Annual Planning with Trello

I literally live my daily life through this Trello board

I initially wrote this post on the Atlassian Community, which I HIGHLY recommend you join if you haven’t already. Lots of fellow Trello enthusiasts like myself over there.

I've been planning my life in Trello for a long time, but this year I decided to bring everything together, make some upgrades, clean up my board, and add some new features and automation with my good friend Butler. 

Here's a template of my board if you want to skip the formalities and get right to it. But keep reading below and I'll explain how it works!

I started out by doing some reflection on 2020 (a good exercise in which I realized it wasn't actually a total dumpster fire), and then I did some planning for what I wanted to accomplish in 2021. (Here's a cool annual review I found - just copy this doc and go through the prompts. Thanks, Morning Brew for the recommendation.)

All of that planning then was “tangibilized” (a word I created recently to mean “to make actionable”. Webster will be publishing it soon) inside of Trello.

1) The Table of Contents List

I created a card with my word for the year as a reminder.

Next, I created a card where I listed out my annual goals. 

Markdown formatting makes it look nice 😎 I broke out my goals into three main categories and listed specifics below them. Each week, I copy the description in a comment and add notes next to each bullet point about the progress I made toward that item. It’s a handy way to make sure every week I’m making progress towards my goals.

Keeping track of things I learn is really helpful to me, so I also made a card called "Things I learned this year" and every week, I add something to a checklist inside of it. I write down something that I learned that week - could be about myself, about life, about my friends… anything! I started doing this about halfway through 2020 and it was actually a really fun exercise and very helpful to look back on at the end of the year.

Lastly, I made some templated cards with checklists for daily, weekly, and monthly habits.

And that's the table of contents list, which is the base of the board that everything else is formed off of.

Next, I created my "working board" section. This is where all the action takes place. 

2) Scrum/kanban lists

I organize my life in an agile methodology, so I start with a Backlog, then have To Do, Doing, and Done lists to track what's going on. Each week is a sprint and I pull things from my backlog and add to my To Do list. 

I call my backlog "Ideas for 2021" as anything that comes up gets dumped in here and then re-prioritized when I do my weekly planning. (I do that - you guessed it - weekly.)

This is the list where I take my annual goals and turn them into bite-sized tasks that I can accomplish throughout the year. I also use labels with the category of my goal so that I can keep track of them and make sure everything on the board falls under a goal so I'm not just adding random things. 

Part of my weekly checklist includes reviewing tasks completed at the end of the week and moving any special tasks to my "Yay" list for celebration. This is fun to look back on over the year and see what I've accomplished.

I created a card in "Doing" for Ongoing tasks and used the card cover setting to make it seem more like a divider. My weekly and monthly checklists will sit under here as they will spend more time "in progress" than most of my other cards and they're not necessarily meant to be cleaned out at the end of every day or week.

3) Now make it easy with Butler automation

I used Butler to create rules to make my daily / weekly / monthly checklist cards. It was actually super easy. I used to use the Card Repeater Power-Up to accomplish this, but it got a little messy and didn't give me as much customization as I wanted. 

With Butler, I can actually name the card by the date, so it's super easy to keep track of. 

Here are some screenshots of my rules if you want to set them up for yourself. 

I also used to have problems with these getting a little clogged up. For instance, if I went on vacation or got behind a few days, I’d come back to a handful of daily cards and felt like such a failure for missing all of those days 😭. I created some Butler rules to move these over to done if 1) I complete all the items in the checklist, OR 2) the due date has passed. (Hey I’m not going to be perfect every day, and every day is a new day to try again.)

4) Additional lists to keep my life organized

I have a list called "Things to Buy", and this is basically an "Add to Cart" button for my life. When I come across something I want to buy, rather than instantly buying it, I just add it to this list and periodically review this list when I actually am ready to buy things. It gives me time to decide if it's an impulse purchase or if I actually want it, and it helps me spend money better by comparing it to other things (do I need both of these programming books or just one?) 

It's really easy to do this because if I'm on my phone, I just click "share" and there's an option to add to Trello. (If you don't see this, you might need to configure it in your phone’s Share settings.) If you're on your computer, you can just use the Trello Chrome Extension and click the Trello icon and add it to your list.

And then lastly, I have a list of other boards or things that I might want to reference, such as other boards that I am working off of, links that I want to keep handy, or just other things I might want to reference throughout the year.  

5) Now spruce it up and make it yours!

This board looks very nice in the screenshots, but I started out by just building the layout and then adding stickers and custom backgrounds and card covers. It was really fun to design as this is basically a vision board for me, and something I am LITERALLY in every single day of my life. (Thanks, Atlassian for the lovely background image.)

So now it's your turn! Feel free to copy it and customize it to work for you!

Can’t wait to hear about what fun additions you add!