by Peter Cosgrove, MD of Futurewise Ltd.
Workcations (where employees work remotely from holiday destinations without using annual leave) can be a divisive concept. While they can be a useful talent attraction tool, they also raise genuine concerns for employers, particularly around potential misuse. When someone says they enjoy a workcation because they can “be on holiday and work at the same time,” that’s exactly the kind of comment that makes employers nervous. After all, no manager wants their team dialling into meetings with one eye on their holiday and one on work.
From a financial perspective, the appeal is clear: spending a month in a lower-cost country might save money. But in practice, you’re often still paying rent at home while also covering accommodation abroad, so the cost savings may not be as real as they appear.
Having a flexible policy like this can enhance your reputation as a progressive employer. That said, there’s a noticeable shift back toward in-office mandates. HSBC recently announced employees need to be in the office three days a week to qualify for bonuses. Amazon is reportedly pushing for five days a week on-site. While some may see these companies as old-school, there’s a broader move to bring people back together physically.
I would also have both employers and employees consider the following:
Tax Implications Companies that aren’t well-versed in international tax laws risk significant issues if employees spend too long working in another jurisdiction. It’s difficult to monitor where remote staff are actually working from, and a permanent establishment could be created accidentally — exposing the company to unexpected tax obligations.
Data Protection Risks If you’re based in the EU and start working from outside the EU — especially in countries with incompatible or stricter data protection laws (e.g., UAE) — you could unknowingly breach regulations. Most organisations aren’t equipped to manage cross-border data risks on an individual employee level.
Blurred Boundaries and Burnout Holidays and work should be distinct. Workcations blur that line, and rather than offering relaxation, they can lead to overwork and burnout. Always being “half-on” is not a recipe for rest. The concept of work from anywhere is now becoming work from everywhere.
Family-Friendly Flexibility On the plus side, workcations can work really well for dual-working parents who struggle with differing holiday entitlements. Being able to work remotely for a few days before officially starting means you can be at your destination on the first day of your holiday.
Like most things, the challenge isn’t the policy itself — it’s how it’s applied in practice. Personally, I believe that blending work and holiday time risks making breaks more stressful rather than restorative. But if managed well, workcations can be a genuine and great perk. After all, starting your day overlooking a beautiful landscape or ocean might just spark fresh creativity and leave you feeling more energised for work.
About the author
Peter Cosgrove leads Futurewise and is an expert on future trends and a much sought-after speaker on talks related to the future of work. He has over 25 years business experience on executive teams as well as on not for profit boards as board member and Chairman. He has been Chair of Junior Achievement Ireland, the National Recruitment Federation and currently serves on the 30% Club Steering Committee tackling gender balance and is Vice Chairman of Aware, a leading mental health charity. Peter has served as a Board adviser for a number of Staffing organisations and has been a contributor to the Expert Group on Future Skills.
