How to Plan an Entrepreneurial Vacation

10 Factors to Consider


Do bosses take vacation? Depending on what company you work for, this answer may vary. Some CEOs have no problem leaving early and coming in late. Others work around the clock to ensure everything is running smoothly. Of course, bosses should take vacation. Everyone should. However, planning for an entrepreneurial vacation is key.

Why Some Bosses Don’t Vacation

As businesses across the country gear up for a long Labor Day weekend, many business owners may be struggling to leave the office. Why? Some fear processes will fall apart, opportunities will be missed, and nothing will get done correctly. Some call these bosses micromanagers.

The fact is, it’s not only important for the success of a company for bosses to take time off, but it’s crucial for maintaining mental health. There’s a way to help ensure the ship doesn’t sink while the captain is away. It all starts with proper planning.

Planning for an Entrepreneurial Vacation

Whether you’re a solo business or manage a team, you still deserve time off. The key is to properly assess and plan for any time away. Here are some tips on how:

  1. Timing. Of course, you don’t want to take time off during the busiest time of year. Pick a period when you expect a lull.
  2. Communicate. Make it known to your team, clients, and customers when you plan on being out of office. Give them plenty of advance notice and clearly state if or how you’ll be reachable. Most importantly, stick to the boundaries you set.
  3. Categorize tasks. What are your daily and weekly responsibilities? Is there a way to work ahead, automate, outsource, or delegate these tasks?
  4. Automate. Some of the more administrative tasks like responding to emails, scheduling, and invoicing can be automated through software.
  5. Delegate. Make sure the point person understands their role and has the necessary training and resources to carry it out.
  6. Plan Bs. Outline emergency protocols and clearly define the steps to address it. Expect the unexpected, but set realistic expectations.
  7. Emergency contacts. Share a list of contact information for all key players in the company and how each can help with certain issues before reaching out to you.
  8. Trust. Empower your team to manage the business while you’re away. If you’re a team of one, trust that you deserve a break and you’ll only come back stronger and ready to pick up where you left off.
  9. Recognition. Once you’re back, acknowledge the efforts made during your absence. Not only does this reinforce the importance of those around you, but it helps boost morale.
  10. Reflection. Debrief for yourself and your team on what worked and what didn’t. This will help adjust the plan for future vacations.

Like anything in business, taking a vacation requires proper planning to help ensure continuous, efficient workflow. It may seem easy to skip the planning and never take time off, but this only breeds burnout. Take a little time and trust to prepare yourself and the team for a well-deserved break without compromising the business. In fact, notice how it makes you a more effective leader.