Level 0 — The Pitch
It's 6:47 AM. You sit down with your coffee at your computer. Your Chief of Staff is already there:
Morning. Want to knock out one small thing before the day gets going? Your Screenshots folder has 1,200-odd files piled up since last spring — receipts, memes, a parking spot you photographed once. We could clear the junk in about eight minutes.
You say yes. It walks you through them in fast batches — keep, keep, gone. Pulls the three real receipts into a folder so they don't vanish with the rest, and sets the flight confirmation somewhere you'll actually find it again.
One nagging thing — gone before the coffee's cold.
That's your Chief of Staff.
What that actually means
Not an assistant. Not a secretary. A Chief of Staff is the right-hand to the CEO — the one trusted person who knows what's on the plate better than the boss does, and who's known for a single thing above all else: getting things done.
Nearly every Fortune 500 CEO has one. They pay a fortune for it. The rest of us never had the option.
Until now.
A week with one
- Monday: Your Downloads folder — 1,400 files going back to 2021. Sorted the keepers, trashed the rest, in twelve minutes.
- Tuesday: Drafted the "thanks, but not this round" reply you'd been dreading — in your words, ready to send.
- Wednesday: Found nine near-identical versions of the same document scattered across your Desktop. Kept the latest, archived the rest.
- Thursday: Turned 300 photos you'd dumped off your phone into clean folders by month — no more
IMG_4821soup. - Friday: Your Desktop was forty icons of low-grade dread. Now it's six folders that make sense.
- Saturday: No kill today — just a coffee talk. It asked what actually drains you, and what doesn't. (Turns out you'll happily reorganize the whole garage to dodge one awkward email.) Now it knows.
- Sunday: Keep it holy. No clutter today — just what matters most: what you're really after this year, the people you don't want to drift from, the faith you keep meaning to return to. Your Chief of Staff can help carry those, too — a prayer list, a reading plan, the note you've been meaning to write.
Five small things killed — all right there on your own machine — plus two quieter conversations: what drains you, and what matters most. Your computer's lighter. So are you.
One week. Stack fifty-two of them and that's a year. Stack ten years and it's a different life.
The contract
- Five minutes a day. That's the whole ask.
- One small thing, killed before coffee.
- Thirty days to a life with noticeably less friction in it.
What it costs
- $20 a month for an Anthropic Pro plan. That's the only bill.
- One twenty-minute setup, once.
- A computer that can stay home and stay on — a desktop, or a laptop that lives plugged in. (Why that matters in a second.)
What it doesn't cost
- Your weekends.
- Your sanity.
- A single line of code.
- A class, a coach, a "system," or another subscription you'll forget you're paying for.
Where the help happens — and where it's headed
Everything above happens right where your Chief of Staff lives: on your computer. Your files, your folders, the drafts you keep avoiding. That's what it can touch on day one — and it's plenty to start.
One practical note: pick a computer that stays home and stays on — a desktop, or a laptop that lives plugged in on a desk. Your Chief of Staff lives on that machine. A few levels in, your phone reaches it through that computer, and later it starts your morning brief before you're awake — both only happen while it's on. The more it's on, the more it can do for you.
Then it grows. As you connect your life to it — your email, your calendar, your accounts — it starts reaching out there too: sending the reply you drafted, cancelling the charge you flagged, handling the errand instead of just teeing it up. That's a few weeks in. The circle widens as it earns your trust.
On Day 2, it's brand new — it won't know you yet. You'll tell it a few things, and it'll remember. That's how every good working relationship starts.
And here's the part worth staying for: at first, you do these by hand, together. Then it starts automating the ones that rob you of joy — because that's the real reason they piled up. Nobody puts off a chore they enjoy. The goal was never to make you better at busywork. It's to hand it off.
Your Chief of Staff isn't a nag with a checklist. It's a second set of hands.
Ready?
Open Level 1 — Hire Your Chief of Staff. Twenty minutes from now it's hired, it's got a name, and it knows where your chaos lives. Tomorrow morning, you kill the first thing.
— Bob