LearnDoBecome Holiday Planning Workshop

Ready to enjoy a calm, organized holiday season? The Command Central we teach inside our Steps to Everyday Productivity (STEP) program helps manage ALL the details of life.

But whether you have your full Command Central up and running OR you’re just getting started with our free resources, this Holiday Planning Workshop (which builds on David Allen’s Natural Planning Model from the book Getting Things Done®) will be your guide to mental clarity and peace. Enjoy!

Lesson #1: Begin With the End in Mind

Your Assignment:

Take 20-30 minutes to meet with your family (or have some casual conversations with your family members individually) and walk through the questions on the template–or use questions you’ve created on your own! Make sure you don’t miss this step, as this will help to make sure everyone’s expectations are aligned and will ease a LOT of stress in the long run.

Click here or on the image below to download your own Family Discussion Guide!

Or click here to save the Family Discussion Guide to your Evernote account!

This is an example of how our family “began with the end in mind”:

And as you’re planning, here are a few more ideas to consider:

(1) Focus on the 9s and 10s. You can ALWAYS add things in later, so let’s imagine you rated each of your traditions, activities, expense items, etc. with a 1-10 scale, you’ll want to focus on the ideas that are 9s and 10s.

(2) Remember that “life” is going to happen. People might get sick, unexpected expenses might come up, or you might have some new challenges/opportunities occur. These unplanned events PLUS the need to continue doing the regular laundry, meal prep, email management, etc. AND the fact that you’ll most likely be having cards, treats, gifts, etc. coming into your life that you’ll want to enjoy and accommodate–can easily lead to overwhelm.

(3) Remember that even 2-3 magical memories can “make” the season. There was one year that we went to make candy cane airplanes with my mom and dad. This was one of the last years my mom was able to actually come out to the living room and sit with us. (She passed away from Alzheimer’s.) I remember my dad sitting with us, and my mom singing songs while we made these candy cane airplanes. Looking back, this is one of my only memories from that season, and it was a beautiful moment.

A book I’ve been reading, called The Power of Moments, explains that even if MOST of an experience isn’t awesome, your brain will highlight the “magic” moments within it and will most likely remember those moments. We’re so thrilled for you to have your best holiday season ever!

Lesson #2: Brainstorm

Your Assignment:

Take 30-40 minutes to identify your categories onto a piece of paper and brainstorm all the details of the season that you want to remember and/or implement. By the end of this step, you should have everything in front of you that you really want to do–not that you feel you have to do. And if it feels overwhelming, don’t go any further until you’ve renegotiated with yourself (and/or your family) and made things as simple as possible.

More Details:

Simply identify the categories of holiday plans you’d like to organize–and then write down as many details as come to mind.

My personal categories were as follows:

• Service opportunities
• Family activities at home
• Family activities outside the home
• Gifts for children/spouse
• Gifts for extended family members
• Gifts for friends, neighbors, teachers, etc.
• Card/mailing
• Decorations
• Food
• Travel

And my brainstorm looked like this:

Lesson #3: Organize (Paper Version)

It’s now time to take all the projects and tasks from your brainstorm and organize them by time frame. This is going to reduce the feeling of overwhelm you might otherwise feel because you’ll be able to look at a small list of things that need to be done in the short-term–instead of a huge list that needs to be done by the date of your special holiday.

Your Assignment:

Spend about 30 minutes writing your sub-projects and tasks onto sticky notes. Then group them into clusters based on the approximate time frame in which you’d like to accomplish them. Label those clusters once you’ve organized them onto one big sheet of paper (or use one sheet of paper per cluster and label each sheet separately) and then you’ll be ready to move onto the next lesson!

(In the next lesson, we’ll be explaining how to do this using Asana or a digital project manager, so if you’re not sure if you want to go paper or digital with this project, you may want to make that decision after viewing Lesson 4.)

More Details:

Step 1 – Move sub-projects from your brainstorm onto Post-it notes. 

Get out a stack of Post-it notes and write out one project from your brainstorm on each Post-it note. Combine ideas from your brainstorm into one project where it makes sense.

Step 2 – Group your Post-it notes into clusters based on when you’d like them done. 

Using a large sheet of paper (or an empty surface), begin moving these Post-its around and grouping them together. Put things that feel more urgent near the top, less urgent things near the bottom.

Step 3 – Label your clusters.

If you’re using a large sheet of paper, add labels for each grouping according to your timeline onto that paper. If you’re using an empty surface, pull out some sheets of paper (one for each cluster), and label each sheet.

These timelines will depend on when you are starting to plan, but may include things like: Early November, Mid-November, After Thanksgiving, December, Today, Tomorrow, Christmas Eve, etc.

***Note: While this workshop is focused on how to structure your projects and tasks, I want to just take a moment to talk about budgeting.

Eric and I have made the choice to only spend money that we have agreed upon and saved for the holidays. That way, when we are buying stamps for the cards or supplies for baking, we aren’t feeling stressed in the process. So if you need to cut back on some of your activities and gifts to protect your budget, please know that that is absolutely okay!

You don’t have to have a ton of presents or take an expensive trip to celebrate the holidays. Often the inexpensive, simple experiences are the most memorable.

Lesson #4: Organize (Optional Digital Version)

Your Assignment:

If you’ve decided you’d like to organize this project digitally, spend about 30 minutes typing your sub-projects and tasks from your brainstorm into a new project inside Asana. Then group them (using the drag-and-drop feature) into clusters based on the approximate time frame in which you’d like to accomplish them. Create “Headings” inside Asana to label the clusters.

More Details:

If you’d like to organize your Holiday planning using Asana, or another digital project management software, this video will show you exactly how to do that.

Reasons I love Asana:

• It is easy to create sections and subsections.
• You can assign due dates to as many (or as few) tasks as you’d like.
• You can potentially delegate tasks to others.
• You can search all of your tasks by keyword or tag.
• Reminders to complete the tasks can be emailed to you automatically.
• You can link the software to your digital calendar.
• Plus, Asana, has a great app that works with your smartphone.

The process explained in this video is exactly the same as the process using paper, with a digital twist!

Step 1 – Move sub-projects from your brainstorm into Asana. 

Combine ideas from your brainstorm into one project where it makes sense.

Step 2 – Create “Sections” for each timeframe and begin to organize your sub-projects.

Create the timeframe sections that make sense to you. These timelines will depend on when you are starting to plan, but may include things like: Early November, Mid-November, After Thanksgiving, December, Today, Tomorrow, Christmas Eve, etc. (Using a colon at the end of the line changes that line into a section.)

Then take a few minutes to put things that feel more urgent near the top of your list, less urgent things near the bottom.

Step 3 – Move sub-projects into the appropriate timeframe section.

Try to make things towards the end of the year as simple as you can. If your list does not feel doable after this step, this is where you would want to think about delegating and having a conversation with your family to decide how you can simplify. 🙂

Lesson #5: Review and Do (Paper or Digital)

Your Assignment:

Take all the ideas you generated and organized in the previous lessons and incorporate them into your Command Central so they will actually happen. If you don’t yet have a STEP Command Central, we’ll walk you through the basics of using an optimal calendar, Routines List, Current Projects List, and Next Actions List. (And please don’t feel intimidated…these will set you up for success and will be a boost to your life throughout the holidays and beyond!)

Tips for success:

• Make sure to put anything date-specific on your calendar.
• Make it a routine to look daily at your Current Projects list (maximum of 7-8 projects per month) and work on those current projects.
• Simplify other routines as much as possible to give yourself time to work on these.
• If you’re using Asana, use copy/paste to move sub-tasks into your sub-projects and add due dates for date-specific tasks. Consider using tags to add contexts to each next action.
• To learn more about how we recommend you use your calendar, Routines List, Current Projects List, and Next Actions List, check out Episode 26 of our podcast by clicking here!
• Below are a couple of images to show a sample Current Projects List and a sample Next Actions List.

Hopefully you can see how beginning with the end in mind–and then filtering all the details into very manageable lists of events, tasks, routines, etc. can change your life! Our goal is for you to feel calm, present, and organized during the holiday season and throughout your life, and we are so thrilled to have you with us!