Making Space for Planning and a Little Fun

If you run a small business, the holiday season tends to arrive the same way every year: slowly… slowly… and then all at once. One minute you’re planning your end of the year promotions and reminding yourself to order more coffee for the office, and the next minute you’re juggling client gifts, year end paperwork, and a staff potluck signup sheets that somehow still has seven desserts and zero actual food.

It’s easy to get swept up. December has a way of convincing us that we should be able to run at full speed and enjoy the holiday magic and finish our strategic plans for next year, all simultaneously. But as leaders, we know better. Doing everything at once usually means we enjoy nothing fully.

So, here’s the leadership opportunity tucked inside the busyness of the season…make space. Space to plan, space to rest, and space to have a little fun along the way.

Why planning in December actually makes January easier

You don’t have to do a full strategic overhaul before the calendar flips over, but carving out even a couple hours for intentional planning creates real relief. Holiday downtime (even if you have to be the one to manufacture it) gives the mental distance leaders rarely get. When the phone slows down and inbox traffic gets sleepy, your brain can finally stretch out a little and look at the bigger picture.

A simple, light-touch December planning session might include:

• A quick review of the past year: What worked, what didn’t, and what was just plain exhausting.
• A shortlist of 2026 priorities: Not a full strategy, just the “these three things matter most” list.
• A few boundary decisions: What you’re no longer willing to hustle for, say yes to, or carry alone next year.

You’ll walk into January with direction rather than overwhelm, and your team will feel the difference.

But let’s be honest, you also need some fun!

Leadership can get very serious, especially at year end when finances, people issues, and deadlines stack up. If you’re not careful, the holidays become another project to manage instead of a season to enjoy.

But fun matters. Not the forced, elaborate, picture perfect kind. Just the small, human moments that remind you why you enjoy the people you work with (and why you do this work in the first place).

A few low-effort ideas:

• Invite your team for a 20-minute “holiday beverage break.” Hot chocolate, cider, or whatever fits your culture. No agenda. Just connection.
• Do a “year-in-review gratitude round.” Everyone shares one thing they appreciated about the team this year. (Keep it optional for introverts!)
• Create a silly office tradition. Ugly sweater day, “best decorated desk,” or a friendly competition for the most over-the-top holiday playlist.
• Take yourself out for a solo celebration. Leaders rarely celebrate themselves. One hour. Your favourite treat. No work allowed.

Fun doesn’t have to be complicated. It just has to be intentional.

The leadership twist: your team follows the pace you set

If you, as the leader, sprint nonstop until December 23rd, your team will think that’s the expectation. If you act like the sky is falling every time a year end task appears, they’ll respond the same way.

But if you stop for a breath, protect an afternoon for planning, or take 30 minutes to laugh with your staff… they’ll follow that too.

People don’t need a perfect leader heading into the holidays, they need a present one.

One small action you can take this week. Book one uninterrupted two hour block in your calendar in the next 10 days. Label it: “Planning and Pause.”

During that time:

1. Write down your top three priorities for next year.
2. Identify one thing you want to delegate or stop doing.
3. Do something relaxing for at least 10 minutes, walk, stretch, read, breathe.

That’s it. You can do a lot with two hours of intentional thought and a short reset.

A final thought to close the year

Leadership…real leadership is mostly about modelling the behaviours you want to see. Calm, clarity, focus, community. These aren’t December luxuries; they’re strategic advantages and the holiday season is a perfect time to practice them.

So. plan just enough to set yourself up for a strong January. Make room for joy so the season doesn’t become another checklist. And remember: you don’t have to “manage” the holidays, choose to experience them.

Here’s to a season of breathing room, meaningful connection, and just enough planning to feel good heading into the new year.