12 tips for taking time off from your business

Taking time off as a small business owner is a challenge. Whether you’re going on holiday for the summer or enjoying a weekend break during the festive season, stepping away from your business can lead to guilt and stress. When a business’s success depends on its owner, you need to learn how to take annual leave strategically. 

While small business owners often manage paid time off (PTO) policies for their employees, they aren’t the only ones who need a break. Time off is necessary for your physical and mental health, and you can enjoy a well-deserved break in several ways. By planning your time off, you can get the rest you need while pushing your staff to grow. 

Jump down to a particular tip or read them all to ensure your next leave is stress-free. 

1. Start planning your time off early

The earlier you can start planning, the better. You need time to get organised before you disconnect. Putting yourself in a time crunch ahead of your break can lead to a stressful leave. You can plan your time off based on the number of employees you’ve hired: 

• If you’re the sole employee: give your customers advanced notice about your upcoming absence, consider taking on additional work beforehand to help offset, and wrap up pending work ahead of your departure.
• If you have employees: let them know you’ll be taking time off from work early so they can get familiar with the processes, your coverage plan and tasks that’ll be new to them.

A good rule of thumb is to prepare for your absence in advance, knowing that more time off should equate to greater advance notice.

2. Decide how long to take off

There’s no one-size-fits-all approach to planning your time off. Coverage and planning will vary greatly depending on your industry, timing, business structure and other factors. Generally speaking, typical spans for extended and small leave periods include:

• Public holidays: taking 1–2 days off 
• Long weekends: taking 3–5 days off
• Annual leave: taking 4–5 weeks off
• Sabbaticals: taking months or even years off

Use short leave periods as a test

The best way to see how your team runs your business without you is to take a short leave first to test out logistics – from there you can make necessary adjustments and be better prepared for an extended (and well-deserved) break.  If your business runs into problems, note what they are and what caused them. That way, you can put systems, lines of communication and backup measures in place for next time.

3. Set clear expectations for employees 

When communicating with staff members about your leave, give them the necessary details about your plans:

• How long will you be gone?
• Will you check in occasionally or stay unplugged?
• Is there a protocol in place for emergencies?
• Who’s their best point of contact in your absence?

Getting on the same page about these parts of your trip will ease your concerns and anxiety.

Delegate your work

Many small business owners take a hands-on approach to help their employees offer the best possible service. However, you need a trustworthy employee to handle your day-to-day tasks when you're out of town. In fact, you might need to delegate your work to more than one employee. 

When delegating, you should always:

• Assign tasks based on a partner or employee’s strengths
• Provide clear instructions
• Offer resources and training on new tasks
• Practice with your replacement and give feedback

So long as you follow these tips, your replacements should perform at their best.

Choose a second-in-command

A trustworthy second-in-command should handle your most important tasks. Instead of only delegating work, choosing a second in command means delegating authority. Not only will your second-in-command work on your behalf, but they will also help you relax during your leave. 

A good second-in-command is trustworthy and experienced. Long-term business partners and employees with seniority make the best candidates.

4. Consider closing up shop

Did your chest get tight just reading those four words? Temporarily shutting down seems counterintuitive, but it's a realistic option for a worry-free leave. You don't need to obsess about your business running smoothly if it's not running at all. Additionally, you save on operational costs while shutting down. 

If you do plan to close up for a brief period, communicate that early and often:

• Let your current clients know that you'll be out and for how long. 
• Post signage if you run a bricks-and-mortar shop. 
• Publish reminders on your social media accounts
• Include a reminder in your email signature.

These frequent nudges ensure that you don’t take anyone by surprise and leave customers in a lurch. They have time to plan around your time away. 

5. Avoid operational slowdown

On the other hand, not all businesses can face the risks that come with shutting down. If you plan to keep your business open, owners can't risk service slowing down or worsening in their absence. To ensure every customer gets the best quality service, make sure to:

• Handle tasks your team can’t before you leave
• Schedule trustworthy employees while you’re away
• Leave your employees with instructions and resources
• Monitor employees’ productivity and check in if you see issues
• Leave emergency contact information in case they need your help

6. Carefully consider the timing of your leave

Seriously thinking about the best time to step away from your business will save you a lot of unnecessary stress. Of course, it's unlikely you'd plan your Caribbean cruise for the busiest time of year. All the same, you should make sure your leave doesn't coincide with other important dates for your staff or clientele.

Major public holidays are trickier. You know your business better than we do, but it's always worth asking, "is it necessary to stay open today?".

If you’re considering closing, remember to review entitlements like public holiday pay to ensure your staff are compensated fairly.

Plan leave during slow periods

Each industry faces slow periods. Construction winds down in the winter, and retailers often see a summer slowdown. While these periods cut into your bottom line, they simplify time-off planning. By leaving your team during a slow period, there's a higher chance they can handle operations without you. 

Check your ERP (enterprise resource planning) or CRM (customer relationship management) tools to see when you get the most business. Alternatively, check month-by-month income statements to see when you bring in the fewest customers. Take time off if it costs more to keep the lights on than you will make in the day. You'll save yourself stress and money in the long run.

Learn more closing your office for the holidays.

7. Prepare for potential issues

When owners leave their business for a trip, it’s better to be proactive than reactive. Even if there’s only a slim chance something could go wrong, you should prepare your business and staff to handle it. Whether you can prevent the issue in advance or train your staff to respond, you want to put out all potential fires. 

If you want to rely on your team, lean into your employee’s specialties:

• Managers and department heads can handle administrative and executive issues. 
• General staff members can handle delays and shortages while explaining any issues to customers.

8. Notify important clients

Before taking time off work, give your most important clients advance notice. This way, you can work out potential issues or project details before they become a problem. Additionally, considering a customer’s needs before starting your leave shows how much their business matters to you. 

If you can’t work out their needs in advance, introduce them to a temporary point of contact. Your employees, including a second in command, should understand how they can assist your most important clients before you leave. Customer relationship management will help ensure your most important clients stay satisfied in your absence.

9. Check in with your employees 

When taking time off, you should plan far in advance so you don't have to communicate while you're out. While taking a complete break from work guarantees the most rest, you may need to check in occasionally.  For example, over 58% of self-employed individuals between the ages of 18–54 state that they do some work while on leave.

You don't want to go overboard and work through your whole break, but a few minutes here and there won't hurt. Again, the important thing is to ensure that the people with you are aware of your plans to stay connected so they don't feel ignored or deceived.

Set up a check-in schedule

If you're going to contact employees during time off, let them know when to expect you. Whether you want daily reports or meetings at the beginning of each week, preparation will keep your check-in on time and productive. For the best results, agree on a check-in schedule before your trip starts. 

Note: while short check-ins can’t hurt, don’t forget to disconnect and set boundaries. If possible, limit communication with your team to short calls and quick email exchanges.

10. See if your trip qualifies for a travel expense write-off

If you conduct business during your time off, you can earn a travel expense tax deduction for some or all of your trip. For example, when you take a few days to focus on business-related activities—such as meeting a client or attending a conference—you can write off certain expenses. Business trips offer write-offs for:

• Travel and fuel
• Meals 
• Lodging
• Event registration
• Equipment rentals

Some owners schedule a few days of leave between business activities. With the right schedule and selection of activities, you can write off most of your travel and lodging fees. 

11. Take advantage of work automation

Business process automation uses software to automate and streamline business tasks. Depending on your vertical, there are many ways to incorporate automation. Some of the most popular include: 

• Automating payroll
• Collecting customer payments
• Setting up automatic reporting and analytics
• Implementing auto-responses on email and social media
• Automating workflows
• Managing recurring invoices
• Sending an out-of-office message or reminder

All-in one business software offers integrations and out-of-the-box options for automating your core processes like data reporting, customer support and sales.

12. Maintain healthy boundaries and take the time you deserve

After deciding how much you want to disconnect from work, stick to the boundaries you set up. For example, if you schedule check-ins and daily email reviews, only engage with work at these times. Likewise, avoid spending all your time thinking about work so you'll get the rest you need. 

While some business owners think their businesses will crumble without them, that’s rarely the case. Taking time off as a small business owner requires thought and prior planning. However, you deserve hard-earned time off – plus, your mind and your body need it. The stress of overworking can take its toll in the form of insomnia, depression and reduced cognitive function. Setting up effective holiday mental health strategies can help business owners manage stress and support overall well-being, making it easier to disconnect when taking a break.

So, take a few deep breaths, put some of these tips into action and then enjoy some time away from your business. It’ll be there waiting for you when you return, and healthy work/life boundaries ensure you’ll come back ready to work. 

While you’re away, time-tracking software will help you track employee productivity to streamline time management and boost efficiency.