Stress-free holidays as an entrepreneur? We’ve got you covered.

Do you always return from holiday to an overflowing inbox? Do you find it difficult to properly switch off because you’re worried about missing something important? We often see entrepreneurs relying even more on their VAs during holiday periods. That way, you can actually enjoy your time off.

In this article, we share five tips to help you go on holiday stress-free with the support of a VA.

Door Lisette Immink
Op 1 May 2026
Blog
Stress-free holidays as an entrepreneur? We’ve got you covered.

1. Map out and delegate tasks before your holiday

Before you go away, create a clear overview of all ongoing tasks. Set priorities and decide which tasks can be delegated. Our Virtual Assistants can support you with this. They manage your inbox, schedule appointments and take care of administrative tasks, ensuring important work and communication continue without you needing to stay constantly involved.

We also plan ahead together. Is your VA going to be away for more than a week, for example due to holiday leave? Moneypenny arranges replacement support so work can continue uninterrupted. Thanks to clear processes and a proper handover, another VA can temporarily take over tasks without compromising quality or continuity.

2. Availability vs accessibility during your holiday

You can choose to set up an out-of-office reply explaining that your VA is monitoring your inbox and handling or escalating urgent matters. Or you can fully disconnect and simply let your VA reply to your emails directly, of course using their own “assistant to” signature. That way, everything keeps moving while you stay offline.

Beforehand, we make clear agreements about how we work, what takes priority and what matters most to you. Our Project Delivery role also plays an important part here: from the very start of the collaboration, we ensure clear processes, proper documentation and a structured setup.

This not only makes it easier to hand over work before your holiday, but also to temporarily scale or switch support when needed. Read more here: Project Delivery: the key to a strong start and smooth collaboration.

3. Finally clear those lingering tasks

And imagine how nice it would be if your VA could finally tackle all those loose ends you never get around to.

Think about updating old blog posts on your website, cleaning up your overflowing inbox or finally setting up that Calendly link that’s been sitting on your to-do list for months.

Your VA can also review administrative processes, update employee handbooks or take on other tasks that usually get lost in the day-to-day rush. That way, you come back from holiday to a fresh inbox and a clearer head.

4. Planning and communication

Create a solid plan for the days before and after your holiday. Make sure ongoing projects are fully up to date and communicate clearly with your team and VA about the current status.

You can also ask your VA to schedule a few catch-up meetings for your return, helping you quickly get back up to speed with everything that happened while you were away.

5. Let go of work and enjoy your holiday

Agree on fixed moments when you’ll be reachable for urgent matters and when you’ll briefly check in online. Or decide within what timeframe you’ll respond if something important comes up.

Inform your team and your VA about your availability. This gives you the peace of mind to properly enjoy your holiday without work-related stress.

Ready to enjoy a stress-free holiday?

Get in touch with us to learn more about our subscriptions or our services. Schedule an introductory call and we’ll show you how our VAs can improve your work-life balance.

We specialise in supporting busy entrepreneurs and managers. Our Virtual Assistants are ready to support you, so you can genuinely enjoy your holiday without stress. Curious which other tasks a VA can take off your hands? Read our article What does a Virtual Assistant do? and discover how they can support you long after your holiday ends.

Curious what Moneypenny can do for you?

Get to know us online and ask all your questions. Or read more about our VA services.

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