Forget ChatGPT... Have you tried a Workcation???
Get permission because we are headed for the ultimate bleisure trip

Forget ChatGPT... Have you tried a Workcation???

Welcome to 2023... The future has arrived! According to the headlines (Bill Gates) the robots are coming for our white collar jobs ??!

Don't panic just yet. There is a way you can enjoy your life to the max while simultaneously keeping on top of your work priorities to beat that bot. It's called the Workcation. This month in Mobility Matters I'll be discussing this trend what you need to think about before you give it a go.

What in the world is a Workcation?!?!

The workcation is making a conscious decision to optimise your work location for a very short period of time in a place that you would want to take a vacation.

I first saw an advertisement in 2022 that suggested you fly to Fiji and work by the pool all day and drink cocktails all night. Sounds pretty good but is the reality that simple. When I work all day I am tired. The novelty of resort life sounds glamorous but is the average person going to want a night of vegging out in front of the tv instead of raging at the bar before the alarm goes off the next day to work again.

in my opinion, the most outrageous workcation location would have to be a cruise ship. On the surface it sounds amazing. Daily cleaning of your room, never cooking, all the amenities at your fingertips. The cruise lines promise that the internet will work the whole time but I am sceptical.

Why would you sign up for such a thing?

Having an experience of taking a laptop on a holiday in the past, I know how you can feel overwhelmed when you blur the boundaries of work and leisure. So why would you want to experiment with this trend.

  • You have no more annual leave and you want to get away
  • You have a major project or work deadline that cannot be delayed and you want to get away anyway
  • You want to explore the limits of how far you can take flexibility

A few tips before you head off

To have the most successful workcation you need to plan ahead. The tips are not dissimilar from what I provided in my #WorkfromAnywhere article in 2022. Here are a few more to add to the list:

  • This is NOT the answer for burnout. If you need a break just take one. In fact, being away from all of the creature comforts of your office (home or in the CBD) can be more stressful!
  • Communication is key. If you will remain in the same time zones it's easy to stay connected to your colleagues, clients and the core of your work. Even two hours can wreak havoc on your diary as you realise that you have meetings booked for 7am or pm which can eliminate the time for fun.
  • Check the treaty. Changing your location for a couple of weeks within your current tax jurisdiction isn't going to be a problem but if you decide to travel further afield then you need to check if there will be tax issues. Some countries don't even allow one day of work without creating an individual income or social security tax liability!

Is it really that easy?

With everything in life there are inevitably risks and rules that you need to consider before you proceed.

Perhaps a worked example is the best way to illustrate:

Sam decides that they can continue their project work asynchronously from the team for awhile. Sam is Australian and books a flight to New Zealand for 9 days. They are keen to make the most of their time so 5 workdays and 2 weekends.. Woohoo!

Issue 1: Immigration - On arrival in Queenstown with their family they need to complete the arrival card.

No alt text provided for this image
Most countries will have an arrival card where you need to state why you are coming to visit.

Sam is fairly comfortable that the main reason for boarding that plane was to have a good time so they tick holiday/vacation. If there is any doubt to the main reason for your trip then you need to consider if a work via is required. Going to detention because you are in the country illegally would ruin the fun.

Issue 2: Comfort is Critical - Sam and the family arrive to their Airbnb to find spectacular views but there is no work desk ?? and it's a bit smaller than the pictures might have implied. They hot desk in the office so a crammed atmosphere shared with others isn't insurmountable. They have headphones. During Covid lockdowns many people worked from kitchen benchtops so that's not the end of the world either. it's just 5 days right.

But the last straw is discovering that the stellar view comes along with a working construction site next door... Sam has a few important calls to make throughout the week so this is far from ideal.

No alt text provided for this image
Queenstown is beautiful from many angles... just don't look down

Issue 3: We live in a VUCA world which doesn't care about your plan

Sam is quite senior in their organisation and is a point of escalation and decision making at times. On day 2 they are called into a strategy session for a new opportunity. It's great for business and everything moves fast. By day 4 they need to sign a contract with the new client. Wait... could that be creating tax implications for the company eg a Permanent Establishment in New Zealand?

Issue 4: No one wants to go to the hospital - Insurance

Queenstown is the adventure capital of New Zealand. Sam intends on working hard during the day and playing even harder at night and on the weekend. The fine print is so important and this becomes very apparent while they are riding in the ambulance to have a broken arm mended after a zip lining adventure takes an unexpected turn. Good thing they purchased travel insurance but what if it was something more severe and unpredictable like an earthquake or a volcano eruption?

These four issues are just the easiest ones to share with you. So many other things could go wrong while you are away from home.

Or everything could go to plan. I hope it does when you venture out there ??.


If reading this makes you wonder what your employees are doing you might want to have a chat. We can discuss what policies you have in place and what might be required to keep your company and team capable to continue their work while remaining compliant as they workcation.

You can message me here on Linked In or book a time in my calendar.


American by birth, Australian by choice.?Ursula Lepporoli?has lived experience. She brings compassion and understanding to the tax and policy expertise she provides to expatriates and employers. Sharing knowledge with the wider mobility community brings her joy.

With more than 17 years of Global Mobility experience she brings a strategic and practical perspective to every interaction. She prides herself on making tax fun but takes the responsibility of cutting through complexity seriously.?Follow her, and?subscribe?to the Mobility Matters newsletter?here.

**The views expressed above are mine alone and are not tax advice. **

Nick Cooke

Tax Director | High-Net-Worth Individuals | Employment Taxes | Fringe Benefit Tax | Holidays Act Remediation | Expatriates | Cross-border Workers | Remote Workers | Employee Share Schemes

2 年

Insightful articile Ursula Dyer Lepporoli as always! I've always liked the idea of workcations but tend to end up forgetting the vacation part. I don't feel it's a break (and in fact can be more stressful) unless I disconnect completely, giving ?? of my attention to family and friends, as they deserve. Kudos to those who can balance both however!

Justin Kabbani ????

AI Coach & Consultant | Helping CEOs, Execs & Marketers Scale with ChatGPT & Copilot | Keynote Speaker

2 年

???? The benefits for creativity are massive! A change of scenery, culture and environment and an opportunity to see the world from a different perspective is almost always a buffet for the brain! I'm sure Ivy Xu would have some hot tips to add!

Julious Dyer

Instructional Designer & Voice Talent

2 年

Bleisure trip? I’ll take a nice Cozumel trip and enjoy the sights while catching meetings. ??

Nadia Beedeison

Reward & Benefits | Workplace Culture | Employee Experience | Recognition

2 年

Kitty Hibble a timely one perhaps, given our conversation last week

Stuart Norbury

Assisting organisations identify Finance, Risk, Compliance, Legal, and Governance Professionals. Brand Partner for AI CV Sifter from KTB Technologies

2 年

I had an extended "workcation" in 2022 where I was away for about 2 months - despite time zone differences, I adjusted my day and made myself available for Zoom/Teams call when needed (usually up to 11pm local time) and allowed for for those hours during the day. Also recently returned from an Australian workcation, or perhaps rather "work from anywhere", where my itinerary was such that I could work during the main business hours and take advantage of the 1hr time difference to go and watch my son compete in a national tournament. You make a good point about a workcation not being a break, and I think employers are beginning to recognise that an employee that is allowed balance between work and life is a productive and loyal asset.

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