I Put a Random Question on My Calendar Every Week. Here’s Why.

Last updated: 2026-09-08

I used to sit down for my weekly review and stall. Blank page. The session was supposed to be thinking time, and I’d burn the first chunk just trying to pick a prompt worth answering.

So I automated it.

I have a Lindy agent populate my calendar with a random journaling question every week. I show up and I answer it. The blank-page friction of starting a retrospective is gone because the question is already waiting. I used to invent those prompts myself. Now an agent handles that routine cognitive task and I spend the slot answering.

When I’m traveling, or when I have a thinking-time slot, I still reach for a physical book: 3001 Questions All About Me. I open to a random page and journal for 10-15 minutes on a single prompt. One of them was “What is my definition of beauty?” AI can generate questions. For this specific workflow, the book is more tactile and more reliable.

Here’s the thing. Generic productivity advice fails when it doesn’t fit your personality. Self-awareness is how you filter it. If you don’t know how you actually think, you’ll keep borrowing systems that were built for someone else.

That’s the ultimate productivity act. Figure out who you are. Then pick the strategies that match.

Finish the work you already started

Brooks has a filter for books. He looks for underrated ones: books that significantly impacted him, that aren’t in the top tier of over-recommended classics (Atomic Habits is the obvious example), and that he hasn’t already discussed extensively on the podcast. You get high-value resources the productivity space tends to skip.

His pick for getting projects out the door is Start Finishing by Charlie Gilkey.

Atomic Habits is about daily habit formation. Start Finishing is about the mechanics of finishing. Limit your active projects. Park the non-urgent items. Use a structured workflow so head trash (Gilkey’s term for mental clutter and resistance) doesn’t run the week. If The 12 Week Year felt too rigid, this is the more flexible alternative for the same problem: too many things in motion, not enough completions.

Are you collecting systems, or are you closing projects?

If finishing is the actual bottleneck, start with Gilkey’s workflow. Cap what’s active. Park the rest. Work through the resistance with a structure.

Then give the framework to the model

Once you have a framework you trust, AI is rocket fuel.

I uploaded Start Finishing to ChatGPT and asked it to map a specific project (launching a members club) using that framework. Creating a structured plan went from hours to minutes. You still need the domain knowledge to evaluate the output. Skip that step and you’re letting the model guess your strategy.

Stop doing that. Upload the book you actually use. Point it at one real project. Then edit.

Brooks makes the same case with Slideology by Nancy Duarte. He reads it as a manual for visual communication and persuasion. AI can generate images and slides all day. You still need the domain knowledge to tell whether a visual is effective. Story structure and visual hierarchy are how you direct those tools so the deck actually persuades.

If your AI-generated slides look boring, the gap is usually that you generated before you could evaluate. Learn the communication piece first, then generate.

AI speeds up execution. Human domain knowledge is what keeps the quality.

Zoom out on the humans

If you’re a manager and your team keeps doing things that look irrational, read Sapiens by Yuval Noah Harari. I recommend it as a foundational text for understanding human psychology and behavior. Cognitive dissonance. Tribalism. The evolutionary roots of both. Once you can see those patterns, team dynamics, persuasion, and decision-making get easier to navigate. It’s a zoom-out book. You start recognizing subconscious patterns in how people show up at work. Read it if you want to understand why your team behaves the way it does.

Brooks also points to The Four Obsessions of an Extraordinary Executive by Patrick Lencioni as a companion to The Five Dysfunctions of a Team. The Five Dysfunctions of a Team is about team building. Lencioni’s executive book is about individual behaviors: build the leadership team, create organizational clarity, over-communicate that clarity, and reinforce it through systems. Short. Written as a fable, which helps if you bounce off dry business texts. Ideal for an annual reread when the principles have gone fuzzy. A 3-hour read that can save an organization from chaos.

Do the Pre-Mortem first

One more mechanic, and I run this before any new initiative.

Keith Cunningham popularized the Pre-Mortem in The Road Less Stupid. Before you start, list all the ways the thing could fail or negatively impact you. The decision rule is simple: if you cannot live with the downside, you should not do it.

A post-mortem tells you what broke after the fact. A Pre-Mortem is the 5-minute risk check you run while you can still walk away. Excitement will hide the downside. Write the downside down first.

Put a question on the calendar

Don’t overhaul your system. Put one random journaling question on next week’s calendar. Use a Lindy agent if you want it automated. Or grab 3001 Questions All About Me, open to a page, and sit for 10-15 minutes.

If a project is stuck, upload Start Finishing to ChatGPT and have it map that project using the framework. Then run a Pre-Mortem before you start.

If you’ve got an underrated book that actually changed how you work, drop it in the comments. Skip the classics everyone already recommends.