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Why planning my entire week doesn’t make me a sad robot like I feared it would

March 17, 2021

I found a way forward. I have found some BALANCE, specifically in the way of planning my day/week and then showing up for it. A quick timeline:

  1. Dylan thinks of something that she either “needs” or “wants” to do. The “important” things get put on a to-do list/schedule, the others just sort of…float around
  2. Dylan makes a schedule/plan based on the “important” items. She tries to not overwork herself, while also being productive 
  3. Dylan does not show up for her to-do list. She doesn’t want to do that stuff. She’d rather be free and do nothing or decide what she’s going to do in the moment
  4. Repeat

I am a black and white thinker, and it was becoming IMPOSSIBLE to find middle ground between the me that wanted to be freeeeeee, and the me that had even basic ambitions.

Found it. Not where I expected. 

A coach I hired (I’ll talk more about that in its own post), suggested I plan everything in. Nail painting, showering, client work, birthday brainstorming…it ALL goes on the schedule. If you’re having a knee-jerk reaction of “ew gross” to the idea of that much scheduling, I get it. But we’re wrong! (And it’s a good thing). I told her “but, sometimes I like to be able to decide in the moment what I’m going to do..”, and she said… “schedule it in!” As in literally, schedule a block of however many hours on any given day to have free time, to get to pick ANYTHING to do. (Mind blown at having that much authority over my life…I thought I’d turn into a pile of ash if not diligently working between the hours of 8am and 5pm).

The problem before wasn’t with planning itself – the problem was WHAT I was planning. I was always scheduling in things that I needed to do, the obligations, and therefore ANYTIME I made a plan, I was making a big list of obligations. My plans essentially equaled “obligation” in my mind, and as you’ll remember, mama likes to be FREE, not obligated. So I didn’t show up. Unless, of course, an external deadline was close enough that I had no choice but to boogie and get it done – but I wanted to be able to get things done without a looming deadline, at least sometimes. By adding in ALL the things I love, things like an hour for “fun brunch”, or three hours in the middle of the day to read, my plans started feeling so much more…enjoyable. And when time came to show up for a less desirable task, it was okay, because I knew how long it would last, and knew fun was coming after, so I actually showed up. Not to mention, if it made it on the schedule in the first place, it must be important to me or urgent in my life in a meaningful way, which helps the medicine go down a bit.

Photo by Estée Janssens on Unsplash

It does take some work, to get things out of your head and calendar and create a plan, but I can’t express my surprise at my own calm, my ability to show up, to follow through, and to give myself REST, and fun (!) all while being productive on work and dream tasks. What I thought would mean rigidity, coldness, and boredom, has actually been flexibility, connectedness (to myself and values), and freedom. And a cute, color-coordinated calendar. And time for real housewives!

Here’s how to try fully planning your week for yourself:

1. Gather the urgent items

Start by looking at the calendar for this week to see if there are things already scheduled in (appointments, deadlines, birthdays, etc), or any things that have a hard, external date/time tied to them. Write those down.

2. Add in the usual, regular, and/or expected business

Next think of any obligations and things you know need to happen this week (don’t forget meal times, grocery shopping, showering, childcare, etc) and add them to the list. No need to get exhaustingly granular – “meal time” covers prepping, eating, and cleanup when I plan. Expect to forget things, and expect to get better at this part as you practice. Don’t stress though, the schedule will be FLEXIBLE to account for our humanity.

3. Add in the fun and meaningful

Next think of the things that you really want to do this week. At this point you don’t need to worry about “too much” or “too little” – whether your list just has “reading” on it, or is a major list of every whim you like, let it out. If this feels foreign at first, it’s okay.  

4. Order the items

Now it’s time to order our list. You can do this intuitively, or use a method to help you sort. I love the Eisenhower matrix (what’s important versus what’s urgent). “Urgency” is dictated by how hard a deadline is, or how close a deadline/date is, whereas “importance” is the more intuitive and flexible of the two, and I judge based on my values and gut reaction to the task at that time. For ordering:

  1. Tasks that are urgent and important go first
  2. Tasks that are important but less urgent go next
  3. Followed by urgent but less important (try to delegate these tasks if possible, or whittle them down to their most essential part)
  4. And lastly are the less important and less urgent tasks (review these and ask yourself why they’re on the list and if they need to stay). 

Depending on your urgent items and ability to delegate, you may need to prioritize zone 3 (urgent/less important) above 2 (less urgent, important), and schedule the less urgent but still important tasks for further in the future. This scale is relative, and tasks may move around the matrix from week to week, and season to season. Email may be more urgent and important some weeks, while art-making and rest may be more important others.

An alternative method is to take it one item at a time, and asking “is this more important or need to be prioritized over _(other item on the list)_?”, over and over until it’s sorted.

5. Add some time estimates

Go through the now-ordered-list and add some time estimates next to each task. It’s okay if you have no clue at first – this method will allow for flexibility and adjustment if you end up needing more time or need to move things around. You’ll also get better at time tracking as you do it more often. Tools like Toggl are awesome to get you oriented in your own time needs, and doesn’t need to be done forever to be beneficial. Vague tasks like “check email” can either be made more specific (i.e. read and respond to 5 emails, or, delete 15 emails) to help with time estimation, or you can allot a reasonable and specific amount of time to generally spend on that task, (i.e. 30 minutes to check email). 

6. Start scheduling!

I love Google calendar for this because it’s free, can be color-coordinated, and is easy to move things around and change event times and durations. For this step I literally go top down from the ordered list and create a block of time on the calendar for that task. If things have specific dates/times they need to be scheduled, work those in first, then let the other tasks float around them – they will be adjusted after it’s all on there, so don’t worry about getting the order correct yet. So, I may not yet know when I’ll get to read, but I know I want to dedicate 2 hours to it, so I’ll just throw it on there where it fits for now.

7. Adjust!

Begin moving the blocks around to fit in an order that makes sense to you. For example, you may notice there are a few errands that could be grouped into a single trip/time slot, or maybe you know you’re more creative in the morning and want to move your creative tasks to earlier in the day. Seeing the reality of all we’re trying to do and how long things take can be deflating at first, but it’s actually empowering! The reality creates a limit, something to help us make decisions about what’s worth doing and what isn’t.

I like to have a schedule that feels full-ish, with areas of gaps and white space to know I’ve got some totally free and flexible time to play with. I also know things take longer than I expect, and that I like space between tasks so I don’t feel constantly rushed from one thing to another.

As you move through the week, you may need to move things around, or even schedule in another session if the one you scheduled didn’t end up being enough time to finish. For example, last week I gave myself a half hour to clean up the mountain of clothes in our closet. When the half hour was up I still had work to do, so I opened my calendar, found an open slot for later, scheduled in another session for cleaning, and moved on with my life. You’re also empowered to intentionally change your mind – just because a plan made sense at the beginning of the week doesn’t mean it needs to look exactly the same by the end – in my budget software they call this “rolling with the punches”, and they remind us that no budget is perfect unless it can be flexible and change with our reality. The same is true for our schedules. A caveat to this though is if you’re using the flexibility to support procrastination and spend more time moving your schedule than showing up for it, you need to adjust and work in some more fun, and also may need to coach yourself on showing up for the less desirable tasks. Once my schedule is set for the week, it only needs to be touched a few times, here and there. If you have kids or more variables, you may require more shifting time, but again, not longer than the tasks themselves.

8. Show up.

This used to be the mountain step for me, the showing up. Now with this method, the planning is the mountain (a much smaller one) and the showing up is…fun! Or at least clear. Sometimes it’s hard, but I know I only need to show up for that task for the next 30 minutes, or hour, or whatever. When plans change, the schedule can be moved. 

Photo by Danielle MacInnes on Unsplash

No more to-do lists

As you come across new things to add to your schedule, instead of making a “to-do” list, make a “to-schedule” list, and add those items to your calendar as soon as you have some planning time. Now when I think of a task, I open Google Calendar, make a default one hour block for the task, and push it out to the following week to be dealt with/scheduled for real later.

If new things are ideas for later later – bigger dreams or things that might not fit on the plate now – collect them in an email folder to yourself, or a notebook, or even the notes app on your phone (that’s what my coach uses!). Check back in with these to feel out when they’re ripe for the schedule plucking.

Tasks that have a regular schedule to them, like monthly bills, weekly email sessions, and birthdays, can all be put on a repeating schedule, so you don’t even have to think about adding in an hour and a half for bills on the first of each month, or an hour to fill out next month’s birthday cards – it’ll already be there!

Here’s hoping you find as much freedom through your planning as I have. There’s room for all you need to do and the things you find important, and it’s much easier to show up for them when you create and dedicate time to them. No more to-do lists! 


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  1. L.F. says:

    Very cool, I usually schedule “transition times” too because I can’t stop one thing and immediately begin the next. I need water, stretching and other stuff between tasks. If I don’t schedule those, I “fall-behind” on the schedule and then I get anxious and start rushing!

    • Dylan says:

      It’s nice that we can take these things we know about ourselves and make them work for us in our schedule.

  2. Ayoka says:

    VERY inspiring – I love the way you put things into words, it feels personal and human and connected.
    I am struggling with planning and showing up too and this sounds a lot more grown up than my current way of dealing with things. Thank you for sharing this – I’ll give it a go. (Fits in VERY well with my word of the year which is “honest” :-))

    • Dylan says:

      I’m so glad this resonated with you, Ayoka. I hope you’re able to show up more and more moving forward.

    • Kristen says:

      This is a great read, Dylan. Your honest, open and oh-so-human tone always resonates with me. Thank you. Now excuse me while I go start my “to schedule” list…

  3. Shweta says:

    Very inspiring and practical! I just scheduled my Friday & the Weekend! My brain feels so much lighter now. Thank you for sharing!

  4. Judy says:

    Wow! This whle beginning part is me. When you said about not being able to find the middle ground between the me that wants to be freeeeee and the me that has even basic ambitions I’d never read a more apt descritpion of myself.

    I’ll do this method. ! kind of had a suspicion that something like this was needed. I really do have things I want to do and make, and it’s discouraging when “for some reason” I can never seem to get them done!

    Thank you!

    • Dylan says:

      ooooh Judy well let me give you a big old hug because I know this problem so well, and the shame and confusion that comes with it. I hope you’re able to put this method to good use! I’ll be writing another blog post soon about how I’ve been focusing on day planning when my depression is stronger and planning a week is too much. <3

  5. Joana Velozo says:

    Thank you so much for this post. It resonates A LOT with me. I always felt the fear of being like a little robot version of myself and now I feel I can make this happen in a generous way.

  6. Hilary says:

    Overwhelm and procrastination has been plaguing me lately, so just reading this post is giving me hope. Thank you for all the tips and tricks! I’m really excited to try this method for the upcoming week. <3