On Workcations, Part 2

My family and I just got back from a week in Cabo, Mexico, which we approached as a workcation. I say that because it was not meant to be a full-on vacation like many assume it was (say Cabo and it’s hard not to think that!).

We were there meeting with business friends and doing a kind of mastermind group, but I was able to bring the family along, so I considered it a workcation. Half work, half family and fun.

I’ve written about workcations before, so this is part 2.

I have some updated thoughts on them. And to save some suspense … they’ve lost a little luster in my mind.

A workcation in my definition is where you are able to work in a remote (awesome and different) location from your norm, while blending family and fun.

But I want to give you the cold, sobering truth about workcations … and then after that awakening offer you a new twist about what they really are for me.

So let’s get to it … here are 5 new things I learned about workcations last week:

1. Your well-established routines will be completely upended.

You’ll be adjusting to new time zones, potentially jet lag, and most importantly new routines.

If you think you’ll be able to set a regular or consistent schedule, then maybe you don’t have kids. Maybe also you don’t realize that you have 1,000 routines and hacks and shortcuts that you take for granted at home because they are … yes, routine.

Everything gets turned upside down … and just about the time you get into a rhythm (where to eat, where to find web, a semi-set schedule) … it’s time for you to leave.

Sometimes just trying to find your toothbrush can throw you off.

2. Say goodbye to stable, fast, reliable Internet.

Or heck, Internet at all.

Yeah, I know you think that 5-star hotel or cabin in the woods will have blindingly fast internet like you do at home or your office … they don’t.

We were at a VERY nice resort in Mexico and the web was shaky at best. So there’s no Skype video (or even audio) chats going on. Sometimes I’ve had to enter chats several times to make sure they went through.

Before that, last summer in the mountains of New Mexico, I explored every option under the sun … and finally had to resort to going to public libraries and the parking lot of a chamber of commerce.

In Europe a couple weeks ago, I found the same scenario … just because you have fast, reliable web in your home, or office, doesn’t mean it follows you all over the planet.

Yeah, you’ll say, but Philly or Spain or wherever will have great wifi. Or You’ll just get a mobile hotspot. Good luck. Everything you do at home or the office with ease … will be exponentially harder to do away from that web paradise.

So pan to forever be hunting good web.

3. You might work 4 “on the grid” hours a day. Maybe.

But really count on two hours.

I planned to be on the grid a lot in Cabo. And in the past. And it’s hardly ever worked out.

By “on the grid,” I mean being readily accessible for chats, conversations and calls.

I maybe got 4 hours once or twice. And they were chopped up. I was also an hour or two off most of our team too, so when I’m ready to chat, found decent web at the moment, they are at lunch or busy. Or [insert any reason to be disrupted].

4. Your 14-month-old baby doesn’t care that you forgot your headphones.

… and that’s ok.

Although my wife Lindsey worked very, very hard at helping me maintain my work and my focus while we were on this workcation, little babies don’t really care.

See No. 1 about routines.

But suffice to say, babies change things. In a very good way.

because moments like this are priceless and forever.

5. This isn’t for everyone.

In fact, not everyone CAN do workcations.

I’m the founder and CEO. I collaborate and have conversations and make decisions etc but over the years, I’ve been able to establish an amazing team around me that makes me look better than I am.

I don’t have a deadline project.
I’m not collaborating with anyone.
No one is looking for an answer that only I have and that they can’t figure out or else can’t easily find without me.

In other words … they don’t need me immediately available and accessible 8 hours a day (which I actually am if there is a fire that big — the good ole telephone still works!).

Also, I think, frankly, our team operates better sometimes without me getting in the way. Plus, I have an outstanding COO who I’m in daily contact with, but who is more than capable of leading without me.

They are all put in the roles they are in because I believe in them, in their talent, in their passion, in their commitment. They can make decisions and do things without me holding their hand 9-5 for a couple of days, or weeks if needed.

Additionally, this is why we give and encourage our team to take actual, real VACATIONS. They need to check out and unplug and go completely OFF the grid.

I don’t expect them to work while they are with their family and enjoying time away together. Most people I’ve met want nothing to do with a “workcation.”

In fact, this week I’m here with other entrepreneurs in WordPress (my industry). Even when I’m not officially on the grid, I’m still doing things and having discussions that will build our business and lead our team into the future.

But as entrepreneurs, we like the balance of work and play … we just don’t expect others to.

(But one thing is for sure though … workcations are NEVER substitutes for the real thing! And we take several week-long type vacations a year, including weekend getaways, where no work is allowed.)


OK, so that’s mostly downer stuff, but it needed to be said. My rose colored glasses have finally come off.

Now I want to share the very positive part of workcations, and how they’ve changed for me.

They aren’t meant to be 40 hours of “on the grid.” They can’t be. For those able to do that, I’m happy for you. But a 40-hour work cation just isn’t reasonable or practical or realistic. It’s idealistic. And that bubble got popped for me.

What workcations are for me is … enough time “on the grid” to stay connected as needed … but truly, they are times to get away to think, reflect, read, plan, strategic, talk, debate, discuss.

They are simply about DISTANCE. About being somewhere else, with your family, enjoying times together … so that you can recharge some and be better when you get back to the grid and grind.

I need this space to be able to see things better.

So the work part of the workcation is simply … perspective … recharging, reflecting and getting re-energized about what we’re doing and where we’re going.

Last week … I also get to spend it with some great business friends and cultivate and deepen relationships with them (and who knows what comes of it) because no matter how beautiful the scenery is … we’re probably always talking shop together and sharpening each other to do and be better. (Thanks, Chris, for putting that together!)

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