Working Through the Holidays: How to Turn a Christmas Trip Into a Productive (and Tax-Smart) Business Getaway
The holidays don’t have to pull you away from your business — and they don’t have to break your productivity flow either. If anything, a Christmas trip can become one of the best times to plan, reset, and move into the new year with clarity.
Whether you're flying home to see family, taking a winter escape, or squeezing in some end-of-year strategy on the road, here’s how to blend business and holiday travel the OOO way: intentionally, calmly, and tax-smart.
🎄 1. Set Your CEO Intention Before You Leave
Holiday travel gets chaotic fast — delayed flights, last-minute shopping, family demands, and end-of-year deadlines.
Before you pack your suitcase, set a clear intention:
What business goal needs your attention before the year ends?
What projects do you want to review for next year?
Do you need quiet space to brainstorm without day-to-day distractions?
OOO Tip: Create a simple Holiday CEO Plan — 1–3 tasks max. You’re not trying to run a full workweek during Christmas; you’re aiming for clarity.
🛫 2. Yes — Your Christmas Trip Can Be Business Travel
Holiday trips that serve a legitimate business purpose may still qualify as business travel.
Examples include:
Meeting with clients, vendors, or collaborators during your trip
Working on next year’s business strategy
Content planning and creation for Q1
Scouting locations for events, retreats, or future business travel
End-of-year bookkeeping and tax preparation
As long as the primary purpose of the trip is business-related, you’re operating within IRS rules.
(And yes — this applies even if you blend in holiday activities.)
🎁 3. Plan Work Blocks Around Holiday Activities
To keep your trip peaceful rather than stressful, think in blocks:
Morning Focus Block (30–60 minutes): Strategy, content planning, tax prep, or reviewing financials.
Afternoon Flex Block: Quick client emails or time-sensitive approvals.
Evening Off: Enjoy family, food, lights, and Christmas traditions.
When you work in intentional blocks, you avoid feeling like you’re “working the whole time” — and instead move into the new year already ahead.
📸 4. Capture Travel Content That Actually Converts
Christmas environments make for excellent content — cozy, warm, aesthetic, and relatable.
Ideas for your business:
“Working from Anywhere” shots in a holiday setting
Flat-lays with your laptop, coffee, and Christmas décor
Behind-the-scenes of planning your Q1 business goals
Travel logs for documenting deductible business time
B-roll of airports, packing, journaling, or route planning
OOO Tip: Holiday content feels personal and genuine — perfect for humanizing your brand.
🎄✨ 5. Track Your Trip Like a CEO
If the trip includes business activity, track it properly:
Save your flights, hotel receipts, and transportation receipts
Write down your business purpose for each day
Keep notes of meetings, planning sessions, or content days
Keep screenshots of digital planning (Notion, Google Docs, etc.)
A simple Travel Log is usually enough.
OOO Tip: Treat your Christmas trip like a mini retreat — and document it clearly and consistently.
🔋 6. Protect Your Energy (and Your Boundaries)
Balance is everything.
Don’t overstuff your schedule
Communicate your availability before the trip
Take breaks when you need them
Protect your mornings if that’s when you do your best thinking
You are a CEO — not Santa. You don’t have to give all your time away.
📅 7. Use the Trip to Launch Into a Strong Q1
This is the real magic:
A Christmas business trip creates momentum at exactly the right time.
Use quiet pockets of the holiday to:
Map Q1 campaigns
Review revenue and expenses
Set your 2026 business goals
Update workflows and systems
Plan your upcoming OOO-style business travel
When everyone else is “waiting for January 1,” you’re already aligned and ahead.
Final Thought
A Christmas business trip isn’t about working through the holidays — it’s about using intentional moments to prepare for a profitable, organized, and inspiring new year. When you do it right, your travel becomes part of your growth story.
Because that’s what OOO is all about:
Work Smarter. Travel Better. Live Like a CEO — anywhere, even at Christmas.
