I’ve been doing a morning routine for at least the past four years. I’ve written several blog articles over those years (For the last post, see Create the Day You Want: The Power of a Proactive Morning Routine) about my practice.
My recent work with Claude Cowork has led to three changes: how I plan, how I journal, and how I handle ideas.
1. Your Plan Is Already Set Before You Wake Up
The first change comes from the shutdown routine skill I run every evening. My old way of planning for the day was to do it all in the morning. I’d look at the task list in the NotePlan app, decide on three priorities, and flag everything else as lower priority.
Now the shutdown routine helps me to figure that out the night before. When I wake up, the plan is already set.
Morning becomes implementation, not deliberation. That’s a quieter, cleaner, and more intentional way to start the day.
I feel more prepared and grounded before the day even starts. As Saul McLeod, PhD wrote in his article “Shut Down Ritual: A Practice for Productivity,”
“Prioritizing your tasks and outlining the most important next steps for the following day reduces morning friction and allows you to start immediately with focused energy.”
The result is that I’m getting a running start on the day and knocking out my priorities almost every day.
2. The Day My Journaling Started Talking Back
The second way Cowork has had a major impact on my morning routine is through journaling. In the past, I journaled in the Day One app, but I almost never went back to reread what I had written during my weekly, monthly, and quarterly reviews. It stayed hidden.
My journaling did have value as self-therapy, helping me work through and acknowledge my own thoughts. However, it didn’t contribute to my reviews.
Cowork reads entries regularly, pulls out themes, and connects dots across days and weeks.
I’m journaling six or seven times more than I did before because it now serves a practical purpose: it has a reader and reminds me of what I wrote during reviews.
My journaling is a part of my Claude Cowork skills for my evening shutdown, the journal interview, and my weekly, monthly, and quarterly reviews. Cowork weaves my journaling through everything.
Because it uses those entries as context, the journaling actually matters in a functional way, not just as a personal practice.
It feeds back into the work. The journaling doesn’t just capture thinking; it prompts thinking.
Different threads surface. Things I wouldn’t have worked out otherwise get worked out.
That feels like much more than a productivity shift. It feels like a change in how I’m living, how I understand myself, and how aware I am of my own life and thoughts over time.
Day One has always captured the day. With Cowork’s MCP connection, it now feeds the day, surfacing emotional themes and contributing context to the shutdown review, my evening journaling interview, and informing weekly, monthly, and quarterly reflections.
I find that giving Cowork access to my journaling helps it better understand what’s on my mind and what I’m thinking, as opposed to just drawing from Tasks and Calendars, which are extremely incomplete. There are Tasks and Projects that don’t show up in my task list, but they do in my journaling. Cowork helps me capture them and keep them on my radar going forward.
The shutdown routine picks up on some major themes and tasks and asks me a series of questions about them. Key questions in ever session are, “What was your biggest win today?” and “What could you have improved today?” This helps me to do more journaling and bring out my own thoughts regarding certain topics.
In my article “How Journaling Makes Cowork Smarter,” I said:
“Cowork knows the calendar and tasks, but without the journal, doesn’t know what they use, what the user is actually thinking about. Tasks tell you what you do or did. Journal entries tell you why they mattered and why you did them and how you feel about them.”
After I do my evening shutdown routine in Cowork, I run another skill called the Journaling Interview. This interview draws on the journaling I did earlier that day as part of my morning routine and compares it with what I actually did.
For instance, recently, it picked up on a morning journal entry where I expressed some anxiety about talking to a friend about a sensitive subject that day. It asked me if I’d decided to have that conversation (I didn’t) and asked me questions that helped me to clarify my thinking about it.
The metacognitive payoff is that I reflect on my own learning process, a distinctly human skill most people underuse. It’s the gap between accumulating experiences and actually learning from them.
3. The Article Idea I Almost Missed (Until Cowork Found It)
Each morning, I review 10 randomly chosen highlights from my Readwise highlights and look for potential blog post ideas.
I have two shortcuts at the end of my morning routine apps, one that saves blog ideas for Original Mac Guy and the other for Retirement Reinvented. These help me capture both the highlights and my initial thoughts on a topic if I think a highlight raises something I might want to turn into a blog topic in the future.
The new addition to using Cowork is that, during the shutdown routine, Cowork goes back and picks three of those highlights and suggests possible article angles. It does a second pass on the material.
Just a few nights ago, that second pass prompted an actual article idea from one of the highlights surfaced, an angle that I’d missed the first time through. As a result it’s on my blog publishing schedule.
Do You Want to Build Your Own Claude Cowork Robot Assistant?
If you’re not familiar with Claude Cowork or are unsure about how to get started, you’re in luck. David Sparks has produced the Robot Assistant Field Guide, in which he takes viewers by the hand and leads them step-by-step through building their own robot assistant using Claude Cowork. (Note: I do part-time administrative support for David Sparks, but receive no income from Field Guide sales.)
I know the process works because that’s how I learned to use Claude Cowork and build the skills that changed my morning routine. When I started this course, I had no idea how to use Claude Cowork. When I completed the course, I had a basic setup, including some helpful skills, and the abilty to start creating my own Cowork skills to fit my workflow.
It Turns Out This Isn’t About Productivity
What strikes me most, looking at all three changes together, is that none of them are really about productivity.
The shutdown routine helps me make decisions for the next day, so I fall asleep and wake up knowing I already have a plan. The journaling gives me a record of my own thinking that actually gets used. The Readwise second pass means fewer good ideas fall through the cracks.
That’s not efficiency. That’s a different relationship with your own day — one where you’re not just moving through it, but actually paying attention to it.
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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