How to Take Time Off This Holiday Season as a Business Owner

Plane flying overhead

Being a business owner is rewarding. You love the work you do and “getting away” may feel counterintuitive to your passion for work. However, taking time off is a great opportunity for you to shake up your process. Challenge the way you view time off as a way to unlock new perspectives while recharging your battery. The interruption to your routine will force you to think and act differently. 

Feeling confident about taking time off will not come overnight. If you simply decide one evening you’re taking a two-week vacation at the end of December and announce it to your team the next day, you’re in store for poor reactions. As the fall season settles in, getting away may be the last thing on your mind—but if you’d like to take time off this holiday season, the countdown to prep for your vacation has begun. 

Consider These Factors

The size of your company will make an impact on your ability to completely unplug from business operations during your time off. In either case, ensure your customers know you’ll be offline and provide the contact information (of yourself or someone from your team) so they feel confident they have somewhere to turn should they need to. 

One-Person Operation

With a one-person operation, you might explore outsourcing tasks to: 

  • A temporary virtual assistant to help respond to emails.
  • A web designer to monitor your site for issues.
  • A social media manager to be active on your marketing accounts.
  • Accounting software to handle your financial operations. 

If information must go out and you don’t feel comfortable delegating it, take advantage of things like Google’s email scheduler or other third-party applications available to handle this.

Robust Team Operations

In a robust team with well-defined roles, it will be simpler to divvy up responsibilities while you’re away. While working with your team you’ve likely inferred many of their strengths and weaknesses, and you can use this knowledge to determine who should take over certain tasks. If you are having trouble assigning a particular duty, ask! You may be surprised by who volunteers and the hidden talents of your team.

If you have a business partner or management team built around you, discuss vacation plans as a group to ensure you have ample coverage for both your customers and your lower level team. Find ways to empower them prior to your vacation to ensure they feel confident in themselves to make decisions and move forward without your immediate input. Give them the directions and resources they will need to make decisions and then get out of their way. Notice where they excel and where they struggle while you’re present and available to coach them.

Your ultimate guide to SMB accounting

Let’s get those books in order.

Create an Out-of-Office Plan

In preparation for time off, spend one week tracking your activities on your calendar—double check that it’s an accurate representation of what you did or accomplished. At the conclusion of this week you’ll have a comprehensive list of what you need to outsource, schedule, or delegate. Keep in mind, experience is the most effective teacher available to your team and you should plan to delegate the majority of these tasks.

Whether you choose to outsource or delegate, a quick instruction sheet for how you typically complete these tasks will be helpful for the person taking over. In the long run, this will also prevent them from contacting you while you’re on vacation with how-to questions. Without getting too into the weeds, create these instructions and leave room for them to improve the process. They may create efficiencies that you’ll be able to adopt in the future. 

Have the team keep note of any holes or issues they spotted in your out-of-office plan. Work to get honest feedback about the time you took off, what worked or didn’t, and information regarding anyone who took initiative during your time away. A retrospective on your vacation is a great opportunity to determine if you need to work additional promotions or hires into your budget for next year.

The Worst-Case Scenario

Worried about your worst-case scenario? Think of that, too! Brainstorm with your team what they would be most worried about handling themselves in your absence. Use this as a blueprint to lay out what would constitute a true crisis in which they would need to contact you. They may define a “crisis” differently than you, and the more you can discuss what true crisis scenarios would look like, the more confident you’ll all feel in their ability to handle it. This way, you can rest easy knowing you’ll get an email or phone call only if they truly need your input. 

As part of your out-of-office plan, create a communication strategy that includes times you will commit to checking your email—if at all! This way, any smaller escalations can be emailed to you and the team will know when to anticipate your responses.

Learning to Live Offline

Most importantly, your time off should be an opportunity for you to relax. Don’t cause yourself extra stress by checking in too frequently— or by not checking in at all. If you’re experiencing a nagging feeling that something is wrong, go ahead and check your email for any fires. Coast is clear? Take a deep breath and find comfort that you’ve adequately prepped your team and business to function without you. Then, get back to your vacation.

Ready to learn more about how to put your accounting on autopilot with ScaleFactor ahead of your time off? Request a demo today.

Reader Interactions

Put your accounting on autopilot

Schedule a free consultation today.

Scalefactor dashboard desktop graphic