Practical tips for a successful workcation

It’s been a big few weeks of travel, with Kristen stuck in Sydney, Nat swanning around Singapore, and gale-force winds at home.

As a global career accelerator, we knew Powrsuit had to be remote-first by design. Theory and practice are two different things—in the early days (aka a year ago 😅), we were anything but. However, as our global membership base grew, we started evolving how we work to be flexible about what we’re doing and where we need to be. 

The past few weeks have been our first ‘proper’ test of what work looks like when you can’t look your colleagues in the eye. We’re sharing what we’ve learned for anyone else considering a sometimes-digital-nomad lifestyle. Because, while moving to Portugal may not be on your 2025 bingo card, the odd workcation may be more feasible (and beneficial) than you realise.

Caveats a-plenty here: We know this isn’t relevant to all – many Powrsuiters are in jobs where in-person is the only way. If that’s you, we hope there’s still something you can take away from this. 👩‍🔬👩‍🍳👷‍♀️👩‍⚖️👩‍🔧

As always, we start with an experiment

With the prospect of three public holidays in one 10-day period, Nat and her girlfriend Kyla decided to turn Powrsuit’s Singapore soft launch into a 3-week workcation. The ‘holiday extension’ tested whether it’s possible (and enjoyable) to combine the two, and eke out the warmth a little longer.

Singapore is expensive, so using it as a base for a typical work week wasn’t feasible. However, Vietnam is close by and incredibly affordable. Nice accommodation (aka a one-bedroom apartment) is circa $35 USD a night. Throw in $4 USD meals, and that means (airfares aside), it costs a little more than a typical week at home. 

While Nat chooses her own hours, Kyla works for a larger company. She’s usually in the office a few times a week, and while their team is geographically spread, remote work isn’t the norm. So, alongside all the other unpaid hours labours of love she contributes to Powrsuit, she’s agreed to share her perspective too.

Here are six lessons we learned:

1. Start from a strong foundation

If you are a strong performer with solid working relationships and self-leadership capabilities, you’re much more likely to get a green light on a workcation. If your employer knows you’re adept at managing your calendar, priorities (and yourself), they’ll be less inclined to care where you do it from. No, that isn’t always the case, but if they won’t budge, that may be a sign of a wider values or expectations misalignment. 

Take a few minutes to honestly reflect on your current state. Do you need regular guidance? Rely on in-person catch-ups? Struggle to focus without structure? All perfectly normal, but all will make it harder to succeed remotely, even in the short term. So, before you even consider a trip, put some self-reliance habits in place:

• Build your professional board of directors so that you can turn up as your best self at work.
• Bring a solution with every problem.
• Ask for regular feedback around key gaps and capabilities.
• Use performance reviews to proactively share your career goals and what you’re doing to get there – members, look out for our upcoming mini-masterclass on how to do just that.

2. Plan in advance

We’re not fans of Hush Tripping – sneaking off to an exotic location without informing the boss. Alongside chronic cancelling, it’s probably one of the fastest ways to break trust (and fuel the return-to-office movement). 

As Kyla says, “If it’s a change in how you usually operate, plan for it”. In the months leading up to the trip, she shared her intentions with all relevant stakeholders (aka everyone she regularly works with) and sought their feedback. She proactively – and with plenty of notice – made sure in-person only meetings were scheduled for the weeks before or after, and updated her working hours and location in her calendar and Slack status. 

Travel time is a great time for focused work. Without the usual distractions and with all the inspiration that comes with a fresh environment, you should be extra productive. Ensure you are by having (and sharing) a clear plan for the work you’ll do – Nat had several mini-projects, and a week with fewer meetings was exactly what she needed.

This level of preparation may feel like hard work, but it actually relieves others of extra work (and pain). If you want to go, it’s on you to make it a success.

3. Timing is everything 

Take advantage of ‘low periods’ – during school holidays, productivity bottoms out. The addition of 3 public holidays meant ten days of blissful break for very little annual leave. 

The week after school holidays is a catch-up week for many – one of the least disruptive times to transition your vacation into a workcation (and to protect time for deep work).

4. Build in discipline 

The call of cafes, cooking classes and walking tours can be loud. Structure shuts out the noise. 

• Have a short holiday or weekend first. You’re in a new place! It’s exciting, so make time to explore so you’re not tempted to cut work for pure play.
• If you’re going with others, make sure they’re working too. It’s quite depressing to be stuck on your laptop while everyone else is on holiday.
• Set and stick to office hours. Your usual approach to work is probably a strong start.
• It can help to wake up and get started straight away. A dip in the pool can easily turn into a day of sunshine and good books (or a challenging mental shift back to work mode).
  

5. Invest in an office

It might look cute, but in our experience, cafes quickly become distraction zones. Finding one, buying coffee, moving around, and poor wifi all become annoyances.

If you have lots of calls and need a quiet space, book a good place to stay or a co-working space with great wifi. We usually work from home, so slide easily into working from a temporary one. We booked one apartment for the whole week and stayed put.

6. Match your hours to your Timezone 

After a recent workcation in the UK, a Powrsuiter returned to New Zealand exhausted. The time zone made the work/holiday juggle almost impossible. Lesson learned. 

Find a destination with as much timezone crossover as you can, and adapt your hours to fit. At Powrsuit, we don’t have fixed hours, but we don’t usually start at 7am. The big takeaway from this trip? We should! 

Many working parents have experienced the benefits of a 7-3 day (or 6-2), but as temporarily remote workers, it was a revelation. Afternoons and evenings are a perfect time to explore a new city – it’s enough time to fit in a cooking class, walking tour, beach trip or river cruise (we know, we did!).

Again, this requires discipline. Little distractions during the day will either make your work take longer or less effective. So, focus is your friend. Our tip: pretend the outside world doesn’t exist until you sign off for the work day.

What are your workcation tips?

In the lead up to this trip (and during it!), Powrsuiters have been sharing what has and hasn’t worked for them. From too many moves and activities to struggling with motivation and distractions, workcations can quickly go awry. However, with a bit of planning, they can be a great way to find a fresh perspective and a different way of working, because work really is no longer a place, it’s an outcome.