The Paradox of Chasing Your Dreams

The Paradox of Chasing Your Dreams

February 2, 2025
A minimalist staircase rising steadily into a soft gradient background representing gradual progress
Last updated: May 21, 2025

Human-authored, AI-produced  ·  Fact-checked by AI for credibility, hallucination, and overstatement

Introduction: The Paradox of Chasing Your Dreams

If you’ve ever felt stuck chasing that “big break,” you’re in good company.

I’ve seen it play out firsthand—not just in others, but in my own life too. There’s always that friend with the next big idea: a glossy magazine, a clever app, maybe even a taco stand with a twist. He’d dive in, heart racing, convinced this was finally it. But then—maybe it’s the first slow week, or the spark starts to fizzle—he’d pivot. Again. And again. A year later, he was surrounded by unfinished projects and that gnawing question: “Why isn’t this working?”

On the other hand, I’ve watched someone else take an almost painfully slow path. No splashy launches. No viral moments. Just one customer at a time, steady as sunrise. From the outside, her progress looked invisible for years. Then suddenly—at least to everyone else—she was an “overnight success.” All anyone saw was the summit, not the endless uphill climb.

Here’s the paradox that trips so many of us:

The more we chase easy wins and lightning strikes, the more real success seems to slip away. It’s only when we commit to the unglamorous climb—stacking small wins, enduring setbacks, refusing to quit—that we get anywhere worth going.

Real achievement is rarely about that single leap; it’s about showing up, day after day, and inching forward even when nobody’s watching.

I keep coming back to the Iceberg Illusion: everyone admires the peak poking above the surface, but beneath? Years of effort. Doubt. Learning. Failure. That hidden mass is what actually holds everything up. It’s changed how I see success—and maybe it’ll do the same for you.

Why We’re Drawn to ‘Big Breaks’

Why is it so hard not to fall for the myth of the big break? There’s more at work here than impatience—it’s something we’re practically wired for.

Take a look at what gets celebrated. Everywhere you turn—on social media, in business magazines, on your favorite podcasts—the stories that go viral are about startups that explode overnight, writers who land six-figure book deals on their first try, athletes who seemingly emerge from nowhere. Our feeds are highlight reels, and it’s easy to feel like everyone else is lapping you while you’re stuck at mile one.

This is where the ‘Expectation vs. Reality Gap’ quietly sneaks in. All these stories set our expectations sky-high, but reality? It’s much messier and slower than any Instagram reel suggests. Recognizing this mismatch isn’t just a comfort—it’s a necessity if you want to stay sane and actually make progress.

But there’s another reason these stories hook us: instant gratification. Our brains are wired to crave fast results. The idea that one lucky break could change everything is magnetic—who wouldn’t want to skip the grind and go straight to the finish line?

The problem? Chasing that feeling leads to restlessness and self-doubt. When results don’t materialize on schedule, it starts to feel like proof you’re on the wrong path—or worse, that you’re somehow falling behind. So you pivot. Again and again. And momentum dies before it even gets going.

If you’ve ever felt like you’re just seeing the highlight reel while everyone else seems miles ahead, know that you’re not alone—and that real progress is built in those quiet, imperfect moments no one else sees.

The Reality: Success Is a Climb, Not a Leap

Let’s get real: Progress almost never comes from one electrifying moment or sudden breakthrough. It’s usually the unsexy stuff—the showing up, the late nights, the second (or tenth) draft—that moves you forward.

If you’re constantly jumping from project to project, nothing gets enough sunlight or water to grow roots. Imagine planting seeds but digging them up every week to check if they’ve sprouted yet—nothing thrives under that kind of impatience.

Think about J.K. Rowling—her Harry Potter story didn’t explode out of nowhere. She spent years writing in cafes and collecting rejections before any publisher said yes. What looks like magic was really built on grit and a pile of “no”s most people never see.

Every time you chase quick wins and walk away when things get tough, you’re not just wasting time—you’re chipping away at your own confidence.

So next time you see a headline about an “overnight success,” pause and ask: What’s missing from this story? Because the truth is always quieter—building something great takes time. The ones who make it are often those who simply kept climbing long after everyone else got bored or discouraged.

A lone climber ascending at sunrise, symbolizing steady progress
Image Source: I am addicted to mountains and sunrise

Building Momentum: The Power of Small Wins

So how do you break out of this cycle? Stop waiting for seismic shifts and start building momentum through small, daily wins.

Here’s what’s worked for me—and for just about everyone I’ve coached or admired: Shrink your goals down until they’re manageable enough to tackle today—not someday. Instead of fixating on launching a million-dollar business or writing a bestselling novel, focus on what moves you forward now. Can you land one new client? Can you write one page?

These steps sound tiny, but they add up faster than you think.

The American Psychological Association has found that people who break their ambitions into smaller steps are far more likely to reach them than those who don’t. Small wins reduce stress and build confidence. That’s what keeps you moving forward when motivation inevitably dips.

Worried that small wins are too insignificant? Think about compound interest in finance: minor gains each month snowball into dramatic growth over time. If you improved just 5% every month for a year, you’d transform your process according to insights on building momentum with small wins.

James Clear puts it perfectly in ‘Atomic Habits’: Small daily improvements create massive change over time. Systems that prioritize tiny progress keep motivation alive long after the initial excitement fades.

If consistency is a challenge, focusing on just hitting play with small wins can be surprisingly powerful—and help fuel those bigger ambitions over time.

  • First, making progress a habit builds confidence—each small win is evidence that you’re moving forward (even if only by inches).
  • Second, it lowers the emotional stakes of every action. When you stop betting everything on lightning strikes and just focus on what you control today, disappointment shrinks and growth feels manageable—even sustainable.

Try this: At the start of each week—or even each morning—choose one action that moves you closer to your goal. Celebrate completion over perfection. Stack enough of those actions together and suddenly you’ve got momentum (and a tangible record of progress).

If you’re looking for practical ways to overcome inertia and start building better routines, the 7-day cure for laziness offers some actionable steps to help get unstuck and create lasting change.

Enduring the Grind: Turning Frustration into Progress

This is where so many people stumble: when things slow down or get messy, it feels like failure—or worse, proof that maybe you were never cut out for this in the first place.

Pause here for a second—because frustration isn’t failure; it’s often progress in disguise. That tension you feel? Nine times out of ten, it means you’re pushing into new territory—not spinning your wheels.

There’s a book I keep coming back to called ‘The Dip.’ Maybe you’ve heard of it. The gist is that every worthwhile pursuit has its own rough patch—a slog that filters out everyone who wants instant results from those willing to stick around for real growth.

The dip essentially functions as a filter. Those who push through come out stronger and more successful; those who give up miss out on fulfillment.

So how do you keep going when things get tough?

  • First, reframe setbacks as milestones—not dead ends but markers on your path of growth. This is where adopting a ‘Growth Mindset,’ as Carol Dweck describes it, makes all the difference. If you view abilities as something to develop—not fixed traits—then every challenge becomes an opportunity to improve, not evidence of your limits.
  • Second, remember: visible progress almost always lags behind real progress. What feels like stagnation or failure might actually be compounding beneath the surface—like roots growing quietly before a seed breaks ground.

Angela Duckworth’s research is clear: Grit—not raw talent—is what separates those who achieve long-term success from those who fade out early. Grit keeps you moving even when progress is invisible or achingly slow.

And finally? Don’t try to muscle through alone. Keep reminders handy—old journals showing how far you’ve come, notes from friends cheering you on, visual trackers where you can see your streaks—to help regain perspective on tough days.

Sometimes it’s about recognizing when persistence serves you—and when it’s time to stop. Knowing the difference can be just as important as grit itself.

Taking the First Step Today

All right—how do you actually put this into action? Start by shrinking your biggest goal into something doable right now.

If your dream is to replace your full-time income with a business, don’t let that huge finish line freeze you up. Ask yourself instead: “What would it take to get just one new customer?”

Want to write a novel? Forget 80,000 words—aim for one solid page today.

This approach breaks inertia and shifts your focus from daydreaming about someday to actually doing something today. And here’s why that matters most: You start measuring your progress by what you control (your effort), not by unpredictable outcomes (overnight results).

Quick gut check: Do you tend to stick with things long enough for results—or do you bail when things get hard? What would change if you committed to just one next step instead?

For instance, if public speaking terrifies you but deep down you want to get better at it, resist the urge to sign up for a giant keynote right off the bat. Start smaller—record a short video for a friend or practice in front of your bathroom mirror. One simple action at a time builds comfort (and courage) for next time.

Standing atop McAfee Knob after a long hike—every summit is reached step by step
Image Source: McAfee Knob

Here’s what I hope sticks with you: The paradox of chasing your dreams isn’t complicated—but it is powerful. Slow progress is usually the fastest route to lasting success. Stop waiting for lightning—start climbing.

Every journey worth taking is made up of countless small steps—each one building on the last, sometimes painfully slowly, sometimes so subtly that nobody else notices but you. When you embrace steady progress and honor those quiet climbs—even when nobody’s watching—you don’t just inch closer to your dreams; you become someone who can actually sustain success once it arrives.

If this resonates and you’re ready to commit to your own unique path, embracing your journey—even if it’s unconventional can make all the difference in staying true through every stage.

That’s my invitation to you (and honestly, my reminder to myself): Trust the process. Keep climbing—even when the trail disappears or your legs ache or progress feels glacially slow. With every step, your story gets richer—and your summit comes closer into view.

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  • Frankie

    AI Content Engineer | ex-Senior Director of Engineering

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