The Permission You Didn’t Know You Needed to Give Yourself

If there’s one lesson that keeps showing up in every conversation about success—whether it’s building a seven-figure business, creating content, or pursuing an unconventional path—it’s this: the biggest obstacle isn’t opportunity or talent. It’s giving yourself permission to do things differently.

Most people operate with an invisible script running in the background. “You should get a real job.” “You should settle down.” “You should stop chasing crazy dreams.” The voice might belong to a parent, a teacher, society at large—but the result is always the same. A life that looks good on paper but feels hollow underneath.

How “Should” Becomes the Enemy of Everything Interesting

The word “should” is a freedom-killer. It’s the difference between living your life and living someone else’s expectations.

During the dot-com boom, I was building affiliate-based websites while everyone told me I should pursue a “real job” because internet businesses were just a fad. Sound crazy now? At the time, it was the conventional wisdom. I ignored it, followed my instincts, and ended up with a seven-figure acquisition deal when Yahoo! bought my game site. That wasn’t luck—that was me refusing to let someone else’s “should” dictate my future.

The same pattern has repeated throughout my career. A school counselor told me I should focus on chemistry to get into a prestigious college. I got a D in chemistry. But the moment I gave myself permission to follow computers and business instead—the moment I stopped listening to “should”—everything changed. That permission led to content empires, published books, a podcast with thousands of listeners, and a life that actually feels worth living.

Why Society Loves “Should”

Every “should” someone hands you is a compressed prediction about what they think will make you safe. Go to school, get a job, climb the ladder, retire. Repeat.

The formula works. It keeps people predictable. It prevents chaos. It doesn’t bankrupt anyone or cause embarrassment. But predictable isn’t the same as successful. And safe rarely leads to interesting.

The entrepreneurs, creators, and innovators who actually move the needle don’t follow “should.” They follow what lights them up, even when it doesn’t make conventional sense. They give themselves permission to be weird.

The Real Cost of Saying Yes to “Should”

I knew someone—let’s call him Dave—who became a lawyer because his father said he should. It’s a respectable profession. Good money. Stable. On paper, it was the right move.

But Dave hated law. Every day felt like drowning in someone else’s expectations. His real dream? Opening a food truck. Not because it would make him rich, but because it would make him happy.

Dave listened to “should” for a decade. Ten years of burnout. Ten years of coming home drained. When the divorce came and the reality hit, he finally did the math: saying yes to “should” had cost him not just income, but his marriage and his time.

I’ve been there too. During a rough financial patch, I almost walked away from everything and took a job selling encyclopedias. It was the “responsible” move. The “should.” But standing in that office, my entire body screamed that this wasn’t me. I walked. A week later, a random email from a company in Japan landed in my inbox offering to license my content for $7,500 a month. That deal saved my family from financial disaster. If I’d said yes to “should,” I would’ve missed it entirely.

How to Build a Life of Your Own Design

Rejecting “should” isn’t about being reckless or irresponsible. It’s about recognizing that you—not your parents, not society, not the status quo—get to decide what success looks like. Here’s how to actually do it:

Listen to Your Instincts: Your gut is a built-in navigation system for what’s real and what’s not. When someone says you “should” do something, check in with yourself. Does it feel right, or does your entire being resist it? When I took a minimum-wage bookstore job just for the fun of it, people said I should be doing “serious” work. But that job sparked ideas and led to speaking opportunities I never could’ve predicted. Your instincts know something your rational mind doesn’t.

Question the Source: The next time you feel the weight of “should,” ask yourself: who exactly is saying this? Is it your mother projecting her own fears? Society’s default script? That insecure coworker? Most of the “shoulds” we carry come from people handing us their own regrets. When people told me I should stop pursuing cryptocurrency content because “it’s too niche,” I asked them to show me the data. They couldn’t. That question—”who says?”—has been worth millions.

Start Smaller Than You Think: You don’t need to burn your entire life to the ground tomorrow. Pick one small thing that defies your personal “should.” Skip one networking event you feel obligated to attend. Say no to one project that drains you. Start a creative project just for yourself. I began writing parody lyrics just for fun—nobody was paying attention. That small act of permission created a cultural moment that got shared millions of times. Small acts of rebellion build the courage for bigger ones.

Find Your People: Surround yourself with people who celebrate your weird ideas instead of questioning them. My podcast co-host and I actively encourage each other’s ridiculous ideas because we know that’s where the breakthroughs come from. Find your tribe—people who remind you that “should” is just noise, and what matters is what you actually want to build.

The Unexpected Gift of Permission

When you stop carrying someone else’s expectations, something shifts. You get lighter. More creative. More willing to take intelligent risks.

Saying no to “should” doesn’t mean ignoring responsibility. Bills still need to be paid. There’s still structure and discipline required. But even within those constraints, you can carve out space for what makes you feel alive. When I was broke, I still made time for the creative projects that kept me energized. Those weren’t luxuries—they were what kept me sane and eventually led to the biggest opportunities.

Life’s too short to be a supporting character in someone else’s story. The person who knows what’s best for your life—the only person who actually knows—is you.

What’s Your “Should”?

Right now, there’s probably a “should” sitting on your shoulders. Something you feel obligated to do. Someone else’s version of what your life should look like.

What would change if you said no to it? Not recklessly. Not irresponsibly. Just clearly.

If you’re interested in exploring how to build a life and business on your own terms, listen to the AI For Everyone Show or check out my upcoming book, “AI Made Simple,” where we dig deeper into how to stay authentic while using tools and strategies to scale what matters.