Calendar Templates 2.0
How I use Reclaim to automatically make every day my ideal day
In 2019, I wrote about how I use a calendar template to balance my schedule and make sure I’m spending time on the things that matter.
The basic idea of a calendar template is simple: Create a repeating schedule of calendar blocks that contain all the elements of a good day. When you start with a template, you don’t need to exercise willpower in the hour-by-hour decisions about what to do. In the words of Annie Dillard, a calendar template acts as scaffolding for your life, freeing you to “stand and labor with both hands at sections of time.”
I still use a calendar template—it’s one of my most valuable tactics for making time—but a lot has happened since I first wrote about this idea three years ago!
Evolving my calendar template
First, the Covid pandemic made my calendar template even more valuable. During lockdowns and the initial WFH period, my template gave structure to days that were unstructured and full of stressful distractions. And as I began to resume work and play IRL, my template evolved, helping me maintain the rebalanced priorities and norms I wanted to continue.
Then in 2021, I launched Character, my new venture capital fund. My schedule changed—I still needed time for deep work (writing, design sprints, etc), but now I have a lot more meetings and emails. My template evolved again.
But there was a problem: With more meetings, there were more people who could affect my calendar. I began spending more and more time managing my calendar. My calendar template was now more like a rough sketch than a template.
Around this time, I learned about Reclaim. (Founder Patrick Lightbody actually emailed me about it in response to a Covid-themed newsletter about templates as scaffolding! Full circle!)
Reclaim, which is now a Character portfolio company, is a smart calendar assistant that dynamically schedules habits, tasks, and meetings, and makes adjustments when things change.
In other words, Reclaim automates my calendar template. I love the product and consider it an essential part of my daily tool stack. Reclaim helps me focus on what matters, and it saves me tons of admin time (scheduling, rescheduling, etc).
And with the beta launch of Reclaim scheduling links a few weeks ago, I realized I could get pretty close to giving Reclaim complete control of my calendar. So, a few weeks ago, I had my first “all-Reclaim week” and it went really well.
I thought this was a good opportunity to share how I use Reclaim to automate my calendar template and help make every day a good day.
(This post reads like an ad, but it’s not an ad, although my VC fund Character is an investor in Reclaim, so I’m biased 😌)
How I use Reclaim to automate my calendar template, step by step
Step 1. Build a foundation
I started by getting all of my calendars in one place using Reclaim’s Calendar Sync. If you have multiple calendars (work, personal, family, etc), it’s essential to see everything together before you can begin to design your days.
Next, I set my Working and Meeting Hours in Reclaim. This is the most direct representation of my calendar template, giving me the ability to define when I want to work and when I want to meet.
Step 2: Create structure with habits and tasks
Now it starts to get interesting. I set up a handful of Reclaim Habits to ensure I make time for the most important building blocks of every day.
If I schedule a meeting at 12:30, Reclaim moves lunch to 11:30 so I still have time to eat. When my afternoon starts to fill up, Reclaim automatically schedules a 15–30-minute afternoon break. For some reason, I seem to organically have fewer meetings on Thursday afternoons 🤷♂️, so I specified a “Soft Hold” with low defensiveness that Reclaim schedules if things are looking light.
Not every habit is managed by Reclaim. I have four workouts a week, plus a weekly review and lunch with Eli on Fridays, that always happen at the same time—those are just regular repeating events in my calendar.
Finally, I tell Reclaim which Tasks I need to get done and how long they’ll take to complete. Reclaim takes over from there, scheduling these tasks within my Working Hours and around my Habits and meetings.
For long-standing Time Dorks readers (hello 🤓), this level of detail—narrowing defining tasks and estimating duration—may sound like the sort of overly-precise productivity optimization I hate.
And it is. The truth is, I rarely use Reclaim Tasks. Normally, I schedule my projects (like writing blog posts) manually and try to build in a certain amount of slack.
But some weeks, I simply have lots of small tasks to complete—Reclaim shines in those scenarios, and helps me avoid the schedule paralysis that can sometimes accompany “busy” weeks.
So far, all of the above is relatively straightforward—Habits and Tasks are solo events, and repeating events certainly don’t require Reclaim.
A smart software assistant that dynamically adjusts my calendar is super handy, but the real Reclaim magic didn’t start until I began using it for meetings.
Step 3. Get smart about meetings
Late last year, Reclaim launched Smart 1:1s, a mind-blowing feature that automatically schedules recurring 1:1 meetings on a frequency you define. Reclaim looks at both participants’ calendars, finds available time within their Meeting Hours, holds the slot, then locks it in as the time approaches or the day gets busy.
A few months ago, they added the ability to create a Smart 1:1 with any person—not just Reclaim users—as long as you have the ability to see free/busy status on their calendar.
Character is very small (only two of us full-time!) so I don’t have a lot of internal meetings, but Smart 1:1 is still a tremendously useful feature. And on bigger teams with lots of internal 1:1s, it’s a game-changer.
From here, we can imagine two ways for Reclaim to expand their meeting capabilities:
- More powerful tools for 1:1 meetings, both internal and external
- Bring these tools to group meetings, not just 1:1
For now, Reclaim is focused on #1, and they recently launched Scheduling Links, making it easier to schedule one-off meetings with people inside or outside your company. (Although I am practically giddy for #2; imagine an automatic Doodle poll!)
Reclaim Scheduling Links are like a smarter Calendly, incorporating everything Reclaim knows about your priorities. For example, I have a high-priority scheduling link I can give people in certain situations—it allows them to book over any Habits or Tasks that Reclaim controls, knowing they can be rescheduled.
Putting it together
This is a lot of steps, but most of it is one-time setup. In the language of Make Time, it’s creating new defaults for your time so you don’t have to rely on willpower to make the right decisions about what to focus on.
Once the system is running, it creates a magical, dynamic, intelligent, automated calendar template that I could only dream about when we wrote Make Time. (And that was only five years ago!)
Here’s how it looks in practice—my actual calendar for this week, November 28, 2022. (Since it’s only Monday, I expect a few more meetings to get scheduled throughout the week.)
Humans are great at lots of things, but fiddling with calendars is not one of them. With Reclaim, I can let software take over. It’s already super smart, but will only get smarter as the Reclaim team continues to build the product. I can only imagine what it’ll be capable of in five years … who knows, maybe by then it’ll be able to attend my meetings, too? 😉