How I Made Daily and Weekly Planning Effortless
I may not work as an engineer anymore, but I still consider myself an engineer in the domain of life. I still rely heavily on systems and processes to make my life easier. If I’m going to do something more than once, I come up with a system for how to make it great every time. And once that system is in place and running smoothly, I’ll tweak it and upgrade it as I go to make it even better.
Weekly and daily planning are great examples of recurring events that can be chores or optimized awesome sessions, depending on your approach. You’re doing them all the time, so you might as well make them awesome sessions.
So here’s what I do for my planning sessions, and why I love it so much.
I have a calendar event at the time I’ll do the planning. And I treat it the same as any other calendar event — that is to say, I do it at the prescribed time. If it doesn’t matter whether it happens at that time or not, it shouldn’t be on the calendar, it should be on a to-do list. The problem with using the calendar wrong isn’t just a semantic one — when you use it as a to-do list you diminish its power to be an effective calendar, which is a bad idea. I’m generally a big proponent of using tools for their specific purpose. I find this ultimately requires less effort and gets better results.
In the calendar event I embed a link to a to-do list in Google Keep with all the things I’ll do during the planning session. The list lives in the archive, because that’s my favorite place, and I don’t need it cluttering my main page. The calendar event is recurring, the note is static and gets reused each time. There are ways to create automations for this kind of thing on monday.com, Trello, and lots of other platforms. I’ve tried many of them, and ultimately I find that simpler is better. But more important than simple is what you’ll actually use. So pick something that you feel comfortable with.
If it happens at a certain time, I use my calendar to handle it. If it needs to get done, but isn’t tied to a specific time, I use a to-do list. I want to have a third thing here, but there isn’t really one?? It either happens at a time or it just happens. I suppose if it happens at a specific place that could be our third thing. Mostly this means you should put something at that location, or maybe use Google Keep’s location based reminders if you’re into that.
Before I get into the details of what’s on my checklist for planning, I want to get a little philosophical and give some context on why I find this part of the process so powerful.
Making decisions is one of the most mentally demanding things we do. It involves the exercising of autonomy, the engagement of our cognitive powers, confrontation with uncertainty, and ultimately acceptance of risk and consequence. I don’t know about you, but that feels heavy to me. We even decide what to think about, and decide what to decide. These meta decisions are probably the two most important ones there are, and have correspondingly high mental costs.
The main reason systems are so powerful is that they unburden us from the weight we typically carry around making decisions. They turn a series of decisions into a series of actions. Deciding to act is more difficult than acting itself. I know this sounds backwards, but think about the last time you had to do something difficult. Once you made the decision and stepped into action, I’d be willing to bet it got easier. This unburdening offered to us by systems is why it’s important to be disciplined in the way we use them. If we use them erratically, they lose their potency and value. The other potent piece of good systems is that they unburden us from remembering, the other cognitively demanding task. Maybe I’ll get into that elsewhere.
Okay, so back to the specifics. Within my to-do list I have a concrete set of actions that I check off as my daily or weekly planning routine. This routine is broken down into small steps to make it smooth and effortless. At the very beginning of the list, I have a link to tomato-timer.com, so I can set a timer and stay focused without having to remember to do that. In my daily plan, I include a task to review the days accomplishments and celebrate wins with some dancing, an inbox zero task (I cheat a little, I cut some slack for the daily inbox zero but generally am very strict about the weekly inbox zero), look at what went poorly with curiosity and compassion, review the calendar for tomorrow (this is actually really important — by having a set time to do this every evening, I can unload yourself from the need to check the calendar every 15 minutes — it’s called deliberate worrying), and finally plan tomorrow’s tasks.
For the weekly planning session, I start with a link to tomato-timer.com again, and then I organize my desk. Fully and completely. All that’s allowed on my desk at the end of this first ~5 minutes are the permanent fixtures: lamp, speaker, mouse, keyboard, pens — and books: the book I’m currently reading plus my various journals/notebooks. Post-it notes get thrown away or converted to a more permanent digital or paper format. Anything that accumulated over the week (gloves, hats, junk, mail, boxes) gets put in its proper place. This step goes first because it’s critical for me to have an uncluttered workspace before I start to plan my week. I find that clutter makes me more likely to get distracted and procrastinate, so I take care of it first.
After my workspace is clear and ordered and I’m feeling very zen, it’s time to do the same for my digital workspace. This is when I do an Inbox Zero sweep. I’m usually fairly strict about the weekly Inbox Zero. If it isn’t handled yet and it actually matters, I’ll convert it to a task on my to-do list and then archive it. If it doesn’t matter…this is when I bite that bullet and just archive it, probably never to be seen again. I’ll also declutter my digital notes and archive and organize writing from the week here.
Now that my physical and digital worlds are clean and organized, it’s time to get into it. I’ll start by reviewing the past week, this is important because I usually forget what and how much I got done, and when I review my wins from the week it gets me excited and motivates me to have another great week. If it wasn’t a good week, I’ll take this time to highlight the few things that did go well, and thank myself for handling whatever challenges made it difficult. I focus on self-compassion and empathy here, which works better for me these days than my old strategies of beating myself up and putting myself down.
With my energy and inspiration high, I jump into the new week and dump everything in my head out onto the electronic page. I’ll usually have my general to-do list up on the other screen and pull from it as needed, but mostly I’m just writing down whatever’s on my mind and whatever I remember. I don’t worry about prioritizing, deciding, planning, or any of that. I just write it down. When I can’t think of anything else, I’ll pull up my tickle lists (I prefer this to the term trigger list) and remember some things I’ve forgotten. I use one straight from GTD, and another I created myself roughly based on the 7 areas of life framework. These two lists will shake out anything I’ve forgotten, and more importantly the second one will force me to bring my priorities and what’s truly important back into focus.
Once everything is out on the page, I’ll drag and drop it into priority order. I’ll take the top 10 or 15 items and port them over to my Productivity Planner (highly recommend this tool), and then I’m ready to seize the week. Finally, I block out time on the calendar for non-work. I usually put two adventures to go play in nature, one or two blocks to work on my artistic projects, and Friday afternoons for friends and community.
Some optional add ons are sending a gratitude text and reviewing my spending on Mint. I don’t always do these because they’re less essential to the purpose of my weekly planning session, but they’re nice to haves.
If you made it this far, I won’t be offended if you’re exhausted. The first time I went through this weekly planning process, it took me 4 hours. I was mentally exhausted to the point I had to lie down and cover my eyes. I suppose a lot of this had to do with the fact that I was coming up with this process as I was doing it! I’m kind of amazed I stuck with it, but now I can do it with fairly minimal mental drain in 30 to 45 minutes. So if this is new to you, go easy your first couple weeks!
If I sum it up, the process is to have a recurring calendar event at the time I want to do the planning, and a link to a checklist embedded in the event. On the checklist is a set of actions that I don’t have to think about, I can just execute on. When I put it like that, it seems so simple. But that wouldn’t make for an interesting post! The whole process of weekly planning (which uses a checklist to minimize decisions) is to create a checklist for the week that you can focus on acting on to minimize decisions. Ah, don’t you just love it when that happens?
I hope you’re making it a great week, happy planning!
