One of my longest-standing professional values can be summed up with a simple phrase:
Never go fishing off the company pier.
That principle can apply to customers, coworkers, professional contacts, gambling, relationships, and just about any other situation where personal decisions can become tangled up with how you earn your living.
Recently, I picked up a passenger at MGM Springfield who needed a ride down to Foxwoods in Connecticut. She was rather cute, and we had a good conversation during the trip.
That does not mean I was going to turn the ride into anything more than a ride.
I was later talking to a friend about it, and I already knew what his reaction would probably be:
“Why didn’t you go inside and play some blackjack?”
Because that was not what my day was about.
My passenger wanted to get out of Springfield and go to Foxwoods. My job was to take her there safely. Once she arrived, my part of the transaction was finished.
There was no reason for me to follow her inside, sit down at a blackjack table, or create a situation that could blur several different boundaries at once.
First, she was a customer.
It does not matter whether a passenger is attractive, friendly, flirtatious, or simply interesting to talk to. The relationship began because the person paid for transportation. That is the company pier.
You do not fish off it.
The problem is not only what happens during the ride. The problem is what someone might say afterward.
A satisfied customer may remember that you were pleasant and professional. A dissatisfied customer may suddenly remember the entire interaction differently. Once personal interest becomes mixed into a professional transaction, every conversation can be reinterpreted through that lens.
That creates risk without creating much value.
The same principle applies to gambling.
I know people who work at MGM. Some of those people have hired me privately to DJ or perform other work for them. I value those personal and professional relationships.
That does not mean MGM hired me as a DJ. It means people I know through that environment have trusted me enough to hire me independently.
I would rather remain known as the person who can be trusted to show up, perform the work, and act professionally than become known for hanging around the tables trying to demonstrate how clever I might be.
Being an advantage player is not something I particularly want attached to my name, either.
It is not necessarily difficult to understand the mathematics, patterns, habits, and conditions that can improve a player’s position. The greater challenge is doing it without drawing attention.
When you already know people who understand those methods—and other people know that you know them—you have another reason not to create unnecessary suspicion.
The question is not whether I could sit down and play.
The question is what I would gain by doing it.
I have more to lose from damaging a professional relationship than I could reasonably expect to win from a blackjack table.
That is where professional judgment comes in.
A lot of people focus entirely on whether something is technically allowed. They ask whether there is a rule against it, whether anyone could prove anything, or whether someone else has done the same thing without consequences.
Those are not always the right questions.
Sometimes the better questions are:
What could this look like afterward?
Who could become dissatisfied?
What version of the story might they tell?
Could this affect how someone views me professionally?
Would I have to explain myself later?
If the situation creates more possible explanations than benefits, leaving it alone is usually the better decision.
That applies when you are driving.
It applies when you are DJing.
It applies when you are consulting.
It applies when you are dealing with customers, clients, coworkers, and the people who may hire you again.
Keep the roles clear.
When I am the driver, I am the driver.
When I am hired as entertainment, I am the entertainment.
When I am repairing equipment, I am there to repair the equipment.
When someone is a customer, I treat that person as a customer.
It is not about pretending that attractive people are not attractive, that gambling cannot be entertaining, or that professional contacts can never become friends.
It is about recognizing that dissatisfied customers often find additional things to say afterward.
Once a professional interaction becomes personal, the story is no longer completely under your control. Whatever happened can be retold, reframed, exaggerated, or misunderstood.
The easiest problem to manage is often the one you never create.
That is why I still live by the rule:
Never go fishing off the company pier, because you never know what you might catch—and you never know what it might say afterward.
Stay fun, stay profitable, and stay safe.