Dreams tend to get the Hollywood treatment.
We see the entrepreneur ringing the bell on Wall Street, the athlete holding the trophy, or the newly minted executive walking into the corner office. We see the moment when years of ambition finally become reality.
What we don’t see nearly as often is the car wash.
Or the online classes. Or the failed test. Or the DoorDash deliveries made because bad weather meant you couldn’t earn money doing the job that was supposed to get you to the next job.
Those are part of the dream, too.
Benjamin Bressler knew what he wanted to do when he was 10 years old. A family friend owned a small four-seat airplane and took Benjamin and his father flying for his birthday. Benjamin even got to take the controls, with plenty of assistance.
He was hooked.
“I knew this is absolutely what I want to do,” Benjamin remembers.
More than 15 years later, he is flying professionally as a first officer for a regional airline.
The distance between those two points is what makes his story interesting.
A Dream Isn’t a Plan
There is nothing wrong with telling people to dream big. We should.
But dreams become useful when we start attaching actions to them.
For Benjamin, becoming an airline pilot required years of flight training, certifications, studying, testing, and building the flight hours necessary to qualify for an airline cockpit. It also required money — lots of it.
So, while friends his age were experiencing a more conventional college life, Benjamin chose online college because it was less expensive and gave him the flexibility he needed. He worked primarily at a car wash while simultaneously going to school and paying for flight training.
For several years, he describes his life as essentially three things: work, college, and flying.
There was a social cost. There was a financial cost. And there were moments when the payoff remained years away.
That distinction matters because persistence isn’t simply wanting something badly enough.
The American Psychological Association defines persistence as maintaining a course of action despite obstacles, discouragement, or the effort involved. Research also suggests that people are more likely to reach goals when they regularly monitor their progress toward them. In other words, ambition works better when the distant destination gets translated into smaller, measurable steps.
Benjamin wasn’t simply trying to “become an airline pilot.”
First, there was a private pilot certificate. Then additional training and ratings. Then instructing. Then accumulating hours and experience. Then airline training.
One runway at a time.
Failure Is Part of the Flight Plan
And sometimes things go wrong.
Near the end of his training for his private pilot certificate, Benjamin failed his first check ride.
The technical reason was relatively minor. The emotional impact wasn’t.
“I definitely had some serious self-doubt in the days after that failure,” he says. “Can I? Am I really cut out for this? Can I really do this?”
That question isn’t unique to pilots.
It happens after the business doesn’t take off, the promotion goes to somebody else, the prospect says no, the investor passes, or the career change turns out to be harder than expected.
Failure has an interesting way of transforming a long-term question — Where am I going? — into a much more immediate one: Do I really want to keep doing this?
Benjamin did.
A couple of weeks later, he retook the check ride and passed.
The lesson isn’t that perseverance guarantees success. Life doesn’t offer that contract. It’s that a setback provides information, not necessarily a verdict.
Sometimes Success Calls While You’re Delivering Dinner
Years later, Benjamin had become a flight instructor, building the hours and experience he needed to reach the airlines.
There was another problem: weather.
If conditions were bad, he couldn’t fly. If he couldn’t fly, he often wasn’t getting paid. So, Benjamin started making DoorDash and Uber Eats deliveries to supplement his income.
Then, one day, while making a delivery, his phone rang.
It was an airline.
He had the job.
Not only that, but he already had a class date to begin airline training.
“I was actually shaking,” he recalls. “I got the call.”
There’s something wonderfully appropriate about the timing.
The call confirming the dream didn’t arrive while Benjamin was sitting in an airplane. It arrived while he was doing one of the decidedly unglamorous things necessary to keep pursuing it.
That’s how many accomplishments actually happen.
The highlight reel comes later.
Turn Left
Benjamin describes another moment that might resonate with anyone who has spent years imagining themselves somewhere they haven’t yet earned the right to be.
On his first trip as an airline pilot, he walked through an airport he had traveled through countless times as a passenger — except now he was wearing the uniform.
Then he approached the gate before boarding had begun, scanned his badge, and walked down an empty jet bridge.
He stepped aboard the aircraft.
Instead of turning right toward the passenger cabin, he turned left toward the cockpit.
After roughly 15 years of imagining that moment, he belonged there.
Mostly.
“Two words: imposter syndrome,” he jokes about wearing the uniform for the first time.
Maybe that’s another useful lesson about achieving something meaningful: confidence doesn’t always arrive at the same moment as competence.
Sometimes you have to grow into the place you’ve already earned.
The Dream Is Just Happening
There is a temptation to put a neat bow around stories like Benjamin’s.
Dream accomplished. Roll credits.
Except that’s not how he sees it.
During a rapid-fire round on On the Right Stack, Benjamin was asked whether his dream was “achieved” or “just happening.”
His answer was immediate:
“Just happening.”
That’s probably the best definition of a worthwhile dream.
Benjamin wants to upgrade to captain. Eventually, he’d like to move to a major carrier and fly internationally. There are new airplanes to master, new destinations to reach, and new milestones ahead.
The original dream didn’t disappear when he achieved it.
It got bigger.
And perhaps that’s the universal lesson in his story.
Dreams matter. But the people who eventually live them are usually the ones willing to turn them into a series of decidedly undreamlike things: work, sacrifice, learning, failure, adjustment, and another day of showing up.
Sometimes that means studying when you’d rather be somewhere else.
Sometimes it means retaking the test you failed.
Sometimes it means delivering somebody’s dinner while waiting for the phone to ring.
And sometimes, after years of turning the dream into work, you finally walk onto the airplane — and turn left.
Stories like Benjamin’s are worth telling — not because the ending is a fairy tale, but because the middle is so relatable. Part of why we do this work is to hand something useful to the people coming up behind us: proof that the car wash shifts and the failed check rides and the DoorDash runs aren’t detours from the dream, they’re the road to it.
Hear Benjamin Bressler’s full conversation about dreams, setbacks, sacrifice, and the surreal experience of becoming a professional airline pilot on On the Right Stack, available on your favorite podcast platform and at Right Stack Advisors.