Five Steps To Take a Vacation in a Highly Connected World

What? Are you serious? Who needs a guide on how to take a vacation? As we become more connected through mobile devices, our always-on jobs, and our expanding online social networks, it’s harder to break away from the physical aspects of work, and even more importantly, the developing mental separation from work and daily life woes to really relax and recharge.

This was my first time unplugged in a few years, and now that Altimeter Group is continuing to safely grow (and hiring) it was a good time to take two weeks completely away from work, and week completely unplugged in the remote Fiji islands.

Well, I should point the finger at myself first, as I live and work, a highly connected lifestyle. It was hard for me to take time off, but I was successfully able to disconnect, both the wireless connection –and mental disconnection from work. I want to share five steps on how to have a successful vacation when you’re a highly connected individual.

Five Steps To Take a Vacation in a Highly Connected World:

Step 1: Take a Vacation. Really. Take one. Or at least, plan for one right now. In fact, the American workforce is less likely to take vacation than many other industrialized nations. Even if your budgets or schedule is limited, take a staycation. Lower cost alternatives include camping at your local beach and national park, or even staying in a nice hotel in your home city on the other side of town.

Step 2: Properly Plan To Leave Woes Behind. make some deals with your colleagues that they will cover for you when you’re gone, and you’ll do the same for them. Then, let your customers, clients, partners, and other important folks, at least 30 days in advance, to set expectations. Lastly, let folks know you’ll be completely disconnected, and they should send you important emails that require action to your colleagues, or after you return: set expectations. Special thanks to Altimeter’s Julie Viola, Christine Tran, Andrew Jones, Charlene Li, and others for covering for me during my downtime.

Step 3: Unplug, Even Forcibly If Needed. So the best way for me to be unplug is to go to an area where there’s no electronic devices, and spent time island in the remote Fiji islands where there’s no cars, TVs, radio, internet, for most islands, you don’t have to go to the other side of the planet to do this, just leave your electronics in the hotel safe. If you truly lack self control, you can disconnect, unpower your devices, or even have your carriers cut off access for a short period of time. Taking time off from social networks (even beyond your vacation) is a good ideas. See what happened when I took a few weeks off from Twitter, my world was just fine.

Step 4: Use Your “Idea Freezer”. Physically being on the beach is much different than mentally being on the beach. One trick to deploy is having a way to shed ideas, so you can resume them after you return –without them interfering into your peaceful brain. The best way is to have a ‘mental freezer’ such as a notepad (I always carry a Moleskine see how I use it to stay organized) by the bed stand to write down any invasive work idea came into your head whatever they are. Quickly slay those ideas, by putting pen to paper, and leaving them in the freezer and expanding your mindshare for other ideas. After a few days, you should settle into your relaxing vacation, worry-free. The great thing about the idea freezer is that they will be there when it’s time to come to reality, all thawed out.

Step 5: Do a Counter Cycle. It’s so easy to yearn to go back to our daily routine so try new experience to expand your mind. Do something opposite to your daily routine (hence the “counter cycle”): exercise, read leisurely books, or just get some sun I find that mixing with different cultures gives me a unique perspective I can take home and reapply to life and work. For example, spending time with the leisurely Fijians on “Fiji Time” (which is far slower than Hawaiian time) helped me to refocus on what’s really important in life.

If you’ve followed these steps, of actually planning, unplugging, then mentally refreshing yourself on your holiday, congratulations, you’ve successfully taken a vacation in a highly connected world, and are ready to return to the land of the connected. Update: Also see Boston Innovation’s group “Why you need a vacation“.

(Update: Fiji pics are now live on Flickr)

  • As a freelancer I find it nearly impossible to even take weekends off let alone plan any “real” vacations. I don’t have colleagues to trust my work to, so it’s difficult to plan around deadlines. These points you made are great advice, but I wonder if you have any suggestions for us “lone rangers” that can’t rely on coworkers to help us through off-time.

  • Thanks Jenn, a really great question.

    First of all, congrats to you in be a freelance “lone ranger” a lot of respect to you and what you do.  With that said, it’s even more important for your clients that you’re always in your best condition, so taking a vacation should be something you need to do.

    I work (hire) a few freelancers, and they still take vacations, even if it’s a sole propertierships.  One graphic designer lets me know a few weeks in advance, and I’m able to prepare to give her work before or after, so setting expectations will still be ok.

    Secondly, I recommend hiring a temporary Online Admin, or Virtual Assistant, in order to manage your business while you’re away.  Like a paging system, they can manage incoming leads, or client requests, and triage the MOST important to you (only if truly urgent) to you while on vacation, giving you peace of mind.

    I hope this helps Jenn, and good luck with your continued mission.

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  • Congratulations on what I consider a remarkable feat: taking a vacation from the connected world. Last year I spent six months living in Guatemala. Before I left, I had fantasies of having to walk 3 days through the mountains in order to find a dial-up connection. Boy, was I shocked when my home-stay family had wireless internet in our home (no hot water, mind you, but internet). I have to say I was slightly disappointed. If I wanted to disconnect, and I didn’t want to lie about the dial-up, I was going to have to own up to it myself. Use the ‘foreign country’ excuse (which works quite well). There was a bit of guilt (…I never called her before I left), and a little anxiety (I know that there is something I am supposed to be doing…) – but after pinpointing that these were everyday ‘connected life’ feelings which I inadvertently packed  in my suitcase…I was able to completely let go. Believe me I went through the scenarios of the possible horror stories that might await me upon my return from the ends of the earth…though my logical brain knew the real horror stories were much more likely in a 3rd world country.
    PS – love the “staycation”

  • Thank you for your reply, Jeremiah! A Virtual Assistant is a great idea; I should check that out one of these days. Most of my clients are very reasonable when it comes to my needing time off, but I have one client (the largest portion of my income) that is extremely demanding, and has expected me to be available over stat holidays, weekends and practically every waking moment of life. It is this client I have the most difficulty with in figuring out how to handle when I am needing some away time.

    Thank you for the article and great advice. Keep up the good work!

  • Sounds like you need to set expectations with the client, wishing you the best.  I’ve had to learn a lot of this too Jenn after starting with Altimeter.  

  • Sounds like you need to set expectations with the client, wishing you the best.  I’ve had to learn a lot of this too Jenn after starting with Altimeter.  

  • Tiffany, thanks, it’s interesting how each culture has different expectations of ‘response time’ depending on where one is from. I hope I can slow down just a bit after this experience.  A bit of “Fiji time” has rubbed off on me.

  • Tiffany, thanks, it’s interesting how each culture has different expectations of ‘response time’ depending on where one is from. I hope I can slow down just a bit after this experience.  A bit of “Fiji time” has rubbed off on me.

  • Jenn

    One other thing, congrats on being wanted, that’s a nice feeling, yes?  It also means your clients want you, and will wait for you to return and even appreciate you more when you’re back.  Get some ‘me’ time. 

  • Great advice and as you mentioned not enough people actually do this to enjoy their vacation time.

    Or you can do what I did a couple of years ago and go into the remote woods where there isn’t even cell service or electricity. That felt good!

    Loving the pictures.

  • Great advice and as you mentioned not enough people actually do this to enjoy their vacation time.

    Or you can do what I did a couple of years ago and go into the remote woods where there isn’t even cell service or electricity. That felt good!

    Loving the pictures.

  • words that rein very very true Jeremiah, I’ve followed them all except the destination being Fiji… dammit I better try it all over again.  Great photos and thanks always for your insights.

  • Paul R.

    On a slightly different tack, I’ve used the ubiquitous connectivity to extend my vacation. Take the first week off, then a few weeks of working Tuesday through Thursday, use the long weekends for relaxing and sight seeing.  And then another week off prior to heading back to work full time.  Spent five weeks in Europe last year.  While all locations had internet service, the “service” was questionable in many places.  After the fact one friend recommended buying a monthly data card and using that, instead of relying on service from various hotels, etc.

  • Smart thinking.  Extending the trip and integrating travel with work.  Nicely played.

  • Hah, you don’t need Fiji to win at this one, but glad you liked.  Thanks Mike.

  • Thanks CC!  Glad your book is doing so well, I still read it when I need some inspiration for content.

  • I managed to do more or less the same last week and I had a great and relaxing holiday. My island was not disconnected from the Onlilne-World, but it was easy nevertheless to stay away from work, I probably needed it badly. However, social media offer new challenges concerning “out of the office”-messages: Difficult to handle are Xing, LinkedIn, commentary part of the blog 😉

  • I managed to do more or less the same last week and I had a great and relaxing holiday. My island was not disconnected from the Onlilne-World, but it was easy nevertheless to stay away from work, I probably needed it badly. However, social media offer new challenges concerning “out of the office”-messages: Difficult to handle are Xing, LinkedIn, commentary part of the blog 😉

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  • Useful tips, its really concern that when we are on vacation nobody disturb us. I am pretty much concern about it. Most of the time when i need to spend some time alone or go to somewhere, first i switch off my mobile. Thats the first and important step to disconnected all.

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  • The only problem with ignoring all emails etc when on holiday is that you get swamped when you return with thousands of emails. Personally I chip away at them on my vacation. 30mins a day. MAX!