Keep Calm and Holiday On: How to Plan for the Holidays Year-Round

When you're prepared, you have a system readied in case things go wrong. The same rules apply to the holidays -- and even more so to business during the holidays.

learn more about David Osborn

By David Osborn

Stefanie Grewel | Getty Images

Opinions expressed by Entrepreneur contributors are their own.

I was that guy. The one who scrambled from store to store on Christmas Eve in a mad dash for small yet thoughtful treasures for each of my family members and friends. But a visit to my mentor's house one July changed that.

He and his wife live in this huge house on a lake. They were showing me around (as you'd expect on a first visit), and we came across a room that changed my thoughts on the holidays forever: the gift room.

After seeing what was in it, I came away impressed and in awe. Like many great entrepreneurs, they'd leveraged something -- in this case, the holidays -- with a system.

Preparing for the holiday rush year-round

Staying calm in business is about preparation. When you're prepared, you have a system readied in case things go wrong. It's a system that supports your work and your life. The same rules apply to the holidays -- and even more so to business during the holidays.

So why do I bring this up when the holidays are barely a twinkle in anyone's eye?

In a recent Healthline survey, 65 percent of Gen Xers reported feeling stressed during the holidays. Baby Boomers came in second at 62 percent, while 61 percent ofMmillennials said they felt the weight of the holiday rush. So, it's never too early to start planning. Leaving anything to chance just increases the likelihood of a stressful holiday season.

Related: By Failing to Prepare, You Are Indeed Preparing to Fail

How early you start preparing for the holidays is entirely up to you. I book my schedule as far in advance as I can. Everything goes on my calendar for the year -- all the holidays, big work events, trips and family gatherings.

I do the same in my business, making sure my staff is ready for anything that comes its way. I don't do this just to benefit the company; I do this to keep those working for us in good spirits all year. The following can help you do the same:

1. Build a culture of year-round planning.

My mentor's gift room was a lesson in the value of being proactive. All year long, he and his wife go ahead and buy this or that if it's perfect for someone on their list. My visit was in the middle of summer, yet their holiday shopping was nearly halfway done.

On top of that, they had birthday gifts for their kids, anniversary presents for their friends and housewarming tokens for that odd invite. Imagine the weight lifted off their shoulders come holiday or birthday time!

That said, in business, planning ahead only gets you so far. Actively check in with employees to make sure things are going as planned. Adjust schedules as necessary.

2. Don't wait until the last minute to find gifts for clients and co-workers.

It may sound simplistic, but we encourage our staff to get a gift box and try to fill it throughout the year. It relieves some of the pressure going into the holidays, so they can enjoy the season and not focus too much on those things that "need" to get done.

A recent survey found that 21 percent of consumers start buying holiday gifts by Halloween, with another 9 percent starting as early as Labor Day. And the practice of shopping early has moved into other retail seasons, such as back-to-school.

Related: How Strategic Planning Turns Chaos Into Confidence

3. Make personal time a priority.

Goals are great. They give you focus and provide a sense of direction and purpose. But maintaining that focus for too long gives your brain no time to repair and recover, leading to a loss in productivity, efficiency and morale.

While taking time off seems to be the answer, four out of 10 workers say that heavy workloads prevent them from using all available PTO. What's more, those who are able to take the time off are considered less dedicated by 17 percent of managers.

We encourage our employees to book four trips a year and ask them to do so a year in advance. Our company doesn't require such regimented schedules, but this level of planning gives staff something to look forward to each quarter.

It also gives them time to better plan their workflow, projects and other responsibilities so the ramp up to the holidays isn't so much of a bumpy ride -- it's more of a smooth ascent.

4. Befriend delegation.

Although delegation is a critical skill, it's often underutilized. In fact, 46 percent of companies have real concerns about staff's ability to delegate. Education can help, but only 28 percent of training programs touch on the topic.

At our firm, we cross-train our employees. Everyone knows enough about what others do to cover during vacations and holidays. This way, no gaps surface in the workflow at any time of the year.

We also ask team members to share their holiday requests with one another to avoid too many people being out of the office at the same time. Over this past summer, our office didn't miss a beat even though everyone took at least a week off.

It's not just about delegating work; it's about making certain that the right people do the right work at the right time. Build capabilities across your staff. Give them opportunities to learn and gain the skills to handle those added responsibilities.

Related: The Secret to Increased Productivity: Taking Time Off

Planning that far in advance may sound like a boring year. Where's the room for spontaneity? Where's the room for fun? But as a father of two who has a large company of thousands, all I can say is that it's all still there -- just planned a bit in advance.

David Osborn

Founder at David Osborn

David Osborn is an Austin, Texas-based entrepreneur, public speaker and author. He is a principal owner of Keller Williams, a real estate company in the U.S. that grossed more than $5.2 billion in sales in 2015. 

Related Topics

Editor's Pick

Have More Responsibilities at Work, But No Pay Bump? Use This Script to Get the Raise You Deserve.
Black and Asian Founders Face Opposition at All Levels — Here's Why That Has to Change
Business News

'This Made Me Physically Recoil From My Phone': Lingerie Brand Apologizes For 'Creepy' Ad Referencing Ryan Reynolds and Bras

Online lingerie retailer Harper Wilde is under fire for a bizarre sponsored post it has since pulled from Instagram.

Thought Leaders

5 Small Daily Habits Self-Made Millionaires Use to Grow Their Wealth

We've all seen what self-made millionaires look like on TV, but it's a lot more subtle than that. Brian Tracy researched what small daily habits these successful entrepreneurs adopted on their journey from rags to riches.

Business News

Viral Sensation 'Popcorn Guy' Has Earned a Gig at the 2023 Oscars

Jason Grosboll first went viral on TikTok for his theatrical method of buttering popcorn in a Texas movie theater.

Business News

The Scam Artist Who Robbed Backstreet Boys and NSYNC Blind. 'Some of the Guys Couldn't Pay Their Car Payment.'

In the 1990s, Lou Pearlman made millions creating the Backstreet Boys and NSYNC. It was all a giant Ponzi scheme.