This is the first post in our 5-part series, Undivided December: A Holiday Survival Guide for Founders & Operators. Each week from now until Christmas, the Plumb team will explore how startup founders and operators can use AI and automation to get more done and be more present this holiday season. So grab a cozy sweater, a cup of hot tea or cocoa, and settle in around our figurative fireplace — it’s time for festivities! 🎄
The December Dilemma ❄️
I've spent enough December months as a startup operator to know that the intersection of business demands and holiday obligations creates a special kind of chaos. As someone who manages operations and strategy, I've seen firsthand how the pressure to simultaneously handle year-end business planning and holiday preparations can break even the most organized systems.
Here's what I've learned: what we optimistically call 'multitasking' is actually just rapid task-switching that leaves us operating at about 60% effectiveness (and that's being generous). For those of us trying to wrap up Q4 while also coordinating holiday plans, this cognitive drain isn't just annoying — it's actively sabotaging both our work and personal lives.
Context-Switching Gets You Coal 🪨
Last December, I found myself on a critical strategy call while simultaneously trying to order gifts online. I completely missed a key point from our CEO because I was distracted by a 'limited time offer' popup. Not my finest moment. But it illustrated something I've been thinking about a lot: we can't actually multitask, we can only divide our attention — and usually pretty poorly.
The worst part? December is exactly when we need our strategic thinking capabilities the most. Instead of having the mental space to plan for the upcoming year, we're caught in this exhausting ping-pong match between professional obligations and personal festivities. I've watched too many smart founders and operators (myself included) make rushed decisions about next year's initiatives simply because they were stuck in survival mode.
How to Avoid the Holi-daze 😵💫
After a particularly chaotic holiday season last year that left me feeling like I'd neither served my team well nor enjoyed the festivities, I started rethinking my approach. Here's what's actually working:
Walking in a Workflow Wonderland ❄️
Word to the wise: you’re probably doing too much, and you’re probably doing it by hand. And while “automation” may sound daunting, I promise it will help you tackle your most annoying (but necessary) tasks and free up hours of your time. Spend a few minutes customizing your workflows in Plumb, then let them go to work for you. Here are some of my favorites:
AI-generated blog posts and social content, written in your voice and for your audience
Auto-transcribed meeting notes, with AI-generated analyses and action items (a true life saver for any season)
A daily, AI-generated meal plan tailored to your dietary needs, complete with a shopping list
Time Blocking ⏰
Here's what I've had to accept: trying to be equally present for everything just means being partially absent from everything. When I'm in a strategic planning meeting, that's where my head needs to be — not mentally cataloging my holiday shopping list. And when I'm at a holiday dinner, nobody is served by me checking Slack under the table.
So instead of pretending I can smoothly switch between work and holiday prep all day, I now block my calendar into focused chunks. Mornings are for strategic work when my brain is fresh. Afternoons might include a mix of operational tasks and personal errands. And some days are just designated holiday days — no guilt about ignoring work emails included.
Let It Go, Let It Go, Let It Go 🎶
Sometimes, winning requires narrowing your scope. When we’re inundated and overwhelmed, everything can seem like a priority — but not everything is. Channel your inner Santa Claus on this one: make a list, take a few deep breaths, and check it twice. What can wait?
That’s A Wrap 🎁
Borrow this simple framework to thrive through the holidays this year:
Identify your non-negotiable December work priorities (be ruthless about this)
Set up basic automation for the routine stuff
Communicate clear boundaries to both team and family
Protect your strategic thinking time like it's gold
Accept that some tasks are better left undone
The truth is, there's no perfect solution to the December dilemma. But I've found that acknowledging the real cost of constant context-switching and setting up intentional systems makes a huge difference. It's not about doing more — it's about being more effective at what we choose to do. And sometimes that means accepting that the holiday cards might go out a little late, or that some strategic planning might need to wait until January. That's not failure — that's just being human.
In our next post, we’ll dive a little deeper into one of the workflows I mentioned above, and demonstrate how Plumb is helping startup founders and operators thrive — through the holidays and beyond. 🚀
The Magic of Plumb
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