Sole Proprietors: How to Take a Real Vacation Without Losing Business

  •    A freelance reporter and writer based in Philadelphia, Pa., Dinah previously worked as a staff reporter for The Associated Press and Dow Jones Newswires.

Solopreneurs — freelancers, contractors and other sole proprietors — need vacations as much as anyone else, maybe more. So how can you get away without disappointing, or worse, losing, customers? Can you even afford a trip, and can you really disconnect from work once you're there?

We touched base with several sole proprietors to find out how they take a break while keeping their businesses intact. The answers are as varied as the entrepreneurs involved. Some ideas may not work for everyone, but perhaps you can borrow a few and take some much-needed time away from the office or shop.


While any trip takes some planning, solopreneurs may need to take extra steps to assure a worry-free vacation.

"I notified all my clients weeks ahead of time, and more than once, that I would essentially be off the grid for my vacation," says Beth Beutler, a virtual-assistant-business owner who recently took a getaway.

"I worked consistently to help them with their needs before I went. I worked ahead and used tools like Buffer to preschedule social media. I cleared out my recurring-task list so when I returned, I had a clean slate," she says. "Financially, a portion of my earnings each week are deferred into a (paid time off) fund for myself. I scheduled a paycheck out of those funds to be paid into my personal account the week of my vacation."

Gerald Aguilar, sole proprietor of Pest Control Pro in Jupiter, Florida, also shores up business in advance.

"I service all my customers before going on vacation. I call and text all my customers weeks before leaving to make sure no callbacks are needed," Aguilar says. "I upgrade my cellphone plan for overseas usage." He also halts advertising for a month before vacations.

"Most importantly, I don't stress it. Family and friends come first," he says.

Lisa Chu, who handles shipping, packing, customer service and marketing for her online children's clothing shop, Black N Bianco, didn't take a break her first few years but realized she needed to "rejuvenate my passion and energy for my business." She wrote a plan so she could get away without losing customers or sales. Chu didn't unplug completely but found a way to take a break.

"Going on vacation meant my customers would not receive any packages for those weeks I'm away, but I would still be able to communicate with them via my smartphone, tablet and laptop computer." Her website notified customers that no packages would be shipped for two weeks.

To avoid a sales hit, she offered customers incentives — free samples, extra discounts or coupon codes — to make purchases while she was away. "Advance preparation was vital to going on a stress-free vacation while not losing my customers," she says.

Impact-measurement consultant Brandi Olson has managed to take two maternity leaves and a vacation.

"The key for me has been in getting my behind-the-scene systems in place for project management, invoicing and workflows. That has allowed me to automate a lot of small tasks — thanks to Zapier and Buffer. This means that some parts of my business can keep on running even when I am personally off-line. As for actual client work, it all comes down to communicating and planning in advance," says Olson.

Olson stopped taking intensive client work about a month before she anticipated the start of her maternity leaves, conducting only minimal work from existing clients.

"I communicated clearly with my clients what they could expect from me while I was away, and I asked what kind of support they might need as well," she says. Olson relied on a colleague with whom she trades "on call" time-off duties, and her automated workflows kept her connected to new leads when she was out of reach.


Other solopreneurs also outsource work to family, friends, colleagues or support services during vacations.

All it takes for a sole proprietor to take vacation is fair notice to clients, a continuity plan and an emergency plan, says Lauren Milligan, a self-employed career advancement coach who has a dedicated assistant. Smaller businesses can outsource tasks to virtual assistants, she says.

"An emergency plan could simply mean that your (virtual assistant) has your cell phone number, or is able to reach out to another person in your network who would be able to deliver more personal help," she says. "When things are set up properly and clients are advised, the likelihood of emergencies is minimized."

Michael O'Meara, a Chicago solo criminal-and-DUI-defense lawyer, says he typically knows well in advance when he will be away so he can schedule hearings and trials for other times. He also depends on a call center, a live-chat web service and other attorneys, letting clients know in advance if another lawyer will be covering a court appearance.

"As a lawyer in a highly competitive market, I don't want to miss calls or queries from potential clients. At the same time, it is incredibly important to get some time away from my practice occasionally to recharge my batteries so that I can continue to deliver strong defense work for my clients," O'Meara says.

The call center can do intake and send him questions so he can follow up with the potential clients — remotely or when he returns to the office. "It's also very important to have a great network of fellow attorneys who practice in the same area. This helps while on vacation because I can call upon them to cover my court appearances while I am gone," O'Meara says.

Mix Work & Leisure - Or Don't

While some solo entrepreneurs aim to take real, business-free vacations, others say mixing leisure with work helps them get needed rest and relaxation. They tack on a few vacation days to a professional conference or take business with them via the Internet, setting aside time to get work done before playing with family or friends.

Others suggest scheduling vacations for your slower times of the year.

While disconnecting entirely "is a good thing to do periodically, vacations can actually be more relaxing if you are tapped in to your business and know everything is running smoothly. This is much preferred to not taking any time off at all, because you feel you cannot afford to be completely disconnected," says Dave Scarola, vice president of The Alternative Board, which provides peer advisory boards to business owners.

Sam Butler, a solo PR adviser and founder of 35th Avenue Partners, suggests solopreneurs rethink the meaning of vacation. "A week off to refresh is reasonable. If traveling, look for somewhere relatively close so you're not wasting rest time on the road. And don't forget weekends; when you're completely unplugged, they can be completely rejuvenating," he says.

Bryan Clayton, CEO of GreenPal, which he describes as an Uber for lawn care, favors short, plugged-in getaways.

"Look for every single means available to conduct your business from your mobile device," Clayton says. "This can include mobile apps for your accounting software, and letting your customers know you'll be gone so they can text message you. Google Docs and Google sheets apps are also great ways to have information at your fingertips should you need to access it."

Most sole proprietors can be gone for three or four days, he adds, "so long as they are willing to check in for five times a day and tend to any emergencies that may be blowing up at home."

Not everyone shares the working-vacation philosophy, however.

"Unless it's completely unavoidable — and it probably isn't — do not check your email while on vacation, especially if you're just going for a week," says solo PR man Henry Stimpson, suggesting you have someone else check it for you. Solopreneurs also might tell clients they won't be checking email, but provide your cell number in case of an "absolutely dire emergency," he adds.

"For most solopreneurs, it's probably best to take vacations no longer than about 10 to 11 days. It's probably better to take two one-week vacations a year than one two-week one, but of course it depends on your business," Stimpson says.

In addition to advance planning and hiring people to handle essential business in her absence, PR firm founder Ciara Pressler enjoys an exotic "workcation" strategy.

"I found an inexpensive condo in Mexico, AirBnB my place, and go for as many weeks as possible in the winter. I invite business friends to join and we make it a business retreat," says Pressler. Both clients and fellow entrepreneurs participate. "My clients love this — my quality of work is actually better because there are fewer distractions."