Staying calm in the holiday chaos: advice from e-commerce leaders

The countdown is on—Black Friday and Cyber Monday are just a week away, and the holiday shopping season is already shaping up to be a whirlwind. To add to the stress, this year’s season is the shortest since 2019, with just 26 days between Black Friday and Christmas Eve—16% shorter than last year! That means efficiency is the name of the game, from managing inventory to staying visible in a crowded inbox.

But in the middle of all the hustle, there's one thing we don’t often talk about: the importance of staying calm. With all the deadlines and to-dos piling up, it’s easy to feel like you need to be everywhere at once. However, sometimes the key to making it through the season is just as much about what you don’t do, and how you give yourself (and your team) the grace to navigate the chaos.

To help you keep your cool during this fast-paced time, we reached out to some industry pros for their best advice. Here’s what they had to say:

Trust the process—and the people around you
Jesse Kaufman, CEO and founder of ShippingTree (now a WSI company), has a simple yet powerful piece of advice: trust the process. “The most important thing for us, aside from all the preparation we do going into peak, is to trust the process and stick to the plan! Things will inevitably go sideways in some shape or form, and you have to trust the systems you've built to properly execute your way out of the problems that arise,” he shares.

When you’ve put the right systems in place, it’s easier to handle whatever comes your way. While things may not go exactly as planned, knowing you’ve prepared well helps you stay calm when the unexpected strikes.

Communication is key (and so is staying human)
Matt Hertz, CEO and founder of Third Person, shares his perspective on how peak season feels: “Peak season is a stressful moment for everyone—not only for you, but your partners, and your customers. Think of it like the night before college finals, or the morning of a home move—stress and anxiety is high! The best way to limit these stresses is through planning and communication. Sharing your goals, expectations, and plans with your partners—all of them—and staying in daily contact will allow you to adjust to real-time needs. Stay calm, appreciate that no one is perfect, but that most are trying their best.”

Plan ahead to manage the chaos
Cullen Sanderson, VP of Strategy at DSV, emphasizes the importance of planning: “Planning is key. Knowing your customer’s plans and expectations makes or breaks you. Having your labor and staffing partners prepared makes the variance more manageable. Lastly, making sure you’re planning with your carrier partners for extra trailers, pickups, etc. could be the difference in delivering that present on time vs delivering a bad customer experience.”

Take a deep breath—and don’t forget to rest
Amid all the planning and coordination, it’s crucial to give yourself space to breathe. Sometimes, the best way to stay calm is by stepping away for a few minutes to recharge. Whether it’s a short walk, a cup of tea, or simply closing your eyes for a couple of minutes, finding moments of calm can help you reset and return to your tasks with a clear mind.

As much as we focus on doing more during the holidays, sometimes the secret to surviving (and thriving) is simply about not doing it all at once. Allowing yourself a breather and embracing the chaos with a calm mindset will help you maintain your energy and stay grounded throughout the season.

If you’re looking for even more ways to manage stress and stay grounded this peak season, check out this episode of Working with Feeling, hosted by Oren Shai. In this episode (How to beat burnout and thrive in uncertainty), Rachel Hamlin, an executive coach and somatic healer, shares her approach to overcoming burnout and thriving in uncertainty. Through a blend of somatic healing and neuroscience-backed strategies, Rachel offers practical tips for navigating stress and creating balance—even in the busiest of times.