I read Austin Henley’s post Automating my job away on a Friday night and did the laziest possible thing with it.
Henley’s whole piece builds to one prompt. A friend who runs a startup tells his team don’t do anything three times - if a task comes round more than twice, automate it. Henley took that to its logical end and pointed his coding agent at its own history.
So I copied his idea, swapped “Copilot” for “Cowork”, and pasted this in:
The work I’ve been doing between Claude Cowork and Excel lately has been considerably more involved than what follows. But this example makes the pattern clear - and it captures exactly why the combination saves so much time and frustration.
I had a list of 20 ASX stocks in an Excel file. Two columns: ticker code and company name. I wanted two more: market cap and 12-month return, pulled from most recent data.
A confirmation email landed in my inbox this week. VIC N Drive Meet. A curated backroads blast with a bunch of fellow Nthusiasts, organised by Hyundai N Australia.
I’m a lifelong revhead. The smell of a good back road on a cool morning, a car that actually wants to be driven hard, and people who feel the same way about it - that’s a perfect Saturday. The i30 N is the best bang-for-buck hot hatch on the market, and I’ll die on that hill.
I’m registered, I’m keen, and I already had the booking email and a calendar entry sorted.
Then I asked Claude Cowork a simple question: “I have these details in my calendar and Gmail - should I capture this information elsewhere? Why? How?"
Every few months, another “how to set up Obsidian so it really works for you” essay does the rounds.
This morning I found yet another one. It looked good. Genuinely thorough. The kind of post where someone has clearly spent weeks refining their setup and another week writing about it.
And I had absolutely no idea what to do with it.
Do I read it now? File it somewhere? But where? The irony of not knowing how to file a productivity system article inside your productivity system is not lost on me.
Relentless Productivity™ has a dark side. The more capable your tools, the faster the work accumulates - and with Claude Cowork, that accumulation happens session by session, each one spawning its own entry in an ever-growing sidebar list that becomes harder to read by the day. I know this from experience. My Cowork sidebar had grown to the point where I could no longer tell what was live, what was done and what was waiting.
As I prepared to race out the door this morning, I snatched up the hand-scribbled agenda for the team meeting and thought: “Oh, at a minimum, I should photograph this.” So I don’t lose the piece of paper. The next thought was: “Hey, I should send this to Claude.” Before I knew it, Claude had read it and turned it into a proper document - ready to throw into the stack for the day ahead.
A friend of mine, let’s call her Jane, runs a marketing consultancy. Fifteen years in, small team, strong client list, had used Claude for chat only. I offered to spend an hour showing her what’s possible now we’re well beyond that. Wednesday night I realised winging a 75-minute demo next morning would burn too much time on navigation and too little on value. I opened Claude Cowork, uploaded a brief I’d quickly hacked together from emails and went on with my evening.