How I Learned to Stop Dreading Vacations and Have Some Damn Fun

Old-timey postcard of Oquaga Lake, N.Y. where last week the author took a REAL vacation. Author’s note: boaters are no longer required to don formalwear whilst boating.

Hello, my name is Ed, and while I have struggled with many things (i.e. playing basketball, determining whether neckties are in style, determining whether neckties I own will eventually come back into style, and other non-necktie struggles), for the purposes of this article, I am not particularly good at taking vacations.

(This is where anyone who has been in “the program,” would say, “Hello Ed!” and add, most likely under their breath, “Jesus, that was a long introduction.”).

Except that now I am much better at taking vacations. I returned from a week away yesterday, had a pleasant Sunday that was not filled with dread, and am ready today to hit the ground running at work.

Clearly, for me, it has not always been this way

Two Decades in High-Tech PR

Since 1996, I have worked in PR for technology companies. Public relations is consistently listed among the most stressful of jobs. The self-importance of this has always baffled me: yes, our work is important and stressful, but we are not scientists discovering new cures for important diseases, doctors upon whom someone’s life depends, or air-traffic controllers using decades-old technology to keep planes from crashing.

(Again, no doubt, what we do is important, particularly for any enterprise/B2B technology companies looking for PR, social media, design and branded content services — drop me a line, OK?) … but, come on now.

15 Years in New York’s Southern Tier

Each summer, for a decade-and-a-half, I have taken a week’s vacation with some of my best friends. We stay at a beautiful, rustic cottage on the shores of Oquaga Lake in Deposit (or Sanford, it’s sort of confusing), in the heart of New York State’s vastly underrated Southern Tier region.

Two of my fellow vacationers are scientists or something like that (what do they do? great question! something scienc-y?); one works in communications at an Ivy League university, the name of which rhymes with “Barvard”; another is a published cookbook author and my lovely wife is a human resources manager at a large software company that is constantly voted one of the nation’s “Best Places to Work.”

Blueberry cobbler prepared by one of my traveling companions. You can purchase her book here. In fact, you SHOULD purchase her book. Do it. I said DO IT! And don’t cheese out and buy a used version. Come on, pony up the dough for a new hardcover.

I include this background as while, yes, I consider my job important, it is no more important than that of anyone else with whom I have travelled. Yet for many of our 15 years at the lake, I thought it was important enough that while I was away from work, I wasn’t entirely present, either mentally or physically.

Does Unlimited Vacation Have Limits? Sometimes.
I was with a PR firm that, like many tech companies, offered “unlimited vacation.” Sounds great, right? There are, however, unintended consequences to such policies. According to Bruce Elliot of the Society for Human Resources Management:

In Elliot’s estimation, and in his informal survey of companies that do offer unlimited vacation, it yields an interesting observation: when given the freedom of taking as much time off as they want, employees don’t actually take more time off than usual. “From all the things we are seeing and companies we talk to, it seems to indicate that employees are not taking any more or less [of vacation days]. We don’t see that.” — “Why Unlimited Vacation May Sound Better Than It Is,” Fortune, March 10, 2016

Let’s Get Right to the Lowlights

I have committed the following atrocities whilst on vacation with my family, the worst of which occurred from 2005-2013 or so …

  • I made our family leave early twice because I “had” to be back for a product launch/meeting with a new client contact/something to which I just couldn’t say “no”; mind you, I didn’t have the guts to tell my wife until midway through the week.
  • Until around 2006 the home was a blessed haven bereft of cell service or WiFi  — so I would find an excuse to trek into town “to pick up a few things” (and manically check my email).
  • I groveled to a client (who was, in retrospect, an asshole who knew I was on vacation) to reconsider his decision to fire my firm whilst at the breakfast table, in front of my children and friends.
  • I snuck out to our house’s dock to take calls deemed “critical” from colleagues that were, upon further review, in no way critical.
  • I checked my email while playing whiffle ball with the kids (go back and read that again; wow, that is bad). Most of the time I would call timeout, respond to the note and then give up a gopher ball (not even an intentional one!) to one of my sons.
  • I had a constant mental countdown of dread (“great, vacation is 75 percent over”) — not the sadness of vacation being over, but pit-of-your-gut dread and fear.

A parade of studies and articles illustrate that I was not alone — as Americans, even with unlimited time off, we suck at relaxing and/or disconnecting.

Image courtesy of Project: Time Off and Fortune. Used with questionable permission. Um, fair rights? Let’s go with that.

The U.S. Travel Association’s “Project: TimeOff” refers to the reduction in annual paid vacation time from 1978 to 2015 as “the lost week”:

“Previous research conducted by Project: Time Off found our nation’s vacation usage had fallen to 16.0 days a year—nearly a full week less than the average between 1978 and 2000. This is America’s Lost Week. In the latest analysis of vacation usage, American workers took 16.2 days of vacation in 2015.”

I will give you that this research was conducted by a trade association advocating for the travel industry … but besides this data, the once economically-driven “staycation” has devolved into a much more sinister portmanteau: the “workcation.”

 “More than a quarter of workers say they are expected to stay on top of work issues when they are away and jump in if necessary, according to a recent national survey by the online jobs site Glassdoor. A similar share said they had been contacted by a co-worker or boss while they were on vacation.” — “‘Workations’ blur line between jobs and time off,” Boston Globe, June 29, 2017

Then It Got Worse, Yet … Better 

Last year, I had parted ways with my previous firm and was consulting. I decided to be upfront with my clients: I will be UNREACHABLE during vacations. I found a trusted colleague (thanks Chuck!) who could (and did!) serve as an able surrogate in my place. And I took TWO WEEKS off. And it was amazing.

I was truly re-charged and came back without dread — refreshed and ready to get back to work. Sure, I didn’t get paid while I wasn’t working, but I also needed the time to recharge, think about my future, and have some fun with my family, my friends, my wife and by myself.

Looking back, I attribute my earlier problems to two key factors:

  • While I had great account teams, I truly thought things would fall apart if I didn’t “keep up” — and the world would collapse, or I’d feel like a slacker.
  • While I was working at an operation with “unlimited” vacation, it never truly felt “unlimited.” While I acknowledge much of this was on me, I couldn’t help but feel that I still had to remain connected even while away from the office.
The author, tubing this past week with his incredibly patient wife

And Then Things Got Much Better

The author, carrying a ludicrous amount of ice cream.




It’s 2017 — and I now have a great gig at a wonderful PR firm that truly encourages us to unplug, providing unlimited vacation with active encouragement from our CEO.

“For example, we established an unlimited vacation policy, and we are flexible about how and where people work. I want them to do the things they need to be creative, whether that’s taking a few days off after a busy month, or going for a run before a brainstorm. I know I, for one, have never had a good idea while tethered to my seat and staring at my email.” — “Women in Business Q&A: Beth Monaghan, Co-Founder and CEO, InkHouse, Huffington Post

So, a few takeaways to make “unlimited vacation” work (stolen/borrowed liberally from the HR blog Workology and the SHRM):

1. The shift to open PTO must be cultural to be effective

2. Management must work closely with employees to plan time off

3. Management should actively encourage employees to take time off to recharge

4. Management should lead by example (see above quote-ed.)

5. Talk about the open PTO policy and be transparent with employees

So, this year, a few things happened. Most were awesome (particularly if you skip the first two bullets):

The author, with his family’s schnoodle puppy (name pending)
  • I couldn’t help myself and I responded to a few emails. I was gently told to stop.
  • Nevertheless, I persisted … and responded to a few more emails. The reminders then became less gentle, so I stopped.
  • I put away my phone and had fun:
    • Ate a lot of ice cream.
    • Started running again.
    • Went tubing with my wife.
    • Slept late (usually I was up by 6; this past week I slept past 9 a few mornings).
    • Took naps.
    • Swam — a lot.
    • Had many mystical adventures and near-naps on an inflatable unicorn perfect for a 6-6 guy.
    • Took in some great minor league baseball.
    • Met our new schnoodle!
    • Ate a lot of bacon.
    • Was insufferable about coffee.
    • Had great conversations about life and/or stupid stuff with my wife and friends.
    • Had similarly great conversations about the book Loose Balls, Terry Pluto’s wonderful history of the American Basketball Association, with my eldest son.
    • Had an amazing twilight football toss with my youngest son as he recounted his day of barefoot waterskiing with another pal who visits the lake.
    • Took in a movie at Deposit’s grand old movie house.
I will miss you, Princess Sparkle Pony Unicorn

Most years, the drive home has been an exercise in finding ways to prolong our “escape” from reality — desperately meandering just to push out the return to the anxieties of “real life.”


The author, with a cut-out of our nation’s 8th president.

This year, our travel was leisurely, not maniacal: we finally took in the birthplace of Martin Van Buren (I’ve been begging to do this for 15 years, so thanks, family) and the artisanal, hipster vibe of Hudson, N.Y.


So in closing, thanks for reading this far. Was I psyched to get up early this morning? Not really. But am I relaxed, recharged and ready? Hell yes.


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