Episode #369 – Holiday Planning Like a Boss

This is episode 369 of the Brilliant Balance podcast: Handle Holiday Planning Like a Boss. Here we are, right at the beginning of yet another holiday season. If you’re someone with a high degree of complexity in your life, with significant responsibilities in multiple arenas, you probably have a lot going on at work. That doesn’t let up at the end of the year, and you also have a lot going on at home—maybe with children, maybe with parents, or maybe just with the responsibilities of running a household. The holidays can feel completely overwhelming to anyone.

They can be almost shockingly overwhelming to those of us who are typically pretty good at keeping our arms around our schedules and maintaining a high level of productivity. Somehow, this time of year can reach a breaking point even for the best of us—those who are usually pretty good at running a plan day-to-day.

The reality is there’s a good reason for that, a particular reason I’m going to dive into in this episode. I’ll also give you some strategies to help you handle the holiday planning season without it taking you under.

One of the ways I want to equip you for this is with a playbook I put together—your personal holiday playbook. This is a simple, straightforward printable that you can grab for free on my website. You can use it to help you plan and stay on track during this holiday season. Think of it as a roadmap for the holidays.

Before I forget, I’ll give you the URL. Go to brilliant-balance.com/holiday—that’s the page you’re looking for. You can download the playbook from there. This playbook provides a roadmap for the season. It helps you outline milestones and tasks by working backward from the key holiday dates. It gives you a framework for when you might want to tackle these tasks and helps you block time in advance for holiday essentials, like shopping or getting tickets for events, so you can avoid last-minute stress.

If you’re feeling stressed right now as we stand at the beginning of this season, this is going to help a lot. Again, it’s brilliant-balance.com/holiday. I’ve also linked it in the show notes. Go grab your download so you have this playbook in hand as you work through the season.

The reason having a playbook is so important is due to an insight we often miss. In our drive to get a lot done, we skip past a big idea: the holidays are essentially a project—a complex project with multiple parts and sub-projects within it. All the work associated with it would be like if you were handed a big new project at work. If you’re a business owner, it’s like taking on a big initiative. If you work for someone else, it’s like your boss saying, “Hey, you’re going to get this done by the end of the year, too.”

That’s what it feels like. It feels like someone handed us this giant, complex project with many stakeholders, a lot of people involved, and emotions running high. There’s so much tradition baked into it. There are family members, friends, and colleagues. There’s a lot of money involved, and a lot of time involved. All those hot buttons get pressed at once in this project we call the holidays.

I don’t want to diminish the holidays to something as boring as a project, but it’s a helpful construct to handle the work associated with it. The spirit behind the holidays, the “reason for the season,” is a completely different thing. If you’ve listened to this show for any length of time, you know my priority for the holidays is to protect both the joyfulness and quietude they bring. I aim to preserve both the magic of the season and those quiet, reflective moments that connect us to the purpose of the season.

Creating space in your calendar for what I call the “holiday project” will help you acknowledge that holidays don’t just happen. You’ll need to make choices about things you won’t do during this time, probably from now until the end of December, to create space for this extra work. Here’s a hint: don’t create room for this extra work by eliminating the foundational practices that keep you healthy, whole, and happy during the season. These include things like sleep, which is often the first to go; quality food; moving your body in a way that feels good; and simple, quiet breathing, like meditation or journaling.

Instead, set aside non-essential household projects, work tasks, or regular activities with the kids to make room for the special things that happen just once a year. This approach frames the holidays as a project. How are we going to create space to do the work of the project?

When you’re running this project, grab that playbook as a guide. First, have a meeting with your family—the key people you’ll be celebrating with, like parents, in-laws, children, and your partner. Decide what matters most to you and yours. You could think of it as: “most important” (things that are paramount and absolutely cannot be altered or skipped), “great if we can get to them” (but not essential), and “we don’t have to do that at all, and we’d be completely fine.”

This exercise is shockingly clarifying. I’ve done this for years, and every year, I get surprises on both sides. I discover things that are really important, usually to my children or other family members, that I would have missed. Every year, I also find things that I thought were critically important that it turns out we could skip.

This sets you up to do three more things. First, say no strategically to invitations or obligations that don’t align with your priorities this year. Second, delegate or outsource with confidence. Think about which tasks you don’t need to do personally. Lastly, adopt a “good enough” standard. Focus on how you want people to feel, rather than on everything looking perfect.

Remember, you don’t have to do it all. A well-balanced holiday is absolutely possible—one that creates space for you to enjoy the magic and wonder of the season. I hope you find something in this episode that you can use. I’d love to see you doing it in the real world. If you’re willing to share, just respond to the email that announces these episodes or drop a comment on the podcast and let me know what you found valuable from this episode and how it’s helping you have a fabulous holiday season.

That’s all for today. Till next time, let’s be brilliant.