There is a special kind of silence that only shows up around Thanksgiving.

The phone slows down. The inbox cools off. For a day or two, the calendar finally stops yelling at you.

And in that quiet, a dangerous thought sneaks in:

“Is this how I want to keep living and leading?”

I have spent Thanksgivings in just about every role:

• Running big box retail and praying the Black Friday setup worked
• Leading Chick fil A and hoping every cooler was properly closed and every door locked
• Now, coaching owners who are somewhere between “I am tired” and “I am done”

Through Cymilleum AI and my work as an Exit Strategist with Exit Factor Atlanta South Metro, I see the same question come up in different words:

“Can my business support the life I actually want, or is it running me into the ground?”

Two Thanksgiving Leaders

If you zoom out, there are really two kinds of business owners during the holidays:

1. The “Please Do Not Break While I Am Gone” Owner This leader:
2. The “I Miss Them, But They Got This” Owner This leader:

The difference is not just staffing or luck. It is systems, visibility, and trust.

And this is where AI becomes practical, not futuristic.

What AI Has To Do With Thanksgiving

AI is not about robots replacing people. It is about building margin back into a life and a business that has been running on fumes.

Here is how I think about it:

AI gives you the room to breathe that you thought you would get when you finally hired that last manager, opened that second location, or hit that revenue goal.

For a service based or franchise style business, that can look like:

• Automated forecasting and prep So you are not guessing how much product or labor you need after the holidays.
• Standardized, AI assisted SOPs So the way things should be done does not live only in your head or your best manager’s head.
• AI powered training and coaching So new team members ramp faster, and your veterans get reinforcement without you holding every hand.
• Decision support dashboards So you are not digging for the three metrics that actually matter. They are brought to you in plain language.

When I work with owners on exit readiness through Exit Factor, we talk about “life after the deal.” When I work with owners on AI readiness through Cymilleum, we are often talking about “life during the grind.” Those two lives need to line up, or the future you are chasing will not feel any better than the present you are escaping.

The Guilt You Feel About Changing… And What It Is Really About

Many owners quietly wrestle with guilt:

• “If I automate this, am I abandoning my team?”
• “If I make life easier for myself, am I being selfish?”
• “If I start using AI, am I cheating the way we have always done things?”

Here is what I have learned in more than 20 years of operations:

Your team suffers more when you are exhausted and constantly in reaction mode than when you use technology to lead with clarity.

AI does not replace the heart of your leadership. It protects it.

• It pulls you out of the weeds.
• It catches issues earlier.
• It gives your people clearer expectations and better tools.

That is not betrayal. That is stewardship.

A Post Holiday Reflection Exercise (AI Edition)

As you move through this holiday season, try this simple reflection:

1. Where did I feel most anxious about my business while I was away?
2. Where did my team have to improvise because our systems were not clear?
3. Where did information live only in one person’s head, usually mine?
4. How much of that is fixable with better systems, and how much of those systems could be powered or supported by AI?

Now flip the script:

“If AI could quietly sit in the background and stabilize one part of my operation before next Thanksgiving, which area would change my life the most?”

That is your starting point.

How Cymilleum AI Helps Owners Redesign the Next Season

At Cymilleum AI, I do not start with tools. I start with the life you are trying to build.

Then we work backward:

1. Clarify the lifestyle target.
2. Identify the operational friction.
3. Design AI supported workflows.
4. Pilot, refine, then scale.

On the Exit Factor side, those same improvements often increase business value. Buyers and successors pay more for a business that does not fall apart every time the owner leaves town.

Your Next Right Step

Between the leftovers, football, and naps, ask yourself:

“Do I want to feel the same way about my business next year at this time?”

If the answer is no, then this season is not just about gratitude. It is about redesign.

If part of that redesign involves AI that is truly human focused and operator aware, that is exactly the work we do at Cymilleum AI. And if you are also thinking about an eventual exit, just know that every smart AI move you make now is a gift you are giving your future self and your future buyer or successor through the Exit Factor work I do as well.