Vacation Time: Six Tips Entrepreneurs Can Take For Stress-Free Travel

by / ⠀Personal Branding Startup Advice / August 20, 2012

According to a recent survey by Staples, Inc., 67 percent of small business owners are planning to take a traditional vacation this summer, and 89 percent are planning to leave town instead of taking a “stay-cation” at home.

For young entrepreneurs, vacation time is a much-deserved break. But letting go of the reins for a week of rest and relaxation is difficult if your mind is constantly focused on your business.

After all, you’re constantly focused on day-to-day business issues, branding and client services – let alone handling emergencies when they arise. And of course, stepping out of the office doesn’t mean those responsibilities go away. So separating work from leisure time is not such an easy task for any small business owner.

To help manage being away and alleviate some of the stress, Travelers recommends making a pre-vacation checklist to get prepared. The six tips below can help ready your staff to manage mishaps and keep the business booming while you’re on the beach.

1. Find replacement management, and pick the right person to manage the business.

Handing off the torch while you’re away can be difficult, so it’s important that the right person is in place. Clients and customers should not notice that you’re away on vacation, so identifying replacement management is an all-important task. This person should be trained and given a “test-run” as manager for a few weeks, or even months, prior to your vacation.

Choosing the right person could mean the difference between smooth business operations and potentially devastating effects on employee, client and consumer perceptions of the business. The solution: choose wisely.

2.  Train employees to manage while you’re away.

Employees are your most important resource, and establishing a succession plan is vital to keeping the business going while you’re away. In the short-term, it is important to communicate that a core group of reliable employees understand how to manage the business.  They’ll need to know the day-to-day operations and what to do if there’s a crisis.

In the long-term, it is important to develop strong hiring practices (making sure the right employees are hired from the get-go) and holistic management strategies. Adopting these practices sets the stage for a stronger workforce that is better able to lead while you’re out of the office. Simply put: business owners who focus on smart hiring processes have businesses that are better able to handle the unexpected. We call this “front door management.”

3. Make sure a business continuity plan is in place and that your employees know about it.

Not being prepared for a disaster can have serious implications for the business, yet many businesses do not have a plan in place. According to a recent Travelers questionnaire, only half of the businesses surveyed have a written business continuity plan or some other disaster recovery document that identifies and mitigates potential threats to a business, its employees and its customers. The right insurance protection coupled with a strategic business continuity plan provides the necessary resources needed for a prompt recovery.

The best way to have peace of mind is to have a business continuity plan ready and clearly communicated to your staff in case of an emergency. In advance of traveling, make sure employees understand the plan and their roles if an unexpected event occurs. Employees should know where they can access important information and whom they should contact, such as vendors or customers. And if you are one of those businesses operating without a business continuity plan, your independent insurance agent can help you get started.

4.  Make sure managers know who to turn to if something goes wrong.

Ensuring that managers understand the proper steps to take in the wake of an unanticipated event is vital to the safety and resiliency of your business. Managers should know where to find the insurance policy and who to contact for questions if something goes wrong. They should also have a basic understanding of the business’ insurance coverages, such as business interruption, extra expense coverage, etc. All of this information should also be included in a business continuity plan, which is yet another reason why it’s so important to have one.

5.  Create a list of to-do’s and inventory of recent and expected projects.

In the same way that business owners ask employees to report to them with updates on projects, you should report to your employees before leaving for vacation. If you expect business operations to run smoothly while you’re out of the office, Travelers recommends closing loopholes on projects, relaying recent client conversations and outlining expected and anticipated projects.

6.  Tap into your advisors, like independent insurance agents, for advice.

Small business owners should consult with industry experts, such as independent insurance agents, attorneys, accountants and other small business owners before setting travel plans. Each can offer invaluable advice on managing risks while you’re away from the office. For example, such advice could include insight on the best times of year to take time off, and tips on how to reinforce aspects of a business continuity plan.

Today’s technology allows you to check in (even if the goal was to check out and enjoy your vacation!).  Odds are you’ll stay connected to the business through your laptop or cell phone – important “safety nets” in case something unexpected happens.  In fact, according to the annual SMB Wellness Index study from Manta, 71 percent of small business owners say they access emails or documents from mobile devices while on vacation, and 60 percent say they enjoy their vacation more because of their mobile devices.

Understandably, trying to tie up loose ends and cover tasks at the office, before leaving for vacation can be stressful. However, with proper preparation, you’ll be on your way to a guilt-free getaway.

Judy Coblentz is Vice President and Chief Underwriting Officer for the small commercial division of Travelers. Travelers is a leading provider of auto, home and business insurance. For more information go to

About The Author


Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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