One last-minute decision in Air Force flight school left Rico Racosky filled with regret for years—until it revealed a bigger lesson about choices, identity, and long-term growth. This episode explores how a painful career decision became the foundation for clarity, resilience, and better decisions.
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My guest for Episode #15 of “My Favorite Mistake” is Rico Racosky, a retired 737 pilot for Southwest Airlines, who previously flew jets in the United States Air Force — fighter jets (F-16 and A-7) and transports (C-141). He's the author of the book Just 2 Choices… It's Your Life.
From his bio:
“Rico grew up in a small coal mining town full of self-doubt and lacked a clear direction in life. Along the way to living his dream of becoming a fighter jet and airline pilot, he developed a strategy for clear and effective decision-making that launched his entrepreneurial path, and he’s now determined to share his strategy and impact as many people as possible.”
In this episode, retired Air Force and commercial pilot Rico Racosky joins Mark Graban to share the story of his “favorite mistake”: a last-minute decision to switch his “dream sheet” from fighter jets to transport aircraft. Driven by a logical head-over-heart choice to prioritize military seniority and promotion, Rico spent years grappling with deep regret as he watched his peers take to the skies in F-16s. However, this detour eventually provided him with a global perspective and a unique professional trajectory that he never could have anticipated, proving that even a perceived career disaster can carry a hidden silver lining.
Rico translates his decades of aviation experience—where every moment is a binary of being on or off course—into a universal framework for decision-making called “Just 2 Choices.” He discusses how the same personal discipline required to follow a cockpit checklist can be applied to daily life, helping individuals and business leaders move toward their goals with incremental, positive actions. Whether you're deciding between career paths or simply choosing how to spend your evening, Rico’s insights offer a powerful reminder that our big results are almost always the sum of small, intentional choices.
Video of Rico:
Here is a talk he gave at a Harvard event:
Quotes
!["It was really a painful time [after choosing to fly transports]. And that went on for probably a couple years, until I started to see that something better was coming out of it."](https://www.markgraban.com/wp-content/uploads/2020/11/My-Favorite-Mistake-Rico-Racosky-1.png)
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From Fighter Jets to Final Decisions: Rico Racosky on the Power of Choice
Mark Graban:
Episode 15: Rico Racosky, retired Air Force pilot and retired commercial aviation pilot.
Rico Racosky:
I never, never would have dreamed that would have led to something better. And at the time it was just such a disaster.
Mark Graban:
I'm Mark Graban. This is My Favorite Mistake. In this podcast, you'll hear business leaders and other really interesting people talking about their favorite mistakes because we all make mistakes, but what matters is learning from our mistakes instead of repeating them over and over again. So this is the place for honest reflection and conversation, personal growth and professional success. Visit our website at myfavoritemistakepodcast.com. Thanks for listening and now on with the show.
And I'm really excited. We're joined today by Rico Racosky. In his career, he was first off an Air Force fighter pilot. He is also a recently retired airline captain, and I will try to avoid making bad jokes about our podcast having an on-time departure or an on-time arrival. You do not need to buckle your seatbelt before listening. Rico is the author of a book called Just 2 Choices, and we're going to also have a chance to touch on that today. So Rico, welcome on board. How are you today?
Rico Racosky:
I'm doing fabulous. Thank you Mark. It's an honor and a privilege. I really, really appreciate the opportunity to chat today and I love the title of your show; it is perfect.
Mark Graban:
Well, thank you. I hope the line for security wasn't too long getting into the podcast.
Rico Racosky:
Well, we did have some challenges didn't we?
The Dream Sheet Dilemma
Mark Graban:
So looking back, you know, your work in your career, you know, as we talk about here on the podcast, what would you say is your favorite mistake?
Rico Racosky:
Well, my favorite mistake that has really contributed to even writing the Just 2 Choices book is that growing up, I was interested in art and aviation. I started off going to art school, and at the last minute, got a call from the Air Force for an opportunity to have a flight school slot. Having, oh, let's just say a strong interest in both travel and in flying low and fast and flying fighters—when I went to flight school, it was the night before we made our decisions to put in our choices for which jets we wanted to fly.
It's called your “dream sheet” in the Air Force; you write down which airplanes you wanted. I was all set on going fighters right up to the point I was on my way to bed that night, the night before we had to have the sheet turned in, and I switched over to transports.
Now, the reason I switched over to transports was that I'd already had about two and a half years in the Air Force as an aircraft maintenance officer in the transport arena. And I was looking at creating, you know, staying in the military and making that a full-time career. And so I chose to go the career path because if I switched over from fighters, I'd have lost, let's say, about three years' worth of seniority, so to speak, in the military.
And so I chose at the last moment to head over and actually just fly transports. And after I made that particular choice and I got the assignment—the assignment I wanted for flying transports—and it was time to go to school for transports, by that particular point in time, I just had an enormous amount of regret. An enormous amount of, you know, pain actually as to why I made that particular choice that way, because I really preferred, let's just say it was probably 60/40 flying fighters over flying transports.
By making that switch, I just felt I'd made a really, really big mistake in my life. And fast forward through the rest of my life: the beautiful part about it is that with all the work that I've ended up doing with Just 2 Choices and some other books that I've written, that world travel as a transport pilot for six years before I switched over to flying fighters in the military was just an enormous gift that I never, never would have dreamed would have led to something better. At the time, it was just such a disaster.
I know for some people it might be kind of hard to relate—you know, “it's just an airplane”—that's understandable, but it's something I grew up with as a kid, all my life on the fly and knowing the distinction between those two different kinds of flying. It was really, really a painful time. And that went on for probably a couple years until I started to see all this “something better” that was coming out of it.
I think you probably have a similar approach to things, Mark, and a lot of guests and folks listening have this similar kind of an approach, which is: there's always going to be something good, it seems like, that comes out of something that at the moment seems like a disaster, or it seems like it's not going to work out or you're not going to be able to recover from it. And so the gift to me has always been to use the Just 2 Choices approach: I can complain, or I can look for the silver lining, so to speak. I think that really put me on that path for making sure I always look for the best opportunities to come out of something, even though at the time, it didn't seem like the best thing.
Evaluating Choices in Uncertainty
Mark Graban:
I mean, look, there are often career choices or transition points that we go through. I mean, just to share a little bit about my background, I'm an engineer. I started my career focused on manufacturing for the first 10 years of my career and I thought that was going to be my entire career. And then 15 years ago I had the opportunity to start doing similar process improvement consulting work in healthcare. I thought, well, this could be a mistake, but I thought at the least I'll learn something from that experience so that I could take back—I can get back onto my primary career path.
The thing I couldn't predict is that 15 years later, what I thought might have been a temporary detour into healthcare turned out to be more of a sustained change. So I think, you know, sometimes when we make choices—and I'd be curious to hear your thoughts on this—when making a choice or as you know, we'll talk about your book, Just 2 Choices, maybe you can help with that framework a little bit. How do you help evaluate choices when you're really uncertain about which one is the best for the long term?
Rico Racosky:
Well, I kind of look at it as—and that's why I call it the Just 2 Choices book. And again, that's why I mentioned my background in art. It's a visual; there's a diagram that has—if you were to take your hand and put your hands about 90 degrees and, you know, take the peace sign or a V sign with your fingers and turn it horizontal. The upward vector of the index finger is the choice it's going to take you in, let's just say, the positive direction. And your middle finger pointing down is the choice that's going to take you in the opposite direction or take you in a direction of what you necessarily don't want.
And so that's how I look at it. And that's a great question because thinking back on it now to that day in flight school, the “just two choices” moment, right? When you make one, and there are only just two choices. That's why computers are binary; everything's a zero or a one, it's not zero and one. And so, you know, when you energize one choice, you de-energize the other, so you kind of get a double benefit.
So what I chose to energize in the long term, at a time when I had to make the choice to turn the paperwork in, was the choice that a career in the military was going to be my long-term goal. Prior to that particular point, I was thinking about promotion; I was thinking about upward movement within the Air Force. If I stuck with having been an aircraft maintenance officer on transports—on two different kinds of transports—and then I went and flew the bigger transports, there was also a thing called the C-17 that was coming out at the same time, a new transport jet. I could be an initial pilot on the C-17, all of which translated militarily into promotion.
And so I decided to say I'll go the promoted route. And so that was the long-term choice. It's just that after I had made the choice, I started to have those second thoughts. So to answer your question, the vector that goes up in the upward direction, which I call choice number one, did have that long-term factor in it at the time I made the choice. And then you just have to ride it out. You know, unless you've got a crystal ball or you're psychic, you just gotta ride it out. Does that help in terms of what you were asking?
Mark Graban:
Yeah. Well, and I'm thinking of one other question that comes to mind. Was there a conflict, do you think, between let's say your heart and your head? Like, was your heart in flying fighters, but your head said the rational, better choice, as you were saying from a career perspective, was to switch to transport? Was it like that? Or was it something different?
Rico Racosky:
You know, I think that's a good way to describe it. I think if I look back on it now—and especially having been blessed to have been able to switch over to flying fighters, which is a rare, rare, rare thing—once you've gone the transport route, to be able to switch over and do that and having flown F-16s… it definitely is where my heart is. It's in the speed and the kind of precision that goes into all the thought process of aerial engagements and those kinds of things. I think that is much more of my nature over transports, although I do love world travel and there are fabulous people there. I wouldn't trade it. It's just that, to answer the question, yeah, the heart is probably more in that fighter range.
Managing Regret and Moving Forward
Mark Graban:
So as you're going through—you described those years of regret—what was your strategy for sort of trying to manage that regret or cope with it? Was it a matter of reminding yourself why you made that choice to switch to transports, or what else did you do to just help manage your feelings about that?
Rico Racosky:
Well, at first, because I had been in the Air Force for about two and a half years as a non-flyer, I kind of knew how the system works. So at first, I tried to work within the system to get them to change the assignment. And if you believe in divine intervention, every call I made to the different fighter people who coordinated those kinds of assignments… I just missed the cutoff. You know what I mean? It was like, “Ah, if you'd have called last week, we could have switched you.”
So I think it kind of made me laugh and say, well, I guess there's more to this than what I'm seeing, because there were several phone calls where it was just, “you just missed it, man.” And so that kind of settled things in, but that was my first response for dealing with the situation and the stress and the conflict within myself.
And then, overall, I'm a positive guy. So it wasn't serving me well to stay in a negative state. So it was one of those things where the Just 2 Choices idea didn't come until many years later, but basically I was using that process to sort it through and to help myself continue to choose to feel better and incrementally better about the outcomes. And like I said, going all over the world? Not a bad gig. Especially with the way the military gives you the keys and says, “Call us if you've got a problem, but get this stuff there.” So yeah, it was very, very tremendously rewarding.
Art vs. Aviation: The Choice Points
Mark Graban:
Now, you had mentioned earlier your interest, if not aspirations, in arts. Looking back and maybe weaving in your Just 2 Choices framework, you have this choice of pursuing arts or pursuing aviation. I can share a little bit more about myself—growing up as a kid, I was really into music. I played drums and percussion, and I was really serious about it. I had a choice of pursuing music or pursuing engineering. I chose engineering and I don't have pain or regret over that. But I was curious: how do you look back at your choice?
Rico Racosky:
Well, the one thing I did know was—even as an 18-year-old kid—I figured out that it's rare to get another opportunity to go fly for the military. And so art was something that it seemed to me that if flying didn't work out, I could always go back to doing art or pursuing art. And so that's what drove that decision.
I'm from a small coal mining town and steel town in Western Pennsylvania, just a couple hours from Pittsburgh. I knew intuitively that I always wanted to travel. I knew that I always wanted to see more than my hometown—and I love my hometown and I love my relatives and the people I grew up with. It's just that I felt there was something bigger out there in the world and I wanted to see what it was like. And so all of that rich aspect tap is what helped that “just two choices” moment be the choice when the aviation opportunity came.
So I mean, how about you? What was your choice point there that drove the one direction?
Mark Graban:
I was influenced heavily by my father, who is an engineer. Music would have been—I have friends who are professional musicians and it is a really tough living. And I had the opportunity to continue enjoying music as a hobby. I was in the marching band; I was very heavily involved in music through college and that's dwindled. I still have a pair of drumsticks here in my office, but I think part of that “no regrets” is like, I don't think I had the passion.
What I had learned when I was a senior in high school—I was taking private lessons with a graduate student at the University of Michigan—and this really sealed it: I had enough talent to do really well and to be the best drummer in my high school and to enjoy playing with minimal practice. I enjoyed performing. This graduate student from Michigan basically opened my eyes to the fact that if I did not love being alone in a practice room for hours upon hours every day, then it wasn't for me.
Rico Racosky:
Yeah, no, I hadn't thought of it that way. That's a great way to put it; I can relate to that very well.
Mark Graban:
And I think that's different than saying I'm lazy, but that idea of being so alone and having to be that dedicated to that craft was… I decided that was not for me. And I think that was the right decision.
Rico Racosky:
Yeah. And so, the thought that crosses my mind is: how far do I want to take this? At the time, how far do I want to take my art? How far do I want to take my aviation? I wanted to take my aviation as far as I could take it. And now, the layout of the book has a lot of art and graphics in it. And so now I'm satisfying that artistic side of myself. And the great part of it is there's just so much more I can do.
Actually, the thing I look forward to most is being able to do animation of a lot of the topics that I'm working on. But the technology wasn't there back then to be able to step into that. And so now it's almost like the aviation gave me that springboard and interfaced with technology and those thoughts, and now the art has kind of caught up to being able to graphically design 3D models of choice and Just 2 Choices.
Aviation Safety and the Discipline of Choice
Mark Graban:
If you'll forgive me, one more question about aviation. One of the themes on the podcast here is learning from mistakes and that we all make mistakes, but clearly in aviation, there are a great number of mistakes that could end up being deadly. So I was wondering what your thoughts are about preventing mistakes and some of the things that aviation does to be so effective at preventing major mistakes.
Rico Racosky:
I think you summarized it real well. That's exactly what aviation safety is about: think first of the consequences of the choice that you're about to make. Somebody asked me one time, “Do you fly an airplane with just two choices?” And I said that's the only way to fly an airplane, because you're either making the jet perform within the parameters it's meant to perform within—either using the simplicity of airspeed, altitude, or direction—it's either on course or it's off course.
And then to what degree are you going to allow the jet—because it's under your control—how far are you going to allow the jet to go either off altitude, off airspeed, too fast, too slow, too fast in terms of fuel consumption, or miles off course? And so that very much of what you just described is what goes on in aviation all the time. It's just two choices, and where are you going to catch that aspect that keeps the situation from exacerbating to something that could create a lot of problems?
Mark Graban:
And it seems like there's—from what I've talked to other pilots about—obviously training and focus on communication and teamwork and breaking down hierarchy. My work in healthcare often brings me across hospitals and surgeons who are trying really hard to learn from aviation because of the advances in safety and how the track record has gotten so much better over recent decades. It does seem like on another level, when there is a really bad event, there is a strong focus on learning from that event and pulling it apart.
Rico Racosky:
Yes, and I'd say one thing with aviation and healthcare is our use of checklists. Whether you're putting a person on the moon or you're just flying by yourself, the checklist really drives keeping things as tight as possible. When I say “tight as possible,” I mean that you're going to be within the parameters of the performance of the airplane that allows you to fly safely and minimize the risk of something catastrophic happening.
And yet there's still that human factor. If you're the kind of person who really doesn't have the personal discipline to care about the checklist, then you're probably not a person who would be a good person to fly with, because it's all about being able to have that personal discipline. But then that goes to engineering, that goes to music; that same kind of discipline idea applies to those things, too. And as they are “just two choices” moments, every one of those: what level am I going to participate in this music? What level am I going to participate in this engineering? Or am I going to participate in this flight?
The Origin of “Just 2 Choices”
Mark Graban:
So as we wrap up here—I guess we're starting to prepare for arrival—what led to your writing of the book, Just 2 Choices, and who is the book for?
Rico Racosky:
It's for broad choices in everyday life, although I'm starting to tailor it toward the business side of things as well. If you're a CEO of a company and you want to make sure that your vision and your mission are understood all the way to the frontline level, then the Just 2 Choices model is a way of being able to translate your vision and mission. So at the frontline, the people who are eyeball-to-eyeball with your customers are making the kind of choices that are consistent with the vision and mission of the company.
Overall, the book itself is a general thing because it was birthed in a lot of ways by aviation visuals. When you look in the cockpit, there are hardly any words; they're just visuals. You fly by graphics and you know exactly where to move your controls and stuff. And so that's how the book is laid out.
But there's another factor: I was working for about 15 years with elementary school kids on goal setting, teaching a process called “Dreams + Action = Reality.” For many years, I'd say, “Hey look, there are just two choices. Which choice of action are you going to take? Is that action going to take you closer to what you want, or is it going to take you further away from what you want?”
I kept saying “just two choices” over and over again, and that evolved into the book because I was going, “Oh, all of life is just two choices,” no matter what we do—our health, our wealth, relationships, career. Every moment we just have to, as I was listening to Karyn's broadcast, realize it's the little choices that all add up to the big results. Pay attention to being in the moment and making the choice now, and then you won't have to make a drastic choice later.
Mark Graban:
I think about the choices I'm going to have ahead of me this evening. I have a choice to exercise or not exercise. I have a choice of eating something healthy or not eating something healthy. I also have a choice to go sit and watch the hockey game instead of exercising. Maybe I can figure out how to do both, but there are two choices, right? As you frame it: a choice that takes us to our goal of let's say health, or a choice that takes us away from that goal.
Rico Racosky:
Can I add one thing there? Because you just inspired another thought. I'm of the similar philosophy, which is: all right, I'm not going to go do an hour workout, but I am going to do something for 10 or 15 minutes, and I'm still going to watch the hockey game. Or I'm going to do situps while I'm watching the hockey game. It's the incremental stuff that allows us to create those new habit patterns that build the momentum. That's the shift in the long run.
Mark Graban:
Yeah. It seems like lots of little good choices prevent the need for a really difficult, “good” choice down the road.
Rico Racosky:
Yes. The big “high ocha” at the last moment. Yeah.
Closing Remarks
Mark Graban:
So again, our guest has been Rico Racosky, author of Just 2 Choices. Rico, how can people buy the book, learn more, and connect with you online?
Rico Racosky:
Well, thank you Mark. Just go to Just2choices.com. Actually I've got three free downloads if you go to Just2choices.com/radio. You can get the welcome and chapter one for free, and then you can also get the Just 2 Choices diagrams that you could actually cut out and paste around your house. One of them will show you how to make positive choices toward a new and better direction as opposed to getting hooked back into your same old choice that gets you into that frustrating place. Or if you're thinking about whether you should go after something or not, there's another visual there. You can just download all those at Just2choices.com/radio.
Mark Graban:
Well great. Well thank you Rico and thank you for those giveaways. I'll put the link to that in the show notes and encourage everyone to go check that out.
So I feel—I haven't been flying as much recently because of the pandemic, but my brain is making me say something like: I know you have a lot of choices of where to come on as a podcast guest, so thank you for choosing My Favorite Mistake. To our listeners, I know you have a lot of choices about what to listen to, so thank you for joining us here. I don't have a loyalty program; maybe I'll have to look into that.
Rico Racosky:
Well, there you go. That's a great idea.
Mark Graban:
So again, Rico Racosky. Thank you for being a guest and thank you for being a good sport with my attempts at airline talk.
Rico Racosky:
Well, it's an honor and a privilege, Mark. Thank you for having me on the show. I really, really appreciate it. God bless you. Thank you.
Mark Graban:
Thank you. Thanks for listening. I hope this podcast inspires you to pause and think about your own favorite mistakes and how learning from mistakes shapes you personally and professionally. If you're a leader, what can you do to create a culture where it's safe for colleagues to talk openly about mistakes in the spirit of learning? Please subscribe, rate, and review the podcast. Our website is myfavoritemistakepodcast.com. See you next time.
This episode explores a career decision mistake and how reframing choices can lead to unexpected growth. Listeners will learn how pilots—and leaders—can make better decisions before mistakes become irreversible.