How to Chase Sky High Dreams: A Pilot's Perspective

With a little perspective, chasing your dreams can be fun, light and the thing that makes you feel fulfilled.

My boyfriend tells me all the time that I inspire him. I love him for that.

He listens on as I play personal growth podcasts or audiobooks. He watches as I wake up before the sun rises so that I can work toward my goals. He takes notice of my meditation practices and roots me on in the garage gym.

He tells me all the time that I inspire him. But the truth is, he’s the reason I do any of this. He’s the reason I believe in chasing dreams in the first place.

Ask us what our dreams are…

A few years ago, the answer to that would maybe have been to get a pay raise. That’s IF we had anything to say at all. We weren’t the dreaming type.

Dreaming up big dreams and going after them—that was for other people, not us. People with money and other resources were the ones that aspired for big lives. We didn’t have resources so what was the point in dreaming then? For us, It was safest to be content with who we were as we were. You can’t fall if you aren’t off the ground.

We did do things like Spartan races. I think that was probably the closest resemblance of ambition that we ever had before. We were content with stagnation. That sounds bad but it’s the truth.

Today, our aspirations are much different than they were before.

Pay raises aren’t even near the top of our goal list (though they are really nice!).

I don’t know what changed us but we are no longer content with living a life half lived. Going to a job day in and day out, answering to other people, making other people money—that sounds like a new kind of hell, to be honest.

Now don’t get me wrong, we are both extremely grateful for our cush corporate jobs. We need to be able to eat after all. And in the event that our dreams crash and burn right in front of us, our cush corporate jobs are the best plan B that we could ask for!

But at some point between then and now, we realized that the only thing that sets us apart from people who achieve massive goals is the belief that they could do it. Somewhere along the way, we changed our minds about what we are capable of and now, we want more.

So what are our dreams?

Me, I’m doing part of it now!

Blogging is so 2008 but I love writing. I’ve loved the process of finding my voice and sharing it with others—I want to keep doing that. I’d like to find a way to help people who may be experiencing similar hardships that I’ve faced in the past—life coaching has crossed my mind a lot. Writing a book one day? Why the fuck not? My dream list seems to be expanding by the day.

He’s going to be a pilot!

Very soon actually. After that, he wants to get a number of other ratings and become a flight instructor. He has high hopes of using his piloting skills for non-profit purposes too. What that looks like is taking shape as he moves through the process but goodness, what a testament to dreaming!

Our ambitions have changed quite a bit in the last few years. From thinking we achieved all we ever could, to dreaming bigger and figuring out how to make it happen.

As I’ve watched him pursue his piloting license, he’s taught me a lot along the way. My ideas around dreaming are very different because of him. Here is what I’ve witnessed along his journey.

Aim high. Really high.

The guy aimed so high he looked straight to the sky.

When he set out to do this, did he know the vernacular to communicate with ground control and other pilots? No. Did he do well in school which meant he would do well in ground school? Nope, he hated school, he didn’t even know studying best practices. Did he ever have to monitor and maneuver 3,000 things all at once in a moving metal vehicle? No, he was a double-tasker at best.

He wasn’t the kind of person that you’d look at and say “There’s a pilot.” He didn’t know the skills it would take to do well, he didn’t even know how to study. He didn’t know these things… YET. But he set his sights so high he knew he had to change who he was, just a little bit here and there, to become who and what he wanted to be.

So when it comes to dreaming, why aim for mediocre? Why set your sights on attaining what you are capable of now? Instead, aim so high that you have to change who you are in order to achieve it.

They said the sky’s the limit and he took that very literally.

Call your shot! Scream it out loud even!

Javi told me about the day he knew he was going to give this piloting thing a shot. He might be embarrassed that I share this story but I think it’s important.

During his morning commute one day, he was listening to The Bobby Bones Show. Bobby talked about speaking your dreams into reality—if you write them down or say them out loud, you’ll have a greater chance of achieving them.

He asked his listeners to say their dreams out loud.

In a car on a highway full of hundreds of other morning commuters, Javi decided to play along.

“I’m going to be a pilot,” he said out loud.

“Again,” Bobby said.

“I’m going to be a PILOT!”

“Again, and louder!” Bobby instructed once more.

“I’M GOING TO BE A PILOT!!” Javi yelled.

Javi yelled at the top of his lungs in a car all alone “I’M GOING TO BE A PILOT” and for the first time in his life, he believed that it might be true. He believed that maybe, just maybe, he might be capable of making it happen.

When he got to work that day, he looked up a local flight academy and set up his first discovery flight…

At the time, I didn’t even know that was a dream of his.

I had no idea that he wanted to be a pilot. I suspect that I never knew that because he never before believed he could become one. But that morning, he called his shot, he said it out loud, then he screamed it. And something changed.

Let’s call our shot—let’s focus so intently on it, let’s get excited about it so much so that we actually start to believe it will come true.

Don’t be fooled by your age.

The day Javi decided he was going to give his dream a real attempt, he was 31.

At 31, most other pilots have been flying for at least a decade. At 31, other pilots have tons of ratings and can fly commercially. At 31, many pilots already own their own planes. For him, at 31, the idea of attempting this had just been born—he’d be starting from square one and very behind the pack.

I’m sure his age prevented him from chasing this dream before. But today, he doesn’t think anything of it.

For him, the achievement of this dream is more important to him than the age he achieves it at. He’d rather say “I did it!” then say, “I wish I would have started at some point.” So he doesn’t compare his journey to that of other pilots, he just keeps flying along his own path, grey-bearded and all.

The time will pass anyway.

Today, Javi is 33. That means he’s been at this for over two years. Many pilots complete receive their license in a single year or even a few months. But Javi has a full-time job which means he can only fly on the weekends. He doesn’t have the kind of money or time on his hands to knock the flight hours out all at once.

He could have gotten discouraged by this. He could have said that it’s taking too long or that there isn’t enough time. But he didn’t. Instead, he kept telling himself, “The timing doesn’t matter. What matters is that I accomplish this.”

So many of us get caught up in how long it will take us to make something happen for ourselves but why? What does it matter if we’re 40 or 50 or 60 years old when we finally achieve what we want? God willing, we’re going to reach that age anyway, might as well get there with a smile on our face and pride in our hearts. The time is going to pass by no matter how we spend it. How do you want to spend your time? Doing or just dreaming and regretting?

You may not have all you need, but you can create it.

During all of this time, this future pilot faced obstacles, mostly when it came to resources.

He didn’t have enough time to study. If you recall, he didn’t even know effective study habits. All he knew was that the textbooks were large and the material was hard—he had to study. But with a full-time job and a long commute, an admittedly needy girlfriend, a social life, and a commitment to his personal health, time was hard to come by.

He didn’t complain though. He made the time.

He’d leave for lunch every day and study in his car where no one would bother him. He would study after work with me by his side on the sofa. Quality time and study time—what a nice little time hack. When he would relax and unwind, he would watch piloting Youtube videos so that he was still learning. He squeezed in as much study time as he possibly could.

But that was just the pen and paper part of becoming a pilot.

He had to find time and money to actually get flight hours in. So he’d save and save, sell some stocks and pay for the hours as he could.

When too much time passed between flights, he’d get rusty. I know he felt disheartened each time he saw how rusty he was. But instead of allowing that to weigh him down, he came up with a solution.

He built a flight simulator.

He didn’t have a computer capable of running a flight simulator. So what did he do? He built that too!

Again, we don’t have the kind of money it takes to do all this. Money isn’t dripping out of our asses as much as I would like that (or wait, would I? gross) So he bought each piece one... by... one...

Each week, there was a new amazon box at our door. They added up. We had enough boxes to build a fort! Instead, he built his computer and flight simulator. Now, when he can’t fly, he goes upstairs and flies in his office. It’s not exactly the same but it gets the job done. He’s rust-free!

We get so caught up in all we don’t have that we forget about what we do have that can help us inch towards are goals. What we don’t have, we can create! I know this is true. I’ve seen it with my own eyes.

Fail and fail again.

Fail as many times as it takes. I know that failing sounds like a weird thing to take away—it’s definitely weird advice to give. But here’s the thing. We will all fail. Likely more than once. The most successful people have the most stories of failure and still, they kept going.

Practice test after practice test—I saw him take the written test too many times to remember. In the beginning, he’d check his score and get upset. 50s and 60s. The textbook part of becoming a pilot was hard and more than his brain capacity would allow.

Yes, he’d get discouraged.

Sometimes, a look of defeat would come across his face and my heart would hurt for him. But he never let it sit for too long. He let his wrong answers provide the direction for what he needed to focus on.

He’d study more and take another test. After a while, he started to churn out 70s and 80s. He’d study more. One day, he said he felt ready to take the actual written test—the one you have to pay cash money for. Again, that isn’t dripping out our butts but he was ready.

He took it in the morning before work one day. I kissed him goodbye and wished him luck just before he set off to the airport. I wondered the whole morning how he was doing.

Several hours later, I got a text.

He scored a nearly perfect score! All his hard work and preparation paid off. Had he let his past test results deter him from taking a new test, he never would have realized how capable he was of passing with FLYING colors.

Failure isn’t the end of your journey, it’s just the opportunity to redo and redirect—only this time, smarter!

Do it, even if you worry about what others think of you.

When he set out on this path, he worried about what other people would think of his dream. He also worried about what people would think of HIM attempting to achieve this dream. He thought that maybe our friends would smile to his face, but secretly think he’s too dumb to accomplish this. Or that maybe people would think he’d never follow through. For those that did believe in him, he worried that he’d disappoint them if he didn’t do what he set out to.

He worried about the opinions of others.

We all do—almost always. Fear could have stopped him. It would have been so much easier to simply be the funny friend that everyone loved vs. the interesting guy attempting to make a career out of piloting. That didn’t stop him though. He decided to do this in spite of caring about what other people thought.

I’m not going to sit here and tell you to not care about the opinions of other people.

I’d be a hypocrite if I did that. I still care so much about what other people think of me. That’s also not what I learned from him. What I learned is that we’ll care about what other people think, maybe a little too much. But we can’t let that be the reason we don’t move forward. We can’t hold back for fear of judgment or disappointing others.

You have to go full force in the direction of your dreams no matter how much you worry about what anyone else thinks. “Go balls to the wall,” as a pilot would say!

Lastly, Don’t worry about the ‘How’ part of your dreams.

I think the most important thing I’ve taken away from watching him pursue his passion is this… He doesn’t get caught up in how scary or unattainable the big picture might seem.

He focuses on one thing at a time, then the next, then the next. One foot in front of the other. If he focused on the biggest picture of his dream, it would seem too massive to attain. It could seem so massive that it may have caused him to pause. So he focuses on what he can accomplish right here and now.

Instead of worrying about how on Earth you’ll make this massive dream become a reality, think of one thing you have the ability to do at this moment, and do that. Cross bridges as they come. The full process will come together in due time.

What have I learned by watching this guy chase his dreams?

So much.

Your dreams are yours and yours alone. They’re put in your heart so that you can go out and work towards achieving them—so that when you do, you can feel an immense amount of pride and gratitude. They’re there to light you up and get you out of bed in the morning. They’re there to show you what you are capable of if you have the belief that you can.

I feel a new kind of fire for life now. Watching him go after something that might seem out of the norm to others has made me realize so much about my own ability to achieve dreams. I get excited to think about what our lives will look like in 5, 10, and 20 years from now! And if nothing... absolutely nothing comes from any of this… we can say we tried. We can say we gave it our best effort and it lit us up in a way he never could have imagined. For that, I am so thankful!

Chasing his dream of becoming a pilot

If you have some pretty audacious dreams of your own, I hope you’re working towards them a little bit each and every day. I hope you’re making yourself proud as you do.

Just remember, aim high, call your shot, don’t worry about your age or how long it will take. Do what you can when you can—make a little progress as often as possible. Do this in spite of how much you care about other people’s judgment. And don’t be discouraged when you fail. It’s part of the process. Fail as many times as it takes. Fail so often and get back up so much so that getting back up feels more normal than staying down. Eventually, you’ll land where you dreamed of.

Happy chasing, ya’ll!