The Most Expensive Question You’ll Never Ask Yourself
By Gabe Salinas, Founder of Window Ninjas
What are you actually chasing?
Not what you tell people at dinner parties. Not what looks good on a LinkedIn post. What are you, in the quiet of your own head at 6am, actually chasing?
I’ll be honest with you. I picked this one back up this week and it stopped me cold. I first read The Great Gatsby in ninth or tenth grade, the way most of us did, as a homework assignment, probably highlighted the wrong things, and moved on with my life. But reading it again as a business owner and entrepreneur? Completely different book. This time it didn’t feel like literature. It felt like a warning.
A 5.0 Golden Squeegee warning.
The Story, In Case It’s Been a Minute
Jay Gatsby is one of the wealthiest men on Long Island in the 1920s. He throws the most extravagant parties anyone has ever seen. His mansion is legendary. His shirts, famously, are imported. He is, by every visible measure, a massive success.
And he is completely, utterly lost.
The whole empire he built, every dollar, every party, every carefully constructed persona, is aimed at a single target: winning back Daisy Buchanan, the woman he loved before the war, before the money, before any of it. Daisy is now married to Tom Buchanan, old money, arrogant, and the kind of man who steps on people without looking down to see what he’s crushed.
The story is narrated by Nick Carraway, Gatsby’s neighbor and Daisy’s cousin, who watches the whole thing unfold with clear eyes and a quiet heartbreak. By the end, the parties are over, the mansion is empty, and Gatsby is dead. Not one person from his famous guest lists shows up to his funeral.
The Lesson That Hit Me Like a Truck
Here is what Gatsby got wrong, and I mean this in a business sense as much as a human one: he never stopped to ask himself what he actually wanted.
He was so locked in on the pursuit that the pursuit became the entire point. He didn’t want Daisy the person. He wanted the feeling he associated with her. The validation. The proof that all of it had been worth it. He built a fortune and an identity around a dream that, if he’d been honest with himself for five minutes, he might have realized had already passed him by.
Sound familiar?
I’ve been around enough entrepreneurs to know this pattern. I’ve felt versions of it myself. You set a goal. The goal becomes an obsession. The obsession takes over. And somewhere in the middle of all that relentless pursuit, you forget to ask the most important question of all: is this still what I actually want? Or am I just too deep in it to change direction?
Gatsby never asked that question. It cost him everything.
Nick Carraway Is the Most Underrated Character in the Room
Reading this as an adult, Nick hit differently. He’s the observer. He watches Gatsby’s world from the inside and sees it with perfect clarity while everyone else is drunk on the spectacle. He’s not seduced by the parties or the money or the mythology of Gatsby. He just watches, and he reports, and he sees what nobody else can see because they’re all too busy performing.
Every leadership team needs a Nick. Every entrepreneur needs someone in their corner who isn’t impressed by the party, isn’t caught up in the excitement, and will tell you the truth about what they’re actually seeing. The people who flatter you are everywhere. The people who see clearly and speak honestly? Those are rare. Find them. Keep them close.
The Green Light and the Scorecard You’re Not Looking At
Fitzgerald gives Gatsby a green light at the end of Daisy’s dock, across the water from his mansion. Gatsby stares at it at night. It represents everything he’s reaching for, close enough to see, far enough to stay out of reach.
That image hit me hard because I’ve seen that green light in a lot of business owners. They’re always staring at the next thing. The next location. The next revenue milestone. The next version of success that’s just across the water. And there’s nothing wrong with ambition. Nothing at all. But there’s a difference between building toward something real and just staring at a light across the bay because you don’t know what else to do with yourself.
The antidote to the green light trap is a scorecard. You want to know where you are. You want to know what’s working and what isn’t. You want to measure what matters and make decisions from facts, not feelings. Gatsby never had a scorecard. He had a dream and a lot of shirts. The dream was borrowed and the shirts couldn’t save him.
The Eyes of Doctor T.J. Eckleburg
There’s a billboard in this book. Faded, enormous, overlooking a stretch of industrial wasteland called the Valley of Ashes. Just a pair of giant eyes behind spectacles, staring down at everything that passes beneath them.
Fitzgerald meant them as a symbol of God watching a morally bankrupt world. I read them as accountability. Those eyes see everything. The shortcuts you took. The foundations you skipped. The questions you refused to ask yourself. The people you stepped over on the way up.
In business and in life, those eyes are always watching. Your team sees how you show up on a bad day. Your franchisees see whether you do what you say you’ll do. Your family sees whether the version of success you’re chasing is actually making you a better person or just a busier one.
You don’t get to hide from those eyes. Neither did Gatsby.
Why You Should Read This Even Though It’s Not a Business Book
Look. I know this is not your typical entry on a business book list. And if you came here for a framework or a four-step system, I understand if this one surprised you.
But here’s what I believe: the best business lessons don’t always come in business books. Sometimes they come from a story written a hundred years ago about a man who had everything and died with nothing because he never once stopped to ask himself the right question.
What do you actually want? Why do you want it? And are you building toward that thing, or are you just staring at a green light across the water because the pursuit feels better than the stillness?
Read The Great Gatsby. Read it slowly. And when you’re done, put it down and sit with those questions for a while. The answers might surprise you.
5.0 out of 5 Golden Squeegees
Keep Shining.
Gabe Salinas
