How to Plan Ahead for a Stress-Free and Successful Holiday Season
The holiday season has a way of sneaking up on us, doesn’t it? One minute, it’s back-to-school sales, and the next, you’re surrounded by decorations, customers, and the chaos of the busiest time in retail. For leaders, this season is an incredible opportunity to finish the year strong, energize your team, and create positive experiences for customers. But it’s also a time when balance can feel unreachable. The good news? With intentional planning, you can achieve your goals, lead your team through the rush, and still carve out time for yourself and your family.
How you approach December and close out the year can significantly impact the year ahead. You can either start January feeling prepared and ahead of schedule, or spend those first weeks scrambling to catch up. Too often, we realize the holiday season has passed without us ever getting a chance to enjoy it. I've found myself in that position many times throughout my career. Here are some tips to help you avoid feeling overwhelmed and missing out on the season's joy, even during the busiest days of this retail period.
Map out your holiday strategy
I do like finding new ways to say, “it all starts with a plan.” Once again, it is critical to know, up front, what you want to accomplish in the remaining days of the year. So layout what you would like to have happen, ensuring you are specific about how you want to schedule yourself both for work efforts and family efforts.
Set Clear Goals: What do you still want to achieve before the year ends? Prioritize these and block time for them now.
Prep Your Team: What responsibilities have you assigned? Does your team have what they need to be successful? Review their schedules and make adjustments to ensure everyone can enjoy the season while managing work priorities.
Define Personal Plans: Schedule your time off early, and coordinate with your team. Planning now will help avoid last-minute conflicts and ensure everyone gets the time they need.
Own your time with intention
With your plan taking shape, determining what can happen when, and what needs to be done ahead of time can ensure that you are setting yourself up for success.
Focus on ‘Domino Tasks’: Identify tasks that need to be completed first to make other actions easier or more efficient. For example, a well-organized stockroom can save hours of stress during peak replenishment times.
Distinguish ‘Must-Do’ vs. ‘Nice-to-Do’: Tackle critical tasks first and let go of perfectionism on smaller, less impactful items. This is also the right place to define what you ‘won’t do’. Not everything has to fit in right now. Ensure you remove non-critical things from everyone’s plate.
Pause to check progress
Determine the right point with your remaining time this year to also schedule a check-in time to see where you are at with your plan. Often we build the plan and get caught up in the activities, forgetting to pause and check to see how we are progressing. This can be especially true when you’ve experienced some unexpected shifts in your business, your team, or even from your manager. Check in with your team. Getting their feedback on what is and isn’t working can help reshape any changes that need to happen. Building in flexibility to your initial plan is a good idea, but you’ll still want to have a defined (and scheduled) time to check in with the plan you’ve built for the remainder of the year.
Schedule time to recharge — midway
Having a plan to get it all done, and even the plan for taking off time at the holidays, should not prevent you from having a plan to catch your breath during the month. Even if it is an afternoon, or a day off where you can ensure you have time for yourself to pause and relax for a little bit. It will be easy to say, “I can power through this month. I have time off during the holiday, so I just need to work hard these next few weeks to get to that.” Then that holiday time off arrives, and you are worn out, or worse, sick, and don’t get a chance to enjoy it. Plan to pause now to recover during the month so you can not only get the things done you want, but be rested when you get to that holiday time off.
Start planning now and watch how preparation transforms the season. The holidays don’t have to be chaotic. With a little work up front, you can make this season one of accomplishment, balance, and fun. Define what you want the remainder of the year to look like, for yourself, your team, and your family.
What steps will you take today to make this holiday season your most balanced and successful yet?
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