My husband says I’m cheating: Digital Planner Pros and Cons 📝

This blog post is a great accompaniment to Gab & Jam

(video: podcast:

Bruce says that the year hasn’t started and I am ALREADY “cheating” on my Plum Paper Planner—that I JUST unboxed ( )! 😳🙄🤷🏽‍♀️😬

Plum Paper Planner Unboxing 3.0:

Let me explain....

You know how much I appreciate the feel and experience of using a pen and paper for ALL kinds of things (like journaling, taking notes, and planning). There is just something the experience of flipping pages and wielding a writing utensil that sends me to another Zen-like mental space. So, when I tell you that I have resisted going digital and paperless for everything (including bills), you really must believe me. However, in the past 2 years, I have finally made the switch to a digital, cloud-based daily journal and that experience has been life-changing. (—This post is NOT about this, but I can just say that I have benefited from having my journal with me every day and everywhere, so that I can do it WHEREVER I am—especially and even on the treadmill!—has me journaling everyday religiously. And the fact that I can copy and paste my ad hoc list of intentions and ideas from these entries from one place to the next has made me more mindful and has meant that I have unlocked the secret code to that superpower of multitasking. You see, many of these journals are not only helping me navigate my feelings, but they OFTEN become the beginnings of blog posts, song lyrics, and other long-range plans, so I can’t stop talking enough about how this has revolutionized my life!)

2019 Plan With Me video:

Still can't shake paper….

However, I have continued to insist that a paper planner is REALLY the way to sit down and bask in the glow of vision board-type planning. There’s something about seeing the entire year spread out before me that gives me a reason to set some time-dependent goals in place. It also gives me the motivation to check our progress on previous goals. That’s why I couldn’t even imagine going digital with my planning.

How it began

So, I had just shot the unboxing video for our latest Plum Paper Planner ( ) and was browsing Pinterest for decorating planner ideas when I ran across a couple of digital planner posts, which I promptly ignored. It wasn’t until a little birdie turned me on to Procreate—which ALSO recommended the use an Apple Pencil ✏️ to get the best out it—that the window for “noticing” digital planner posts opened again.

What can a digital planner do better?

In my quest to exploit using Procreate and, subsequently, learning about the Apple Pencil, that it became clear that a digital planner might offer solutions similar to my digital journal. ✏️ 🍎 However, as I have mentioned before, I thought that if I was going to do the digital planner thing that I was going to have to create my own. After that, I watched a two-hour video of how painstaking this process is to make one from scratch and I scrapped that idea pretty quickly. 🙄 And, again, I shot the idea down and went back to learning about Procreate. 🤷🏾‍♀️

Layout options (similar to last one; )

It was inevitable

Going down my YouTube rabbit hole for Procreate, I found a video where a person said that you should just download a free one to see if it’s for you. 🐇 That’s the moment that the switch got flipped just a little.

Here was the first Plum Paper Planning unboxing:

Biggest benefit?

What I realized is that one of the BIGGEST benefits of having the digital planner is customizing it —a problem I had for the latest Plum Paper Planner is the lack of a financial page to meet my specific needs—but with a digital planner, not only can you import specific PDF pages in (that have exactly what you need), but can also create your own and put it in there as well. Huh. Realizing this was a game changer! So, off I went in search of my first digital planning experience! ✏️


Because we took advantage of the Black Friday special, not only was everything 30% off, but a free gift of planning stickers were thrown in (see Unboxing video timestamp here: ). This was a nice bonus, because while I have been very curious about their stickers, I would have NEVER have ponied up the cash to throw it in the cart. —While I am a sticker whore, I tend to get mine from the dollar section of Target or on sale a Meijer; I would NEVER spring for premium planner stickers, because I buy so many stickers, so often, for so many other purposes. —So, it IS nice to be able to try them without paying extra for them.

Pros and Cons?

Here are some important Pros and Cons of the digital versus paper planner experience:

Pros to using a digital planner:

  1. —Don’t have to lug around a thick paper planner (which often gets left behind when I am carrying quite a lot to and from work) (My planner "fits" in my iPad, so I don't have to carry any more than the planner to be armed for planning!)

  2. —Don’t have to limit the number of pages (to limit size) (You can have as many pages as you'd like. Really. It's amazing how wonderful it is to decide you want to add a trip packing list page for everybody in the family and then be able to add it on a whim!)

  3. —Don’t have to worry about leaving it open and out (for people to see; when I am at work, I don’t share what I am doing) (All I have to do is to slam the cover of my iPad shut and ALL of our side hustle work is securely out of sight.)

  4. —Can add in your own pages, as well as reorder and copy more to insert wherever you’d like in planner. (This means that I can have any and all the financial pages that I want—and, again, they can be private.)

  5. —Can customize cover and pages with your own photos (so that it can become more of a scrapbook and journal). (One of my favorite digital planners that I've found is the "Life Planner" by Amanda Davis. It includes a bucket list, a vision board for each month, habit trackers for books read and movies watched--along with space to insert cover images and a short review. While I did NOT end of purchasing hers, I am super inspired by her example to make my planner into more of a lifestyle experience. Here's her link, if you'd like to check out how her planner works: )

  6. —Can copy and paste plans, ideas, etc. from my digital journal into planner. (As I have mentioned, often the plans for my day or date-sensitive project details are often started in my daily Google Docs journal. It's great to be able to simply copy and paste any of the goodness that I stumble upon while journaling right into my digital planner, right in the moment, on my phone.)

  7. —Works even when not online (can be synced up later)

  8. —Don’t need the more expensive iPad Pro in order to use it (I have a 2018 iPad and it works fine.)

  9. —Undated version means you can use it again and again (by just downloading a fresh file); whereas even undated paper planners can’t be reused, because you won’t be able to erase all that you’ve done to it.

  10. —There seem to be an infinite number of outlets to find a planner system and general style that works for you. (Etsy has a bumper crop: Here’s the one that I settled one: )

  11. —Yes, you can access your digital planner from your phone, so that you can stay on top of all those wonderful things you wanted to do with your time, but might need reminding of.

Here are the Cons that I have realized about using a digital planner:

  1. —Not crazy about my handwriting (and it only looks less good on iPad), so it’s not a pleasure to behold

  2. —Must carry the pencil around, for best results (which is fragile and requires protection and charging)

  3. —Planner is NOT available when either the iPad or Apple Pencil doesn’t have a sufficient charge. (My iPad is only compatible with the older Apple Pencil 1, so it has to be physically connected to a lightning charger; unlike the new Apple Pencil 2, that has the magnetic charger when stuck on top of most iPad Pro cases.)

  4. —Undated version means that you either have to manually write in all dates correctly or try to copy and paste digital sticker dates—which is what I am going to attempt to do (AND which is painstaking, but necessary if I want to be able to see and plan for future activities 🤷🏽‍♀️).

  5. —Because there are so many places to get a digital planner, it is quite a time-suck and can be an overwhelming process to find exactly what you want. (In the end, it was inspiring, but it was nerve-wracking too, because, as you know, my schedule is ALWAYS full of other things I need to be working on.)

  6. —There is a learning and a cultural curve. (If you want to get the most out of your planner, you will need to invest time learning how to do all the basics in whatever planner app you choose to store your planner, in my case, GoodNotes; also, you have to make peace with the differences between using a digital medium and a paper one and not try to force it to be something that it is not. )

  7. —There are some extra expenses involved in using a digital planner. [Not only do you need the basic equipment of a new-enough iPad and a compatible Apple Pencil, but you need to pay for your note taking app to hold the digital planner (in our case GoodNotes cost $7.99), our Toscan-styled planner ( ) cost about $25, and I bought some “official” digital planner stickers—even though, eventually, I plan to make my own—and paid less than $12. for a variety of basic, functional elements (like date numbering) and fun stickers (like ones to remind me to do laundry and other daily tasks, but in a fun way (search "Digital Planner Stickers in Etsy or in Pinterest). ]

  8. —No, the Apple Pencil doesn’t work with your phone. So, even though you can access the planner with your phone, you are hard pressed to be able to add to it in a meaningful way, which is a REAL bummer, because as I may have mentioned in passing, I do MOST of my journaling when I am on the treadmill from my phone, so it would GREAT to be able to update it then—before my day gets started good). —I am going to investigate ways around this limitation. Even if I can copy and paste from my journal into my digital planner on the iPhone, I will be pretty happy, so I will try this out and let you know if it works.

  9. —There are no pre-made stickers dedicated to what we plan to use it for (i.e., record release dates, YouTube video making/uploading/promoting, podcast publishing, etc.), so all of these need to be made from scratch—which adds yet another task to my already toppling-over list…

One way to make digital stickers is Procreate.

Here is the Procreate “How To” Playlist:

After using it for one full week, here are a few realizations....

The ONE thing that I assumed would be the biggest pain in the ass—the fact that the planner is undated—may turn to be INCREDIBLY useful for me to actually START using the planner fir this week on (instead of waiting until two weeks from now—January 1—to get started). However, it IS a pain to have to physically add in the date numbers one at a time. 🙄 You best BELIEVE that once I get one month done, I will copy that whole motherfucking configuration and paste it onto the next month! 💥 —I am assuming that, except for a few tweaks, it should be MUCH easier to move them around slightly than to have to place them AGAIN. 😳🤷🏽‍♀️ So, that’s my grand plan with that.