How founders can take a holiday (and how your Virtual Assistant can help)

For many founders, the idea of taking a real holiday can feel impossible. With clients to serve, a team to manage, and a business that depends on you, stepping away, even for a few days, can feel daunting. In fact, only around half of business owners take a proper holiday each year.

But the reality is, regular breaks shouldn’t be a luxury, they’re essential. Time off gives you the headspace to reflect, recharge, and return with fresh ideas and renewed energy. With the right preparation (and the right support), you can take a summer break or prioritise family time during the school holidays without your business losing momentum.

Be proactive and transparent

First, own the fact that you deserve a break. The old narrative of the “always-on” founder doesn’t serve your wellbeing or your business long-term.

Let your clients, suppliers, and team know well in advance that you’ll be taking time off. Share the exact dates, set expectations around availability, and introduce them to the person who will be their point of contact while you’re away, whether that’s a team member or your Virtual Assistant. Clear communication means you’ll avoid last-minute panics and keep everyone on the same page.

Plan like a CEO, not a firefighter

Look back at this period in previous years. Were there spikes in client activity? Recurring tasks that crop up? Anticipating demand and planning accordingly is key.

Create a simple scenario plan with your team: ‘If X happens, then Y’. Map out who handles what in your absence so that everyone is empowered to make decisions. This not only gives you peace of mind (and means less phone calls on your break!) but also strengthens your team’s confidence and autonomy.

Automate where you can

Automation is your secret weapon, not just for holidays, but for smoother operations year-round.

Set up:

• Auto-responders on email and social media
• Scheduled content for your blog, newsletter, or social channels
• Automated invoicing and payment reminders
• Tools like Zapier or Make (formerly Integromat) to streamline routine admin

Your Virtual Assistant can play a key role here, helping you audit your processes and implement automation tools tailored to your business. 

Set clear boundaries (and stick to them)

If you don’t set boundaries, your holiday can quickly turn into ‘working remotely’ rather than taking a real break. Define your rules:

• Will you check in once a day? Once a week? Not at all?
• What qualifies as a true emergency worth interrupting your holiday?
• Who is empowered to make decisions in your absence?

Make sure your team, and you! stick to these rules. Your time away should be protected, not eroded by constant notifications.

Plan around seasonal peaks

If you’re juggling business with family life, especially during the school holidays, planning your time off becomes even more important. Many founders feel the pressure rise during the summer holidays or Christmas period when both client demands and family commitments peak. Ask your VA to look at your business calendar and pinpoint quieter windows, even if they don’t align perfectly with school breaks. Proactively managing your schedule this way not only reduces stress but will make sure you’re not fighting fires while trying to enjoy family time.

By planning ahead, you can also prepare your clients for your absence and smooth out any seasonal spikes in workload by bringing in extra Virtual Assistant support, to help during these busier months. Remember, founder burnout often builds during these pressure points so building in real downtime is essential.

Model time off for your team

As a founder, the way you handle your own time off sets the tone for your entire business. If you never disconnect, your team will feel they can’t either. Taking a proper, well-planned holiday doesn’t just benefit you, it shows your team that switching off is valued and encouraged. By openly communicating your plans, setting clear boundaries, and trusting your team, you create a healthier work culture where you’ll be getting the best of everyone.

How your Virtual Assistant can support you

This is where a VA can be your holiday hero. Your Virtual Assistant can:

• Manage inboxes and triage urgent messages
• Handle client queries or direct them to the right team member
• Monitor operations and flag genuine emergencies
• Keep your content and marketing running in the background
• Researching and booking kids’ clubs and camps so you have some time to yourself, for work or for rest!

If you have a team, a VA can also take on admin and coordination tasks, freeing up your team members to step up in other areas. That way, the load is shared and your business keeps moving, without overburdening anyone.

Outsourcing during peak holiday seasons isn’t just a safety net; it’s a smart way to ensure your business stays visible and responsive, even when you’re offline.

Ready to take a real break this summer?

Need help finding the right VA to support your summer plans? Get in touch and we’ll help match you with expert support tailored to your business.