How I Plan My Day Using Claude Cowork

I posted recently about my morning writing habit — 15-20 minutes of free-flow writing in Ulysses with brain.fm every morning. No structure, no agenda. Just getting thoughts on paper.A lot of people asked for more detail. So here's the full system — including the exact Claude Cowork setup I use, the prompt, the team role definitions, and what a real morning looks like. Copy whatever's useful.The morning writing follows a framework.There are three parts. The writing happens in Ulysses. Once I'm done, I export it as a .txt file and drop it into my Cowork folder. More on that in a minute.

The Process

Part 1: Free-flow writing.

I open Ulysses, turn on brain.fm, and write about whatever's top of mind. Sometimes it's something from yesterday. Sometimes it's a business problem — pricing, team dynamics, a project that's stuck. Sometimes it's bigger strategic thinking about where NOOON is headed or the new company I'm building.This part is usually a paragraph or two, unless something heavy is on my mind. On a recent morning, I spent most of this section working through office buildout decisions and our financial runway — burn rate, pricing gaps, whether we had enough months of cushion. That kind of thinking needs space, not a to-do list.More problem-solving happens here before 8am than the rest of the day combined.

Part 2: To-dos.

I pull in my running task list. What's in progress, what's high priority, what needs to be delegated, and what's been sitting too long.A real example from a recent morning:→ Revisit pricing for all project types (high priority)→ SOPs due Wednesday (high priority)→ Design support for a client — review feedback and provide direction→ Post 2x today→ Schedule the Pixel Pushers event→ Final files for a client (I need to do this since Tim is already booked)→ Referral tracker — make sure we're caught up on payments→ Reach out to my network for SSD interviews→ Work on Tim's next steps list ahead of our 1:1The critical filter: am I looking at CEO work, or am I looking at work someone else should own?

Part 3: Five Minute Journal.

Quick, structured reflection:→ I am grateful for…→ What would make today great?→ Daily affirmations. I am…→ 3 amazing things that happened yesterday…→ How could I have made yesterday better?Takes five minutes. Keeps me grounded. Some days the best thing that happened yesterday has nothing to do with the business — and that's the point.

Then I hand it to Claude.

I export the whole session as a .txt file from Ulysses and drop it into a folder called "Plan My Day Documents" inside Claude Cowork.Inside that same folder, I have a role definitions document for my entire team. It outlines exactly what each person owns:→ Victoria (Head of Ops & Sales) — proposals, pricing, CRM, pipeline, client onboarding, manages our EA→ Tim (Head of Design) — creative direction, design quality, mentors our junior designer, presents to clients→ Devin (Head of Development) — technical direction, manages dev contractors, scoping, code quality→ Jessie (Executive Assistant) — scheduling, admin, follow-ups, research, deck prep, proposal formattingI also have a transition plan in that folder — a roadmap to fully remove me from day-to-day operations by June 30th. Claude knows the plan.

The Cowork prompt.

Here's the exact prompt I use for the scheduled task:

‍Check Slack, Google Calendar, email, Notion and Circleback to give me a short briefing ahead of the day to get me caught up on everything that needs my attention.Then help me prioritize my work, delegating everything that does not fall within my role as the CEO. I should only be focusing on people, culture and numbers, as well as creating content, networking and speaking.The people who report to me are:Victoria - Head of Operations & SalesDevin - Head of DevelopmentTim - Head of DesignJessie - Executive AssistantYou can find details on roles in the folder to work in, along with a plan to fully remove me from operations by June 30th. I have also included a working plan for building my new hard of hearing company.I also tell it: I want to do one task each day that(1) moves NOOON forward and increases profit margins and revenue, and(2) pushes things forward in getting a clearer idea on what needs to be built for this new accessibility company.And: Check the Daily Writing folder for any new entries that can give you more context on what I'm working on and what still needs to be worked on.

What Claude does with all of this:

It reads my morning writing, checks Slack, email, calendar, Notion, and Circleback (which records our team calls). Then it gives me:

1. A short briefing on what needs my attention
2. My tasks reprioritized through the lens of my role as CEO
3. Delegation calls, "this is a Victoria task," "send this to Tim," "Jessie can handle this"
4. 1-2 high-leverage items for NOOON
5. 1 task that moves the new company forward.

I walk away from the morning with extreme clarity on the one or two things I should spend my time on — not the fifteen things I could be doing.

One more thing.

I frequently search back through my daily writing, pull it into Claude to surface themes, and export files to ideate on content and strategy. The morning writing isn't just planning. It's building a searchable archive of my own thinking that compounds over time.The best system is the one you'll actually use every day. This one stuck because it takes 20 minutes, the output is immediately useful, and it forces me to think before I react.