How to Work Smarter From Anywhere | OOO Travel + Business
The New Definition of “Office”
When I think about my office, I don’t picture four walls or fluorescent lights anymore. My office could be an airport lounge in Miami, the deck of a cruise ship in the Caribbean, or even a sunlit café in Barcelona.
That’s the beauty of the OOO lifestyle: your business doesn’t have to stay stuck in one place. You can work smarter, make your lifestyle tax-deductible, and design a business that supports the freedom you’ve been craving.
In this guide, I’m sharing the systems, routines, and mindset shifts that help me (and countless other entrepreneurs) turn travel into a real business advantage.
Design Your Travel-Ready Workspace
Pack smarter, not heavier: a lightweight laptop, portable charger, and noise-canceling headphones can transform any environment into an office.
You don’t need a giant setup—you need a streamlined one that frees you to move. Remember, too much gear = more stress. These tools help you truly work smarter from anywhere.
Chase working smarter from anywhere on a cruise ship.
Master the 4-Hour Work Block Rule
Instead of spreading tasks over 8–9 hours, create two highly focused 2-hour sessions. This structure works great for entrepreneurs who travel because it protects time for both business productivity and memorable experiences.
Example Travel Schedule:
Morning (9:00–11:00am): Emails, client calls, and high-focus strategy work
Daytime (11:00am–4:00pm): Excursions, sightseeing, or downtime
Afternoon (4:30–6:30pm): Content creation, financial updates, and team check-ins
Evening (7:00pm onward): Networking events, themed cruise nights, or fine dining with clients
Chase’s smart packing capsule wardrobe for business travel and networking on cruises.
Pack Smart, Work Start
Clothes that do double-duty: For example, a blazer that works seamlessly for both a Zoom call and a dinner out.
A capsule wardrobe with versatile pieces reduces stress and ensures you’re always ready to shift from business to leisure and to networking in one day.
Blend Business + Travel (and Write It Off)
Practical Strategies for Blending Business + Travel
Client Dinners: Hosting a meal during your trip counts as a deductible business expense when you’re discussing business.
For example: dinner on the ship with a client or collaborator.
Professional Development: Attending a seminar, training, or conference while traveling allows you to write off registration fees, hotels, and meals. For instance, joining a workshop while docked in Miami.
Content Creation as a Business Expense: If your brand involves travel, lifestyle, or education, creating photos/videos/blogs during a trip supports marketing expenses. Example: documenting Virgin Voyages Scarlet Night for your OOO audience.
Transportation + Lodging: Flights, cruise cabins, hotels, and even Uber rides can qualify if the trip is primarily for business.
Mixed Trips: If your trip combines business and leisure, keep a clear record of which days are business-related. For example: 4 work days (deductible) and 3 personal days (non-deductible).
Networking Beyond the Boardroom
The best conversations happen during unique experiences, not in stuffy conference rooms.
On a cruise, that might mean:
Scarlet Night (playful): Bold, high-energy, and unforgettable.
White Party (elegant): Sleek and elevated, perfect for meeting fellow professionals.
Masquerade Night (creative): A chance to connect through imagination and storytelling.
Build an “Anywhere” Mindset
The office isn’t a place—it’s a system.
OOO philosophy: By embracing flexibility, you not only work smarter but also design a lifestyle aligned with freedom, creativity, and growth.
Your Smarter-Anywhere Plan
Ready to build your smarter, out-of-office lifestyle? Check back here for tips, Amazon finds, and destination guides that help you work—and live—better from anywhere.
Your next adventure could be your smartest business move yet.
Ready to work smarter from anywhere? OOO has you covered
