I once met a man in an airport lounge who wore a suit so sharp it could shave your soul. He had slick hair, a gold watch the size of a moon crater, and a Bluetooth earpiece blinking like a smug little UFO orbiting his face. He said things like “synergy,” “leverage,” and “let’s touch base offline,” which is corporate for “please don’t call me, I’m very busy adding no value anywhere.”
I asked him what he did, and he said, “I empower verticals.”
I blinked. He winked. And somewhere in the distance, a PowerPoint presentation wept.
That, my friends, was the moment I knew: we live in an era where looking successful is a profession unto itself, and actually being successful is something you try to squeeze in between yoga and your fourth Zoom call with a guy named Sterling.
Looking successful is easy. A leased Tesla, a cornflower blue blazer, and a bio that says “strategic advisor” to something vague and possibly made of vapour. But real success? That’s a garage band. It’s a sweaty melody. It’s unshaven in ripped jeans. It smells like burnt coffee, missed calls, and hope. It’s waking up at 2am in a panic because you just remembered you forgot to invoice anyone for anything last month.
Real success is independence. Not just financial — though that’s nice, and helps when you want guacamole and rent — but mental. It’s freedom from performative nonsense. It’s not having to say “circle back” unless you’re talking about a failed moon landing. It’s the quiet power of saying no, of walking away, of choosing your chaos instead of someone else’s calendar.
See, independence doesn’t photograph well. It’s not glamorous. It doesn’t have an elevator pitch. But it’s the warm, perfectly pitched hum of knowing you don’t need to ask permission. You don’t need Sterling’s approval. You don’t have to wear a suit unless it’s a court appearance or a funeral.
The trick is that fake success is loud. It's in your face. It's all caps and glossy and smells faintly of a cologne called “Executive Vision.” Real success is subtle. It doesn’t post about itself. It doesn’t need followers. It’s the ability to spend an entire Tuesday fixing a client’s broken project and adding real value without a single meeting, memo, or middle manager.
Looking successful is exhausting. You’ve got to keep the illusion polished, the mask smiling, the metrics vaguely inflated. But being successful? That’s calm. That’s knowing your bills are paid and your time is yours. That’s sipping bad coffee and smiling because the company you built — the weird, rarely understood, yet beautiful enterprise — is actually working and adding value.
So, forget the slick blazer guy in the lounge. The wristwatch is probably leased, too. The “synergy” is a hologram. My friends, If you are looking for an example of success while you wait for your next flight, look for someone with ink on their fingers, a wild look in their eyes, and a deep, unshakable grin of success because they know:
They don’t have a boss.
They are the boss, which is far more valuable
And they wore ripped jeans to work — on purpose.
Douglas Zhivago
