The Disciplined Entrepreneur: Guest Blogger Dean Van Dyke

The holidays can test anyone’s discipline. Between family gatherings, travel, and endless seasonal distractions, it’s easy to let good habits slide (just like your diet while staring down that cookie tray).

But this week we will give the tips you need to keep your business going strong with the help of Dean VanDyke from The Pillar Group reminds us that discipline isn’t about rigidity; it’s about purpose.

With his military background, Dean shares how maintaining structure during chaotic times isn’t just possible, it’s freeing. It creates space for what truly matters: connection, reflection, and systems.

And from our side of the Live Local team, we’d like to add this: don’t forget to reward yourself when you stick to the routine. That reward doesn’t have to be big, maybe it’s an hour off, a favorite coffee, or a quiet walk. The goal is to remind yourself that discipline and joy can go hand in hand.

This season, let’s finish strong while others lose motivation, stay focused, and celebrate the wins (big and small) that keep us growing.

And now from Dean...

                                                          The 15-Minute Monday Drill

PART 1: The 3×5 Discipline Drill (That Takes 15 Minutes)

Here's what they don't tell you about discipline: it's not about grinding harder.

It's about working smarter—with systems that actually hold. Because let's be real: you're already working 60-hour weeks. You're already showing up. The problem isn't effort. It's structure.

You know what needs to happen. Prospecting. Follow-ups. Content. Delivery. But by noon on Monday, you're buried in Slack, email, and fires. Sound familiar?

The hustle-harder crowd will tell you to push through. I'm telling you something different: stop pushing and start planning.

What I Learned When Failure Wasn't an Option

Quick story. In the Navy, our team lived by a simple mantra: "Plan the work. Work the plan. Debrief the truth."

No jargon. No overnight success stories. Just rhythm. That rhythm saved time, cut risk, and built trust under pressure—radios loud, timelines tight, stakes high. No one cared if we were "feeling it." The mission ran anyway.

Your business is the same. Clients don't wait for your motivation to arrive. Revenue doesn't care if you're having an off week.

I carried that rhythm into every company I've served. Fifteen years later, it still works. And here's the best part: it takes 15 minutes to install.

The 3×5 Discipline Drill (15 Minutes)

This is the exact drill I walk clients through in Week One. It's simple. It's repeatable. And it keeps you on track when everything else tries to pull you sideways.

3 Priorities: Pick the three outcomes that move revenue or retention this week. Not tasks. Not busywork. Outcomes.

Examples:

• Close two proposals

• Book five discovery calls

• Ship the client deliverable by Thursday

Write them down. Make them visible. These are your north stars for the week.

5 Blocks: Place five focused blocks on your calendar to advance those outcomes. Each block = 60–90 minutes. No meetings. No Slack. Phones face-down.

Guard them like your income depends on it. Because it does.

Here's the thing: most entrepreneurs lose the week by Wednesday because they never scheduled the work that matters. They hoped for pockets of time. Hope isn't a strategy.

One After-Action: End each day with a 5-minute review. Three lines in a notebook:

• What worked?

• What didn't?

• What changes tomorrow?

This isn't about perfection. It's about adjustment. Small course corrections compound into big momentum.

Your 20-Minute Monday Setup

Let's make this real. Here's how you install the drill this Monday:

Step 1: Calendar First — Schedule your five blocks before anything else touches your day. Treat them like client meetings. Because they are—meetings with your future revenue.

Step 2: One Scoreboard — Track only what drives outcomes. Calls set. Quotes sent. Demos booked. Cash collected. If it doesn't move the number, stop measuring it.

Step 3: Daily Debrief — Three lines. Every night. Wins. Frictions. Adjustments.

This is where discipline becomes automatic instead of effortful. You're not white-knuckling your way through the week—you're learning as you go and getting sharper every day.

The Question That Changes Everything

"If I repeat today for 90 days, do I like where I land?"

If the answer is yes, you're on the right path. Keep going.

If the answer is no—and most of us know when it's no—then don't wait. Most business owners lose 6–8 weeks tweaking the wrong variables. Adjusting tactics when the real problem is structure.

Wednesday I'll share the PST Loop—the framework underneath this drill that makes it hold when life gets messy. Plus real client results from the first 30 days.

Drop a comment if you're installing this Monday. I want to hear how it goes.