The Holiday Survival Guide For Small Business Owners And Freelancers

How to balance work and life over the holidays without going crazy or losing out to a competitor.

The Holiday Survival Guide For Small Business Owners And Freelancers
[Photo: Flickr user Wilson Hui]

Shutting off during the holidays can be much harder when you’re a small business owner or freelancer. Not only is your work wherever you are; there’s the fear that if you do try to scale back on work over the holidays, your clients could possibly go elsewhere. And, many established companies have set holidays that enforce some downtime, freelancers included.


There’s also the worry that because not everyone celebrates the holidays, competitors who don’t observe them could usurp some of your business during the festive season.

On the flip side, we know how important it is to take a break and recharge. So how should a small business owner or freelancer manage the annual struggle between work and personal life during the holidays? We asked a few in various industries to give us their best holiday survival tips.

Be Extra Organized

Most freelancers and small business owners will tell you it’s nearly impossible to run your own business if you have bad organizational skills. But we all know that the holiday period can be less than organized with impromptu shopping outings, dinners with friends, and events with family. That’s why Tash Khan, director of Blossoming Gifts, a boutique flower and gift firm, says during the holidays freelancers need to be vigilantly organized–more so than normal.

Khan says being organized includes not only setting up meetings and calls with clients, but also scheduling their time limits to stay on track and ensure there are enough working hours to get things done. “Being organized allows you to be more efficient and enables you to find the time to take out of your schedule to be with family and friends,” says Khan. Plan in some padding on either end of appointments to allow for unexpected overruns, so you can still make that gathering with friends.

Build Downtime Into Your Schedule

Not only should you schedule every single work-related call, meeting, and deadline into your meticulous holiday calendar, you should also schedule downtime in too, says Khan.

“It is important to find time to wind down or be around family,” says Khan. “By setting this time aside you essentially give yourself a deadline for when certain things need to be done to ensure that you can have that uninterrupted downtime and not worry about incomplete tasks.”


Khan also notes that this scheduled downtime can have productivity benefits as well. “We all know that stress can get to us at times and stepping away from the task at hand is essentially what we may need,” he says. “Taking a few minutes or even hours is sometimes necessary, and can often help you to generate fresh ideas and discover new ways of thinking.”

Use A Virtual Assistant

No, not Siri. We’re talking human virtual assistants. They can be relatively inexpensive to hire if you use a virtual assistant agency like Get Ahead, says the company’s marketing director and former freelancer Caroline Saunders.

“Our founder and director, Rebecca Newenham, always takes time off over the holidays to spend with her three children. That was the reason she set up the business in the first place–so she could work flexibly around her daughters,” says Saunders.

Virtual assistant services mean that you can have a real person competently monitoring and responding to your work emails and phone calls over a set period of days or even just during certain hours each day. The assistant will reply based on your instructions and only interrupt your family time during your off hours if there is an urgent message from a client that demands immediate action.

Clearly Communicate Your Availability To Clients

It’s important to remember the clients you are dealing with are just like you and probably want to be able to enjoy downtime over the holidays as well. Most of the time they’ll be happy just knowing what days and hours they can reach you should the need arise. So clearly communicate your holiday availability to clients well in advance, says Saj Devshi, owner of educational startup Loopa.

For Devshi this means first sending an email newsletter to his most engaged customers. Next, Devshi posts a note on his company website FAQ listing his holiday availability. Finally, Devshi posts his contact information for any urgent issues and lets his customers know that these messages are only checked once every 48 hours. This gives his customers peace of mind knowing when they’ll get a reply.


“People like to know where they stand with their queries, even if that’s an automated response,” says Devshi. “The thing that’s guaranteed to lose you a [potential] customer is if they get no response,” he adds, “because if you can’t answer their problems when they haven’t bought from you, how can they have faith that you will be there to help them when they have?”

Work When You Are Normally Most Productive

While it might be tempting to try to sneak work in when time allows between family outings and holiday shopping, such a scattered approach will probably mean you aren’t getting your best work done. It’s best to set aside time for work each day when you are normally at your most productive–whether that’s early morning, afternoon, or evening, says Galia Orme, founder of CHOC Chick, a raw chocolate company.

“I’m very much a morning person and am up naturally at 6 a.m., so I start on emails first thing and identify my priorities for the day,” says Orme. “During the holidays and days off I still use my early mornings to identify any important issues that need to be dealt with. When you run your own business, you never seem to stop, so I allocate my time in the morning to focus on any urgent work and [as a result] have the rest of my day completely free to dedicate myself to my family and holiday time.”

Though working during your most productive time might occasionally clash with a holiday event, putting in a few focused hours of work during your most productive time means you’re likely to accomplish a lot more and not have to interrupt family time later.

When You Have Family Time, Absolutely Maximize Its Value

Approach downtime with as much determination as you do your work time, says Tim Cameron-Kitchen, founder of SEO and digital marketing firm Exposure Ninja.

“Just as you are ‘all in’ when running your business, be ‘all in’ during your downtime,” says Cameron-Kitchen. That is more than just turning the phone off and putting the laptop away. “I usually find that planned activities outside the house create a much stronger bond ‘per hour’ than just sitting around watching TV together,” he says. “If your family is used to enduring your crazy work schedule, this is a chance to reward them by being fully present and creating memories that will last.”


“Plus,” he adds, “by being fully present, there’s a chance that they’ll have had enough of you quite quickly and will let you return to work!”

It’s a win-win for everyone.