The Dream-Chaser’s Milestone Dilemma
There’s a feeling I’ve had for the past year that I haven’t been able to articulate until now. Maybe you’ve felt it too - especially if you’re pursuing a creative field where the payout is non-linear.
I’m calling it the “dream chaser’s milestone dilemma.” It’s that feeling of ambivalence when you watch the people closest to you - usually those with salaried, full-time jobs in less-expensive markets - do things like get married, buy homes, and have kids. These milestones feel like a world away when you’re chasing a creative dream that takes a decade(+) to pay off. And it’s not a pleasant feeling.
Here’s the good news though… I’ve also found the cure for it.
What Is The Dream-Chaser’s Milestone Dilemma?
Here’s the definition I’ve made up from scratch. If you don’t like it, well, sorry-not-sorry.
Dream-chaser's milestone dilemma (noun):
The feeling of ambivalence, conflict, and uncertainty that creative individuals experience when they watch their friends and family hit traditional “adult milestones” like getting married, buying a home, and having children, while they themselves are still pursuing their creative dreams.
This dilemma can be caused by a number of factors, including:
The financial insecurity that often comes with pursuing a creative career. Creative individuals often have to work multiple jobs or take on freelance gigs in order to make ends meet. This can make it difficult to save for a down payment on a house or start a family.
The delayed payoff of creative endeavors. It often takes time and many iterations before creative products and services start to generate income. This can make it hard to continue to delay gratification in the hopes of an outsized pay day later on.
The uncertainty of the creative process. Creative individuals often have to deal with rejection, disappointment, and setbacks. This can make it difficult to know if they will ever achieve their dreams.
The pressure to conform to social expectations. There is a lot of pressure on creative individuals to “grow up” and get a “real job.” This pressure can make it difficult to stay true to their dreams.
Not a bad definition, right? For all these reasons, it’s hard to keep going.
But I do have a cure. If you’ve ever considered quitting the path to pursue a more “conventional” life, don’t do so without inverting the problem. Look across the fence to see if the grass is really greener on the other side…
How Do People Live Like That?
There’s a video I found that perfectly articulates where I land on the dream-chaser's milestone dilemma. The video is of Jerry Seinfeld (JS in the transcript below) talking to a fellow (but “unknown”) comedian backstage at a comedy club.
The young comedian (YC in the transcript below) tells Jerry he’s been struggling for 10 years to “make it.” And it’s been hard watching his friends make money and hit milestones that are achievable along a more conventional career path. He wonders if he made a mistake.
Here’s the exchange:
JS: This [stand-up comedy] is such a special thing. This has nothing to do with ‘making it.’
YC: But did you ever stop and compare your life? I see my friends, and they’re making a lot of money. They’re moving up. They’re all married. They’re all having kids. They have houses. They have a sense of normality.
JS (making a disgusted face): Let me tell you a story. This is my favorite story about show business. Glenn Miller's orchestra is doing a gig...They can't land the plane because it's winter, a snowy night—they have to land in this field and walk to the gig. They're dressed in their suits. They’re carrying their instruments. They’re walking through the snow—it's wet and slushy.
And in the distance, they see this little house…They go up to the house and look in the window. Inside they see this family. There's a guy and his wife — she’s beautiful. There's two kids, and they're all sitting around the table. They’re smiling. They're laughing. There's a fire in the fireplace...
These guys are standing there in their suits. They're wet and shivering, holding their instruments, and they're watching this incredible Norman Rockwell scene.
And one guy turns to another guy and goes, ‘How do people live like that?’
That's what it's about.
Here’s the video:
Do You Really Have What It Takes To Live A “Normal” Life?
Can you ever really go back to the steady-eddy, monotony of “normal” life? Especially after having experienced the adrenaline rush (in both good times and bad) of having skin in the game? Of putting your heart and soul into something and letting the market decide if you’re worthy? Of being in control of your time?
As Naval Ravikant says, “A taste of freedom can make you unemployable.”
That’s what happens when you get a taste of real life… when you find something that lights you up… when you realize you have the power to create something from nothing.
Sure, you may go back for stretches - when absolutely necessary. But you are changed, my friend. You can never forget. You can never go fully back. Because you know what it’s like to bite into life and let the juice run down your chin.
So when the dream-chaser’s milestone dilemma starts to creep up inside you, remember that the grass isn’t always greener. You can go back to a “normal” life, but you won’t be alive. And when you’re 90 years old looking back at your life, all that will matter are the regrets you carry with you.
And those are under your control right now.
Thanks for reading.