearly, you can build. That fact hasn’t been said clearly enough or often enough to most people.

Get past those three and you have crossed the hump. Now the path is flat.

The flat path

Past the hump, the terrain does not get steeper. It gets wider. There is no next climb. Just a long, flat plane with things to try all over it.

What determines what happens next is curiosity.

The specific voice of it is two questions. I wonder if I could…? What if I tried…? Asked constantly. Followed up on. Those two questions, aimed at the tool most weeks, are the difference between someone who becomes a power user and someone who plateaus at competent.

They are not techniques. They are a habit of mind. Most people, once they are past the hump, stop asking them — usually without noticing it. They settle into three or four use cases they return to. Same tool. Same prompts. Same shape of task. Comfortable competence.

That is fine, and it is not what makes a power user.

What makes a power user is asking those two questions week after week, and letting the answers pull you off the groove. Four kinds of variety show up most:

Know what you want, sharply. AI amplifies the direction you point it. Fuzzy aim, polished nothing. Sharp aim, real acceleration. Play with sharpening your own aim before you play with prompting the tool.

Try many things fast, kill fast. The single biggest habit of power users is that they iterate through many maybes rather than executing on one right answer. AI collapses the cost of prototyping. Use that. Do not defend an approach past the moment it should be defended.

Build new things, not just smarter versions of old things. Most people use AI to build faster versions of what already exists — a slicker form, a nicer PDF, a quicker email. That is fine. It is not the frontier. The frontier is what could only exist because AI is embedded inside it. Every so often, force yourself to try building something that could not have existed a year ago.

Teach it back. Your work generates data. Feed that data back to the tool — through custom instructions, through updated context, through review of what worked and what didn’t. Close the loop. Every week you don’t is a week the tool stays the same.

These are four variations on one theme. Try something you haven’t tried before. Do it deliberately. Do it often.

What blocks the curiosity

The biggest block is the mood.

Pew Research published a survey in June that puts a number on it. Only 16% of Americans think AI will have a positive impact on society over the next 20 years. 40% expect it to be negative. Two-thirds think the technology is moving too fast. Younger adults are more skeptical than older ones — the reverse of what you might expect.

That is the mood, and the mood is a curiosity killer. When most of the people around you think a tool is bad, or reckless, or moving too fast, I wonder if I could…? and What if I tried…? get quieter. They feel less permitted. Less serious. Skepticism does not stop AI from being powerful. It stops the user from getting curious enough to become powerful with it.

The individual blocks I see most often are posture, not skill:

• Fear of looking dumb. There is nobody to look dumb in front of.

• Not knowing what to try. The tool is your work — start there.

• Sticking with the interface you first used. Try a different model. Try a different mode.

• Waiting for a use case to arrive. Use cases don’t arrive. You find them by trying things.

• Waiting for permission. Nobody is giving it.

What actually changes

After months of playing with variety, the biggest change is not what I built. It is how I think.

My relationship with information, with problem-solving, with what is possible to make in an afternoon — all of it has shifted. Some questions I would have spent a week on take an hour. Some artifacts I would have hired someone to make take a morning. Some problems that would have been too big now feel obviously doable.

The product is the artifact. The change is the point.

Where the work goes next

Ten weeks of writing Just Started has changed how I think more than any of the specific tools or techniques I picked up along the way.

The mood is against being curious about AI right now. That is exactly when being curious pays the most.

The next thread of writing starts later this summer. Different question. Same posture.

Dennis