The Case Against My Own Advice
Two years ago, I wrote a blog post arguing for planning your day in the morning rather than in the evening before. I said that I did my best daily planning in the morning, and that the last thing I wanted to do in the late afternoon was to plan the next day.
Now, I do an evening shutdown routine every evening and plan my next day. Nothing about my morning has changed. What has changed is that I now use a shutdown routine with Claude Cowork, and I’ve received great benefits from it. (For those of you unfamiliar with Claude Cowork, it is a feature of Anthropic’s Large Language Model; an AI service)
Read on to find out why I’ve changed and why you might also benefit from a shutdown routine run through Claude Cowork.
What My Cowork Shutdown Routine Does
When I started using Claude Cowork several months ago, I created a shutdown routine skill. I’m pretty sure this skill was mostly borrowed from David Sparks, who generously shared his as a part of the Robot Assistant Field Guide course.
My shutdown routine gathers all its data sources, then in about fifteen minutes walks me through the day and sets up tomorrow.
What It Does:
- Reviews the day — It presents me with a roles-organized narrative of what actually happened: completed tasks, today’s calendar, and the key threads from my morning journaling.
- Open Task Walk-Through — Next, it goes through each unfinished task in today’s note one at a time; flags “zombie” tasks (open in 2+ of the last 3 days); and acts on my answer regarding what to do with the task — defer it, drop it, or keep it on the radar.
- Four reflection questions, one at a time: (1) biggest win, (2) how I did that day practicing the four virtues (Wisdom, Self-Control, Fairness, Courage), (3) if there’s anything still rattling around to capture, and (4) what happened during the day that I’m grateful for.
- Surfaces the blog pipeline — It gives me a summary of what’s ready to publish, what’s next to build, and where posts I’m working on are in the blog-production process.
- Plans tomorrow — Cowork gives me an estimate of tomorrow’s free time, surfaces the week’s 3 priorities for alignment (from my weekly review), then proposes 3 Priority Actions with reasoning. I confirm or change; it writes the final set into tomorrow’s NotePlan daily note, and pulls Apple Reminders for that day into the daily note. Then a pruning question: is there anything I should drop, defer, or say no to?
Every Source Cowork Pulls So You Don’t Have To
My Cowork shutdown routine skill draws from a number of sources to provide me a comprehensive review of what I’ve done, what tasks remain open, what tasks are listed in Apple Reminders for tomorrow, what tasks already exist in the NotePlan daily note for tomorrow, my calendar, and what I’ve journaled in the morning and during the day.
Frankly, when I did my morning planning on my own, I never took the time to draw on all these sources. I did a much more cursory review, focusing on the day’s Apple Reminders, the tasks already listed in my daily note, and the calendar.
Here’s a list of the most important sources the Cowork shutdown routine draws from:
- Today’s daily note — Looks at notes completed/open tasks and my my morning journaling.
- Today’s and tomorrow’s calendar events — Apple Calendar, in the NotePlan app.
- Tomorrow’s daily note — Looks to see whether 3 Priority Actions are already set.
- Tomorrow’s reminders — Apple Reminders, via NotePlan.
- The past 3 daily notes — for zombie-task detection.
- The previous week’s weekly review (or the current monthly review) — for my stated weekly priorities.
- My roles list, which includes Arete statements (ideal behaviors) for each of my roles — for mapping tasks/events to my roles.
- The blog publishing schedule, to determine what blog topics are upcoming, and where blogs are in the production process.
The Payoffs That Changed My Mind
I’ve gained several benefits from performing a daily shutdown with Claude Cowork:
1. The satisfaction of going to bed with a plan for tomorrow. When I go to bed that evening, I already know what I’m doing the next day. As a result, I can hit the next day running.
As Todd Henry wrote in The Daily Creative,
“As you wrap each project or each day, make an effort to consider exactly how you will begin again tomorrow. Doing so will go a long way toward preventing paralysis. Always end your creative work with the beginning in mind.”
2. Morning Fog vs. Evening Clarity. I used to plan in the morning, but my mind was foggy, and I was half-awake. I lacked the day’s information at my fingertips, and had the friction of needing to look everything up. The evening is simply a better time to think through and plan the next day, especially when Cowork provides me with all the information I need to make decisions and plan the next day.
3. Cowork does the donkey work. The main reason I resisted an evening shutdown routine before was end-of-day exhaustion. I didn’t want to look at several sources, sort out my tasks by role, process them, and set up tomorrow when I was exhausted.
The point isn’t that I have more energy in the evening now; I don’t. Now it’s that Cowork carries the load of gathering the resources, so even though I’m tired, I only have to respond, not assemble. Cowork takes care of the donkey work of assembling all of the information that I need.
4. The interactive walk-through is fun! Being guided step-by-step through the shutdown process by Claude Cowork is kind of fun and more interactive than working from a digital template or printed guide. This is a big part of what makes the evening shutdown worth doing.
5. The surprise-and-celebrate effect. The role-sorted list of what I did each day surprises me almost daily. As I move from task to task during the day I forget what I’ve done. Seeing a complete list of what I’ve accomplished that day becomes a small, motivating celebration.
6. The compounding chain. At the end of the shutdown, Claude Cowork generates a summary of the day. These daily shutdown summaries feed the journal interview I do after the shutdown routine, then the weekly review, then the monthly and quarterly reviews — giving me a comprehensive, role-organized view without having to dig up the information myself. The daily practice quietly builds the raw material for other skills to draw on and leverage.
I recently wrote a post that shows how this pays off: giving Cowork my daily context made the quarterly review sharper and less painful because it could see what I’d actually done, not just what was on the calendar. (Jim Eagar, How Claude Cowork Made My Quarterly Review Better.
7. Nighttime Subconscious Work. Another advantage of doing the planning the night before is that my subconscious works on my plan for the next day while I sleep. Productivity expert Chris Bailey wrote about this in The Productivity Project:
“Your brain also continues to process and consolidate new information into memory as you sleep…This is also a great reason to define your three outcomes for the next day at the end of the previous day.”
Waking Up to a Day That’s Already Planned
In the past, I would get up, head to the kitchen to get a cup of coffee, then sit on the sofa with my iPad and work through my morning routine. Part of that routine was to open NotePlan and, with a still-foggy mind, try to determine what I did the previous day, which tasks I hadn’t completed, and what new tasks were on today’s list. I’d then categorize which tasks were my priority and which others I hoped to complete that day.
Now, my morning experience is much different: I wake still a bit sleepy, open the NotePlan daily note, and everything’s waiting for me there — calendar, Apple Reminders integrated into my task list, and my three priorities already chosen.
Instead of having to collect information and make decisions, it’s all already done. At a glance, I can see what my day is going to look like. In addition, the daily note list doubles as my checklist through the day. I find that’s a much more relaxing and productive way to start my new day.
Try It for One Week Before You Judge It
If you’d told me two years ago that I’d plan every day the night before, I’d have laughed. The objection I had then — that I’m too tired at the end of the day — hasn’t gone away. What changed is that I no longer have to do the heavy lifting myself.
So here’s my suggestion: don’t take my word for it. Design a simple shutdown routine, let Cowork build the skill, and run it for one week. See whether you sleep a little easier knowing tomorrow is already handled, and if you enjoy having your next morning start itself.
If you’re curious where I got started, David Sparks’ Robot Assistant Field Guide is where I learned to use Claude Cowork on my Mac and put together my shutdown routine skill. If you’d like to put your own skill together and do it with Cowork, this is the place to start.
Note: I wrote this blog post myself using my own words and thoughts for the initial draft. I used AI only to suggest headlines, section headings, images and text improvements.
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