Last week I asked whether you were using Claude. The replies split almost right down the middle.

But here’s what actually got me:

Not one person said no because they weren’t interested. Every single “no” was really “no, but show me.”

So. Showing you.

And before anything else — I want to be clear that I don’t get paid a dime to talk about this. No affiliate deal, nothing. I’m just genuinely obsessed and I want you to have something useful out of it.

The short answer: every month my bookkeeper sends me a spreadsheet full of transactions nobody can identify, and I used to dig through Gmail and old Amazon orders to figure out what each one was. Now I hand it to Claude Cowork. I type out — in plain English — where the sheet is, what month I need, and my rules for what counts as business versus personal. It goes through my Amazon orders, my Gmail and my Whatnot activity and fills the sheet in, flagging anything it isn’t sure about instead of guessing. Then I told it to save the whole thing as a Skill, so next month I just say “do the bookkeeping thing.”

What does Claude cost?

Regular Claude — the chat part — has a free version. Actually free, not a trial.

The part I keep talking about, Cowork, is on the paid plans. That starts at Pro: $20/month, or about $17/month if you pay for the year.

One of you wrote back and said you have no money to invest right now. I really appreciated that.

So here’s my honest advice: go use free Claude. Today. It costs nothing, it’s genuinely good, and you’ll learn a ton before you ever spend a dollar. The paid version will still be there when it makes sense for you.

The thing that tripped me up at first

Cowork isn’t the regular chat box.

You download the Claude desktop app, and Cowork is right there next to chat. Same place, different mode.

Chat talks to you. Cowork goes and does things.

The task I handed over: my monthly bookkeeping pile

Every month my bookkeeper sends me a spreadsheet full of transactions nobody can identify.

A Venmo payment. An Amazon charge. A credit card line with zero context.

And I have to go figure out what every single one of them was.

Which means digging through Gmail for old Venmo receipts. Pulling up months-old Amazon orders. Staring at a charge trying to remember whether those storage bins were for inventory or for my closet.

It’s not hard. It’s just tedious. And it’s the exact flavor of tedious my brain refuses to do — so it sits there while I go do 47 more interesting things.

(You know the feeling.)

How I use Claude Cowork to do my bookkeeping, step by step

Here’s what I actually did.

1. I typed something incredibly simple

Not “help me with transactions.” That gets you nothing.

Here’s roughly what I actually typed, and I want you to see how unimpressive it is:

(I opened up Amazon and Gmail and logged in first so it could get right to work.)

“Here’s my bookkeeper’s sheet [link]. Go through my Amazon orders and my Gmail for August, figure out what these transactions were, and fill in the notes column. Groceries and vitamins are personal — shipping supplies and storage bins are business. If one order has both, only count the business part. If you’re not sure about something, flag it for me instead of guessing.”

That’s it. That’s the whole thing.

No special formatting. No prompt template I bought somewhere. Just… what I’d say to a person.

The only real trick is being specific. “Help me with my finances” gets you nothing. “Here’s the sheet, here’s the month, here’s what counts as business” gets you your afternoon back.

2. Then I watched it go to work

It logged into my Amazon. Opened up each order. Reconciled them one by one.

Then into my Gmail, where it found every Venmo payment and logged them all — adding notes wherever it could tell what something was for.

While I did something else entirely.

And I know what some of you are thinking, because I thought it too: wait, I’m giving it access to my Amazon?

Here’s what that actually means. It’s using the browser on my computer, where I’m already signed in. It’s not getting my passwords. And I can watch the whole thing happen on my screen in real time — and stop it any second.

Which honestly I did, a lot, the first couple times I used this. Now I mostly go make coffee.

3. It got stuck, and that’s the part I want you to see

There were 6 charges it couldn’t identify.

So I said: go into Whatnot, look through my activity, and tell me what these were.

And it did.

I want you to notice that, because it’s the thing nobody tells you about working with AI. It’s not a magic button. It’s a back-and-forth. It got 90% of the way there, told me where it was stuck, and I pointed it at the missing piece.

That’s the actual skill. Not perfect prompts — just knowing where the answer lives.

4. And then the part that made me sit back in my chair

When it finished, I just said: “Save this as a Skill so I can do it every month.”

That’s it. Plain English, same as everything else.

And now all of it — the sheet, the rules, where to look, what to flag — is saved.

Next month I don’t explain any of it again. I say “do the bookkeeping thing” and it goes.

Why saving it as a Skill is the real win

That’s what I want you to really hear.

It’s not that AI did one annoying task for me.

It’s that I taught it my process ONE time, and now that task is basically gone from my life. Forever.

Think about what that’s worth on something you do every single month.

Questions I get a lot

Do I need the paid plan to try any of this?
No. Regular Claude is free and it’s genuinely good. Start there, learn how it thinks, and upgrade later if and when it makes sense for you. Cowork itself is on the paid plans, starting at $20/month.

Where is Cowork, exactly?
This is the part that tripped me up. It’s not the regular chat box on the website. You download the Claude desktop app and Cowork sits right there next to chat — same place, different mode.

Wait, am I giving it access to my Amazon?
I thought the same thing. What’s actually happening is that it’s using the browser on my computer, where I’m already signed in. It’s not getting my passwords. And I can watch the whole thing happen on my screen in real time and stop it any second — which I did, a lot, the first couple of times.

Do I have to be technical?
Nope. There’s no code anywhere in this. You saw what I typed. It’s the same thing you’d say out loud to a new assistant.

What if it gets something wrong?
That’s why I tell it up front: if you’re not sure, flag it for me, don’t guess. It got about 90% of the way there on its own and told me where it was stuck, and I pointed it at the missing piece.

What else could I use this for?
Anything repetitive and annoying that follows rules you could explain out loud. Print on demand designs. Whatnot. Research. Getting listings written. That one thing that’s been rotting on your to-do list for months.

What should I walk through next?

Okay, one honest note before you go.

A lot of you wrote back about bookkeeping and accounting specifically.

Which might be because bookkeeping is the thing everyone on earth hates. ?

Or it might be because I’m the one who brought up expenses last week, so that’s what was sitting in your head.

Probably some of both.

So let me widen it: what would you actually want me to walk through? Print on demand designs. Whatnot. Research. Getting listings written. Some specific thing in your business that’s been rotting on your to-do list for months.

Tell me in the comments. I read every one.

I’m Rachel Rofé. I’ve been building online businesses since 2006, I sell luxury resale live on Whatnot, and I’ve taught over 18,000 students how to make money with print on demand and Etsy.