We’ve all learned the proper way to read a book: You begin at the first page, move steadily through the chapters, and finish at the end. It’s a simple, logical progression. But when it comes to an academic journal, the approach flips. You’re supposed to start at the back, skim the headings for a sense of direction, and then circle back to the front. It’s the opposite of what we’re accustomed to doing.

That’s a striking parallel to how life feels for many of us right now. We’re bombarded with the message to chase our dreams––to pursue what ignites our passions––yet despite our best efforts, we often end up feeling empty, anxious, and unfulfilled. What if we’ve been approaching it all wrong? What if the script we’ve been handed is upside down?

In Matthew 20:1–16, Jesus shares a story that challenges this pervasive narrative head-on. It’s a tale about a landowner hiring workers for his vineyard, but it’s also a profound reflection on dreams—both ours and God’s. The script we’re typically given is straightforward and insistent: “You’ve got to chase your dreams.” It’s a rallying cry echoed in motivational quotes, viral memes, and graduation speeches. Yet Jesus introduces a paradox that disrupts this mindset, hinting that chasing our dreams might not lead us to the fulfillment we expect. Let’s dive into this story and unpack how it turns our conventional wisdom on its head.

The Story: A Vineyard and a Generous Landowner

Jesus sets the scene with a vivid opening: “The kingdom of heaven is like a master of a house who went out early in the morning to hire laborers for his vineyard” (v. 1). The master seeks out each laborer, agrees to pay them a denarius each—a standard day’s wage—and sends them off to work in his fields. At 9 a.m., he ventures back to the marketplace, spots more workers standing idle, and tells them, “You go into the vineyard too, and whatever is right I will give you” (v. 4). They agree and head out. He repeats this process at noon, then again at 3 p.m., and even at 5 p.m., just an hour before the workday ends.

What if the script we’ve been handed is upside down?

Imagine this scenario today: A wealthy venture capitalist spots your potential and decides to fund your start-up dream. Suddenly, you’re #livingthedream, as the popular meme declares. It’s the contemporary version of what Jesus is describing—an invitation to break free from the mundane, to stop living the boring life others dictate, and to chase what you truly love. Perhaps you envision yourself as a rock star, a professional surfer, a ski instructor, an artist, or the founder of a groundbreaking shoe company. The message is exhilarating: Don’t follow someone else’s rules; pursue your passions, chase your dreams.

Steve Jobs is the poster child for this ethos. He dropped out of college, had no formal degree, yet went on to found Apple and reshape the world. In his iconic Stanford University commencement address, watched millions of times, he urged graduates that you’ve got to find what you love. It’s a powerful, liberating story that promises freedom and purpose. But if it’s such a compelling narrative, why do so many of us still feel empty, restless, and anxious? Why doesn’t chasing our dreams always deliver the satisfaction we’re promised?

The Paradox: Not Everything Is So Dreamy

This is where the paradox emerges, and it’s a twist that stops us in our tracks. In Jesus’s story, evening arrives, and the landowner instructs his foreman, “Call the laborers and pay them their wages, beginning with the last, up to the first” (v. 8). The workers hired at 5 p.m., who toiled for just one hour, step forward and each receive a denarius—a full day’s wage. Those hired at 6 a.m., who endured 12 grueling hours in the heat, expect a bigger payout for their efforts. But they, too, receive just a denarius. Predictably, they grumble: “These last worked only one hour, and you have made them equal to us who have borne the burden of the day and the scorching heat” (v. 12).

Their dream—fair reward for their hard labor—falls apart. They’re frustrated, unhappy, and feeling shortchanged. Does that resonate? Chasing our dreams doesn’t always lead to the outcomes we envision. Jesus’s story subtly reveals at least three significant problems with this relentless pursuit.

Problem #1: Whose Dream Is It Anyway?

The first problem is philosophical and cuts deep: Whose dream are you chasing? Think back to high school. You may have been required to wear a uniform, adhering to someone else’s standards. But once you graduate, you’re free to choose your style—or so it seems. In reality, you often trade one uniform for another, dressing to match what everyone else is wearing. When you’re told to “do what you love” or “follow your passions,” you assume you’re acting on your desires. But are you?

In their book Clash!, Hazel Rose Markus and Alana Conner point out a cultural divide: As an Asian kid practicing piano, you’re obeying your parents’ expectations. In Western culture, chasing your dreams feels like freedom, but it’s still conformity to a societal norm. Either way, you’re doing what you’re told—the voices directing you have simply shifted.

Problem #2: The Cruel Joke of Dreams

The second problem is pragmatic and sobering: Dreams can feel like a cruel joke. Remember those childhood pranks, like being told you’re intelligent if you can touch your nose with your tongue? It’s a setup—you can’t do it. Chasing dreams can be just as elusive, a promise that’s nearly impossible to fulfill.

Chasing our dreams doesn’t always lead to the outcomes we envision.

Nassim Nicholas Taleb, in his bestselling book The Black Swan, argues that finding your dream is a roll of the dice, dictated by the tyranny of luck. If you opt for something “boring” like becoming an accountant, your life follows a bell curve—stable, predictable, and safe. But if you chase your dreams, you’re on an L-curve: 99.9 percent of us will fall short, while a mere 0.1 percent hit the jackpot.

Consider Harry Styles versus a random YouTuber with zero views. The gap between them isn’t just talent—it’s luck. Phil Knight, the founder of Nike, admits in his autobiography that while hard work is essential, luck ultimately decides the outcome. Steve Jobs could preach to Stanford graduates about finding what they love because they were privileged enough to ride their luck. But what about the factory workers assembling iPhones, trapped in poverty with no such opportunities? For them, the dream-chasing narrative is a luxury they can’t afford.

Problem #3: You’re to Blame If You Fail

The third problem is critical and personal: If you don’t succeed, the blame falls on you. As a junior doctor working on Christmas Day, I’d see dads hobbling in with broken bones from trying out their kids’ new toys. What was meant to bring joy—a shiny new gift—often ended in pain.

Chasing dreams is sold to us as a path to happiness, but it frequently leads to disappointment. Philosopher Alain de Botton explains that in our meritocracy, where you own your success, you also own your failures. If you don’t find your dream, the story goes, you didn’t try hard enough. The weight of that failure rests squarely on your shoulders, adding guilt to an already heavy load.

The Flip: Gift from a Generous God

How do we escape this exhausting cycle? Jesus flips the script entirely. The vineyard owner responds to the grumbling workers with calm authority:

Friend, I am doing you no wrong. Did you not agree with me for a denarius? Take what belongs to you and go. I choose to give to this last worker as I give to you. Am I not allowed to do what I choose with what belongs to me? Or do you begrudge my generosity? (vv. 13–15)

Then comes the radical twist: “So the last will be first, and the first last” (v. 16).

The story is saturated with “gift” language—life and dreams aren’t things we earn through effort; they’re freely given. Jesus offers three transformative flips to reorient our perspective.

Flip #1: Life Is a Gift to Receive

Life is a gift we receive, not a prize we seize. I’ll never forget the day my wife gave birth to our first child at a fancy birthing clinic—no doctors, just us navigating the chaos. She was in labor, and I was too, running around trying to help but feeling utterly helpless. Friends had warned me: There’s nothing a guy can do when his wife is in labor. Offer water? “Stop asking me that!” Try to comfort her? “Stop touching me!” Everything I did just seemed to make her angrier. So I retreated to a corner with a book, waiting until they handed me the baby. I texted my friends, “We’ve got a baby!” They replied, “Congratulations!”—as if I’d done the hard work. I hadn’t. My wife did it all. That child was a gift I received with overwhelming joy.

Life is a gift we receive, not a prize we seize.

In the vineyard, the workers appear to earn their wages through labor, but in truth, their pay is a gift from the landowner’s generosity. Malcolm Gladwell’s Outliers reinforces this idea: Steve Jobs and Bill Gates succeeded because they were born at the precise moment the computer revolution took off—a gift of perfect timing. Hockey players born early in the school year gain an advantage from their size—a gift of circumstance. We don’t choose our parents, our country, or the schools we attend. Life itself is a gift handed to us.

Flip #2: God Has a Bigger Dream

God has a grander dream for us than we could devise ourselves. At an all-you-can-eat seafood buffet, Asian parents drill it into you: “Don’t eat the bread.” There’s nothing wrong with bread—it’s good—but why settle for it when there’s seafood to savor? It’s fine to dream big—become an astronaut, work as a brain surgeon, or cure cancer. Those are worthy ambitions. But God’s dream eclipses them all: life with Jesus, the forgiveness of sins, eternal life, a new heart, a fresh start, purpose, meaning, hope, and peace. That’s the seafood to our bread, a vision infinitely richer and more fulfilling.

Flip #3: God Pays for His Dream for You

God pays the price for this dream. While living in Chicago, I once took my friend Peter out on the town. I parked my car in a sketchy neighborhood because it had free parking, but he cautioned me, “Don’t park your car here—it won’t be here when you get back.” I argued, “But Peter, it’s free parking!” He pulled cash from his pocket and said, “I’ll pay for the parking.” Should I trust my instincts or Peter, who was willing to back his advice with money?

God’s dream for us is so expensive that he pays for it himself. The vineyard isn’t just a workplace; it’s a symbol of God’s kingdom. Jesus dies on the cross and rises from the dead to secure our place in his family, offering a life brimming with peace, purpose, and hope.

New Question, New Answer

We started with a pressing question: “How do I chase my dreams?” The script we’re given shouts, “Go for it—chase them with all you’ve got.” The paradox whispers back, “Not everything is so dreamy; it doesn’t always work out.” But Jesus flips it entirely: Our dream isn’t something we chase—it’s a gift from a generous God. It’s a gift we receive with open hands, a dream far bigger than our own, and one that God himself pays for through his sacrifice.

As a junior doctor assisting a surgeon, I once had the chance to finish an operation. Toward the end, the surgeon said, “Do you want to close the wound as part of your training?” I eagerly said yes. When I asked, “What suture should I use?” he replied, “It’s your case—do whatever you want.” I chose suture number six, but he gently corrected me, “No, you actually want suture number three.” Doing what I want is good, and there’s freedom in that. But sometimes what’s true, wise, good, and beautiful is even better.

We’re told to pursue whatever we desire, and that’s a fine starting point. Yet Jesus offers something greater—God’s dream for us: life with him, the forgiveness of sins, a brand-new heart, a fresh start, and a place in his vineyard, his kingdom, his family. It’s a dream that’s true, wise, good, and beautiful, and it’s a gift we can simply receive with gratitude.