A Reflection on Vacation Guilt

"Czech" out the experience that brought our Director of Account Management on board.

Before I considered joining the Treehoppr team, I had never stepped back and asked myself, "Why don’t I take PTO?" I was in the midst of deciding whether or not to travel to Europe to surprise a childhood friend who was living there. I would need to take six days off work. SIX DAYS! The previous few months at work had been extra hectic and I was leading the charge when it came to a number of projects. Although they were all wrapping up at the end of September, two weeks later felt too soon to go offline. What if something went wrong? Would my boss think I was neglecting to steward the projects post completion? Would my coworkers resent me for the extra work they needed to pick up? How many emails would I return to?

As I stressed about these questions, and also contemplated the opportunity to sign on to direct account management at Treehoppr, it occurred to me I was the classic example of the corporate culture Treehoppr is trying to affect. Even though I had plenty of vacation days, was at a lull in my work cycle, and had just had an anxiety ridden two months of work, I still didn’t feel comfortable taking time off. My boss would most likely agree that I needed the break to recharge and refocus. What was stopping me?

For one thing, beyond the stigma I was worried about, my bank account loomed, wagging a finger that I would dare dip into my savings for a trip. Despite constantly being reminded that I should maintain a cushion for health expenses or car troubles, I wanted desperately to experience the world with it instead.


This makes sense; I’m a millennial. We overwhelmingly prioritize travel above acquiring things or building retirement accounts. For me, this stems from the ways my former travel has informed my worldview and the way I move through life. This has been of value to me personally and at work. Traveling has allowed me to connect with a broad range of friends, coworkers and strangers much more vibrantly and deeply. For example, after traveling to Cape Town, South Africa, I interned at a homeless shelter. Because of the time I spent with impoverished people in informal settlements, I was more able to understand the root causes of poverty, allowing me to empathize with people in that situation and focus on solutions to homelessness in the United States. I’m constantly amazed by how travel reshapes my perspectives and challenges my perceptions. It has genuinely taught me more than I ever learned in a classroom or a book.

So how do employees move forward when they earn and need vacation and place so much importance on it, but still don’t take it? I put time on my boss’s calendar and then sat at my desk debating the different ways I would approach her about my six days of PTO. In the end, I barely had the words “I would like to take a week to visit a friend…” out of my mouth before she said, ‘GO!” Although I was surprised at the speed with which she agreed, in retrospect, it’s no shock that she wanted me to take a break. She recognized that I was burning out and highly values travel in her own life. While not all managers embrace vacation as much as she does, it’s hard to ignore the fact that employees return to work more engaged and productive after a break.

Naturally, I would ascertain that if my company was signed up with Treehoppr, I wouldn’t have been nervous to ask for time off. My boss would’ve already known my travel plans, and potentially helped me contribute to the cost. However, I also learned a valuable lesson to JUST ASK! This is probably good advice for me to take across the board…


So I took my six days off, went to Prague and surprised my best friend of the last 20 years. My bank account shuddered and I jumped for joy. As predicted, I came back to work the next week invigorated and motivated, not just in my current position, but also to ensure every employee feels comfortable taking well-deserved time off. I took a deep breath and dove into my emails.

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About Zoe Pilla

Zoe comes from a background in non-profits and education. She's passionate about all things social-minded, travel and outdoors. Up next on her travel list, South America: Machu Picchu and Patagonia.
  • San Francisco, CA