5 Quick Observations As a Result of Working During Vacation

Watching the sun rise on vacation

“You SUCK at vacations,” my boss replied after I’d answered one too many work e-mails while on vacation.

It’s true. I haven’t truly unplugged and relaxed since my honeymoon over 2 years ago. This is not something I’m proud of, mind you. It’s something I’m hoping to get better at in the future.

Here are few random observations I captured in a notebook on our last day of a week long vacation:

1.) Naps are good when you’re tired.

Most mornings we got up fairly early, worked out, ate breakfast and went straight to the beach or pool. Every day, between 2-4pm when our energy waned, we took a nap. After the nap, we were refreshed and ready to continue our adventures.

I don’t know about you, but I rarely, if ever, take naps when I’m not on vacation. And definitely not during the work week.

What if, at work, when our energy waned we were permitted to take a short nap?

Instead of lethargically stumbling through the last few hours of the day, a nap might (GASP) make us more productive.

And before you start with the “Oh, of course a millennial is advocating for naps in the workplace” nonsense, the research shows that sleep is a vital health, safety, and social issue. Sleep consolidates learning and memory and enhances cognitive performance, physical performance, and creativity. Companies lose billions a year in productivity costs associated with lack of sleep.

Arianna Huffington even had nap rooms installed at the Huffington Post.

“Ultimately, at work, the most important thing is our energy. It’s not exactly how many hours we are sitting at our desks, but how present are we when we’re there.”

Other nap friendly companies? Google, NASA, Zappos, Nike, and the New York Times.

2.) You probably shouldn’t take a vacation during “busy” time.

I’d only taken 4 days off in the last 14 months and with a few huge projects looming in mid-September, I was completely burned out. I was growing increasingly resentful to the point that completing even minor tasks took twice as long. So I did what most people would do, right? Booked a vacation on a beach. Fine, Alaina booked it. She’s my travel agent.

I had convinced myself I deserved it. And maybe I did, but with the big projects looming, and countless tasks still to complete, I thought about work a lot during our vacation.

I ended up answering some e-mails and working on a couple of projects from the hotel room. Worse still, I spent *more* time trying to get my VPN to work than I did actually working. (There’s a lesson in letting go of things you can control buried in here somewhere.)

I’m fortunate that I work with a very talented team completely capable of handling things while I was out; however, it still felt nonsensical and completely irresponsible to be gone during this busy time.

It’s tough to “turn it off” when others are still working — especially if you take pride in the work you do and the projects you manage.

Unlike other countries, like Europe, the closest we get to true down time is the relatively light time between Christmas Eve and New Years Day. It’s hard to turn it completely off when everyone around you is still hustling, still moving things a long — your tasks critical to their deadlines.

Also, because a quiet work environment is so key to my concentration, creativity and productivity, I’ve always (historically) used the time others are out of the office to catch up and/or get ahead.

In the future, I’m going to try and be more strategic about proactively planning a vacation when I can reap the benefits, be more present, and come back fully restored.

3.) But, it is easier to work when you’re unencumbered by distractions.

I told myself I’d work for about an hour each day we were gone. That would help me stay on top of things and not come back *completely* overwhelmed.

I didn’t work a full hour every day, and I didn’t get as much done as I would’ve liked. Though, much of that had to do with my uncooperative VPN.

What was interesting, is that when I did work for a bit, I was not stressed about it and I was not resentful that I was working during vacation.

I wasn’t trying to fit work in between two unproductive meetings. I wasn’t trying to think, write and plan while hearing every word of a meeting taking place in the hallway when there’s a perfectly unoccupied conference room 12 steps away.


I chose to work when it was quiet, when I had energy, and when I felt like accomplishing something work-related. I love my job, and the work that I do, so it made me feel good to make progress on a project. It made me feel like I’d earned a “muy fuerte” margarita on the beach.

It’s not hard to get excited about impactful work when you’re unencumbered by distractions and not chained to a desk or conflicted by a time clock.

4.) Other thoughts on working during vacation:

  • Is it better to be looped in on e-mails and feel compelled to respond?
  • Or is it better to be not copied and wondering “what if” constantly thinking about everything that has to get done?


More than once I woke up at 3-4am thinking about some aspect of our upcoming campaigns.

I ended up e-mailing my team and saying that I’d rather be copied and have the reassurance that things are moving along vs. being in the dark. I also didn’t want to come back to an onslaught that would put me behind from the day I return to the office.

In retrospect, I think that was the wrong decision — one rooted in the anxiety I was feeling about all the work going on.

In truth, I’d like to get better at letting go; therefore, I think having colleagues leverage delay delivery and/or not copying you while you’re out is still ultimately the best solution.


The benefits of vacation are innumerable. In fact, I listed them in my out of office response: higher productivity, stronger workplace morale, greater employee retention, and significant health benefits.

(Let’s be honest, I wrote that for myself more so than anyone receiving that response.)

Nobody will have the intimate knowledge of your projects as you do, but if you properly prepare your team for your time away from the office, they should be able to handle it 80% as well as (you think) you would’ve. As a manager of people, you have to learn to let go sometimes. Even if you’re responsible for the outcome, letting others help you is the only way to scale yourself and for all the work to get done. Being done is almost always better than being perfect.

5.) Be clear on everyone’s expectations

There’s very much this mentality of “This is what you do on vacation.” But, in truth, vacation is whatever you want it to be as long as the people you’re on vacation with are on the same page.

My wife and I worked out nearly every morning on vacation. We ate good food; we drank by the pool/beach; we went at our own pace; we read; we explored the resort; we slept a lot.

And I worked. For the love all that is holy, why would I work on vacation? Seriously? Have you not read *any* of this post?

But here’s the thing. I explained to my wife that I would have to work a bit during our vacation so she knew it going in. She also knows that I’m a Type A crazy person.

So yeah, she probably expected me to work, but she’d also much rather me spend that hour doing something with her. And I don’t blame her. She’s 100% right.

You see, while Alaina is one of, if not the most important thing in my life, she doesn’t always feel like the most urgent thing. This is unfortunate and something, like vacations, I’m going to have to consciously get better at.


On our last full day there was a drunk couple being insanely obnoxious at the pool. I was annoyed. I just wanted to bask in the sunshine and finish my magazine.

Ryan: “Wow. They sure are obnoxious.”

A: “At least they’re having fun.”

OUCH. That one stung, but she was right. She usually is. Don’t tell her that, though.


My job is much different now than when we first met. I have (much) more responsibility. I work on projects that are significantly more impactful. The sheer volume of tasks and projects have more than doubled. There’s more ambiguity, more to learn, more constituents to keep happy.

And yet as my career as grown, I’ve gradually lost the ability to let loose and have fun. I’ve become a buttoned up old man who just wants to work, work out, and read.

It’s time to revisit my 2015 manifesto:

More walks. More listening. More love. More humility. More patience. More perspective. More spontaneity. More gratitude. Always more gratitude. More creativity. More music. More family. More friends. More fiction. More fun. 

I hope this vacation was a wake up call.


This blog started primarily as a marketing blog, but now I think and write much more about work/life, social psychology, health and happiness. I will also continue to explore top performers (authors, entrepreneurs, business leaders and more) and dissect what we can take away to be top performers in our own work and personal lives.

If that interests you, consider subscribing below: