Why I Built a Calendar That Shows 365 Days at Once
1,190 words · 6 min read
By Archie Cowan
Senior Prototype Developer for AWS global and strategic customers, former ITHAKA/JSTOR Chief Architect. Generative AI builder. Aspiring to do everything.
Welcome to 2026. You know that feeling when you're looking at your 2025 goals and realizing you're maybe 30% done with things you thought you'd finish? Yeah. That was me last week.
I had this certification I meant to complete, a side project that's been "almost done" for months, and a trading strategy I never got around to backtesting. All sitting there, mocking me from my abandoned quarterly planning docs.
Planning for achievements I want to make at work, planning trades I want to be able to make in the markets, planning articles I want to write, planning time with my family, planning not to get sick, planning not to get burned out. You know, work hard, play hard.
Last year I found it helpful to look at a week at a time. How am I going to spend my hours throughout the week? This was mostly focused on habits though.
I also tried quarterly planning. There are 13 weeks in a quarter. So, what are the 5-10 things you want to achieve in that quarter? But I haven't latched on to this very well over the last few years.
I realized the problem: I can't just roll with the punches as they arrive. Best defense of your time is a good offense. But weekly planning only handles habits, and quarterly feels too abstract.
I wanted to try looking at an entire year at a time.
Naturally, this turned into a, hopefully short, obsession with year long calendars. Naturally, I didn't want to do it with anything I could have just used and then got on with it. I had to do it a certain way that was in my head. Sigh.
To make an apple pie from scratch, first you must invent the universe.
Daily habits have their limits for getting things done. I've found I can only have so many pans on the fire at once. I can't always be doing customer work, training, side projects, certifications, side customer consultations, trading, and, oh yeah, taking care of myself with good diet and exercise. It's usually here's 10 things, pick 3 that you can do daily. Without more of a macro plan though, things just don't happen.
One thing I used to do is "take a week off" from normal duties. Like, if everything survives a one week vacation, why can't it survive a one week workcation? Clear my schedule of all normal operational stuff and write or maybe build something for the sole purpose of writing about it.
How often can I do this though? Planning this out is hard. What if I could select blocks of time in a year-long calendar in an intuitive way? What if I could see the texture of my schedule aligned to weekly, 2-week, up to 6-week blocks of time?
I've been working with Kiro's spec mode lately for breaking down complex projects into manageable tasks - I've written a whole series about AI coding tool tips that covers this approach. So I let this same systematic impulse play out - what would happen if I built a calendar that thinks in patterns instead of just dates?
The first view shows how I can create a matrix of 28 by 14 rows of days - the entire year in a single view. I can slice through each row with a selection. The second and third views show how changing the matrix shape reveals different time patterns.
1: 28-Day Wide Matrix
2: 14-Day Wide Matrix
3: 7-Day Wide Matrix
The Problem with Month-by-Month Thinking
Here's what I realized: without macro structure for year-level planning, I kept missing things I could have prioritized sooner.
If I'd known I should be 25% done with that certification by March, 50% by June, 75% by September - I would have caught the problem in spring, not December. But monthly calendars don't show you progress against annual goals. They show you meetings and deadlines, not the bigger picture.
You end up with this weird disconnect: big goals live in your head or some planning doc, while your actual time lives in Google Calendar. They never talk to each other.
What Changed When I Could See Everything
Building this calendar matrix was one of those "I'm sure this exists already but I'm handy with AI and I'll make my own" moments. I feel like a thousand developers sometimes with these tools.
Hoping to build more things and share in 2026 more often!
Now I can see an entire year packed with information in ways that actually make sense. I don't have to use awkward calendar software that forces me to click through months. I don't have to redraw paper calendars over and over while I'm experimenting with different time blocks.
Before: "Let me check if March works for this project... wait, what's happening in April... let me write this out again..."
After: I see the whole year. I spot the perfect 8-week window that spans Q2/Q3. I notice I'm clustering all my intensive work in fall - I can spread it out. I can literally see if I'm on track for annual goals by looking at how much space I've allocated.
The spatial aspect surprised me most. When you see time laid out as a grid, your brain processes it differently. Patterns become obvious. Conflicts jump out. Planning becomes visual instead of mental.
Use Cases Beyond My Planning Obsession
Project Planning
- Sprint visualization - See all your 2-week cycles laid out spatially
- Milestone mapping - Spot conflicts between project deadlines months in advance
- Resource allocation - Visualize when your team will be stretched thin
Personal Organization
- Vacation planning - See the whole year's availability at once
- Habit tracking - Mark recurring activities and spot gaps in patterns
- Event coordination - Plan around holidays, conferences, family events
Business Applications
- Marketing campaigns - Visualize launch sequences and promotional periods
- Editorial calendars - Plan content themes, publication schedules, and seasonal campaigns across the full year
- Seasonal planning - See busy periods and quiet times in context
- Compliance tracking - Mark regulatory deadlines across the full year
Try This Tomorrow
Next time you're staring at an annual goal wondering "how am I going to fit this in," try thinking spatially:
- Sketch the full timeframe - Don't just look at next month
- Mark your milestones - Where should you be 25%, 50%, 75% done?
- Look for the gaps - Where are your natural intensive work periods?
The calendar matrix is live. Build your 2026 view and see what patterns emerge when you can see all 365 days at once.
Know someone that likes yearly planning? Make a calendar and share it with them using the sharing feature!
What would you plan differently if you could see your whole year as a landscape instead of a series of monthly snapshots?
© 2026 Archie Cowan