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How To Move To Digital Planning


I have been a tangible, hard copy planner for my entire life. My obsession with agendas started in sixth grade when we were finally allowed to purchase the school's branded agenda for $10 and use it to write down homework assignments and soccer practice dates on corresponding days of the week. For some reason I loved that the school agenda had all the pre-planned dates (like holidays, PA days, photo days, etc.) written into them for advance planning, and this is also when I first learned how satisfying it is to write down something you want or need to do, and strike it off the list when it was successfully complete. I bought a school agenda every year, until one day in high school I realized - you can purchase agendas OUTSIDE of school, different, more aesthetically pleasing ones; agendas you could customize and create based on your preferences. Until that time, I thought "agenda" was literally a school term and that only students used them. 😂 Over the years, especially throughout university and then when I started working, I cycled through various different versions of agendas and day-planners, starting with the daytimer brand (old faithful that I stuck to for probably 5 consecutive years, refilling the paper annually) and then working my way through all different types/brands of planners - the Erin Condren Life Planner, the Happy Planner, the Simplicity Planner, the Passion Planner, Clever Fox, Mead, random Staples house brands, and I even tried my hand at the bullet journalling format for a while there with Leuchtturm notebooks. Needless to say, my planners were spectacular. I was militant about planning, preparing, highlighting, note-taking, post-it-noting... I did it all. My agendas were famously colourful, neat, and kindergarten-teacher-printing tidy. I wrote in pen and kept white out nearby at all times, because I didn't want my calendar to be scratched out and messy. I carried my agenda everywhere and refused to solidify dates to anything unless I could cross-reference with my trusty sidekick. That's where things got complicated. I'd be out somewhere, say, wrapping up at the dentist's office, and they'd ask me to schedule my next appointment. But I never had my agenda with me at the dentist.

So I'd say something like "I'll have to call you to re-book, I don't have my calendar on me"... and then I'd ultimately forget to call and re-schedule anything. (Maybe that's why I've always had cavities at my dentist appointments...😂) This kept happening. Especially after I became a parent, I found it extremely difficult to keep my agenda on me at all times. I would have a purse and a diaper bag and a stroller (and, you know, a baby) to manage, and my agenda started sticking permanently to my office desk, collecting dust. And then, I started getting really unorganized. Which is very uncharacteristic of me. When I returned to my full-time job, I found myself forgetting things, even though I had my agenda nearby. My outlook email had a calendar attached to it, so I had a few haphazard recurring tasks in there - weekly team calls on Mondays, follow-up calls on Wednesdays, and once in a while a colleague (who was really good with sticking to their calendar) would invite me to something and the appointment would go on that digital email-connected calendar... that I never looked at. If I didn't add it to my IRL agenda, I would forget about it. And regularly, I was forgetting to add things to my agenda. So, there were messes everywhere. For some reason, I fell out of the "routine" of tangibly planning. That's not to say I don't still enjoy a good hand-written brainstorming session from time to time, but actively keeping up with the writing, colour coding, post-it-note adding... it became something that was time consuming and I just didn't have the necessary time to consume. I also think I created a crazy expectation for myself, thinking that if I couldn't do it EXACTLY like I used to (pre-motherhood) then I wasn't going to do it at all. This just made my life really messy and I had to figure out how to get it back on track, and fast. I really wanted to be good at tangible organization again, and I did try to psych myself up a few times, purchasing brand new, sparkly, shiny agendas that I thought would be "the ticket" to re-motivating myself.

All that did was have me waste money and time initiating new systems that I was not mentally ready to implement. So, one day (at the dentist office no less) I decided I was going to start using that google calendar app that had been sitting on my phone for ages. Nothing else was in that calendar, but I opened it, looked ahead 9 months, and booked a dentist appointment on the spot, without claiming to "call back later" or "cross reference my agenda" before confirming. I went home and opened the google calendar on my laptop. I had an email address that was a gmail account, and I decided that was going to be my #1 email for life (personal things, like sports teams, dentist offices, family appointments, school correspondence, business calendar bookings, etc.) Later, I attached my business email to the calendar as well. MOMFIDENT BOSS TIP: The very first step to digital planning is to master the use of the digital calendar. Now, you could use a different calendar if you use a different email provider, but google calendar works really well for me and integrates with other systems I use smoothly, too. But don't worry about any of that other stuff yet. Worry about deciding which online calendar you're going to use (I suggest google) and then start using it. It WILL take some getting used to. But you know what's neat? You have that calendar with you everywhere you go, because it's in your pocket at all times. Groundbreaking, I know. But knowing this ONE thing had the capacity to make my life just a little bit smoother, was a big deal to me. Suddenly, my agenda could live in my purse and I didn't have to remember to bring it with me everywhere. Here are some tips for getting started.

1. CHOOSE A CALENDAR PROVIDER: Select the calendar platform you want to use. (Google, iCalendar, Outlook, etc.) I mentioned already that I suggest google; it seems to be the most commonly used one, which is also great for aligning with other people's calendars because chances are, they're kickin' it with google, too. 2. PREP BEFORE YOU BEGIN: First, consider the "buckets" of tasks/to-dos/recurring events, and colour code them by category. Here are some examples of "bucket" categories: perpetual dates/reminders (like birthdays), personal tasks (like if you have a house cleaner that comes every month, if you have dodgeball on Thursday's, you have an upcoming doctor's appointment, or your kid has gymnastics on Saturday's, etc.) work time, morning routine time, fitness time, etc. Obviously, "work" can include many different tasks and appointments, but if you colour code "work" as purple, you'll be able to see at-a-glance on your calendar what times you're working and what times you are free to do other things. I like to keep all my "personal" things as one colour too, whether it's my own appointment, my kid's sports practice, or a one-off family get together, I keep them all green so I know they have to do with personal "stuff". Note: this may take you longer to get used to than you think. Begin by making a list of all the things you did over the past month, or week, and then try to organize them by category. "Personal" can include many tasks, and you'll want to ensure you get into the habit of colour coding personal things accordingly, as you add them to your calendar. Similarly, "work" can include many tasks, so as you start making a list of all the things you need to accomplish, you'll see that "create graphics for blog post", "marketing seminar" and "event planning call" all fall under "work" and though they're different events individually, they can all be colour coded purple. 3. HOW TO START: I suggest you start small by JUST putting in perpetual dates that will save your brain in the long run. Example: put in all the birthdays of the important people in your life, and set them to recur on a yearly basis. If you do something on the 1st of the month, or the 15th of the month, every month - note that and put it in there to recur. If you have a weekly recurring work task, insert it (using the proper colour code, of course!) and make it re-occur every week on that day. Get used to the function of just manually creating an appointment and build competency with how to make things recur perpetually, weekly, bi-weekly, annually, etc. Get used to adding a colour code, or adding notes (if you like) inside the event itself. I like to do this with calls and virtual meetings, and add the exact link I'll need to join the session inside the calendar appointment, so I'm not searching for it later. It will get easier to schedule things quickly if you familiarize yourself with the system and get good at it. 4. HOW TO CONTINUE: After you've gotten used to adding those regular yearly dates, start looking ahead to the next month. What appointments do you need to add to your digital calendar? If you work out of the home, maybe you just mark "WORK" from X hour to X hour, in a specific colour, and start there. If you have weekly sports, meetings, or appointments, add those in and remember to specify them by colour. As you can see from the example above, I have added things like my daily workout time, my morning routine time, and my "house hour" time in different colours. My morning routine time is something personal that involves my whole family, so you'll see other "personal" things are in the same colour (our cleaning team coming on Wednesday morning and a gymnastics practice Wednesday afternoon. Purple items are regular/recurring work tasks. Pink items are one-off work appointments, workshops, etc. Any external meetings booked with my calendar booking software also show up pink because they're one-off and I want it to flag my attention when I look at my upcoming week. I've colour coded any work I do for my podcast in a separate shade of purple - it's still "work" but I need to ensure I'm spending focused time for recording and editing on the show every week, or else things will fall behind. My main tip for you would be to spend some time planning this thing on your computer, and then get used to checking it on your phone on a regular basis. Get in the habit of looking at your calendar maybe in the morning when you have your coffee or are, you know, taking nature's call every day. 😂 You will not create a habit out of it unless you start LOOKING at it. Set an alarm on your phone at a specific time every day that says "CALENDAR REVIEW" and do that for 30 days. Soon enough, you won't need the reminder. I use plenty of other tools for digital planning, but the VERY FIRST tool I started getting excellent at was my google calendar. Only then was I able to add in other digital systems (that I'll talk about in another post) for planning my to-do lists and brainstorming, organizing what I'm DOING during specific work blocks, and planning out my business marketing, content, and strategy.

MOMFIDENT BOSS TIP: Don't try to do everything at once! You will overwhelm yourself, just like when you try to take on anything else in life too much at a time. Don't bite off more than you can chew. Start by implementing this ONE THING, get really comfortable with it, and then you'll be ready for implementing additional digital systems. Let me know if you DO implement a digital calendar, and how it goes for you over the first 30 days of using it. More to come on digital planning. XO Courtney

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