Sales Intelligence AI for sales insights and conversation intelligence

10 Tips for a Successful 'Workation'


Facebook Twitter Linkedin Copy link post URL copied
4 min read

In this, the first segment  of our special series “Beyond the Office,” we take a closer look at how small business owners can leverage today’s innovations to give them more freedom to choose how and where they work.

Small business owners often struggle with the challenges of taking a vacation. Almost all mental health experts agree that time away from work to unwind and recharge the batteries is necessary. However, without paid time off or back-up help, a getaway can be next to impossible for anyone responsible for all the day-to-day activities required to run a business.

Image Courtesy of Nhom Toi on Flickr

Image Courtesy of Nhom Toi on Flickr

Today’s the first segment  of our special series “Beyond the Office,” which takes a closer look at how small business owners can leverage today’s innovations to give them more freedom to choose how and where they work.

With advancements in technology, the “workation” has become increasingly popular. So what is it exactly? Simply put, a working vacation. Maybe it’s not quite as relaxing as a week off without customers, vendors and to-do lists. Yet this hybrid holiday is a smart compromise for business owners, who want time off while also keeping their business running as usual.

To have a seamless workation that gives you the ability to work while granting time for play and relaxation, you need a plan. Here are 10 tips to guide you on your way:

Delegate As Much As Possible
First and foremost, don’t attempt to manage a workation alone. Getting some reliable help while you’re away will make your trip much more enjoyable. Figure out what you can shift to an assistant or coworker – or, if you’re a solo entrepreneur, find a trustworthy neighbor, family member, friend or short-term virtual assistant who can help keep you organized. Give them specific tasks such as answering email inquiries, paying invoices or returning customer calls. By having this little extra bit of support, you’ll buy yourself some more leisure time.

Notify Your Customers
While you probably won’t be able to notify everyone about your upcoming workation, you can certainly let those whom you deal with on a regular basis know that you’ll be away from the office. By doing so, you’ll give them a heads-up that you might not be readily available. Customers appreciate being told your plans and will likely respect the fact that you’re taking a few days for yourself.

Make Sure Your Destination Is Workation-Friendly
Deserted islands and remote mountains make great spots for quiet, relaxing sojourns. But, they can also cause a lot of frustration if they don’t offer Wi-Fi and good cell phone reception. Before your book your vacation in a secluded spot, you’ll want to confirm that your phone is going to work and you’ll be able to access the internet.

Bring the Right Tools
Since you won’t have access to all of your usual office gear, you’ll need to think about the few items that are absolute necessities for getting work done away from the office. Most likely you’ll be taking your laptop or tablet and a phone. But you might also want to sign up for a few workation-friendly tools, such as a cloud-based business phone system like RingCentral, an internet stick or online backup and document-sharing tools.

Set a Schedule
Without setting time aside for leisure, you may find yourself working as hard on a workation as you would any other time. To make sure you have time for fun, figure out what hours you’ll absolutely need to work and when you can take a break. You’ll also want to take into consideration the time difference from where you are and where your customers are located!

Get as Much Work Done Ahead of Time as Possible
The time to finish that big project is before you pack your bags for your trip. By getting as much off your plate before you leave, you’ll buy yourself more free time. Remember, the goal should be to incorporate a bit of work into a vacation, not to fit a little vacation into your work.

Designate a Workstation
Once you’ve arrived, figure out the best place to set up your workation workstation. Whether it be a desk, quiet corner or even a patio, figure out where you can get your work done with the least amount of hassle and disruption.

Stay Professional
Even if you’ve told customers that you were heading out of town, they don’t want to talk to you while you’re drinking beer on the beach or playing volleyball with the kids. If you can answer your phone without too much background noise or disruption, that’s great. But if you’re in the middle of having fun, you’re better off letting the call go to voicemail.

Have Fun
It’s not always easy to juggle a vacation and work, and, for some, it can be downright difficult to completely unwind. However, the purpose of a trip is to get away and relax. Once you’ve finished what needs to be done for the day, put it away and focus on having some fun!

Plan a Future Vacation
Not every trip should involve lugging along a laptop or talking to customers. At some point, you will want to plan a real vacation where you can focus solely on spending some quality leisure time without having to think about work. By planning ahead and having the right people and tools in place, a workation can easily be accomplished and even a vacation is doable.

Bon voyage!

Originally published Jun 21, 2011, updated Aug 07, 2020

Up next

Communication & collaboration

7 Personality Traits of Successful Business Owners

While there is no one winning formula for business success, there do seem to be character traits that most successful business owners share. In a 2010 study by the Guardian Life Small Business Research Institute which polled over 1,000 business owners, the following traits were found to be the most common. Ability to Collaborate At ...


Facebook Twitter Linkedin Copy link post URL copied

Related content