How to Turn Your Holiday Travel Into a Business Advantage
The Season of Travel — and Strategy
Most people treat holiday travel as “the last break of the year.”
But smart entrepreneurs know it’s the perfect moment to review the year, plan the next one, and make strategic decisions — all while enjoying time away.
OOO teaches entrepreneurs how to travel with purpose: part rest, part elevation, part tax-smart strategy.
Turn Holiday Downtime Into CEO Planning Days
What to do:
Review your offers, pricing, and systems
Outline your Q1 goals
Sketch your 12-month content or marketing plan
Reflect on the wins + lessons from the year
Why it works:
Holiday trips naturally create space. New surroundings = clear thinking, fresh perspective.
Tax Strategy Tip (OOO-style):
If you intentionally schedule planning days, coaching calls, business meetings, or strategic sessions during the trip, you can shift certain travel expenses into the business-purpose category when done correctly.
Network Without Trying (Holiday Edition)
Where natural networking happens:
Airport lounges
Hotel bars/lobbies
Cruise ships
Holiday events and mixers
Travel excursions
Holiday travel puts hundreds of motivated professionals in close proximity.
Most are relaxed, open, and actually talking to strangers.
OOO Tip:
Have an easy “holiday icebreaker” ready:
“Where are you traveling from?”
“Do you own your own business or work remote?”
“What are you working on next year?”
It feels natural — not salesy — and can turn into real partnerships.
Build Deductible Content While You Travel
Ideas for content you can create:
CEO-day-in-the-life travel videos
“Working from anywhere” B-roll
Travel tax tips
Behind-the-scenes of your planning day
Packing or gear recommendations
Your 2026 vision
Why this matters:
If your business regularly teaches, coaches, documents, or shares travel, lifestyle, productivity, or business strategy, your trip becomes content-producing, which supports the legitimacy of business intent.
End-of-Year Financial Prep (In a Better View)
Use your holiday trip to close the financial year strong:
Reconcile your books
Categorize expenses
Prepare year-end reports
Review revenue streams
Check your tax estimates
Even one “business day” on the trip strengthens your ability to categorize the trip as mixed-purpose vs business-purpose.
Get Strategic Clarity for the New Year
Travel gives you something your office can’t:
newness, mental space, different perspectives, and clarity.
This is the perfect time to ask:
What needs to change in 2026?
What will I stop doing?
What will I double down on?
Who do I need to hire, delegate to, or collaborate with?
What systems need to be built?
OOO’s philosophy:
Your best ideas come when you step away — not when you’re overwhelmed at your desk.
Practical Ways to Make the Trip Tax-Deductible
Possible deductible activities include:
Strategic planning sessions
Client meetings
Business lunches or dinners
Business-related excursions
Content creation days
Visiting another business, coworking space, or event
Simple Rule of Thumb:
If your primary purpose is business, portions of the trip may be deductible when properly documented.
OOO Documentation Tips:
Keep receipts
Log business activities
Take photos of your work setup
Save notes from planning sessions
Keep calendar entries
Wrap the Trip With an Annual Review Ritual
Close the year with intention:
Write out your accomplishments
Review mistakes without shame
Create a “not doing next year” list
Identify your CEO priorities
Commit to your new habits
This is the type of clarity entrepreneurs don’t get at home.
Travel With Purpose, Enter the Year Prepared
Holiday travel doesn’t have to be “just a vacation.”
It can be your CEO reset, the moment you look at your business from above and decide what comes next.
Work Smarter. Travel Better. Deduct Responsibly.™
