A weekly planning ritual that actually works

Artists need epiphanies. Why not plan for them?

Years ago, when I was living in Brooklyn in my early 20’s, my friend

Danielle Olivarez

taught me how to move. She was finishing up her yoga teacher training and I was an eager guinea pig, which meant I spent an hour or so at the park with her every few weeks, sweating and stretching on the mat.

What really happened was that Danielle gave me cues. Hearing her voice in my head, I’d find myself “rotating my inner thighs” on the subway and “holding a pencil between my shoulder blades” while typing away at my desk. These small somatic suggestions, over time, changed the way my body engaged with the world.

I’m telling you this story because I want to talk about planning your week. Which is really to say, I want to ask you: What are you cueing yourself to do?

Side Note: Hello! If you’re seeing this in your inbox, you might be noticing that I’ve moved my email list over to Substack. This was a long time coming — honestly, I’ve been waffling on the decision for so long that I got stuck in the weeds and completely fell off my previously very consistent newsletter habit. I’m excited to get back into the rhythm of things now that we’re all together here in one place, and I no longer have to negotiate every idea into the most “optimized” route. Thank you for reading.

How To Plan Your Week With Compassion and Curiosity

It’s easy to see a to-do list as a list of demands, which might explain why we avoid planning anything at all.

What I prefer to do is to see your planner as a collection of small cues—a weekly-ish hypothesis about what you think might happen, structured with small reminders prompting you to make time for the life you actually want to be living.

For the last few years, I’ve hosted a live Weekly Planning session nearly every Monday using the Desktop Organizer Notion template I developed in 2020. What I’d love to do today is share that weekly planning ritual with you, offering you a few of the cues that’ve changed the way I (and many others) engage with the world.

You can watch it in video form below, or keep reading for a step-by-step breakdown.

Step 1: Reflect and Review

What happened last week? What went well? What didn’t?

For each of these prompts, I recommend setting a timer for three minutes and free writing. You can reference your to-do lists and calendar apps, or just work from memory. What happened? What might be influencing the way you feel right now?

One note: It’s very easy to remember what didn’t go well (hence the late-night memories of that weird thing you did that one time in middle school). Try to spend a little bit of extra time giving yourself credit for what did, in fact, work out as you intended.

Step 2: Preview and Schedule

What’s happening this week? What are the constraints on your time, and where can you carve out a moment for yourself?

It’s certainly possible to just wake up every day and let your calendar app tell you what to do. Which is why I recommend not doing that.

Instead, take a few minutes to actually copy down your schedule for the week—whether you do it in the Desktop Organizer or just on a blank sheet of paper. Manually sorting through your calendar offers you time and space to notice that 15 minutes of free time you have on a day of back-to-back meetings, or the totally open Thursday you didn’t even realize existed.

Noticing, as a first step, then gives you the opportunity to fill those small pockets of time with things you actually want to do.

Speaking of which…

Step 3: What DO You Want To Do?

What do you want to do this week? What would make you happy, or fill your cup?

Here is my hypothesis: I believe that if you make time for what you want to do, you’ll find more energy and momentum to approach those things you “need” to do. Which is why I always encourage spending a few minutes (before brain dumping tasks and to-do’s) free-writing about your desires.

Your answers to this question will, eventually, be added to your very same to-do list alongside tasks like sending that email, breaking down those cardboard boxes, and mopping the floors. In a way, this affirms that what you want is just as important as what other people need.

Step 4: Brain Dump

What are all the things you need to / get to / want to remember to do this week?

Artists thrive on epiphanies. Coming up with new and novel ideas sources the energy we need to keep going.

Which brings us to another hypothesis: I believe that if you get things out of your head and into a system you can trust to hold them, you’ll have more brain space freed up to stare at a tree and make a connection between seemingly unrelated things (aka be wildly creative).

Which, of course, is why we brain dump. The first few things that come out will probably be those that feel most urgent right now. Write them down, then keep going. Include everything you just said you want to do—even the things that feel trivial or self-indulgent.

Ask yourself, again and again, for at least three minutes: What else?

Even if you don’t end up doing everything on the list this week, at least you know you’ve written it down. Which means you no longer have to walk around thinking “I have to send that email,” and instead can go for a walk or stare at a body of water, which inevitably increases the odds of having a very good idea.

Step 5: Um, Actually…

What do I actually need to accomplish this week?

After brain dumping everything we can think of onto a list, it’s time to negotiate. What’s actually important?

For me, this question acts like a cheesecloth. It squeezes the list I just made, which may very well have been informed by whatever Pinterest rabbit hole I fell down right before starting to plan, and asks me to think about what actually matters.

What I like to do is repeat the phrase, “I actually need to…” over and over again, letting the auto-predict of my brain fill in the blanks until something interesting comes up. Sometimes the responses are spiritual, other times practical. You might actually need to drink water, or you might remember a task you forgot about on the brain dump list.

As always, keep writing and the answers will appear.

Step 6: Prioritization

What progress have I made on each of my top priorities? What are my top priorities?

There are two ways to approach this prompt. If you already know what your priorities are (perhaps you’ve done a Big Paper Planning Day and have a set of abstract goals!), then you can name those priorities and then give yourself credit and gold stars for any and all action you’ve taken in their direction.

If you don’t know what your priorities are, you can try it the other way around. What are you proud of yourself for? Where have you been investing energy and getting something you want in exchange? Where can you give yourself credit?

From there, you might even start to notice that it seems like you’re someone prioritizing XYZ. This is useful. It’s insightful. In fact, this kind of reflexive self-knowledge can spark your response to the next prompt, which asks…

Step 7: Now What?

What’s the least complicated next step? What’s the tiniest, itty-bittiest next thing you can do in the direction of these priorities?

Your least complicated next step is not a project. It’s not 15 tasks hiding in a trench coat pretending to be one thing. It may not even be what you’d traditionally consider “productive.”

Instead, the least complicated next step is a small, manageable action.

If everything feels overwhelming, try a constraint: Do all of my late homework might become Read one page of the assigned chapter.

Or maybe your least complicated next step exists to “set the scene” for the action you want to prompt: Reorganize my closet can become Play music and open the windows.

Whatever it is, go back and add it to your Brain Dump list, along with any other to-do list items that cropped up when you were journaling about priorities.

Step 8: Schedule Your Cues & Pick A Top 3

What day will you do each item on your list? What’s your Top 3?

If you’re following along with this process so far, that means you’ve already reflected, scheduled, named what you want, brain dumped, prioritized, and figured out a least complicated next step.

All that’s really left to do is schedule out your cues.

When do you want to be reminded to do these tasks and to-dos? When do you want to be prompted to read outside or walk to the library? When is the best time to send that email or spend 25 minutes deep diving on that project?

The truth is, picking a “Do Date” is, in itself, a tiny hypothesis. We’re saying, “I think that if I follow this plan, then I will finish this list of tasks by Friday.”

If Tuesday arrives and we don’t actually have the time, energy, or spoons to do the laundry…well, we move the task. With self-compassion, preferably.

The system, wherever it lives, holds the to-do list and is ready to cue you again tomorrow. (The reason I love Notion is it frees me from a haunting mess of scribbles left behind by rescheduled tasks!)

As you pick your Do Dates, this is also a good time to choose your Top 3, or what I like to call your “Good Enough Threshold.”

If a wizard tapped you on your shoulder and demanded you only do three tasks this week, what would you choose?

Your Top 3 don’t have to be the three most productive tasks. One of them might very well be the thing you just said you want to do.

After all, who’s to say going to the library or sitting outside stoned at the café isn’t actually the most important thing you can do for your practice this week? Will any of us ever know, really, if we don’t remind ourselves to try?

Above all, the cue I want to offer you this: We get better with practice.

This was as true for the yoga I practiced with Danielle as it is for time management, prioritization, planning, and creative structure. As you stretch and practice, new muscles develop. One day you wake up and realize you can touch your toes. Another evening you go to bed satisfied, knowing you did do everything you said you were going to do that day.

If nothing else, take my hypothesis out for a spin: Experiment with the idea that if we build a habit of asking ourselves What do I want? before approaching What do other people expect or need from me? then we might end up with a more fulfilling, creatively engaged life.

If you pay attention, you might even notice that the dishes get a bit easier, too.

Thank you for reading.

<3 Lex