We’ve got a three-day weekend right around the corner. Memorial Day is this coming Monday, which means barbecues, family time, and a well-deserved break and the official opening day to summer. For most people, a long weekend is pure celebration.
But if you’re anything like me and you make your living in sales, you might look at a holiday weekend with a little bit of mixed emotion.
Let’s talk about rhythm.
I’m a big believer in consistency. Sales is a game of momentum. You build it up through the week, you stack your appointments, you follow up on leads prepare your proposals, and you roll that energy forward. When the rhythm is working, everything flows perfectly. You know exactly what a Tuesday looks like, how a Thursday feels, and how to close strong on a Friday.
But when a holiday hits, that rhythm gets completely thrown off.
Honestly, trying to work on a Monday when it’s a holiday just feels inherently off. If you try to go out and cold-canvas a retail strip or a restaurant row on Memorial Day, what do you find? Half the business owners aren’t there, the ones who are open are too slammed dealing with holiday rushes to look at a merchant statement, and the corporate offices are entirely dark. You’re spinning your wheels, hitting dead ends, and wasting gas. It feels like swimming upstream against a heavy current.
Everyone is on a different frequency, and trying to pull a decision-maker into a serious conversation about processing rates or hardware upgrades on a holiday is a losing battle.
Then comes Tuesday. You walk into the office or hop in your car, ready to kick off a “short week.” In theory, a short week sounds amazing. In practice? For me, it actually makes me feel less productive.
Suddenly, you have four days to do five days of prospecting, following up, and closing. But it’s worse than that—your merchants are also trying to catch up on everything they missed while they were closed or short-staffed over the long weekend. They don’t want to talk about switching processors on Tuesday morning; they’re trying to sort out inventory, banking, and employee scheduling.
Because of this, I’ve had to completely reframe how I look at holiday weeks. I’ve stopped trying to force regular sales activity into a holiday Monday. It just slows down my overall momentum and frustrates me before the week even officially starts.
Instead, Monday has essentially become my Sunday Prep Day for Tuesday.
I treat Monday as a low-pressure, high-strategy day. While the grills are lighting up, I spend a quiet couple of hours organizing my pipeline, cleaning up my CRM, and pinpointing exactly which merchants I am going to strike first when the doors open on Tuesday morning. Monday builds the blueprint, so that when Tuesday hits, I don’t have to think—I just execute and kick off the week at full volume.
Instead of letting the holiday drag my momentum down, I use it to build a ramp so I can launch into Tuesday at full speed. It’s the only way to counteract that weird, sluggish feeling a short week brings.
Is it just me, or do any of you feel the same? Does a three-day weekend mess with your sales rhythm? How do you handle the shortened week without feeling like your productivity took a massive hit? Let’s figure out how to conquer this post-Memorial Day sprint together—drop your thoughts in the comments!
Happy Selling,
David
