Working But Not: Holiday Travel
Holiday travel season is around the corner, and that often means transforming airports, spare bedrooms, and coffee tables into temporary offices. The work doesn’t stop, but your surroundings shift daily, and what used to be automatic suddenly requires more setup, patience, and discipline. Preparation is what separates a calm, efficient travel week from one filled with unnecessary friction.
Before you leave, take time to run a travel systems test. Don’t assume your setup will seamlessly transfer once you’re out of your usual environment.
1. Test your access: Open every tool, document, and platform you might need while offline or on a new device. Can you log in from your laptop or phone without getting locked out by two-factor authentication? Are your files synced to the cloud and accessible from multiple devices? Do you have a secure password manager and local copies of anything mission-critical? If something stalls, fix it now.
2. Prepare for power: The smallest items are often the biggest failure points when you’re mobile. Bring redundancies for everything: charging cables, adapters, and plug converters. A compact power strip, a high-capacity power bank, and a universal outlet adapter should live permanently in your travel bag, not on your desk. If you work internationally, check voltage compatibility for chargers and laptops before you leave.
3. Think connection-first: Holiday travel means inconsistent Wi-Fi. Assume you’ll face poor network coverage or dead zones, and build for it. Download key files, presentations, and notes for offline use. Configure cloud tools to sync automatically, but also make sure you can work in “offline mode” if needed. Add extra data to your phone plan or hotspot. In travel weeks, connection quality will be your limiting factor, not effort.
4. Build your portable workspace: Test-drive your travel setup before you leave. Use only the gear you plan to bring for a day or two and see what slows you down. Does your keyboard, stand, and mouse fit in your bag without overloading it? Does your webcam handle poor lighting? Can you take a video call from a quiet corner without friction? Most people overpack tech they never use and underpack what keeps them productive, you only learn which is which by simulating the trip.
5. Plan your rhythm: Travel disrupts the routines that hold your focus together. Replace them with lighter, portable ones: one morning block for deep work before everyone wakes up, and one shorter afternoon block for quick communication or project updates. Protect those blocks and release the rest. You don’t need to replicate your full schedule, you need predictable anchors that keep momentum.
To handle remote travel, you don’t just pack hardware, you pack systems. You should plan for power, connectivity, and access as carefully as you plan your itinerary. This level of foresight will turn your trip from a potential source of stress to maximized flexibility. The goal isn’t to tether yourself to work during the holidays, it’s to stay organized so that you can disconnect confidently when the work is done.
Remote Rhythm
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Coverage Without Chaos
The holidays test how well your systems hold up when everyone steps away. For most teams, November and December reveal whether your operations depend on individuals or on structure. When half the team is traveling, clients still expect responses, orders need to ship, the metaphorical “show must go on”. During this time of year, your cracks in communication and processes will show fast. The solution isn’t more hours, it’s better preparation.
High-functioning organizations treat the holiday slowdown like any other operational challenge: something to design for, not react to. They plan for absences, document ownership, and establish clear action paths if something critical happens while leadership is out.
Start with critical coverage: List the work that can’t stop: customer support, finance approvals, active sales conversations, live campaigns, or server monitoring. For each, assign a clear backup. That person doesn’t need deep expertise, just a checklist of key tasks, what “normal” looks like, and where to escalate issues. Even lightweight coverage ensures no area becomes a single point of failure.
Build continuity documents that live beyond the season: Every team member should create a short “If I’m offline” brief, a single page covering current projects, major deadlines, responsible contacts, and open loops. Store them in a shared workspace accessible by anyone. These briefs shouldn’t just serve the holidays, they should evolve into permanent continuity files that reduce dependency year-round. When someone steps away unexpectedly, the system already knows how to keep moving.
Define what counts as an emergency and how to respond: One of the biggest sources of stress during holidays isn’t the emergency itself, it’s the ambiguity around who handles it. Set clear definitions: what’s urgent, what’s routine, and what can wait. Assign one decision-maker per function and choose one communication channel for escalation. If something fails on Christmas Eve, the response should be automatic, not debated.
Shift the focus from presence to preparedness: Encourage everyone to close open loops before leaving, document handoffs, queue updates, and pre-schedule internal communications. Visibility doesn’t mean availability; preparedness means work can continue without check-ins. When your systems are designed to operate asynchronously, people can actually rest without guilt or fallout.
Set the rhythm early and communicate it clearly: Publish the holiday schedule weeks in advance: coverage rotations, expected response times, and blackout dates. Make it visible to everyone, internal teams, clients, and partners. Clarity builds confidence, and confidence allows people to unplug fully. The absence of surprises is what gives a team absolute calm.
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Remote rhythm isn’t about pushing harder through the season, it’s about building enough operational stability that the business can keep moving while people recharge. The true mark of a mature team is not how frenetic it feels in Q4, but how calmly it runs when half the team is offline.
