Vacations for small business owners
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Vacations for Small Business Owners: How to Plan and Execute the Perfect Break

Small business owners often have “vacation anxiety.” They fear that if they leave, everything will fall apart. Or they think that if they go away, they’ll be spending most of their vacation time on the phone. This means that vacations for small business owners don’t happen nearly as often as they should.

I painfully relate to these tendencies and tend to put time for rest and relaxation on the back burner. But the truth is that small business owners should treat vacation time as a necessity, not a luxury.  With some preparation and training, vacations for small business owners can be a reality.

I Get It: You Care About Your Business

The fact that you hesitate to leave your business for a week or two shows that you care.  You want your business to run smoothly and you don’t want to leave your employees holding the bag if there’s a problem while you’re gone.

A survey conducted by OnDeck shows how rare vacations for small business owners are.  In this survey, only 9% of 200 small business owners planned to take a two-week vacation that year.  Only 57% were taking time off for vacation at all.  Most vacations for small business owners are taken only after the company has been around for more than ten years.  That’s a long time to put off taking a break.

Consider Temporarily Closing

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Some vacations for small business owners are possible because the business closes down for a week or two.  This is most common with small businesses that have very few employees such as a boutique, bakery, or small restaurant.   Although you are giving up revenue for those weeks, it can be a good option if you:

  • Take the same week or weeks each year. Consistency will help your customers expect that you are closed every year during that time.
  • Let your clients/customers know far in advance. You can tell your clients in person, with signage, and with social media that you will be closed during that time to avoid surprises.
  • Close during a time when business is slow anyway. If your tax preparation business is slow over the summer, or your ice cream store is usually empty the first week of February, take advantage of those slow weeks to get away.

Use a “Stand-In”

If you have a good business relationship with the owner or operator of another firm in your area, consider working out a deal with them.  You can “pinch-hit” by taking charge of each other’s businesses while you are away.

  • Even business owners who work out this arrangement ask their stand-in to help only when there is something that needs attention immediately and can’t wait.
  • You will still let your clients know that you will be away. Inform them of your arrangement so they know that someone is available if you can’t be reached on vacation.
  • Offer a fee to your “stand-in” if necessary.

Maybe you work in an industry where you can’t have someone pinch-hit for you, and that’s okay. It just means that it may take a little more planning to make your vacation happen.

In the law firm context, I can’t just have another lawyer from another firm sit in my desk for the day. One of the early reasons I wanted to work with other attorneys and have them join my firm was to share some of these small business burdens. The solution for you may also be business growth before you can get away.

Prepare Your Clients

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Keeping the business running by leaving employees in charge is another way vacations for small business owners can be successful.   When you prepare your clients and employees before you leave, you will help your business run smoothly without you.  Then you can enjoy your much-needed trip away.

Inform your clients that you’ll be on vacation

Tell personal clients about your plans.  You may even want to buffer your departing time and your return time by a day or two.  Tell your clients you are leaving the day before your leave and returning the day after you return.  This will give you time to tighten up loose ends before you leave, and time to catch up when you get back.

Don’t plan changes or events right before you leave

Rolling out a new computer system?  Planning a big sales promotion?  Don’t do it right before you leave.  If you start something new and then leave town, you’re asking for trouble.

Be smart about timing

Leave at a typically slow time.  For instance, if you have a tax business, a spring break trip the first week of April is not a good idea.

If you don’t have a clear-cut slow season, look at your books.  Find your slowest week or weeks over the last year (or more), and plan your vacation around that time.

Enjoy the prep time

Vacations for small business owners can drive the owner and the customer to be more productive.  Some business owners say that the weeks before they leave town are extra-productive, since clients are trying to tie up loose ends before the owner leaves.

You can also use your upcoming vacation as an opportunity to make calls, check on your customers, and perhaps drum up some more business.

Prepare Your Employees

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Getting your team onboard can make the difference between a stressful time away and a restful break.

Find a trusted employee to be in charge

Most vacations for small business owners are possible only because the owner has an employee they can trust to lead in the owner’s absence. It can be scary for most small business owners to turn operations over to an employee, but in the long run it’s a wise decision to have a second-in-command.

When you train a trusted employee for your vacation, you will benefit later as well.  In the future you can leave them in charge if you have a family or medical emergency, or even if you want time to explore new opportunities for your business.

It’s a good idea to do a “practice delegation” before you leave. Take a day or a weekend off to see how your employee in charge handles the business on their own.

Prepare other employees too

Even your employee in charge won’t be there every minute you’re gone. Give the other employees the information they will need to handle any issues that come up.  Here are some things you might plan for:

  1. How to reset the internet connection.
  2. Who to call when the computers are down.
  3. How to get in touch with building maintenance in case of a leak, plumbing, or other property issues.
  4. The best way to contact the building’s cleaning service.
  5. Any other suppliers or service contact information that may be needed.
  6. Let your employees know what kinds of problems or issues need your immediate attention.

Some things that come up are not time-sensitive.  In these cases, ask your employees to write out a summary of what happened or what needs to be addressed and leave it on your desk for when you return.

If you are clear with your employees about what constitutes an emergency, you won’t have your workers calling, emailing, and texting you with every issue that comes up.

Take care of all bills before you leave

Even if you trust your employee in charge or the fellow professional that is pinch-hitting for you, you may not want to give them access to your financial information.  Make sure all bills are paid before you leave.  You can schedule automatic payments, or pay them early if necessary.

Set Limits for Yourself

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Vacations for small business owners can only happen when employees and clients understand that the owner is on holiday.  Make sure your employees know that you will not be reachable throughout the day.

  • Check in, then check out. Don’t get sucked in to spending your whole vacation with your face in a smart phone.  Tell your employees that you will check in once or twice a day, then stick to it.
  • Commit to checking in at a time when you know you’ll be hanging around the hotel room, or in a place with few distractions. Many owners check in for half an hour early in the morning, and then half an hour in the evening after dinner.
  • Avoid the temptation to check in more often, even if there is an issue to deal with. If you prep your team for the times you plan to check in, they won’t expect an immediate response.
  • Don’t forward client calls to your cell phone. Unless you want your vacation companions to be very unhappy with you, let someone else answer your calls.  Some business owners use an answering service like Grasshopper and then check their messages once a day.
  • Handle contracts when you get back. Avoid signing or negotiating important documents or contracts while on vacation if you can help it.  You are more likely to miss something or make a mistake on a contract if you are away from your business resources and routine.
  • Setup your autoresponder. When I leave on vacation, I make sure anyone who sends me an email knows I’m away. I sometimes include an extra day of auto-response emails just so I have time to get back and into the swing of things after I return.
  • Stay off social media. It’s a good idea to keep away from your business’s social media site.  Reading comments, messages, and news on social media is just another way to get sucked into working while on vacation.If you like to post on your business page on a regular basis, set up posts in advance.  You can coordinate this either with your employees, or social media programs such as Buffer.

Show Appreciation When You Return

Owners will tell you that vacations for small business owners would not be possible without the one or two employees that they can trust.  When you get back, show your appreciation by:

  • Meeting with them to go over the business decisions, activities, and challenges that came up in your absence.
  • Keeping them in the loop instead of immediately taking back control and shutting them out.
  • Verbally expressing your appreciation (it means much more than you may think)
  • Giving a gift – a bonus, gift card, or item – to show your appreciation.

 Take Care of Yourself

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Vacations for small business owners are as important as vacations for anyone who works hard.  When you are a rested business owner, you are a better boss.

  • Rested business owners make better, more creative decisions. Your body and brain need a break.  Getting away from the daily grind can help you think more clearly.  It can also give you perspective on what your business is doing and why.  You may even visit other shops and meet people during your time away that give you new ideas and inspiration.
  • When you trust your employees and give them responsibility, it boosts morale. We all like to think that the workplace will fall down without us.  But in a healthy workplace, the team can pick up the slack when the boss is gone.
  • Taking a vacation sets a good example. If you want your employees to achieve a good work-life balance, show them by your example.  A boss that never takes vacation only shows their employees how little they value their personal time and their friends and family.  Take care of yourself and your loved ones as a model to your employees.
  • Vacation is part of your salary. You may not be able to give your employees a raise every few months, but when you take a vacation, you can model that time off is part of an employee’s salary, and one of the reasons they like working with you.

Conclusion

You care deeply about your business, but you can’t pour from an empty cup.  Take care of yourself and take some time off.  You can be there to manage your business every other week of the year.

Vacations for small business owners are healthy for the bosses, for their employees, and for their business.

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    JACOB TINGEN

    LAWYER & ONLINE ENTREPRENEUR

    After graduating from law school and passing the bar, I struggled to find work, pay my bills, and make ends meet. That's when I decided to take control of my future and start working for myself. Now, several years and a handful of companies later, I'm sharing how I launched a successful business, and how you can do it too.

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