I regularly hear from people who have what everyone calls a “great job.”

Good salary. Benefits. Corner office. The works.

They all sound miserable.

When I ask what’s wrong, they say some version of the same thing that makes me want to roll my eyes at our entire culture:

“I feel so guilty for wanting more. I should just be grateful for what I have.”

Here’s the thing about that guilt: it’s not yours.

The Gratitude Trap

We’ve been sold this idea that wanting more than your stable 9–5 makes you ungrateful. Selfish. Out of touch.

And I get it. Every time you daydream about starting that business or traveling for months instead of just two weeks a year, that voice creeps in: “People would kill for your job. What’s wrong with you?”

But here’s what nobody talks about: your guilt is someone else’s profit margin.

Every day you stay small, stay grateful, stay trapped in the “good enough” job, you’re building someone else’s empire while your own dreams collect dust in a drawer somewhere.

The system depends on your guilt to function. It needs you to believe that wanting fulfillment beyond a steady paycheck is somehow wrong. That conditioning isn’t accidental — it’s engineered.

Who Benefits From Your “Gratitude”

Let me paint a picture:

You wake up Monday morning and feel that familiar dread. You sit in your car for an extra minute before walking into the office, taking a deep breath like you’re preparing for battle.

You spend 8+ hours making someone else’s vision come true. You sit through quarterly reviews that emphasize “being grateful for growth opportunities” while your salary stays flat. You optimize processes you don’t care about for products you’d never personally buy. You build empires you’ll never own.

Meanwhile, your boss drives home in a Tesla, planning their next vacation to Italy — funded by the value you and your teammates create daily.

And when you express any dissatisfaction? “You should be grateful. Do you know how many people would want your position?”

Of course they want you grateful. Grateful employees don’t negotiate aggressively. They don’t leave for competitors. They don’t build competing businesses during lunch breaks. They don’t recognize their true market value.

Your contentment is their competitive advantage. Your guilt is their insurance policy.

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Permission to Want More

The most successful people I know — the ones who built portfolio careers and reclaimed their time — started exactly where you are.

They had stable jobs. They felt guilty for wanting more. They thought they were crazy for dreaming beyond their corporate cubicle.

The difference? They gave themselves permission to want more.

Not permission to quit tomorrow and live under a bridge. (Although honestly, some days that sounds tempting, right?)

Permission to honor both parts of themselves: the part that values security AND the part that craves meaningful impact.

Here’s what that permission looks like in practice:

Permission to build something on the side while keeping your day job as financial foundation.

Permission to become the CEO of your own life instead of a supporting character in someone else’s story.

Permission to start small — maybe it’s just 30 minutes every morning working on your idea before checking email.

The Truth No One Talks About

Your dreams aren’t too big. Your current life is too small.

And that guilt you feel? It’s not wisdom — it’s conditioning designed to keep you exactly where you are. It’s learned helplessness dressed up as virtue.

The most dangerous thing you can do is spend your entire life being grateful for a life that never truly belonged to you.

Because every day you postpone this conversation with yourself is another day closer to looking back with regret, wondering what could have been if you’d just given yourself permission to want more.

So here’s my question for you:

What would you build if you stopped feeling guilty for wanting more?

Here’s an even better question: What will you start building this weekend?

Because I guarantee someone’s already profiting from the fact that you haven’t answered that question yet.

And it’s not you.

-Matt

Start with 30 minutes tomorrow morning before you check your email. Just 30 minutes working on something that belongs entirely to you. See how that feels. Your guilt will try to talk you out of it — that’s how you’ll know you’re on the right track.

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