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How to Make Your Working Vacation a Success

A working vacation seems like a pipe dream. Hence, Lee Wilson explores five essential tips for a successful working holiday.

On the Road Again: 5 Tips for a Successful Working Vacation | SEJ

Working vacations have a bad reputation; either the assumption is that little if any work will get achieved, or that any notion of having a real vacation is optimistic at best. But this doesn’t have to be the case! In this post, I am going to explore five essential tips for a successful working holiday.

Tip 1: Getting the Work/Fun Percentages Right

On the Road Again: 5 Tips for a Successful Working Vacation | SEJ

This is the initial barrier that frequently causes working vacations to fail, or under deliver on pre-trip expectations. While percentages will always differ depending on the driving force for combining business and pleasure, travel destinations, and myriad other factors, it is possible to combine work life and home life successfully in your travel plans.

Setting expected work/fun percentages before your trip will enable you to plan for delivering on your expectations.

The more forward planning you can book into your holiday from the outset the better.

From advance booking activities, through to identifying ‘between meeting stop offs’, investing in advance planning, will save on disappointing work/fun deliverables.

Tip 2: Using Personal Experiences to Drive Success

Regardless of your industry, there will be logical opportunities to leverage travel plans (or direct work needs requiring travel) for business and home life value add.

The charity sector is a fantastic example of this in action. Companies are able to volunteer time, energy, expertise, and provide real stories to influence the behavior of others. This can encourage user involvement, engagement, and contribute towards business goals, including naturally shareable content and link building, building brand awareness, and adding faces (people) to services provided.

The top countries for contributing volunteering time are currently: Myanmar, USA, New Zealand, Canada, and Australia:

CAF - World Giving Index 2015 - Volunteer Time

Source: CAF World Giving Index 2015

On smaller scales, this is something I like to do every few months with the company I work for – an example below from a recent Dartmoor Challenge. This type of approach can provide employees with an added feeling of personal, or self-achievement, and is great for team building too.

Vertical Leap charity and volunteer work - Dartmoor Challenge

Tip 3: Making the Most From Seasonal Slows

Many industries have some degree of seasonality. The summertime is a regularly quoted slow period, but this can also become a time for innovation, service enhancement, and increased work/vacation productivity.

Companies can leverage seasonal slow times for chances to combine employee efficiency, and work/life balance improvements. When the need for staff numbers is lower, creativity with staff holiday use, wider remote working, and getting flexible with holiday working options, can be a real win-win.

Some tips for using a working vacation to overcome seasonal slumps include:

  • Take time out to re-approach your product/service delivery, refine, and innovate
  • Implement good ideas, and turn existing insight into actionable next steps
  • Experiment – with processes, reporting, and other business approaches (challenge the ‘status quo’)
  • Leverage the season for evergreen content creation, seasonal opportunities, and creative seasonal writing
  • Add new areas of potential positive impact into the marketing mix – develop new ways to turn around business slow times
  • Get to know your customers more – use remote travel plans to have face to face meetings with customers in disparate locations

Tip 4: Save Money by Combining Priorities

Regardless of how much time and money is set aside for work and for fun, there will be scope for combining both outcomes to save money. Part of this is tied to effective and early planning, another aspect of this is prioritizing what outcomes matter the most to you (are finances an issue?), and ensuring you are able to positively impact them from the outset.

If you can make the most out of each location; setting agendas, booking in multiple meetings, and identifying ‘go between’ vacation stops, you are likely to save money before you even leave for the airport.

Here are some extra tips for saving money on working holidays:

  • Expenses: Agree with your company the parameters for what qualifies as a work expense. Having clarity on areas like this helps to avoid disappointment and unexpected costs when you return to the office.
  • Maximize locations: Every meeting destination is an opportunity for exploration and fun. The more you can approach each business requirement as a chance to combine personal and business, the better.
  • Book in advance: From flights and traveling to package deals and more, every day counts when it comes to cost saving with advance booking.
  • Buy in bulk: Food is one of the most overlooked costs with business trips and working vacations. If you are situated in a single location and can plan supermarket trips when on the road, you will be able to save compared to constant eating out. Buying in bulk also covers items like refreshments, which individually are low impact, but can collectively make a large difference between and extra sightseeing or staying in the hotel.

Tip 5: Enjoy Every Moment

If your working holiday is 50% work and 50% pleasure, or any variation on your work demands, the end result doesn’t have to be 50% less fun.

Embrace the moment; look at every interaction, work commitment, and pre-booked event, as a moment to enjoy and be enhanced by the fact that you are on a form of vacation.

The biggest mistake people make on working breaks is forgetting to enjoy themselves, or at the other extreme, neglecting to get the most work value out of the trip. Striking the perfect balance will result in a productive, relaxing vacation.

How Did it Go?

I love to hear about other people’s experiences, so please let me know about your successful (or not so successful) working vacations and share what others can learn from your experiences.


Image Credits

Featured Image:
In-post Photos #1: CAF World Giving Index 2015. Used with permission.
In-post Photos #2: Vertical Leap – ‘Dartmoor Challenge’. Used with permission.

Category Careers
VIP CONTRIBUTOR Lee Wilson Service Operations Director at Vertical Leap

Lee Wilson is Service Operations Director at Vertical Leap, and has led digital marketing departments since the early 2000’s. He’s ...

How to Make Your Working Vacation a Success

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