Calendar wrangler
Take control of your calendar before it controls you
There's nothing more important than time, yet most of us don't pay enough attention to how we use it—especially when it comes to our calendars.
In this article, I'll share some thoughts on how to take control of your time by designing a calendar that works for you, not against you.
Tips'n' Tricks
Ideal Calendar
Plans often fall apart—and that's fine. But that doesn't mean we should let our days drag us along. We still need to fight against entropy.
One powerful tool is the Ideal Calendar: a deliberate design of your week that reflects how you want to spend your time. Then, aim to bring your actual calendar as close to it as possible.
Oren Ellenbogen discusses this well in Leading Snowflakes1, a book tailored specifically for engineering managers. While the concept of time blocking and ideal weeks is covered more broadly in books like Deep Work2 by Cal Newport, Ellenbogen applies it directly to engineering leadership.
He introduces the "Ideal Week" as a tool to proactively block time for your most important responsibilities, such as:
1:1s
Focus / thinking time
Team rituals (standups, planning, retros)
Learning and improvement
Cross-functional collaboration
Strategic work
Without designing your calendar with intention, it gets filled reactively and you drift away from being the kind of leader you want to be.
Context blocks
Not all work is created equal. Some of it is strategic, some operational. The cost of switching between these modes is high.
That's why it's helpful to break your week into context-specific blocks. Cluster similar types of work together to reduce context-switching and reclaim mental energy.
Put all your work in the calendar
Work lives in too many places: Jira, Google Docs, Notion, Post-its, email, Slack, your head. But everything you commit to will take time, so your calendar should reflect that.
No, you don't need to create an event for every single email. But you should absolutely have blocks for things like:
Email and message triage
Presentation preparation
Deep work
Admin tasks
This forces you to reckon with the true cost of your commitments.
Maker Time vs. Manager Time
This concept comes from Paul Graham's 2009 essay, "Maker's Schedule, Manager's Schedule"3. It's essential reading for anyone in a hybrid IC/leadership role.
Maker's Schedule (e.g., engineers, writers, designers) requires long, uninterrupted blocks of time.
Manager's Schedule (e.g., leads, execs) is structured around hourly meetings and rapid decisions.
The two schedules conflict. A meeting in the middle of the day can ruin an entire afternoon of focused work for a maker.
Being aware of which mode you're in, and protecting the right kind of time, makes a huge difference in your productivity and satisfaction.
Color Coding
Color coding your calendar is a simple but powerful technique. You can use it to:
Distinguish between types of work (e.g., meetings, deep work, admin)
Separate planned vs. unplanned work
Highlight strategic vs. operational tasks
What you choose to color will depend on what you're trying to optimize for—and that can change over time. Personally, I tweak my color scheme every 6 months or so.
The visual feedback helps you quickly spot imbalances. Are you slipping back into IC habits? Avoiding strategic work? The colors will tell you.
Measure what matters
People often underestimate how easy it is to measure their time—and how valuable those insights can be.
Google Calendar has an API. You can pull your events and analyze things like:
Hours spent in 1:1s
Time in meetings
Slack or focus time
Work-life balance trends over time
With just a bit of scripting or a spreadsheet, you can get a data-driven view of where your time goes—and start making real improvements.
Final Thoughts
Your calendar is one of the highest-leverage tools you have as a leader. Use it with intention.
Design your ideal week. Block your time. Track what you do. Review and adjust. Your time is too valuable to leave to chance.