Can a Sole Proprietor Take a Vacation?

Date: August 26, 2013

Sole proprietor on vacationHiring someone to fill in is just one option for business owners operating solo.

For a sole proprietor, the worries can be endless. Getting away from them can prove even harder.

Small business owners who have partners can take a vacation here or there, handing over responsibilities for a week or so at a time. For the sole proprietor, life is not so simple, and real vacations—not having to answer calls from the beach or having to work on a laptop early in the morning or late at night—can be years in the making. Here's how a few small business owners make time off happen.

Hire Competent Project Managers

Alistair Herriot, who owns HammerSmith Construction, founded his business in 1999, and for his first six or seven years was the company's only employee. He vacationed so seldom that when he got married, he initially thought to himself that he wouldn't be able to take a honeymoon—an idea that he never uttered to his fiancee. (Spoiler alert: He did end up going on a honeymoon.)

Early after founding his business, Herriot was able to manage time off around projects that lasted just a few weeks. However, now his projects last much longer—three or four months at a time—but he has two employees, both project managers, who enable him to take time away from the job.

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Get Creative with Scheduling

Herriot still has demanding customers who want to see him on a daily basis. So he offered this piece of advice for a sole proprietor when going on vacation: Know your customers. "Customers play a big role," he says. "Some customers can be very, very needy. Some can be understanding and easy-going."

Choosing the scheduling of projects for needy customers, and also the size of jobs for those customers, around vacation can help. "Maybe not having too much going on while you’re away," Herriot suggests. "Otherwise, you won't be able to relax. If there's potential for things not being done 100 percent correctly, the risk is greater. You might even be better off to have less done and then hit the ground running when you get back. You might not lose too much time doing it that way."

Public relations professional Jill Lerner, owner of Jill Lerner Communications, gave her clients one month's notice before she went away. After getting back, she said she found an unanticipated benefit of going away. "You really want to square everything up before you go, so you're extremely productive in weeks before vacations," she says. "It spurs you to be that much more productive. Consequently, you enjoy it more."

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Recruit Pinch Hitters

For those without project managers like Herriot had, finding someone who might be willing to be in charge of your business temporarily while you are away could be another option.

That's what Lerner did when she took her first true vacation since founding her company five years ago. She went to Hawaii for 10 days.

In the event that a crisis situation arose with one of her clients, she had other independent PR professionals whom she trusts lined up to work. She said she had set aside money to pay them if necessary and worked out some guidelines with them as to how she would do that.

"The truth is, I was checking my email probably once a day," Lerner says. "[My clients] all have my cell phone number if anything absolutely needed my attention; I'd be available to them. I also made sure I have my network of colleagues in place, a great network of colleagues I have referred and received business from. If there was something I couldn't handle because I was away, I had people in place."

Lerner returned from Hawaii very much refreshed, a concept that is key for any business owner—no matter how large their company is.

READ NEXT: How Owners of Small Businesses with Multiple Employees Get Away


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