A real holiday as a business owner starts with deciding how available you’ll be, then preparing your business accordingly. If you can delegate essential tasks and set clear boundaries, you may be able to disconnect. If your role still requires your input, plan limited, scheduled work instead. Learning how to take a real holiday as a business owner is less about finding the perfect destination and more about making time away workable.
It’s understandable to worry that customers will need you or work will pile up while you’re away. But waiting until the business feels completely ready can keep you on call indefinitely. Time away can give you room to recharge and return with fresh focus. A clear plan also tells your team and customers what to expect.
This guide covers how to plan a holiday, prepare people and processes, set an out-of-office message, manage notifications and decide whether to disconnect or work remotely. You’ll find practical ways to make time away part of running your business, without feeling guilty about taking a break.
Key Takeaways
- Choose holiday dates early and make time away part of your business plan, rather than waiting for a quiet moment that may never come.
- Delegate essential tasks to a trusted person and give them clear instructions on what to handle and when to escalate an issue.
- Set customer expectations with an out-of-office message, then silence non-essential notifications to protect your time away.
- Decide whether to disconnect or work remotely based on what the business genuinely needs, and set firm boundaries if you stay connected.
- Use a break to recharge and return with renewed focus, while building processes that make future holidays easier to take.
Holidaying as the Owner of a Small Business - Can it be done?
Yes. Plan around essential work, clear responsibilities and a trusted person who can respond if something changes.
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Prepare the Business for Owner Leave
Build a continuity plan before booking time away. List essential daily tasks, key contacts, likely disruptions and who is responsible for each response. For example, a retailer might assign order enquiries to one employee and urgent supplier issues to another. Include guidance on which decisions can wait until you return.
Test the plan by taking a short break from routine decisions. Note where staff get stuck, then update the instructions before a longer holiday. Identify risks such as delayed orders, unanswered customer concerns or missed payments, and give the person covering a clear process for escalating issues.
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Train Staff to Handle Delegated Tasks
Show employees how to complete each task before you leave, then let them practise while you’re still available. Demonstrate the process, provide written steps and explain what needs your approval. Checklists for opening, customer follow-up or payment processing make expectations easier to follow.
Use a practice run to see whether the instructions work without your help. Ask the employee to complete the task independently, then review the result together. Clarify any confusing steps and record the access or information they need. Don’t delegate a responsibility without giving its owner the authority to act.
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Delegate Business Responsibilities
Assign each essential responsibility to a named staff member, trusted contact or person covering your work. Explain the expected result, what decisions they can make and when to escalate a problem. If you work alone, arrange for someone you trust to manage urgent enquiries or coordinate essential orders while you’re away.
Trust the person you choose to follow the agreed process instead of monitoring every action. Set one contact route for genuine emergencies and clarify what can wait. This helps prevent confusion and gives employees room to take ownership of routine decisions.
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Arrange Cover for Deadlines and Daily Tasks
Map tax, payroll and other compliance deadlines that fall during your holiday, then assign responsibility for each task. Deadlines and requirements depend on your business obligations and payroll arrangements. Record the relevant due dates in your calendar and arrange cover before leaving.
Temporary manager or virtual assistant costs depend on the work scope, hours, experience and length of cover; the price is determined for the case after a quote request. Include those costs in your leave plan. Give the caretaker clear instructions for payments, records and urgent queries, without sharing access they don’t need.
Setting an out-of-office reply and switching off notifications
Plan your customer communications and notification boundaries as soon as you choose holiday dates. Give the person covering time to practise, then tell customers when you’ll close, reopen and respond.
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Set Out-of-Office Expectations
Write an automatic reply with your closure and reopening dates, expected response time and an alternative contact for urgent matters. For example, direct order enquiries to your nominated employee and explain that other emails will receive a reply after you return. Keep the message consistent across email accounts so customers don’t get conflicting instructions.
Before activating the reply, send yourself a test email. Check the dates and contact details, and avoid promising an immediate response if you’ll be away from your inbox.
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Set Boundaries for Checking Business Updates
Decide whether you’ll check business updates at all or only during a planned window. If you need limited access, choose the inbox or system that matters and set a clear stopping point. For example, check one urgent-issues inbox at a set time instead of scrolling through all your email throughout the day.
Turn off non-essential work notifications on your phone and laptop. Keep only the alert you need for your agreed emergency channel. This can reduce interruptions and help protect time for the holiday itself.
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Set Closure and Reopening Dates
Put your final trading day and reopening date in your out-of-office reply, website notice and social media posts. If your shop will close, display the same dates at its entrance. Consistent information helps customers avoid arranging collections or expecting service while you’re unavailable.
Update scheduled emails and customer notices if your plans change. Set a reminder to remove the out-of-office message when you reopen, so new enquiries aren’t told you’re still away.
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Choose What Counts as Urgent
Agree with the person covering which situations warrant contacting you. A customer safety issue may need escalation, while a routine invoice question can wait. Put the distinction in writing and share the right contact method, so staff aren’t left guessing or sending every update to your personal phone.
Test the contact route before you leave. Ask the nominated person to send a practice message and confirm that you receive it.
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Prepare Your Accounts and Devices
Review the apps that could interrupt your break, including email, banking and credit card alerts. Keep notifications that help you spot a genuinely urgent financial issue, but silence routine activity updates. Make sure the person covering can use their own authorised access instead of relying on messages sent to your private device.
Before leaving, check your out-of-office reply from an external email address. This final test can catch missing contacts, incorrect dates or unclear instructions while there’s still time to fix them.
Benefits of taking holidays as a small business owner
A planned break can help you return with renewed energy, clearer focus and a fresh perspective on daily work. Use it as an opportunity to step back, notice what the business depends on and remember what your hard work is meant to support.
- Use time away to restore your attention. Before you leave, note decisions that feel difficult or repetitive, such as choosing which customer issue to tackle first. A change of pace can give you space from daily demands. When you return, review the list with fresh eyes and identify what truly needs your attention.
Make the break meaningful by choosing activities that don’t revolve around work. You might plan a coastal walk, a family meal or a day without business messages. A holiday isn’t another task to optimise; it’s time to reconnect with life beyond your inbox.
- Notice whether constant work is affecting your focus. Look out for personal warning signs, such as struggling to concentrate on a routine decision or finding it hard to stop thinking about work during dinner. These observations aren’t a diagnosis. They’re prompts to take your workload seriously and make room for recovery.
Use your first day back to review what changed while you were away. If a staff member handled customer follow-ups or daily decisions, ask what went smoothly and where they needed support. The conversation can show which responsibilities are ready to move off your desk.
- Give your team the opportunity to build confidence. When an employee takes responsibility for a customer enquiry or regular operational task, they practise judgement instead of simply following instructions. Agree on decision boundaries before you leave, then let them manage routine matters without seeking approval at every step.
After the break, thank the person who covered and discuss a useful lesson. They may have spotted a confusing handover or a process that could be documented. Recognising their contribution turns holiday cover into practical development, not just a temporary favour.
- Return with a deliberate reset instead of immediately filling every hour. Set aside time to catch up on messages, review urgent decisions and reconnect with employees. Then choose one change to carry forward, such as keeping a recurring task delegated or protecting a regular day from routine work.
A holiday can reveal how much the business relies on you for small decisions. Use that insight to improve processes, clarify responsibilities and make future absences easier to manage. The goal isn’t to remove yourself from the business entirely. It’s to build a business that leaves room for your own goals.
Choosing whether to disconnect or work remotely
Choose your approach before travelling: disconnect if trusted cover can manage essential work, or set firm limits if your input is still needed. The right choice depends on your situation, responsibilities and the boundaries you can maintain.
- Decide what genuinely needs your attention. List the decisions only you can make, then separate them from routine questions a trained employee can handle. If the remaining tasks can wait until you return, plan to disconnect and give the person covering a clear way to manage urgent issues.
If work must continue, define the specific tasks you’ll handle while away. For example, you might approve a time-sensitive payment while your team manages ordinary customer follow-ups. A short list helps stop remote work from quietly expanding into a full working day.
- If you’ll stay connected, set a daily work window in advance. Choose a start and finish time that fits your travel plans, and tell employees when you’ll be available. Keep the window for essential decisions instead of routine emails someone else can handle.
Protect the rest of your day by closing work apps outside that window. If a request arrives during a family activity or booked excursion, direct it to your nominated contact unless it meets your agreed criteria for an urgent issue. Clear boundaries help make the holiday feel different from a normal workweek.
- If remote work is part of your plan, choose a destination and accommodation with reliable phone coverage and internet. Check that you can access the tools needed for your agreed tasks, such as email or online banking. Don’t assume a travel connection will support a scheduled call or payment.
A portable modem or a mobile phone used as a hotspot can provide another way to connect. Treat these as practical options, not a reason to accept every request. Decide what work can be done offline, and save essential contact details before leaving.
- Account for time zones when travelling internationally. Schedule calls and online banking payments with the other party’s local time in mind. A meeting that seems convenient where you are may fall outside a customer’s or employee’s working day.
If you use your mobile overseas, turn off data roaming to avoid unexpected charges. Ask your mobile provider about unlocking your phone for international use and whether an international data plan is available. You could also consider an international SIM after arriving. These options can support planned communication without leaving your phone open to constant business updates.
How can a small business owner prepare their business before taking a holiday?
Planning how to take a real holiday as a business owner starts with practical decisions about timing, customer needs and essential work.
- Choose dates that fit your business cycle. Look for a quieter period, and avoid scheduling a major launch, stocktake or other significant change immediately before or during your absence. Mark the holiday in your diary early so other commitments don’t take its place.
Plan for work that may come in while you’re away. A retailer might fulfil orders early, pause new orders or arrange for someone trusted to handle them. Allow time after reopening for customer refunds, follow-up service and enquiries that built up during the closure.
- Tell customers when you’ll be away and how this affects service. Share closure dates through the channels they use, such as social media, direct calls or a poster in your shop. Keep the information consistent, and explain when service resumes or where urgent enquiries should go.
Prepare scheduled social media posts and emails before you leave. Check the dates and details, then make sure each message matches your reopening plan. If your business can pause during the break, divert the work phone to an answering machine that gives customers clear next steps.
- Write a practical emergency action plan for the people covering your work. List the tasks, who owns each one and which situations need escalation. For example, a service business can set out how staff should handle a cancelled booking, a safety concern or a customer complaint.
Prepare process notes for recurring tasks and explain what can wait until you return. Give the person covering their own logins and passwords, along with any required remote access, security codes or keys. Provide only the access they need for their responsibilities.
- Complete routine administration before leaving where you can. Review upcoming staff wages, bills, customer orders and payments, then finish tasks that can be handled in advance. Schedule payment reminders where appropriate, and note what the person covering must monitor.
Consider whether artificial intelligence could streamline a suitable process, such as drafting a response or organising routine information. Review its output before relying on it, and keep a person responsible for decisions affecting customers or business operations.
- Rehearse the arrangements before your holiday begins. Ask the person covering to follow the written process and handle a routine task without your input. Note unclear instructions, missing access or decisions that still depend on you, then revise the plan and practise again. This practical test helps turn plans for how to take a real holiday as a business owner into a workable routine.
For help turning leave planning into a workable business strategy, explore business strategy support.
Mark the holiday in your diary early, then prepare and delegate cover before you leave. Rehearse the arrangements so you can spot unclear instructions or missing access in advance.
The Bucket List Accountant: Business Coaching & Strategy
The Bucket List Accountant can help you connect your holiday plans with the way your business operates. If stepping away feels difficult because every decision, deadline or payment relies on you, Business Coaching & Strategy can help you consider your business structure, responsibilities and lifestyle goals together.
For help managing business finances around time away, Business Tax Advisory and Accounting or Small Business Accounting may be relevant. A clearer view of cash flow and upcoming obligations can help you plan leave with greater confidence and decide what needs attention before departure. The aim is a business that supports the life you’re working towards, not one that keeps every personal goal on hold.
If you’re ready to explore a more sustainable way to run your business, contact The Bucket List Accountant.
Make room for the life your business is meant to support
Your next holiday doesn’t have to wait until every task is finished. Choose the kind of break that fits your circumstances, then take one practical step towards it: reserve the dates, identify what needs cover or decide which work can wait. Each choice helps turn time away from a distant intention into part of how you run your business.
Learning how to take a real holiday as a business owner means shaping a business that can make space for your personal goals. If you’d like support thinking through that next step, explore your options with The Bucket List Accountant. You can build towards time away with clarity and confidence.
The information on this website is general in nature and is provided for information purposes only. It is not legal, financial or professional advice. You should obtain specific, independent advice relevant to your circumstances.
Frequently Asked Questions
What tasks should a business owner delegate before going on holiday?
Delegate repeatable tasks that keep customers and daily operations moving, such as confirming bookings, checking deliveries or responding to routine enquiries. Match each task to someone familiar with the work, then explain what completion looks like. For example, a Geelong café owner could ask a trained team member to confirm supplier deliveries and flag discrepancies, while leaving non-urgent decisions until they return.
How do I set up an out-of-office message and emergency contact while travelling?
Include your away dates, when you expect to respond, and a named contact method for urgent matters. For example: “I’m away until next Monday. For urgent booking changes, contact Sarah Jenkins at sarah@thebucketlistaccountant.com.au. I’ll respond to other emails after I return.” Get the contact’s permission first, and avoid sharing personal travel details or confidential information in an automatic reply.
How can Australian business owners manage customer service and urgent issues while away?
Give the person covering a simple way to sort enquiries by urgency and respond consistently. A Geelong service business might treat a booking change as routine but escalate a safety concern or an issue that could stop work. Prepare short response templates for common questions, and record who handles each channel. Review the plan with the person covering before you leave.
How can I disconnect from work and avoid checking messages on holiday?
Choose your approach before travelling, then reduce the temptation to check work. Log out of business email, remove work shortcuts from your phone’s home screen and ask a travel companion to help you stick to your boundary. If a concern comes to mind, note it for later instead of opening your inbox. Give yourself permission to be present.
Article by
David Patterson
With more than three decades of experience helping business owners grow profitable, sustainable businesses, he focuses on one simple idea: Your business should give you a life, not take one away.
David works with small business owners who are doing okay but feel stretched, time-poor, or stuck. He helps them regain control of their numbers, build stronger systems, and create the financial freedom to start ticking off the things that matter most, now... not "someday".
He is the creator of the Bucket List Business Program, host of The Bucket List Accountant Podcast, and a passionate believer that success isn’t measured by revenue alone, it’s measured by the life your business allows you to live.
Disclaimer
“The information on this website is general in nature and is provided for information purposes only. It is not legal, financial or professional advice. You should obtain specific, independent advice relevant to your circumstances.”