The topic of vacation, or the “taking of” vacation to be precise, has become a complicated workplace issue in recent years. Certainly in Silicon Valley the debate swings across a wide swath of norms when it comes to taking time off from work. How many weeks per year are appropriate? Should you be actually doing work while on vacation? And perhaps most importantly, what does it actually mean to take a vacation that is well taken? Since I’m about to embark on my annual family pilgrimage to the Oregon Coast, I figured now is as good a time as any for me to reflect and share my thoughts on this important subject.
First off, a disclaimer: I am not using this post to argue from my role as a startup CEO for or against any specific type of vacation policy. Also, I’m not going to make this a public (or social) policy piece that compares the workaholic approach American’s take to vacation to how our international counterparts embrace vacation. Nope, as I set off on a week off with my family, I’m simply here to ruminate on what I have come to believe are the important tenets of a vacation well taken. Please note, however, as a Silicon Valley resident — and someone who can’t stand playing golf — my definition and approach to vacation may differ from yours.
Let’s start with some definitions. According to the always undisputed results of a Google search (and what other kind of search is there exactly?), the word vacation originates from the Latin “vacare” or to “be unoccupied”. Okay, that’s interesting. Based on this definition, my wife and kids would say I’m pretty much on vacation every waking hour I’m at the house. So how about a few more precise dictionary definitions from the fine folks at Merriam-Webster:
Vacation (n):
1. a period spent away from home or business in travel;
2. (a): a scheduled period during which activity (as of a court or school) is suspended; (b): a period of exemption from work granted to an employee
3. a respite or a time of respite from something
With this as context, let me share my definition of vacation, or at least my personal tenets of how I have come to view the topic of “vacation taking” in today’s frenetic digital age.
Tenet #1 — Take Your Vacations Dang It!
This one seems pretty obvious, but you’d be surprised how many people don’t take their vacations. Not taking vacation is unacceptable, especially for those who work at companies that haven’t instituted formal vacation policies, where it’s truly use it or lose it every year. Even for those working at companies that specify time-off limits, banking those days usually ends up being capped and the small PTO (personal time-off) balance you might accrue isn’t worth the mental health benefits you gain by replenishing and recharging at least a few weeks each year.
Now if you do work at a company that leaves your vacation decisions open ended, you should definitely plan out the right amount of time-off each year. As a rule of thumb, take the vacation you need while living up to the commitments you have to your teammates and your company. Generally speaking, folks know that their contributions are critical to the success of the company and they in turn find the right vacation-to-work balance. Now if you’re not exactly sure how much time to take-off, there are a few obvious signs that you may be overdoing it on the vacation front. For example, you may want to dial back on time-off if people at the office ask you your name when you get back from your most recent trip to Tahoe. Likewise, if you find that new guy from finance sitting at your desk surrounded by pictures of his dog and mom after your two-week sojourn to Mexico, yep, that trip might have been a tad too long.
The bottom line for Tenet #1 is to take vacation, don’t skip it or trade it in for more compensation. With this tenet firmly grounded, the rest of my self avowed vacation advice focuses on how to get the most out of your time away.
Tenet #2 — Set Goals For Your Vacation
This seems a bit counterintuitive doesn’t it? I can hear you all screaming at this right now, “Goals? That’s what I am focused on at work for Christ’s sake!”. Trust me on this one, setting out a few simple goals will make you feel so much better when your vacation comes to an end (and it will come to an end). Setting out, and achieving, a few simple objectives for your vacation will not only allow you to look back and quantify what you actually got out of each vacation, but you’ll also have a bunch of things to talk about with your friends at work (assuming they remember your name!). Mind you these goals can be pretty much anything so long as, like any good goals, they are measurable and they stretch you a bit. A few examples of “vacation goals” (granted, some more “stretching” than others) might include:
Read 2 books (okay how about one book, not counting graphic novels);
Take at least 3 killer hikes (e.g. longer than say five miles each);
Sleep 10 hours each night (see, some of these aren’t exactly gonna tax you physically);
Hit 5 local landmarks (yes, breweries, wineries, and distilleries all count here);
Take away at least 1 historical story from your travels that you’re pretty sure nobody back home really knows about (alas, you need to prove you actually did something more than sleep, eat, and drink beer all week!)
Make your own list of goals for your vacation. You’re human, you have needs related to striving for meaning and stuff like that. Come home with a list of accomplishments that you can brag about. At least have a few things you can tell your grandkids you did on that trip to Istanbul, Havana, or the dude ranch outside of Jackson Hole.
Tenet #3 — No Dieting, Some Exercising
This tenet is pretty simple. If you’re in the middle of some whacky Paleo-intermittent fasting-juice-and-protein-shake-cleanse diet nonsense, stop it the minute you hop in your Lyft ride to the airport. One of the surest ways to ruin your vacation is to start counting calories or picking at your food trying to toss aside anything with white flour or refined sugar in it. Hell, vacations are meant for eating native dishes that might include copious amounts of white flour and refined sugar so please indulge. And don’t limit yourself to simply breakfast, lunch, and dinner. Mix in a few snacks around the big feasts every day; in fact it’s a good practice while on vacation to constantly be eating since you can’t be sure when you might hit a long stretch of walking a city or the wilderness without access to food, God forbid.
It’s this last point that relates to the other half of this important vacation tenet. Doing some exercise is a great way to accomplish a number of things while on your trip. First, it reduces dramatically any guilt you may feel by all the eating (and perhaps wine, beer, and/or distilled spirits drinking) that you’ll be doing. While you may be slurping down upwards of 5,000 calories a day, all it takes is a moderate amount of exercise to convince yourself that you’re breaking even. “Bearclaw and a white mocha frappuccino…30 minute jog at a laughingly slow pace…breaking even!”. Second, picking out a daily exercise activity gives you an instant line item per your vacation goal setting effort. On a week long trip to Tahoe? Great, challenge yourself to do something physical every day and you’ll head home after day seven feeling like a winner. Sit around your hotel room or cabin every day and by day seven you’ll feel like the sloth that you have become (“hey, are those bearclaw crumbs on your hoodie?”). Finally, being even moderately physically active opens up a full array of ways to tap into the local flavor of your vacation destination. At the beach? Super, take a surfing lesson, do some snorkeling (or SCUBA diving if certified and so inclined), or run barefoot in the sand. Out in Colorado? Awesome, how about a crazy hard hike, mountain bike tour, or finding a nearby lake for a swim? Or find yourself in a big city? Well, tie on those sneakers, strap on your Fitbit, and crank out 20K steps a day checking off your laundry list of landmarks along the way.
Tenet #4 — Toggle Between Ritual and Adventure Vacations
I think about vacations in two important buckets: ritual vacations and adventure vacations. It’s important to find a balance between the two versions as they each offer up a different kind of renewal that you need from your time away from work.
A ritual vacation is one that you do over and over. It’s one that you typically do with extended family included (which of course raises the potential of making it quickly not feel like a vacation if you’re not careful). The most obvious ritual vacations are typically anchored around holidays — Thanksgiving, Fourth of July, the last couple weeks of December and first week of January. For my family, the annual trip I am on this week to the northern Oregon Coast is indeed a ritual vacation.
My grandparents started the tradition long before I appeared on the scene, and now it’s become a ritual that my own kids look forward to. The best thing about a ritual vacation are all the “little” rituals that make it a ritual vacation: the trip to the bakery downtown that serves up the most mouth watering maple bars, buying a book at the local bookstore on day one and reading it over the week ahead, crab fishing on one of the local rivers that pour into the Pacific Ocean. You get the point. Ritual vacations also give you a unique opportunity to truly unplug in a familiar environment and reconnect with family members. You get to slow down, create your own space, and think about whatever catches your attention other than work. Maybe sketch the outline of the novel you want write, draft the plan for the non-profit you want to start, or take the time to binge watch the HBO series all your friends keep reminding you how lame you are for not watching (leave me alone about that damn “Game of Thrones”!).
The alternative to the ritual vacation is the adventure vacation. For single folks this can be a solo journey somewhere, or an opportunity to gather a group of friends and set off somewhere never visited. For those of us married with kids, the adventure version might start pretty tame e.g. the time honored trip to Disneyland or the weekender down in Monterey Bay. Later, when the youngsters have the stamina and attention span to handle something a bit more bold, off you can go on the types of car camping trips my wife took our girls on to explore the wilds of Montana, Wyoming, and Vancouver Island in Canada over three successive summers. And in recent years we had the good fortune to visit England, Spain, Greece, Turkey, the Dominican Republic, and Cuba.
My advice on adventure vacations is to explore both near and far. By traveling “near” I mean take advantage of exploring what is literally in your backyard, which for us looks like the trip north my younger daughter and I took a couple years ago where we go to explore Mt. Lassen National Park, Crater Lake National Park, fly fishing and white water rafting in Central Oregon, and a full campus and athletic facility tour at the University of Oregon (her favorite college team of course). By traveling “far” I mean hopping on a plane and flying far away. Flying to a new country, culture, and language that you don’t speak. In both cases — traveling near and far — keep moving and document your travels through photos and the written word. Writing down in detail what you see, experience, and feel is no less powerful a memory than the hundreds of photos you can easily click with your smartphone. The simple act of documenting your adventure vacations in this way help you learn so much more about the places you visit, while giving you something to later peel back when you plan what you would seek out when you go back to this country or destination (and you should go back if you can someday).
Tenet #5 — Don’t Work on Vacation (Unless You Absolutely Have To!)
Full disclosure, I have never lived up to this tenet worth a damn, and I’m not sure I ever will. However, I aspire to achieve it someday as I see it is an important aspect in capturing the true benefits from your vacation time. We live in the always connected age, an environment in which work is always a mere finger tap or two on your mobile phone away. Fear of missing out, fear of being irreplaceable, and fear in general draws all of us to constantly check in on work. Is that product going to ship while I’m gone? Is that deal going to close while I’m gone? Is that campaign going to go off without a hitch while I’m gone? Yes, yes, and yes. Now put your darn phone down and get back to those vacation goals of yours.
Alright, outside the utopian world where vacation life and work life live in absolutely separate orbits, I grant you that there are product ship dates, deal signing deadlines, and campaign execution windows that do land unceremoniously on top of your vacation week (or weeks). For some roles like CEO, startup employee, corporate lawyer, investment banker, doctor, etc., it isn’t typically realistic to go 100% off the grid. Oftentimes vacation days get preempted with critical conference calls, contract negotiations, or at a minimum, the need to respond to emails, texts, or Slack messages. As a CEO, my goal for vacation time is to do my best to find discrete windows to do critical work tasks and check-ins early in the morning before my family awakes or later in the evening after they’ve gone to bed. At the same time, I try with each vacation to do a better job of defining the “critical work tasks” that require my attention by partnering with my teammates on clearly defining what we need to sync on while I’m out versus what can wait until I’m back. Establishing these windows for doing critical work while on vacation creates vital boundaries in this era where it’s all too easy to blur the lines that demarcate work from vacation. Outside these pre-determined times, I try to be 100% on vacation. I have gotten better over the years about not using my phone to constantly look-in on work and I have improved at ignoring the urge to respond to the constant stream of notifications that populate my phone’s home screen. But I can always do better.
A Final Thought or Two on Vacation
No matter your company’s vacation policy, the time you take off from your work enables you to recharge and replenish your mind. If pursued intentionally, vacation time also allows employees to reflect on the important work they are doing and where they hope to go in the future. Active minds tend to stay active, and in this vein vacation periods become important periods where real personal and professional growth happens. So use your vacation time and use it wisely. When you come back to your company and teammates you should feel reenergized and excited about what lies ahead. That’s a sign of a vacation well taken.
Originally published on Medium on July 31, 2017. This Substack version is maintained as the canonical archive.