Christmas Starts in July: How to Avoid Stressful Holidays as a Construction Entrepreneur

As a business owner, I’ve lived through two types of holiday seasons. The first is chaotic, stressful, and full of sleepless nights. The second is calm, enjoyable, and filled with genuine holiday spirit. After many years of lessons—some learned the hard way—I’ve discovered that the difference between the two boils down to preparation.

In this article I will let you know my secrets to a stress-free EOY.

It’s no surprise that I start thinking about Christmas in July. Not only because I’m a recent Christian convert (a story for another day), but because the holidays have a way of shining a spotlight on the cracks in your business. December is a unique beast: it’s when expenses like payroll pile up, invoices go unpaid until January, and personal obligations ramp up with trips, gifts, holiday parties and constant interruptions.

I’ll never forget those holidays when the shutdown meant high payroll, low revenue, and sleepless nights staring at my bank account. Years like this one—where December includes three bi-weekly payrolls—were especially brutal. If you’re not prepared, it’s a perfect storm.

But do I have stress? Nope. Not at all. Sure, I’m handling a tough situation for my Tennessee client, Alliance Global Solutions, but my finances are in order, my New Year’s plans are booked, and I’m looking forward to an amazing 2025.

So, how did I go from chaos to calm during the holidays? By making changes earlier in the year. Here are three things I do every year to set myself up for a stress-free December.

1. Go Hard in August

In August, I focus on marketing to build a pipeline that will carry me through the New Year. It’s all about going hard when everyone else is slowing down and taking a summer break. If it’s a slow year, consider doing something the market wants to augment your income while it’s quiet.

What do I mean by that? Say you want to focus solely on commercial jobs, but there aren’t any RFPs. Take on residential jobs for a few months and build up that cash. When times are tough, there’s always a market for something. Your job is to discover what that is and do it.

2. Plan Your Cash for the Holidays

The holiday season can be brutal on cash flow, but you can avoid the stress by planning ahead. Start predicting your cash needs from Thanksgiving to New Year’s as early as September, and then set aside the funds you’ll need. This takes tons of discipline, but trust me, it works.

You’ll thank me when you’re spraying champagne in the club at midnight on New Year’s Eve instead of stressing about payroll.

3. Lean Into the Parties

Don’t underestimate the importance of holiday celebrations—your company holiday party matters. It should be well planned and fun. Over the years, I’ve done everything from company snowboard trips to restaurant buyouts to beach vacations. Those events are still talked about by former employees and old clients.

Holiday parties aren’t just about letting loose; they’re about building culture, strengthening relationships, and creating memories that last long after the work is done. Plan and pay for this early so you have something to look forward to.

But what if it’s too late? What if this year is already a jingle bell ball of stress? Well then…

4. Remember What Christmas is About

For what it’s worth, let’s not forget what Christmas is truly about. It’s not just about payrolls, parties, or presents. It’s about a child born in Bethlehem—a Savior who came to bring hope, joy, and peace to the world.

If you’re feeling the holiday stress, I recommend you use this time to reflect on that hope. Take a moment to pause, step away from the chaos, and focus on what matters most. Whether it’s through prayer, reading the Nativity story, or simply sitting quietly and reflecting on the meaning of Christmas, grounding yourself in the bigger picture can bring a sense of peace that no financial plan ever could.

Because at the end of the day, it’s not the perfect balance sheet or smooth project schedule that defines a successful holiday season—it’s the joy and hope we share with others.

The holidays will always bring challenges, but they don’t have to bring stress. With a little preparation and foresight, you can turn December into a time of joy and reflection—and fun. So this Christmas, as you sip your eggnog or attend that final holiday party this evening, start thinking about what you’ll do better next year. Your 2025 self will thank you.

God Bless. Merry Christmas, and here’s to a stress-free New Year!