My shadow calendar: an experiment in aligning my time with my values

My shadow calendar for this past week (low quality is intentional 😏)

For the first few days of January for the last couple of years I’ve taken some time to do a personal retreat. The first one (which was only one day long) was in 2015 with my old roommate and dear friend, Annemarie Gray, back when we lived together at 40 Cottage Street. The purpose of the retreat is to keep me on track with my own goals and vision by reflecting on the past year. Taking time to re-center on my goals and vision for my life feels necessary because, without reminding myself where I’m going and why, the forces of the world are likely to take me everywhere else. I’ve spent lots of time around older folks and, having died once, I’m not waiting until I turn 40 to have a crisis that pushes me to get my life in order.

I do several different activities on this retreat (more details here) but this year I upgraded a process I came up with last year. Last year (2016), I took a ruthless look at the difference between how I wanted to be spending my time (based on my own priorities and values) and how I was actually spending my time. Then, as I started planning for the next year, I (roughly) sketched out how I should spend my time each week in order for my values to be clear.

Example: Value – Taking care of my body. Implication –I need to both put good things in it (eat well) and use it (exercise). So, in order for that value to show up in my time, I need to make sure I had sufficient time to go grocery shopping and cook meals for myself. I also need to make sure I have time held each week to exercise (at the gym, biking, or playing volleyball).

Over the course of the year, it felt like a huge personal system upgrade. So when the time came for my 2017 reflection days (which I extended this year to three days), having experienced how much of a difference some thoughtfulness could make, I wanted to put even more intention into how I think about my time (I’m crazy, I know, I’ve been told).

One thing I noticed when looking back was that there were times during the year where I got off track and didn’t have any built in time, tools, or structures to make small course adjustments before the next annual retreat.

So, instead of just having a sketch as something I make once and then leave behind until the next year, I decided to take my sketch (which I have been trying to find an image of without any luck) and turn it into an actual Google calendar. I wanted to do this because it would allow me to toggle the framework on and off (even daily if I wanted to (which I, of course, did)) to see how on or off track I was with my intentions.

My shadow calendar for this past week.

Of course, it’s just a guideline but I think a structure like this will help me more than, say, waiting until I turn 40, looking back on my 20s and 30s, and realizing I’ve spent a bunch of time doing things I didn’t really want to do.

And, although I’ve only been operating this “shadow calendar” practice since January, I can already see at least three lessons emerging.

Lesson 1: It makes knowing when to say “yes” and “no” easier

It’s so nice to have a structure for what I want to do with my time each week. It makes it super clear in most circumstances (though not all) when to say yes and when to say no.

For example, some days I’ll get invited to three or four different events, all of which are amazing. But I feel empowered to say no to all of them somewhat easily because it’s project night or because it’s one of my bi-weekly hangouts with a close friend/woe (ht adrienne maree brown for the term woe (friends who are working on excellence) which was borrowed from Drake who got it from fellow Canadian rapper, Devontée).

Or maybe someone has invited me on a weekend trip. But when I look and see that it’s a weekend I’m supposed to be seeing my little nephew, Jayden? Easy no.

Although I do say no orders of magnitude more than I say yes (which makes sense because there’s so much more I can’t do than I can), my shadow calendar helps me in other than just saying “no.” Having this structure makes it easy for me to understand just how flexible I can be and still get done what I need to get done. For example, when something comes up that I really want to do or go to, if I have a free night open later during the week, I can switch project night (or whatever was scheduled) to that free night and attend the thing. As long as I stick to my overall structure, it’s great to know that I’m still going to have time to keep moving forward the things I want to.

Lesson 2: It’s easier to hold to when my schedule is more stable

For the past couple of years, I’ve been trying to live more seasonally. It started with my diet and I think that experiment (along with these New England seasons and my increased attention to natural cycles) has influenced my activity levels. So I’m noticing that my ability to stick to my regular set of activities is much harder during the summer when I’m really active and/or traveling a lot and easier to do in the winter.

Lesson 3: I haven’t figured out what to do as my woes move

It’s unbelievably helpful to have regular hangouts scheduled with my woes. With most of them, I have some sort of regular, recurring conversation or dinner, usually in the every 2–3 weeks range. But… sometimes they move (like, in the past year, at least four have left Boston, most for NYC. ugh.) and our previously determined catchup/hangout schedule doesn’t work.

I have yet to totally figure out how to deal with this adjustment. Sometimes it means someone comes off the regular hangout list (which is sad but real). Sometimes it means we move our meeting to virtual or phone call. I’m actively wondering about what to do in this area, because “The only lasting truth is Change”… hm!

Lesson 4: Maybe I should hold a group retreat for this?

Well, this one is less of a lesson and more of an idea… A few people have mentioned to me that they really like this idea (the idea of having an annual reflection retreat). One person even said they’d love to go in a group to do this. I love renting houses with friends so now I’m wondering about the idea of prototyping a group annual retreat in a house somewhere outside of Boston this January. I’m convinced (via my experience in my coaching practice) that any sort of self-driven change process is aided by accountability and, although getting away can be pricey on your own, with multiple people to share the cost, maybe this is a two-birds-with-one-stone situation. This is just an idea for now, but maybe it’ll happen…

Anyway, so that’s my shadow calendar. I’m curious to know what folks think about it so feel free to leave a comment here or hit me up on Twitter or by email.

What’s up next in this series? I’m not totally sure, but maybe I should write out some lessons learned the first 15 people I’ve worked with in my coaching practice… or maybe just an overview of my approach and process. We’ll see!

P.S. — Shoutout to Julian for encouraging me to think about how significant this practice actually is and also for pushing me to write this up so that Heather could see it. ❤