You’re always plugged in. Even when you’re not at your desk, your brain is solving problems, managing people, or scanning the next opportunity. That’s part of what makes you successful. But it also makes true rest feel out of reach.
That’s where a workation comes in — part work, part vacation, and entirely designed to help you reset without dropping the ball.
If you’ve never taken one, here’s exactly why it’s worth it — and how to make it a powerful reset, not just a working holiday.
1. Change your scenery
When you’re in the same office or home every day, your thinking narrows. You make fast decisions, but you stop seeing fresh angles. Changing your environment, even for a few days, breaks that mental loop.
Whether you’re in a cabin in Montana or a city café in Lisbon, new surroundings force your brain to engage differently. That mental reset can unlock strategy-level thinking — the kind you rarely access while buried in daily fires.
How to make it productive: Block off time each morning for deep work. Leave afternoons open for exploring or reflection. Use the change of pace to tackle big-picture planning — things like your next product rollout, org chart redesign, or pricing strategy.
2. Step back to see clearly
Being away from your business gives you perspective. You start to see which tasks are essential and which ones you’ve been doing out of habit. That’s gold for leaders who feel overwhelmed but can’t pinpoint why.
One client — a founder of a 12-person marketing agency — took a 10-day workation in British Columbia. By day five, he realized his team ran smoother without his constant Slack messages. When he got back, he restructured how he delegated.
How to make it productive: Before you leave, set your team up to run without you. Give them more autonomy than you’re comfortable with. Then observe. What breaks? What doesn’t? Take notes and apply that insight when you return.
3. Tackle long-overdue work
You’ve got projects you’ve been meaning to tackle for months — updating your onboarding deck, building a partner pitch, rewriting your sales page. But at home, something urgent always gets in the way.
A workation creates the buffer you need to go deep on those long-postponed priorities. You’re away from the buzz. No surprise visitors. No back-to-back meetings. Just you, your laptop, and time to work on the important things.
How to make it productive: Pick one major initiative to focus on during your workation. Don’t overload your to-do list. Set a clear goal (e.g., “write the new investor memo” or “build our 2025 hiring plan”), and carve out 2-3 hours per day to chip away at it.
4. Go solo to reset
If you’re the only one carrying the weight of your business, your mental health is your infrastructure. A solo workation lets you breathe. It gives you space to think beyond operations — to reconnect with why you started this.
Some founders find clarity in hiking trails. Others journal by the ocean. One tech CEO I coached books a cabin in the desert every quarter, just to walk, read, and reset. No team. No meetings. Just him and his thoughts.
How to make it productive: Unplug strategically. Let your team know you’re accessible in emergencies, but set a daily 1-hour window for check-ins. The rest of the time? Reflect, read, or brainstorm without pressure. Don’t underestimate how much this “non-work” fuels your best work later.
5. Pick the right format
Not all workations are created equal. Choosing the right one depends on what you need right now — clarity, momentum, rest, or connection.
If you’re overwhelmed and need to reconnect with your own thinking, go solo. If your team is misaligned or burnt out, take them with you. Domestic options are ideal for low-stress logistics. International trips offer perspective that can’t be matched.
Ask yourself:
- Do I need to think big without interruption, or solve a team problem?
- Do I want convenience, or insight from new cultures?
- Am I trying to reset, accelerate, or delegate?
The right format depends on your intent. Get clear on that, and the rest gets easier.
6. Take your team
If you’re leading a small team, taking them on a workation can build trust faster than any Zoom meeting or office happy hour. The shared experience of working and relaxing together helps uncover strengths, break silos, and align priorities.
One small software company in Boise takes their 8-person team to a lake house every summer. They work in the mornings, then cook, paddleboard, and talk strategy in the evenings. Every year, they come back with clearer goals and tighter bonds.
How to make it productive: Set a theme for the week: “planning next year,” “solving our customer onboarding friction,” or “shaping our new culture.” Keep work blocks structured and short. Allow time for group meals, light adventures, and deep conversations.
7. Budget smart
A productive workation doesn’t have to mean a luxury resort or first-class flights. In fact, many entrepreneurs find more clarity when they keep it simple and intentional.
Start by planning your budget around these categories:
- Travel (flights, gas, or rental car)
- Lodging (hotels, Airbnbs, or cowork-friendly retreats)
- Food and groceries
- Workspace (if not included)
- Tools or equipment you might need (see next section)
Instead of thinking of it as a new expense, reallocate funds from conferences, office space, or personal development. If you’re unsure, try a 3-day domestic workation before committing to something bigger.
A lean, well-structured workation can have a bigger impact than a lavish but scattered one.
What to bring
You don’t need much to work well on the road, but a few key tools can make the difference between smooth and stressful.
Bring:
- A lightweight laptop with good battery life
- Noise-canceling headphones
- A mobile hotspot or SIM card with data
- A universal power adapter (for international travel)
- A cloud-based tool like Notion, Trello, or ClickUp
- A video call app that runs well on weak Wi-Fi (Zoom, Google Meet)
Optional but helpful:
- Portable second monitor (like a SideTrak or iPad with Duet)
- Foldable laptop stand or compact desk setup
- Business travel insurance with gear coverage
Before you go, block your calendar, set your Slack status, and turn on your out-of-office with clear response times.
8. Stay local
You don’t need to go halfway around the world to get the benefits of a workation. Sometimes the best reset is a short drive away. Think national parks, lakeside Airbnbs, or mountain cabins with decent Wi-Fi.
These trips are easier to plan and less disruptive for your team or family. Plus, if something urgent does come up, you’re close enough to handle it.
How to make it productive: Choose a place with reliable internet, good light, and minimal distractions. Set a simple daily schedule: one block for deep work, one for catch-ups, and one for non-work activity. Then stick to it.
9. Go abroad
Leaving your country, even briefly, reminds you how big the world is. It disrupts your assumptions. It makes you question routines and appreciate what’s working.
Entrepreneurs who spend a week in another culture often come back with fresh ideas for how they market, manage, and serve customers. One founder said his time in Tokyo taught him more about product precision than any workshop he’d taken.
How to make it productive: Time-zone shifts can work in your favor. If you’re ahead of your team, use mornings for solo focus work. Afternoons can be for local exploration, and evenings for syncing up remotely. Travel light and keep tools minimal.
10. Set boundaries
A workation is not a sneaky vacation or a disguised work trip. It’s something in between. If you don’t set boundaries, it turns into neither: you’re half-working, half-relaxing, and not satisfied with either.
Set expectations with your team, clients, and even yourself. Define what “productive” means for the trip, and how you’ll measure success.
How to make it productive: Decide how many hours per day you’ll work. Communicate when you’ll be available. Protect time for reflection and play. Most of all, give yourself permission to not be fully “on.” That’s where the real ROI lives.
11. Return stronger
The ultimate value of a workation isn’t what you do on the trip. It’s how you show up when you return. With distance, your mind resets. When you come back, you bring sharper focus, better energy, and stronger leadership.
Several founders I’ve coached say their best ideas came not in front of a whiteboard, but in a quiet moment away from it. One planned her company’s entire 18-month product roadmap during a workation in Spain, then came back and executed faster than ever.
How to make it productive: Schedule a debrief day when you return. Look at your notes, list your insights, and turn them into action steps. Share your biggest takeaways with your team. The real momentum starts when you apply what your break helped you see.
When not to take one
Workations are powerful — but they’re not always the right move.
If your business is in crisis, stepping away can make things worse. If your team is new, absent leadership can rattle their confidence. And if you’re truly burned out, splitting your attention might prolong the problem.
Be honest about what you need. If you can’t step away without things breaking, that’s a sign to fix your structure — not force a break. If you need full rest, give yourself permission to disconnect entirely.
Workations work best when you’re stable but stale — when what you need is not rescue, but renewal.
Re-enter with clarity
What happens after the workation is just as important as what happens during it. The value compounds only when you bring your insights back into the business.
Don’t dive straight into meetings or email catch-up. Instead:
- Block off your first day back to review, reflect, and prioritize.
- Write down 3 key takeaways or ideas that surfaced while you were away.
- Identify 1 or 2 things you’ll do differently going forward.
- Share those insights with your team so they see the value of your time away.
The goal isn’t to resume where you left off — it’s to return with better energy, focus, and leadership.
Conclusion
You don’t need to earn a break — you need to structure one that works. A workation isn’t an escape. It’s a tool. One that recharges your brain, re-centers your leadership, and gives you space to do your best thinking.
Whether you go solo or with your team, local or global, one week or one month — the goal is the same: come back better than you left. That’s what makes it worth it.
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