#23: Adapting Rules

newsletter Mar 18, 2024

You know… it’s okay to think about rules a bit differently.

I certainly do, all the time.

You don’t have to blindly accept everything as black and white.

Many well-intentioned rules and policies impede actual life, unintentionally. If there’s a (positive and ethical) way to honor them while getting around them, lean into it. We have this one life.

Here’s an example.

On my drive to Dulles International Airport in Washington D.C. this month, my son Jalen asked me the following question…

“Dad… are you going to drop me off at departures?”

“Nah kid… I’m going to the gate with you, again.”

Jalen is my best friend.

Had him at age 25 when I was young and broke. In many ways, he was my purpose to get up every day and hustle. Had no choice as a parent. We’ve been through a lot together and have a deep relationship as a result.

So, when he flies up to D.C. from Atlanta to spend time with me and his little brother, I feel whole again.

When it’s time for him to go back to Atlanta, I usually do one of two things:

  1. Fly with him to Atlanta and come right back to DC an hour later.
  2. Go with him to the gate to say goodbye.

I don’t like to drop him off at the curb. I have this perspective for anything you love… treat it as the gold that it is.

I prefer to fly with him and come right back (so many ways to travel hack this) or walk him to the gate and watch his plane take off. I always have intent to fly (airlines have this policy), but truly I make the decision when I am at the airport.

(Note: I am a very frequent traveler so I’m sure not to abuse rules).

The reasons I do this should be obvious, I love my kid.

But how I do it may not be obvious.

I buy a fully refundable ticket or redeem a mileage award ticket and make the decision at the gate as to whether I am going to fly with him or not.

At minimum, I see my boy off at the gate hugging him goodbye. At maximum, I fly with him and spend half a day in airports (which is actually a lot of fun, especially hanging out in lounges).

 It’s my way of Trying Life On with and for my son.


Life has gotten so fast, people are forgetting to slow down, enjoy life and take a long moment to say goodbye.

Interestingly, airports are starting to realize this. They want people to come into the terminals, spending time with family and, of course, shop and spend money. That’s cool. I’m all for it.

There’s now 8 major US airports that offer non-passenger access to the terminal (article). And plenty of airports across the world have this practice as well.


Here’s my point…

Think about rules critically, don’t just blindly accept them.

Find ways to affect the outcome you are looking for in life. Don’t just simply accept the status quo of it all.

We’re in such a rush to get things done. I think we forget what’s important in many cases.

We can be spending more time ‘intentionally’ living with our families and loved ones, and that should be the priority.

Try Life On.

Enjoy your family. Enjoy life.

If there’s a blocker to it all, find a way around it in a positive, ethical manner.

A thought for you as you Try Life On with your loved ones.