I Workationed for a Month

and Hated Every Minute of It

I’m going to start this by caveating that this is an incredibly privileged crib-rant. It’s wild to me that I can just travel for a month and not have to worry about my bottom line. At 23, this would have seemed impossible to me. I want you to remember this as you read- this is a very unusual circumstance that I’m writing about. It’s a very personal experience from which I’m trying to draw universal lessons. Ok, now we can continue.

Picture this: I’m in Sri Lanka, sitting on a plush hotel bed with the sound of waves crashing in the background. My laptop is perched on my lap, Slack notifications dinging in the corner. I’m halfway through a team huddle, thinking about the 17 things I still need to do, and all I can feel is this gnawing, overwhelming sense of stress.

This past month, I’ve been in Sri Lanka (Colombo and Galle!), Dubai, Mumbai, and Rishikesh. Four incredible places, four stunning backdrops—and I (nearly) hated (almost) every single second of it.

The dream of a workation is exactly that—a dream. The reality? Far less glamorous. Between traveling, trying to maintain my workout streak, running WTFund, and being present as a manager, I felt like I was constantly dropping the ball somewhere. At no point did I feel like I was succeeding, at work or at life.

When Work Meets Vacation, Nobody Wins

The thing about workations is they sound fantastic on paper. Work with a view, a cheeky cocktail by the pool, maybe a sunset swim between calls. But here’s the thing: if you’re trying to be a functional human being with a job that requires actual accountability, the cracks show fast.

Sri Lanka? I spent my mornings staring at turquoise waves but feeling this crushing guilt because I wasn’t answering emails fast enough. Dubai? I was half-present in every interaction, mentally calculating how to stay ahead of deadlines. Mumbai? The chaos felt comforting for five minutes before I had to jump back into spreadsheets. Rishikesh? The quiet was supposed to be grounding, but I couldn’t stop checking my phone.

Every single place, no matter how beautiful, felt like a series of missed moments—because I couldn’t stop trying to juggle it all.

The Logistics of a Workation: A Lesson in Chaos

What no one tells you about workations is how exhausting they are. On paper, the schedule seemed fine. I’d wake up, get my morning workout in, settle down to work during the day, and explore in the evenings. But reality? It was logistical chaos.

Flights and hotel check-ins rarely aligned with my calls. I spent hours finding stable Wi-Fi, only to have it crash at the worst possible moment. I tried to manage time zones, thinking I’d cracked the code—work during India hours while traveling—but what that really meant was my evenings, the “vacation” part, were consumed by playing catch-up.

And that’s not even accounting for how physically draining it was. I’d pack up my laptop, chargers, notebooks, and workout gear every other day, hauling everything across airports and hotels, always on the move. By the time I sat down to work, I’d already burned through half my energy just existing in transit.

The logistics extended beyond just physical travel. Every new place came with its own set of challenges: unfamiliar workspaces, unexpected interruptions, and a sense of disorientation that made it harder to settle into a rhythm. A desk in a hotel lobby isn’t the same as the conference room we work out of at office, no matter how nice the view is.

Fitness in the Midst of Chaos

If you’ve ever tried to keep a fitness routine while traveling, you’ll know how impossible it can feel. I’ve worked hard this past year to build a consistent routine—waking up early, going to the gym, and making movement a priority. I thought I could maintain that on the road.

I was wrong.

In Sri Lanka, I’d wake up to the most stunning sunrises and force myself out for a workout or swim. But halfway through, my brain would kick into overdrive: “Did you respond to that email? What about the investor update? Is the team okay?” By the time I got back, I wasn’t refreshed—I was more stressed than when I started.

Dubai wasn’t much better. I’d find a gym, squeeze in a workout, and then rush back to calls. There was no time to savor the moment, no satisfaction from ticking “workout” off my list. It felt transactional—something I had to do rather than something I wanted to do.

By the time I got to Rishikesh, I’d given up trying. My workouts became sporadic, and the guilt piled on. For someone who thrives on structure, the lack of routine was deeply unsettling.

Fitness became less about physical health and more about mental survival. The idea of “showing up”—even imperfectly—felt important, but it also highlighted how stretched thin I was. What should have been a source of energy turned into another obligation on an already overloaded plate.

Work, Interrupted

At the heart of the workation myth is this idea that you can be equally productive in paradise as you are at your desk. Let me tell you—you can’t. At least, not when you’re managing a team, running a vertical, or trying to build something meaningful.

Work requires focus, and focus requires stability. I had neither. Every time I logged into a call, I felt a step behind. Even when I was fully caught up, the feeling of falling behind lingered. It’s hard to explain—it’s not about missing updates or failing to execute. It’s about presence. When you’re leading a team, people don’t just need your output; they need your attention, your energy, your presence. And I couldn’t give them that from a hundred different hotel rooms.

I thought being physically present on calls was enough. But the truth is, being on a video call while you’re mentally stressed and emotionally disconnected doesn’t count as showing up. And when you’re not showing up as a leader, it impacts your team in ways you don’t realize until later.

This lack of connection isn’t just about technology. It’s about the small moments—the impromptu brainstorms, the casual check-ins, the sense of camaraderie that gets lost when you’re not fully present. Those intangibles matter, especially when you’re running a team.

The Emotional Dissonance

The hardest part of the entire experience wasn’t the logistics or the workload. It was the emotional dissonance. I was in these incredible places—places people dream about—and all I felt was sadness.

There was this moment in Rishikesh. I was sitting by the Ganga, watching the sun dip behind the mountains, surrounded by peace and beauty. It should have been transformative. But instead, I felt this weight of guilt and stress. Guilt for not being present at work. Guilt for not enjoying the moment. Stress because my brain couldn’t stop thinking about everything I wasn’t doing.

I realized that I’d trapped myself in this impossible cycle. When I was working, I felt like I was missing out on the beauty around me. When I tried to enjoy my surroundings, I felt like I was failing at work. There was no winning.

This emotional dissonance took a toll on my mental health. I’d look at the photos I’d taken—the serene beaches, the bustling streets, the tranquil mountains—and feel nothing but exhaustion. The gap between how I’d imagined this experience and how it actually felt was staggering.

Workations Aren’t for Everyone

Here’s the thing: I can see how workations might work for individual contributors. If your role is task-based, with clear deliverables, and you don’t need to collaborate constantly, you might be able to pull it off. But if you’re managing people, leading a team, or running a vertical, it’s a different story entirely.

Leadership isn’t just about getting things done. It’s about being present, connected, and responsive. And that’s really hard to do when you’re battling time zones, struggling with Wi-Fi, and constantly on the move. Your team can feel it when you’re not fully there. And as much as we’d like to think otherwise, remote leadership has its limits.

More importantly, workations require a level of compartmentalization that’s nearly impossible for roles involving high accountability. Switching between “vacation mode” and “work mode” isn’t as seamless as it sounds. The overlap creates friction, and that friction drains your energy faster than you realize.

What I Learned

This month taught me a lot about myself, my work, and my limits. Most importantly, it taught me that workations aren’t for me. Here’s what I’d do differently:

1. Separate Work and Rest: Work or vacation. Pick one. Trying to do both will leave you feeling like you’re failing at both.

2. Set Boundaries: If you absolutely must mix work and travel, set clear boundaries. Block time for work and stick to it. But more importantly, block time to not work.

3. Know Your Role: If you’re a manager or leader, understand that your presence matters. It’s not just about output—it’s about energy, connection, and showing up for your team.

4. Don’t Romanticize It: Workations look great on Instagram, but the reality is far less glamorous. Go in with realistic expectations.

5. Prioritize Your Well-Being: Whether it’s fitness, rest, or mental health, don’t sacrifice your well-being for the sake of appearances. No destination is worth burning out over.

The Bottom Line

I’ve always been someone who believes in pushing boundaries, trying new things, and chasing balance. But this experience was a humbling reminder that sometimes, chasing balance creates more chaos. It’s okay to admit when something doesn’t work. It’s okay to say, “This isn’t for me.”

The next time I travel, I’m making a promise to myself: I’ll either work or I’ll vacation. But I won’t try to do both. Because some things deserve our undivided attention—the waves, the mountains, the people around us, and most of all, ourselves.