Working Holiday

How to take a vacation without anyone knowing

Back Web Only Aug 29, 2014 By Janna Maron

Flexibility is one of the greatest benefits of being an independent worker (or freelancer, or solopreneur, or whichever term you prefer). You don’t want to be chained to a cubicle or beholden to the 9-5 schedule. So you go mobile — taking your laptop with you — to keep your job and freedom without having to choose between work and play.

That said, you don’t always want to be broadcasting every time we leave our home base of operation. Although the landscape of work is changing with mobile independents at the forefront, there are still those traditional clients who could be uneasy if they perceive “mobile” as “unavailable” or “irresponsible.”

So, how do you take a trip without anyone knowing?

Set Expectations

Don’t be too available: As an independent, I’ve found the value of setting an important precedent: I’m not too available. Don’t get me wrong, I am very available, especially to my clients. But there’s a fine line between being prompt and responsive and being OCD about checking email. I will always get back to clients within 24 hours. Sometimes that means waiting to return a an email received at 5 p.m. until 9 a.m. the next morning.

Setting these boundaries sends the message that you are doing other important things (like maybe getting on a plane and flying to Seattle or Chicago for a few days). As long as you get back to your clients within a reasonable amount of time, it doesn’t matter where you are geographically located.

Never work from the same place twice: Okay, that’s a bit of an exaggeration. But let’s say you have a standing video call with a client. If you are not in the same place for every meeting, it sends the message that you’re getting work done no matter where you are. Take the call from home one week, from a coworking space the next, from a beachside bungalow the week after that, and none will be the wiser.

Plan Ahead

Find a coworking space: These spaces are huge assets to independents. Compared to a coffee shop, coworking spaces offer a more professional atmosphere, more reliable Wi-Fi and, perhaps most importantly, much-needed privacy. Most spaces offer affordable day passes, and a quick Google search will turn up a number of options, especially in larger metropolitan areas.

Reschedule meetings as necessary: Let’s say you want to go to Chicago for a week. You’ll be in a different timezone so there are two options for that standing video call:

  1. Keep the call at its regular time—if the call is at 1 p.m. in Sacramento, take the call at 3 p.m. in Chicago; or
  2. Reschedule the call—schedules change and it’s not the end of the world to reschedule the meeting. You can say that your schedule has changed (which is has) and ask that the call be moved to 8 a.m. (10 a.m. Chicago time) for that week.

Manage social media appropriately: If you don’t want anyone to know that you’re on a covert vacation, you must manage your social media accordingly. That means:

  1.  No pics of Wrigley Field that reveal where you are,
  2. No Facebook or Foursquare check-ins, or other location-based posts
  3. No out-of-town friends tagging you in their posts

If I’m feeling really clever, I might change the geo-tag of my Instagram, or even pre-schedule some posts from Sacramento to automatically go live while I am traveling.

Manage Availability

Pay for the Wi-Fi: These days most airlines offer in-flight Wi-Fi — for a fee. Some people I know roll their eyes at paying for Wi-Fi. But you want to make the most of all the time available to you. If I can work during a 5-hour plane ride, $5 for WiFi is nothing.

Check in: Regardless of where you are, check your email at the beginning and end of the client’s day. Keeping the client’s day in mind is key, especially if you are no longer in the same time zone. Even if you are in the same time zone, your day might start at 10 a.m. when taking a work-cation (working vacation).

Set an email alarm for the morning and respond to urgent matters right away. That will buy you at least 6 hours of being offline to have a leisurely brunch, go shopping or read in a park for the afternoon. Make sure to check in again at the end of the day.

The reality of an indie life is that you don’t get paid vacations, and often don’t have the option to not work. But that shouldn’t come at the cost of leisure—it just means we have to be a bit more creative with the ever-elusive work-life balance. So far this year I have worked from Seattle, Chicago, Santa Barbara and Lake Tahoe. I always get my work done and no one (except for my husband) needs to know  where I am.  


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Roy (not verified)September 2, 2014 - 4:52pm

Too bad the tone of the article is that independents have to "hide" from their clients to take time off. I am a business owner and it is no different for me. I do believe I deserve time off; that time off will make me serve my clients better.

It all starts with being realistic. If you are the Lone Wolf, don't try to look like you are a big consultant with people and branches all over. Be the small independent. Let your clients know your schedule and availability. You are not on call 24/7. You e-mail a client at midnight, they will think that is the best time to get you.

And, "manage your social media accordingly" looks like you are really trying to hide and this is espionage work. You are killing me.

I could go on and on, but I disagree with the premise of this article.