From Beaches to Boardrooms: How to Mix Relaxation and Revenue on Your Next Trip
The Art of the Workcation
Who says you have to choose between relaxation and revenue?
For entrepreneurs, content creators, and CEOs-on-the-go, the best trips combine both.
A “workcation” lets you recharge your mind and move your business forward. It’s not about working 24/7 — it’s about working strategically while your environment inspires you.
Step 1: Set Intentional Business Goals Before You Go
Before you pack your bags, get clear on what makes this trip a business trip — not just a getaway.
Ask yourself:
What projects or goals will I focus on while I’m there?
Will I meet with clients, partners, or vendors?
Can I document business-related content?
How will this trip support my upcoming quarter or campaign?
Even one clear objective (like “outline next quarter’s marketing plan” or “film travel content for my brand”) helps legitimize the business side — and makes your time more meaningful.
Step 2: Create a “Portable Office”
You don’t need your entire home setup to be productive on the road — just the right essentials:
✅ Laptop or tablet
✅ Portable Wi-Fi or hotspot
✅ Noise-canceling headphones
✅ Cloud-based systems for files (Google Drive, Notion, QuickBooks)
✅ A travel folder for receipts and documentation
💬 OOO Tip: Keep all your business trip essentials in one small tech pouch. You’ll be amazed how much lighter travel feels when everything has a place.
Step 3: Schedule Work Windows
Mixing business with leisure doesn’t mean sitting on Zoom calls while everyone else is snorkeling.
Try structured flexibility — work in short, focused windows (1–3 hours) and then log off fully to enjoy your destination.
Example:
Morning: Strategy time or client calls from your balcony.
Afternoon: Free time — beach, excursion, or spa.
Evening: Recap notes and check tomorrow’s itinerary.
This rhythm lets you stay productive and present.
Step 4: Turn Content Into Currency
If part of your trip involves sharing your journey online — you’re not just vacationing, you’re marketing.
Document:
Behind-the-scenes videos
Travel tips for other entrepreneurs
“Day in the life” posts showing how you blend work and rest
If the content directly supports your business, those travel days may count as deductible — as long as you document your purpose and outcomes.
💡 Example: Filming a video titled “How to Take a Tax-Deductible Workcation” while staying at your resort ties your experience directly to your brand.
Step 5: Keep It Legit
The IRS isn’t against mixing business and pleasure — they just want proof of your intent and documentation.
To stay compliant:
Keep receipts for flights, lodging, meals, and transportation
Track your business vs. personal days
Save your itinerary, meeting notes, and content plan
Add calendar invites or notes showing what you worked on
Step 6: Unplug Without Guilt
Your rest is part of the strategy.
When you recharge, you come back sharper, more creative, and better able to serve your clients or team.
So enjoy that sunset, order the dessert, and remember: balance is part of success.
Working smart means knowing when to work — and when to rest.
Final Takeaway
Blending business and travel isn’t about “doing it all” — it’s about designing a lifestyle that supports your goals and your peace.
The next time you book a flight, think beyond the vacation. Think about the strategy behind it.
💬 Work Smarter. Travel Better. Deduct Responsibly.
📞 (904) 604-6944
