Taking a holiday as a business owner: Is it really possible?

Vacation time and PTO survey 2017

Written By: BOSS Editorial

Published: March 21, 2025 | Updated: May 13, 2025

Reading Time: 2 minutes

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The dream of a hard-earned getaway often feels out of reach for many business owners. The constant responsibility, client demands and weight of decision-making can make it seem impossible to truly disconnect.

With a well-considered approach, though, stepping away for a break isn’t just feasible – it’s necessary. Imagine getting up from your desk and knowing that things will run smoothly in your absence.

It may not be a spontaneous last-minute deal, but a cheap holiday is within your reach if you take the right approach.

Planning to the last detail

When running your own business, an escape often feels like an overwhelming prospect. However, the key lies in thorough preparation.

Start by mapping out every project or task that will require attention while you’re away. What can be put on hold, and what must continue? Set realistic goals for what needs to be done before your holiday begins.

You should also create contingency plans in case of any hiccups. Getting this all together may take a while, but the peace of mind it provides while you’re away will be invaluable.

Delegating responsibilities and trusting your team

If you’ve spent time cultivating a capable team, now is the moment to let them shine. Delegate specific tasks and ensure each person understands what’s being asked of them.

You can empower them to make decisions, although you’ll need to ensure you provide clear guidelines to ensure consistency in your operations. This trust can boost morale, develop a sense of ownership and ultimately give you the space you need.

Setting boundaries for your break

Define what constitutes an emergency and what doesn’t, and communicate this well in advance. Implementing such rules doesn’t just protect your escape – it encourages your team to take responsibility and keep things running smoothly.

Consider setting up an automatic email response that states your absence and directs urgent matters to someone else. Let your clients know well ahead of time when you’ll be unreachable, and, if possible, arrange for them to contact someone else.

Using technology to stay connected

Although the goal is to disconnect, it’s unrealistic to cut yourself off completely. Aim to maintain a light touch by setting up automated systems for communication, invoicing or customer support to ensure opportunities aren’t missed.

Tools like Slack or project management apps can help you stay in the loop without requiring you to engage with every detail. Check in only when necessary and don’t allow yourself to get bogged down in every minor update.

Returning without feeling overwhelmed

Once your leave ends, the idea of returning to piles of emails and a backlog of tasks can feel daunting. Look to ease back in rather than plunging straight into everything.

Block out time on your first day back to catch up on the most important tasks. Use your team’s support to help you ease into your workload. It’s also worth reviewing where you could automate or delegate further to make future breaks even easier.