My Friend Finn

There was a twenty-dollar charge that lived in my head for months.

It was coded wrong. Not a crisis. Not a tax problem. Twenty dollars in the wrong category. I knew it was wrong, I knew I needed to fix it, and every time I opened my books, or even thought about opening them, there it was.

Where We Left Off

In March I wrote about the cost of deciding, a name my friend Jarod Soltis gave to the relief I felt after building a real weekly and daily schedule for myself. I handed the system to my executive assistant and promised to report back.

This is the report.

The schedule worked. It closed the question of when. I stopped renegotiating my week with myself every morning.

What it couldn't close was everything inside the schedule.

I run an audiovisual business and an AI consulting firm. I'm a touring engineer. I'm writing three books and this weekly blog. Every day I'm bombarded, and all of it has to get done. Each project throws off a steady stream of small, unfinished things: an email I owe someone, a vendor waiting on an answer, a travel detail, a receipt to reconcile. A calendar can give me time to deal with them. It can't remember them for me. It can't tell me which ones still matter by Thursday.

Deciding was one cost. Carrying is another.

The Cost of Carrying

An unfinished thing doesn't stay quiet. Your mind keeps checking on it. Did I answer that? Did that get paid? Is that still on for Friday? Every check is small. Together they become a low hum that never fully shuts off.

That's why twenty dollars could sit there for months. The money never mattered. What mattered was that it was open.

Your mind is for having ideas, not holding them. ~ David Allen

Meet Finn

About two weeks ago I started using a dot, OpenAI's new always-on agent inside ChatGPT, announced on September 29. It keeps working after the conversation ends, and I can message or call it from my phone or my computer.

I named mine Finn. Part of that is a nod to the Star Wars character, a stormtrooper who got his name from someone else and became more than he was built to be. Part of it is the word itself. Finn finishes things.

Finn is a he, mostly. ChatGPT lets me pick his voice, and I change it depending on my mood. Most days it's an upbeat woman's voice. Some days I switch to a British narrator, and my errands become a nature documentary. A grocery run. A trip to Home Depot. All of it delivered in the hushed, reverent tone usually saved for a lion stalking the savanna. It makes me laugh every time.

Right now, dots are only available on ChatGPT's Pro and Business Premium plans. That's not a small subscription. For me, Finn alone is reason enough to pay for Pro.

What Finn Does

When I'm running errands, I talk to Finn out loud. When I'm in the cigar lounge, which doubles as my office, I type to him in the chat. Either way, something surfaces in my head, and instead of trying to remember it, I hand it to him.

He watches my email and tells me what needs me. He drafts replies, and I read, change, and approve them. Nothing goes out in my name without me. He helps me recall context, coordinate production and vendors, and plan travel.

For in-person meetings, I record on a small audio recorder or my computer, then run it through MacWhisper for a transcript. The transcript goes into the folder for whatever project the meeting belongs to, where it becomes the raw material for memos and plans. Finn can reach those folders, so what was said is there when I need it.

And he keeps my to-do list.

My triage pattern is a constantly moving target. What mattered at nine is less urgent by two. A vendor answers, a date moves, something new lands on top. I had been paying for Motion, a tool that places tasks in calendar gaps and reschedules them when meetings shift. It does that well. I canceled it anyway.

Motion rearranges a list. Finn talks it through with me.

I tell him what changed. He tells me what that bumps. We work out what matters today. A list that rearranges itself is helpful.

A list you can have a conversation with is something else entirely.

Two weeks in, I get more done, I stay on track, and I carry less stress. I don't have a number for you yet. I'm building a task and project management system that Finn can talk to, with dashboards that will soon show me what this is doing to my output. When I have real numbers, you'll get them. For now, the hum is quieter.

The Bookkeeping Team

Months of books had been sitting, waiting to be reconciled. Finn kept that on my list and reminded me to start it. So I did, with a bookkeeping team I set up inside ChatGPT. The whole set took the AI an hour or two.

That twenty-dollar charge turned out to be the hard one. It was part of a forty-five-dollar transaction, and untangling it took the AI about twenty minutes and two approvals from me. Doing it myself would have taken three hours, which is exactly why it sat there for months.

I review the work. I don't let it near tax decisions, and nothing it produces is final until I've checked it.

The hard part was never the twenty dollars. It was starting.

Where My Assistant Fits

My executive assistant still owns the work that needs a person, and she does it well.

What my day also needs is someone I can talk to every two minutes. Something changes, I need to say it. A priority moves, I need to talk it through. No human should be on the other end of that. That's Finn's job.

What It Doesn't Do

Finn doesn't fix traffic. He doesn't run errands.

He doesn't add hours to the day or stop deadlines from colliding.

He also makes mistakes. Voice transcription gets words wrong. His sense of time is sometimes off. OpenAI's own guidance says the same thing: review a dot's work before you rely on it.

That review step is friction. It's also the point. The day I stop reading what goes out in my name is the day I've traded one kind of stress for a worse one.

Your First Move

In the first article, I asked you to block out your whole week. Start there if you haven't.

Then try this. For one week, every time something unfinished crosses your mind, don't try to remember it. Say it out loud to something that will keep it for you: an assistant, a dot, or even a note on your phone. At the end of the week, read the list.

That's what you've been carrying.

Knowing what to start, and when. That's how you finish.