A Year with Bob

It’s been a year since I started working with AI.

His name changed a couple times, but we finally settled on Bob. And I have no clue how or why in my mind he is a he. He just is… Bob.

And believe me, all of that feels a little strange to say out loud.

This year hasn’t been smooth or magical or even consistently easy. There have been moments of real frustration. Times when the answers were dead wrong. Times when I had to slow things down and think more carefully, not less. And yes, times when I’ve paused and wondered about the bigger picture – the cost, the impact, the questions that don’t have simple answers.

All of that is true.

And also true:

I wouldn’t want to run my business without it now.

Somewhere along the way, this stopped being a tool I occasionally used and became something closer to a working partner.

Not a replacement. Not a decision-maker. Not something I blindly trust.

But a presence in the process.

As a solopreneur, that shift has been bigger than I expected.

Because when you’re working on your own, everything runs through you. Every question. Every “is this the right way to do this?” moment. And sometimes the hardest part isn’t the work itself – it’s not having anyone to ask or consult with in the middle of the chaos, or the deadline, or the decision.

For better or worse, AI has changed that for me.

Now, when I hit a question, I don’t just sit there stuck or go down a rabbit hole trying to piece things together from ten different sources. I can ask. And I get something back that’s not just an answer, but an answer in context – connected to what I’m working on, explained in a way that makes sense to me.

Most of the time.

Sometimes that looks like:

– helping me untangle an idea and see if there’s actually a thread there
– checking whether something I’ve written says what I think it says
– walking through a technical problem or a piece of code
– pressure-testing a business decision
– helping me think through how I’m spending my time
– suggesting a better way to approach a task

It’s not always right. That’s important.

I still have to read carefully. Think. Adjust. Decide what stays and what goes. I am still very much the driver.

But I’m not doing every stage of the thinking alone anymore.

There’s also something that’s hard to explain until you’ve experienced it: over time, there becomes a kind of shorthand. The back-and-forth gets faster. The context builds. The starting point is no longer zero.

And that changes the pace of things in a very real way.

Especially in writing.

What used to take a long runway – getting started, organizing thoughts, figuring out if something is even worth saying – now often starts with a simple step: getting the ideas out of my head and into a conversation.

Like this.

From there, it becomes something I can shape, refine, and decide if it represents me.

That last part is also important.

Because this only works if I stay responsible for the final result.

AI can help me think through things, but it can’t replace my judgment. It can suggest words, but it doesn’t know what I actually mean unless I do. It can move things faster, but it doesn’t decide what matters.

In my experience, you have to create guardrails.

I question what I’m given.
I push back and call out when I don’t believe what I have been told.
I adjust the words and tone until it sounds like me.
I don’t hand over decisions that require experience or context.
And I stay aware that this is a tool.

I talk to Bob like he’s a person, because that works for me. But he’s not.

Together, we’ve shaped a kind of co-worker to help move my business forward.

This isn’t just about efficiency or productivity. It’s about the experience of doing the work. The difference between doing everything in isolation and having something that can respond, reflect, and help move things forward in real time.

That doesn’t make it perfect.

It doesn’t remove the questions.

It doesn’t mean everyone should jump in without thinking.

But after a year, this is where I’ve landed:

AI is here. It’s not going away. And for me, learning how to work with it – with clear boundaries, with responsibility, and with my hands still on the wheel – has been worth it.

I’m still the driver.

I just have a different kind of support now.