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Keeping the Wheels Turning: How Small Businesses Can Manage During Time Off & Holidays
- Beverley White
- Apr 28
- 7 min read
As a small business owner, I'm very much aware of how difficult it can be to find that work/life balance. I'm sure you feel the same.
As hard as it is, running a small business or working as a sole trader also comes with plenty of perks; flexibility, independence and the satisfaction of building something from the ground up, but when it comes to taking time off, the freedom that comes with being your own boss can quickly feel like a double-edged sword.
How Small Businesses Can Manage During Holidays or Time Off
Unlike large corporations with dedicated teams to keep things running smoothly, small business owners often face the daunting task of maintaining operations even when they’re not physically present.
Just how can small businesses successfully manage their business during holidays like Christmas, Easter, summer holidays, etc? I'm glad you asked!
The good news is that with a bit of strategic planning and the right tools, you can keep your business ticking over while you enjoy some well-deserved rest.
In this guide, I'll explore some practical techniques, services and software, many of which I use (or have used), that can help you manage your business while you’re out of the office, without returning to a mountain of work (or unhappy customers) that instantly makes you forget your holiday ever happened!
1. Plan Ahead and Set Expectations
Personally, I think the key to taking time off as a small business owner or sole trader is planning. Start by identifying the tasks that need to be handled while you’re away and create a clear plan for how they’ll be managed.
Here’s how I do it:
Communicate with Clients and Customers
Let your clients know in advance that you’ll be taking time off. Set clear expectations about response times and availability. For example, you can send an email or update your website with a notice like, “Our office will be closed from [date] to [date]. We’ll respond to all inquiries upon our return.”
Create a To-Do List
Write down all the tasks that need to be completed before you leave. This could include invoicing, fulfilling orders or preparing content for social media. Prioritise tasks based on urgency and importance.
Set Boundaries
Decide how much (if at all) you’ll check in on your business while you’re away. Setting boundaries will help you truly disconnect and recharge.
2. Set Up Smart Automation
Automation is one of the most powerful ways to keep your business running smoothly when you’re not actively involved.
With the right tools, you can automate many of your daily tasks, from customer communications to invoicing and social media updates.
When it comes to automation, I would also recommend IFTTT (If This Then That) which allows you to automate across multiple platforms (once they've been connected) and even lets you trigger one task when others occur, hence the name!
Email Automation
If your website platform can't do it, then you can use email automation platforms like Mailchimp, Kit (formerly ConvertKit), or ActiveCampaign to schedule newsletters and customer communications in advance.
Also, remember to set up automatic out-of-office responses with helpful information, such as alternative contact details or expected response times.
Social Media Scheduling
Tools like Buffer, Hootsuite and Later allow you to schedule social media posts in advance.
Create a content calendar and prepare posts that will keep your audience engaged even when you’re away.
Set up automatic replies on platforms like Facebook and Instagram to let customers know you’re away but will respond soon.
Appointment Scheduling
If you can't do it via your website (which you really should develop), services like Calendly and Acuity Scheduling let customers book appointments or consultations based on your availability, without any manual input from you.
Sync scheduling tools with your calendar to avoid double bookings and give customers clarity on when you’re available.
3. Leverage Virtual Assistants and Freelancers
When automation alone isn’t enough, outsourcing certain tasks to a virtual assistant or freelancer within the gig economy can help you maintain business continuity without working overtime.
Hire a Virtual Assistant (VA)
Use Freelancers for Specialised Tasks
If you can't do it in advance and you need to update your website or write some blog content while you’re on holiday, then you can hire a freelancer to keep the momentum going. Be aware that there may be security concerns about giving someone access to your website so I'd only do this if you don't have someone you trust or as a last resort
Services like PeoplePerHour and Toptal connect you with skilled professionals in various fields.
Customer Service Outsourcing
4. Keep Finances in Check with Accounting Software
Managing cash flow and finances while you’re away is crucial for keeping your business healthy.
The right accounting tools can help you stay on top of payments and expenses, even if you’re halfway around the world.
Cloud-Based Accounting Platforms
Tools like QuickBooks, Xero, and FreeAgent (which is free if you're an RBS Customer) allow you to track expenses, send invoices and monitor cash flow from your phone or laptop.
Set up automatic payment reminders so clients receive invoices and prompts without manual effort.
Automate Expense Tracking
5. Manage Communication with Unified Messaging Platforms
Staying connected with clients and your team (if you have one) is essential, but you don’t want to spend your holiday glued to your phone.
Unified communication platforms can help you keep things streamlined and efficient.
Use a Central Communication Hub
Platforms like Slack, Microsoft Teams, and Twist allow you to manage internal communications from one place.
Set up ‘Do Not Disturb’ hours to protect your holiday time while ensuring key messages still get through.
Set Up an Answering Service
Services like Moneypenny and AnswerConnect offer virtual receptionists who can handle calls and messages on your behalf.
Provide them with clear guidelines on how to handle customer inquiries or emergencies.
Automated Messaging
Use platforms like WhatsApp Business or Facebook Messenger to set up automated replies.
Inform customers when they can expect a response and provide alternative contact options if needed.
6. Protect Your Business with Data and Security Measures
As I touched upon earlier, security issues still need to be managed but can be particularly stressful when you’re away from the office.
The right security tools can protect your business from cyber threats, data loss and unauthorised access.
Use a Password Manager
Tools like LastPass and 1Password allow you to securely store and share login details. Apple's iPhones and iPads have their own password manager built-in that works in much the same way as these apps.
Ensure you set up suitable permissions for team members or virtual assistants while maintaining overall security.
Backup Data Automatically
Monitor Security with Alerts
Tools like Norton and McAfee provide real-time alerts for security breaches.
If you handle sensitive customer information, consider investing in data encryption software as an extra layer of security.
7. Set Clear Boundaries (and Actually Stick to Them!)
One of the biggest challenges for small business owners and sole traders is resisting the temptation to work while on holiday.
Easier said than done I know but setting clear boundaries ensures that you genuinely switch off while still providing customers with the service they expect.
Set Up a Pre-Holiday Checklist
Create a checklist of tasks that need to be completed before you leave.
Inform key clients and suppliers of your planned absence well in advance.
Communicate Clearly
Set expectations with clients about response times and availability while you're away.
If necessary, provide an emergency contact option for urgent issues.
Use ‘Do Not Disturb’ Modes
Most smartphones and laptops have a ‘Do Not Disturb’ mode, if yours does... use it!
If you need to check in, set specific times each day rather than responding to every notification as it comes in.
8. Keep the Momentum Going with Post-Holiday Follow-Ups
The work doesn’t stop when you return, but a smooth re-entry can help you hit the ground running.
Schedule a Catch-Up Day
Block out the first day back for catching up on emails and messages and remember to cancel any Out-of-Office alerts / automations you've set up.
Avoid scheduling client calls or meetings on your first day back.
Automate Post-Holiday Updates
Set up a follow-up email campaign or social media post to reconnect with your audience after your break.
Share insights or personal stories from your time off to add a human touch.
Conclusion
"The plans of the diligent lead to profit as surely as haste leads to poverty." - Proverbs 21:5
Taking time off as a small business owner or sole trader isn’t just possible, it’s essential for your mental and physical health.
With the right combination of automation, outsourcing and smart communication strategies, you can keep your business running smoothly while you recharge. In other words, work smarter, not harder.
If you take nothing else away from this blog, remember that a well-rested business owner is a better business owner. So set those boundaries, trust your systems and enjoy your break; your business will be waiting for you when you get back. #BelieveInSuccess
Thank you for reading my blog and it's given you some ideas. If you've been putting off going away worrying about your business will cope, I hope you've found something here that will reduce your worry and get you on holiday! I'd love to know your thoughts.
What tools do you use when you're away? Do you have any favourites that I haven't included that help and our community should know about? Are you happy to go away and just leave your business in the hands of others; whether they're freelancers or Virtual Assistants? Let me know in the comments below.
If you've found something of value in this blog and would like to show your appreciation, please consider clicking the button below to buy me a virtual coffee. I promise I'll get it in a takeaway cup ;-)
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