WHAT’S YOUR CAREER WORTH? 2026 UPDATES – AIRLINE COMPENSATION & TRENDS WITH KIT DARBY

May 4, 2026 | Podcast Episodes

What Is Your Pilot Career Really Worth?

When pilots talk about compensation, the conversation usually starts with hourly pay rates, and that makes sense. Rates are visible, comparable, and easy to track, but as airline compensation expert Kit Darby explains, focusing only on pay rates misses the bigger picture. The more important question is far more fundamental: What is your career actually worth, and what are you doing with it?

That question is at the heart of this conversation, which remains just as relevant in 2026 as when it first aired. While pilot pay remains strong, aviation hasn’t stopped being cyclical. Fuel costs, aircraft delivery delays, hiring slowdowns in certain segments, and broader economic pressure all serve as reminders that high income alone doesn’t guarantee long term security. What matters is how that income is turned into stability, flexibility, and options.

A Life Spent Inside the Numbers

Few people are better positioned to answer questions about pilot career value than Kit Darby. With more than five decades of aviation experience, spanning military flying, multiple airline careers, teaching, consulting, and expert witness work, Kit has seen every phase of the cycle.

He’s flown through recessions, strikes, bankruptcies, mergers, booms, and busts. He’s also spent decades modeling what pilot careers are worth in real dollars, often for legal cases involving injury, lost medicals, or wrongful death. That work requires precision, and the results are eye opening.

Why Pilot Compensation Has Changed So Much

Pilot compensation today looks very different than it did just a decade ago, especially at the regional level. Five or six years ago, some regional airline pilots were starting at $23,000 per year, but today, starting pay around $100,000+ is common. Regional captains can exceed $250,000, and in some training or high demand roles, compensation can push even higher.

This dramatic change wasn’t accidental. It was driven by a genuine and sustained pilot shortage. According to Kit, the U.S. aviation system is currently short around 24,000 pilots across airlines, corporate aviation, and the military. Early retirements during COVID, training bottlenecks, and long term demographic trends all converged at once, without the usual “reset” of a recession to slow hiring. Shortages drive leverage, and leverage drives compensation.

The Hidden Power of Retirement Benefits

While pay rates often grab headlines, retirement benefits are where airline careers truly separate themselves from many other professions.

At the major airlines, company paid retirement contributions have reached levels that are rare in today’s workforce. Historically airlines contributed around 16% of pilot compensation toward retirement, but new contracts are pushing that figure to 18% fully company paid, with no employee match required.

To put that into perspective, the average American worker with a 401(k) typically receives a 3–5% employer match, which requires employee contributions.

For airline pilots, this means:

  • Retirement contributions that are several times higher than the national average

  • Contributions applied to incomes that are already well above average

  • Decades of compounding growth over a 25–35 year career

This is where many pilots underestimate the true value of their compensation package. Retirement benefits are not just an added perk, they represent a substantial component of long-term career wealth and financial security.

What Is a Pilot Career Actually Worth?

When Kit builds career value models, he looks far beyond hourly pay alone. His analysis incorporates total compensation over time, including monthly flying averages, retirement contributions, medical and insurance benefits, travel privileges, and realistic career progression assumptions such as seat upgrades and longevity.

For example, a 40-year-old American Airlines pilot with 25 years remaining until mandatory retirement at age 65 may have an estimated remaining career value of approximately $10 million in today’s dollars. Importantly, that estimate is based on conservative assumptions, including a captain upgrade around year 11, long-term retirement growth of roughly 5%, and no reliance on unusually favorable contract improvements or aggressive investment projections. For many pilots, the actual number could be even higher.

YOUR CAREER HAS A NUMBER ATTACHED TO IT, WHETHER YOU’VE CALCULATED THAT NUMBER OR NOT.

High Income Is Only the Starting Point

One of the most important themes from this conversation is that earning a high income is not the finish line, it’s the foundation. The real opportunity lies in how that income is transformed into long-term stability, flexibility, and financial independence.

For pilots, this means building more than just a strong paycheck. It means creating financial resilience through disciplined cash flow management, maintaining liquidity outside of retirement accounts, and building diversified investments that provide options when the industry inevitably changes.

The risk is assuming today’s conditions will last forever, relying on maximum flying hours, locking away every dollar in retirement plans, or building a lifestyle that depends on peak earnings indefinitely. Aviation has always been cyclical, and history consistently reminds us that downturns, slowdowns, and disruptions are part of the business.

The goal is not simply to earn more. The goal is to use today’s opportunities to create lasting flexibility and security for the future.

Cycles Are Not a Theory, They’re a Fact

Kit describes aviation as a “sharks teeth” industry, a business defined by repeated cycles of expansion and contraction. Throughout history, pilots have experienced furloughs, bankruptcies, strikes, mergers, pandemics, hiring booms, and sudden slowdowns. While today’s compensation environment is exceptionally strong, aviation has always been cyclical, and there is no reason to believe that reality has changed.

COVID was unique in one important respect: unprecedented government intervention through the CARES Acts helped prevent furloughs on a scale that would normally have occurred during such a severe downturn. Without that support, tens of thousands of pilots likely would have lost their jobs temporarily. That level of intervention was extraordinary, and there is no guarantee it will happen again in the future.

For pilots, the lesson is clear. The objective is not to perfectly predict the next downturn, slowdown, or disruption. The objective is to be financially prepared for it when it eventually arrives.

The Real Question Every Pilot Should Ask

When you step back, this conversation isn’t really about contracts or compensation tables, it’s about intent.

The questions you should ask:

  • Do you know what your career is worth?

  • Are you protecting it?

  • Are you using today’s income to give your future options?

  • Could you reduce flying, absorb disruption, or pivot if you needed to?

If the answer to those questions is unclear, that’s not a failure, it’s an opportunity. Because a pilot career is incredibly valuable, but value only matters if it’s managed intentionally.

As always, I love hearing from you. Send your questions to info@pilotsportfolio.com, and we’ll get them answered in an upcoming episode.

Until next time, thanks for listening, and thanks for reading.

TRANSCRIPT

[00:00:00] Tim: Before we jump into today’s conversation, I wanna give you a little context. This is a re-release of one of our most popular episodes at an earlier conversation with Kit Darby, the airline compensation expert. And the reason we’re bringing it back is fairly simple. The core question has only become more important with time.

What is your career actually worth? When this episode first air pilot compensation was moving quickly, contracts were being reset, the pay at the regionals has changed dramatically through LOAs. The post- COVID hiring surge was still shaping the industry. Now, looking at it through a 2026 lens, the picture is, I’d say, a little bit more nuanced, right?

So pilot pay is still strong. Retirement benefits are still a major planning opportunity. Long-term demand for pilots is still very real. We’ve all seen the studies, but we’re also seeing pressure from fuel cost, aircraft deliveries, slower hiring in parts of the market, and renewed reminders that aviation is [00:01:00] still a cyclical business.

So as you listen to this conversation, I don’t want you to just to think about the big compensation numbers. I want you to think about what those numbers are supposed to do for you. So high income is powerful. It should help you build resilience. It should, of course, help you build a strong foundation, and quite frankly, we all go to work so we can do the things that we enjoy doing with the people that we love.

So it should be helping your family as well. And so you wanna make sure that your strong income is giving you these options, not only when times are good, but when the industry changes, and that’s what this episode is about.

You’re listening to The Pilot’s Portfolio, the show dedicated to guiding professional pilots towards a future of financial success and stability. Fly along with your host, Timothy P. Pope, as he provides financial planning insights and answers to your burning questions and dives into real life stories from fellow [00:02:00] pilots who share their successes and cautionary tales.

The pilot’s portfolio takes off now.

Kit brings over five decades of active aviation experience and over three decades of aviation consulting experience specializing in the area of pilot compensation. For the past 15 years, Kit is president of Aviation Consulting, LLC, where he specializes in litigation support for you guessed it, pilot career earnings.

So there is nobody better to talk about airline pilot compensation. If there is an authority on the subject, it is Kit Darby. So with that, let’s jump in to this conversation with Kit Darby from KitDarby.com and Aviation Consulting, LLC. And be sure to stick around to the end where I’ll break down the top three things that I want you to think about from today’s conversation.

Let’s jump in. [00:03:00] Kit Darby, welcome to the program. We’re happy to have you on the Pilot Money Podcast. 

[00:03:04] Kit: Glad to be here. Thanks for the invitation. 

[00:03:06] Tim: I’d love for you to share a brief background of your aviation experience. I see that you have over 23,000 hours that spans military and civil. So I’d love for you to walk the listeners through where you’ve been in aviation and where you are today.

[00:03:20] Kit: Well, I, uh, entered the service out of college during the Vietnam War, not exactly my choice. Went off to Army flight school. They had, uh, mostly helicopters as they still do, but they had a fixed wing section and I got some advice from a existing Army pilot to hold out for fixed wings. I became a fixed wing army pilot.

I did that for seven, eight years. Never actually went to Vietnam. I was supposed to, but, uh, they sort of started cutting back. So I stayed back, became an instructor, got lots of flight time. And as I was getting out, I was looking at the airlines. And right when I got ready to get out initially in 76, there was sort of a recession [00:04:00] going on, so I stayed a couple of years and got out in 78.

At that point, I got out, went to work for Braniff. I got my engineer ticket and a type rating, uh, on the GI Bill and then got my … I got hired by Braniff worked there as a DC8 engineer and DC8 copilot in just nine months. But they grew rapidly and eventually failed. At that point, I worked in a family publishing business, which sort of got me into this part of it where I’m, you know, providing information.

Joined the Georgia Guard, flying my military airplane, the, uh, OV1, and, um, got hired the second time right by Republic, which was, of course, eventually merged into Northwest. But I didn’t know that. I didn’t know they were … Who they were gonna merge with. Their leader was a, a known mergermeister, so I was, uh, pretty sure they were gonna merge, and I couldn’t be sure with who.

So I went back in the job market, and, uh, I got hired by Capital for a little while, which was a, a military charter that went scheduled after Vietnam. And I was a [00:05:00] DCA co-pilot and even a captain there in about a year. But they weren’t a career position. So I was applying to the major airlines. I got hired by Piedmont, eventually merged to US Air, but I did not, uh, stay there.

I also applied to United, which was a larger company with much better retirements. And I went to United. Uh, they had a strike in 85, and I was in the process of selection and training, and I elected not to cross picket lines in a primarily unionized business. So I got to work in more like 86 and, um, spent 23 years there, progressed through the airplanes, retired as a 767 captain in 2007.

And then, uh, went to work for Boeing, teaching here in Atlanta at the Airtran Training Center on the 737 and eventually the 717. The 717s went to Delta, and I was fortunate enough to go with them. So I spent 10 years at Delta after retirement at [00:06:00] age 60, first, initially on the 717, and then I began teaching the ATP CTP course, which is a new course required to get your ATP in the multi-engine airplanes.

I did that for 10 years, and, uh, now I’m teaching that same course at, uh, a smaller school, uh, Sanders Aviation, teaching the ATP, CTP. So along the way, I got into the resume business and then the information business with a company called FAFA, Future Airline Pilots at the time, became future aviation professionals.

Worked there, grew the business from, uh, 300,000 to 3.6 million. Had a falling out with my partner, left, started my own. Uh, it grew to the, about the same size, four million or so, and nine eleven hit, and that was coming pretty close to my retirement age. So I downsized the business, and now it’s myself and a few retired captains and resume writers, and we are a, a much smaller business.

The, the business at its [00:07:00] peak was 20,000 members. 80% of the people hired were members of the company, civilian or military. But today, it’s just a few of us, and we, we do resumes, application reviews, interview prep. And we’ve always maintained this salary survey, which was one of our most popular products at FAPA and as well at Air Inc.

So what we do is turn those salary surveys into, uh, earnings models or earning capacity. My main job as an expert witness provide career values for pilots injured, guilt, delayed. That’s my main business. Although I still teach on the side and work with individual pilots, we pay the bills with the expert witness work where we determine career values for current pilots.

We work airlines primarily, but we also do corporate, smaller airlines, military, uh, various number of career options for professional pilots. 

[00:07:52] Tim: Let’s talk about the salary work. And I love this because you’ve seen all kinds of ups and downs, right? You can bring [00:08:00] contacts to the salary conversation. So for the past 14, 15 years, you’ve been running aviation consulting.

You just mentioned, you know, a focus on airline pilot compensation. Can you talk to us about what is going on in the airline compensation environment right now? 

[00:08:18] Kit: You’d have to call it a wild and crazy time. Typically, you know, airline pilots do better when their airlines do better, and they were out of extended profitable period going into COVID.

The typical business cycle is seven to 10 years, and at COVID, we were 11 years without a recession. It was time, you know, nobody knew what the cause would be. And then coming out of COVID with the shortage, which developed from a whole variety of factors, we’d actually seen the shortage coming several times before, and each time we were saved by a recession or SARS or some other event would ease the market and the, the severe shortage didn’t develop.

But in this time, we [00:09:00] retired 5,000 pilots early, and we haven’t been saved by another downturn. So we are seriously short of pilots. I estimate, uh, in the US, looking across airlines, corporate, military, we’re probably 24,000 pilots short right now today. There are 500 airplanes at the regionals park. The majors wanted to expand 10 or 15% this year.

They couldn’t do that partially due to a lack of pilots. So there’s a real shortage, and shortage, of course, drives up wage and benefits. So on the low end, on the regional airlines where they didn’t make hardly anything, you know, it’s five or six years ago, the starting pay was 23,000, which is clearly not a living wage for a professional.

And today, it’s 108, so it’s gone up 400% starting pay, 108. And the captains maxed out at 120 or so. Today, they maxed out at 250, and if you were a instructor or in demand position, it could go as high as 350, which is [00:10:00] pretty comparable to major airline pay. I mean, the pay has come up so much that it’s, could be a career option for many people.

[00:10:06] Tim: So let’s talk about that for a moment. It could be, right? “Hey, 250, Max and Allen, if I wanna teach, maybe I make a little bit more. “So it could be a long-term career option, the regionals, but how is that impacting then the majors? Some of these are wholly owned. If you’re paying the guys at the regional that rate, what have we seen happen to the guys on the mainline or ladies?

[00:10:27] Kit: Well, the mainline was making a little more, a lot more before they pay came up. And right now, they’re going through another round of contract increases. I have a chart which I’ll make available after the talk that shows the pay raises, uh, from 2010 till today. But the, all the airlines that have new contracts, so they’ve gotten them in late 2022 or, or 2023, they have gone up about 20% more than the already great rates they already had.

[00:11:00] Along with the retirement improvements, the retirements, uh, Delta United American were 16%, 100% company paid retirement programs. And in these new contracts, they go up to 18%. I never thought I would see it go above 16, but it has, and it, and it’s a significant increase over the next few years. It doesn’t happen right away through the length of the contract, which was typically two to four years.

These retirement contributions, 100% paid by the companies will increase at Delta United and American at least to 18%. But put that in perspective, the average 401 in America, if you have one, it’s three, four, 5%. At 18% company paid 401 most 401ks require a match or participation by the, the employee. In this case, it’s 100% paid by the company at 18%.

That’s like four times the national average on a paycheck that’s four times the national average. I mean, we’re talking 15 or 20 times better retirement [00:12:00] income and, and contributions than you would expect as a normal corporate employee in America. 

[00:12:06] Tim: There’s two observations, as you mentioned that, that I think about is number one, the regional pilots don’t have the 16 going up to 18% and 2026 direct contribution that the mainline carriers do.

[00:12:20] Kit: Yep. That’s the big difference. You talked about the pay was comparable, but the retirement is not. Although if they do their maximum match, in other words, if the pilot participates at a high level, they do have a very good retirement. It starts out low, but if, if you spend time there and make your career there, it comes up to 12, 15% as well.

But you have to make your matching contribution and you have to stay long enough to benefit from that. But if you did stay, it would also provide a substantial retirement. 

[00:12:49] Tim: Right. So you can make it at the regional level. It requires a little longevity, requires work, but at the mainline, a lot of times what we’re seeing is with these new contracts anyway, day one, [00:13:00] 16% scheduled to go 18%.

And then the 401 contributions are so attractive so much in terms of total dollar amount that we’re seeing a lot of these market-based cash balance plans being added for money that can’t go into the 401. Love to hear your thoughts on those. 

[00:13:20] Kit: Again, you have options, the investments that you make or who you have make them makes a big difference.

You, there’s a lot of money there. How much it grows is a function of the, how adept you are at playing the market. I have to confess, I’ve been very busy doing the other things and very simple. I, I put all mine in the Standard Force 500 and I took it out when I retired. But there were guys that, that actively managed their retirement or had somebody else actively manage their retirement, their whole career, and some of them did a lot better, and some of them did.

Standard Poor’s 500 yielded a, a very good retirement s- total sum for me. It wasn’t the best, but it was far from the [00:14:00] worst either. So I wasn’t an active manager myself, and I didn’t pay anyone to do it. I do now, but at the time, it wasn’t foremost in my thoughts. 

[00:14:09] Tim: I wanna pause here because this is one of the most important planning points in the whole conversation.

So when pilots talk about compensation, we naturally focus on hourly rates, and I get that, because the rates are visible, they’re easy to compare, they tend to get the headlines. But for a lot of professional pilots, the retirement side of the equation may be just as important, and in some cases, more important over the long term.

Now, since this conversation first aired, the planning issues have become even clearer, higher pay, stronger employer contributions. A IRS contribution limits can create a situation where pilot’s income starts to outgrow the basic retirement framework, and if you’re at the majors, that is absolutely the case.

So that’s where things like market-based cash balance plans, brokerage accounts, raw strategies, coordinated withdrawals, alternative investments, all of those things [00:15:00] become even more important. So the question is not just how much am I making? So the better question we should be thinking about is, “Hey, what are my dollars doing for me?

Like, what goals are they accomplishing for me? Where are they going? How are they going to be taxed? Is my strategy optimized?” And that’s the shift from shift from earning a, a great income to building long-term financial independence, financial success, and wealth, right? Now, before we keep going, I’d like to mention this.

At 360 Aviation Advisors, we help successful professional pilots who have outgrown DIY investing. We help them coordinate retirement planning, investments, and tax decisions with ease and clarity, because at a certain point, building and preserving wealth to support the life you enjoy takes a team. To learn more, visit 360Aviationadvisors.com.

[00:16:00] That’s 360Aviationadvisors.com. Now back to the show. 

[00:16:06] Kit: Now, I see that you just put a slide on the screen. Walk us through this. This was the one I was looking at for career values, so career value being a sum of pay, benefits, and retirement. Pay rates come right off the contract based on longevity airplane, pretty easy to figure that out.

And then you have to multiply at times your average flying, anywhere from, you know, 80 to 92 hours a month average for pilots, depending on the company. Some companies have 13, 28-day months, and they get the same amount of flying per month. Consequently, with an extra month, they end up with additional flying.

So they might be the ones that would average 92 hours a month where the actual FAA hard time limit flying in the seat, a thousand hours divided by 12 is 83, somewhere around 80, 85 hours for most people, a little bit more for those companies that have 13, 28-day months. So that’s the pay element, the [00:17:00] hourly rate times, hours flown.

And then benefits, and of course, benefits include retirement, but we have a specific formula for retirement. So we use that formula. Each airline’s a little different, and we use that formula, and what’s left are non-retirement benefits. So what I do is I, I go to the Form 41, the government accounting of airline operations and income, and I look at the benefit value for pilots and the compensation value for pilots, and I divide.

It comes out that the average percentage of benefits provided by the airlines are somewhere between 25 and 35%. If you take away the 15% that’s going into retirement, you end up with 15 or 20% non-retirement benefits. So that’s what I use. 

[00:17:46] Tim: And when you say benefits, are these tangible cash in your pocket benefits?

[00:17:50] Kit: No, those are insurance, you know, medical, dental, uh, life insurance, travel. And again, it’s, it’s a sort of a buffet, you know? I mean, you have different things you [00:18:00] can elect to do. It depends on the size of your family, all that stuff. So rather than trying to figure out what each individual pilot does, I just take the total benefit value and divide it by the total compensation value, and that is the percentage that’s being spent on benefits, regardless of how you might choose to use it.

[00:18:18] Tim: When I look at this chart, say I’m 40 years old, I’m in Charlotte, so let’s say I fly for American, I’m gonna fly ’til 65, so I’ve got another 25 years in the game. How much total value is the remainder of my career? What’s that worth? 

[00:18:33] Kit: That’s a $10 million career. That’s today’s dollar. So it will be a much bigger number when you get it 25 years, some of it 25 years from now.

But there’s a number of accounting ways. When I go to trial with these things, some jurisdictions require that you increase it for the future raises and then decrease it for the inflation. There’s another method which is called the offset methods, which assumes that the increases are offset by the decreases, which is pretty close, [00:19:00] usually.

So s- some courts will allow you to simply say that the value today is the same as the value tomorrow, because you’ll get increases and decreases, then they offset each other. Others make you make the maneuver, and pilots have kept up amazingly well. If you talk to a pilot, he’ll probably tell you it hasn’t.

But he doesn’t have the actual data, and I’ve got the data. 

[00:19:22] Tim: Before we go to the next chart, for the listeners at home who can’t see what you’ve put on the screen, we’re gonna make this available. It’s gonna be in the show notes, but you could choose your airline, you could choose your seat, you can choose the amount of years left that you have.

And the example that we just talked about was a $10 million career value. You’re not thinking about future increases on the contract. Are we putting any kind of return assumptions on 401k? 

[00:19:50] Kit: You don’t really pick your seat and plane. I mean, seniority controls that to some extent. 

[00:19:54] Tim: Sure. 

[00:19:55] Kit: So I have an 11-year captain in my calculations, which is very [00:20:00] conservative today.

People are, you can make captain much sooner, but not as far off as you might think. I mean, everybody talks about the most junior pilot that made captain. In many cases, that’s in a year or two or three now. But the average person in a court case, I would have to work probabilities. So I can’t assume captain until the majority, until 51% make captain.

And that’s probably running six to eight years today, but over the long term, it runs more like eight to 10. So I’m using 11, the 10 million dollar number assumes captain in 11 years. If you make it sooner, the number would be higher. And then we look at the return. I’m using 5% as a very conservative estimate of a long-term return on the 401.

That’s what I use. I feel it’s conservative. It’s certainly conservative compared to historic values. 

[00:20:50] Tim: I think the big takeaway is, hey, there’s a tremendous opportunity here, right, as a professional pilot. A little earlier, you talked about the shortage, you talked about the 5,000 pilots [00:21:00] that retired early with COVID.

You talked about there was a shortage before COVID, and the industry hasn’t been rescued by a downturn to kind of soften the blow. We all read the Boeing studies of how many pilots we’re gonna need by 2050, the CAE studies. When do you anticipate things kind of leveling out, so supply, leveling out with demand, and it no longer being a wild and crazy time for airline pilot compensation?

[00:21:27] Kit: Well, the demand for pilots has got two main factors. One is growth, and growth is directly related to e- economic factors. And regrettably, those are extremely difficult to forecast, and I’m not gonna try to do that here. 

[00:21:42] Tim: Sure. 

[00:21:43] Kit: But I would say that if we have a mild recession, hiring will decrease substantially.

If we have a long, severe recession, hiring will stop. We might even go negative and have pilot furloughs. On the other side, the retirements themselves remain strong for another four or five [00:22:00] years. So we’ve got half of the formula remaining good for another four or five years. We have the economic portion unknown and when we’ve been expecting, anticipating a recession ever since COVID, and it simply hasn’t happened.

So COVID would be considered a downturn in, by almost any measure. So maybe that was our 10-year downturn. Maybe we’ve got 10 years left. I don’t know. Like I said, very difficult to forecast. We have one war, now we’ve got two wars. Who knows? There’s so many variables, very unstable right now, and the economy really is the wild card.

[00:22:34] Tim: Sure. As a financial planner, I always like to tell clients, “Hey, we treat the future with the deference it deserves,” right? And I think that’s what you’re saying as well, but the things that we know is, “Hey, it’s a great time to be a professional pilot when it comes to compensation.” I’d love to get your thoughts on this.

We’re recording this near the end of 2023. We’ve heard some weird and interesting things coming out of [00:23:00] the cargo side of the industry. We saw that UPS gave an early retirement bonus. I can’t remember the number. I think it was a couple hundred pilots that took that. And then more recently, we saw FedEx tell its pilots to consider flying with a regional carrier.

What’s going on in the cargo space? 

[00:23:18] Kit: On the surface, that was pretty offensive to the pilots because the last time they looked, everybody was making 23,000 a year. When you look back at it now, with the bonuses that are offered between the job itself and the bonuses offered, you could easily get into the 250 to 350 a year range, which should not insult anyone.

This is a boom and bust industry. We call it Sharks teeth, up and down, up and down, up and down. I mean, and that’s for the cargo business, it was up artificially due to COVID. It’s down a little bit now. It’s not down horribly, but it’s down. That leaves them with too many pilots, much more efficient for them to buy out early retirements just like we did for COVID, or to [00:24:00] find other things for them to do if they’re attracted to that.

Those are reasonable solutions. Although I’d have to say, when you talk about the job and the seniority and working within the job, it’s not always logical. A lot of times it’s more like religion or politics. It’s an emotional thing. So that offer was poorly received. When I look at the numbers though, I understand why, and I’m not offended.

I’m not the one making the choice, but, uh, at the same time, those are viable choices. And I would say the, the lifestyle of a cargo pilot is different than the lifestyle of a passenger pilot. And when things are even, and they’re not even right now, but when they’re even, we actually see more people go from cargo to passenger than we do from passenger to cargo.

That’s not been true during COVID. You know, cargo was a great place to be, but not everybody wants to be on the backside of the airport in the dark. I mean, a lot of people, and myself included, I like being on the front side of the airport with TGI Fridays and Ann Annie’s pretzels and [00:25:00] people going by.

[00:25:00] Tim: Right. 

[00:25:01] Kit: Many people derive their pleasure in life interacting with other people, and some people consider the lack of that an advantage. I mean, some cargo pilots cherish the fact that they don’t have to deal with flight attendants and all that. But for me, I sought to like it. So, like I said, when things are even, we see more people go to passenger than cargo, and the route that was offered was a route to passenger, if you were thinking about going there anyway, might not be a bad idea.

If you were for there for the money, FedEx and UPS do have a higher career value, higher pay, better retirement program, and I would say there’s a reason for that. That’s a tougher job from my perspective than the, the big three, Delta United American or somebody like that. 

[00:25:43] Tim: Yeah, you pay for it in terms of the kind of flying.

Yeah. We’ve talked to clients at FedEx and there’s the emotional component that you just mentioned, “Hey, I f- I fly for, for FedEx. Like, what am I doing flying for a regional now?” And then of course, the regionals, you’ve got more legs in a day kind of thing, so that flying might wear you out. [00:26:00] But then there is the money.

Now, let’s talk about potentially moving to a regional or, or just the idea of staying at a regional long term. We have relationships with a lot of career coaches like yourself, interview prep and things like that. And part of the conversation is like, look, when the music stops, folks do not want to be sitting in a regional jet.

They’d much prefer to be sitting at a main line. 

[00:26:25] Kit: There are reasons when you move from one to the other, you’re at risk again. You go through training, you’re on probation. So you go through a risk area. You, you’re on the bottom of the list. So if there’s a substantial furlough, you could be furloughed. So you could reach for the better job and end up without a job.

That’s the worst case si- scenario. So it, it is risky business in the first few years. So the typical furlough is under 5%, you know, two or 3%. A bad one is 5%. The worst one ever is 10%. So until you get [00:27:00] 10% behind you, you’re at risk. And I might add that had there not been the CARES Acts under COVID, CARES one, two, and three, we would’ve probably furloughed 20 or 25,000 pilots.

25% of the pilots in the US would’ve been furloughed without government rescue. And by the time that government rescue was over, a light at the end of the tunnel, the recovering traffic and growth again was to the point that, you know, you can’t furlough a pilot for three months and save money because of the training up and back.

If you’re not gonna furlough them for six, nine months a year, then, then you’re saving money by not furloughing them. So CARES Act one, two, and three, and the introduction of the vaccines, which moderated the virus, saved the airline industry in a, in a way that it’s never been saved before. In my previous life, I’ve been furloughed three times and bankrupt twice, and nobody ever saved me, you know?

But in this case, they saved the whole industry, and it was genius because we’re in a world market, [00:28:00] and this world market, uh, we have a very viable, very vibrant, growing, capable airline to take advantage of this growing market now, and the rest of the world didn’t do that. The rest of the world wasn’t supporting their airlines and preventing furloughs and keeping the airplanes flying.

They didn’t do that. So we are in a very powerful position right now to take advantage of that market due to the incentives support from the government through the CARES Acts one, two, and three. 

[00:28:27] Tim: Certainly, it’s earned its spot in the history books there. Now, the cargo discussion is another place where the episode has aged, may I say, in an interesting way, right?

So when we recorded this, FedEx was already a major example of how quickly the tone can change in aviation, right? So cargo had been a great place to be during COVID. And when the industry started dealing with excess capacity or uncertainty and some very difficult career decisions, I think were at hand where folks had a dream of going to cargo for a long time and went, “Hey, should I go to cargo or should I go [00:29:00] to passengers,” right?

But now in 2026, we’ve seen that the story continues to develop. FedEx pilots have, uh, been working through a long contract cycle. The broader airline industry is also dealing with fuel pressure and capacity decisions and margin pressure, right? Those are things that, as a pilot, you can’t ignore, right? So your career is incredibly valuable, and while it is incredibly value, it’s still exposed to forces that you cannot control to fuel prices, aircraft delivery, geopolitics, merger activity, labor negotiations, consumer demand, cargo demand, the broader economy, like all of those things.

And I think, I mean, I’m not a professional pilot, but I have to deal with all those things, right? So I say that to say, look, it doesn’t mean you should be pessimistic, it just means you should be prepared. So what is your financial plan doing for you to help you, number one, have a great foundation? Number two, help you have insight in what your fixed and variable expenses are, [00:30:00] help Help you quantify and identify the risks and then figure out how you’re gonna mitigate those risks, you know, a thoughtful investment strategy for a given timeline and goals.

And then plans for, hey, what if things become not as great or as they currently are because it’s just a matter of time, right? It’s cyclical. So we wanna make sure that your success, your comfort at home, your ability to provide yourself and your family the life that you want is not contingent on just being able to fly an extraordinary number of hours per month.

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So how does the airline pilot use your services? 

[00:31:57] Kit: So the other thing I do is work with individual pilots, [00:32:00] their resumes, applications, and prepare them for interviews with a goal in mind of getting the job as soon as possible. We review the resume and many of them need to be redone. People say, “Well, it’s a modern age.

I don’t need a resume,” but that’s really not true. Your resume at every airline is a part of the screening and interview process. So we want you to have a good professional resume. You would also give it to the people recommending you because recommendations are very important. The application is really the key document.

And I got into the application business because I was writing resumes and people would send me their application to gather their information and I would look at the application and go, “Oh my God, you can’t spell, punctuate, or answer the question. This isn’t gonna go well.” So the application is scored, the number gets you the interview.

And then when you walk into the interview, the person interviewing you has reviewed the application usually right before you walk in, and that is your first impression. So we all know im- how important first [00:33:00] impressions are. So the application is really key to getting the job. And then finally, the, you know, knowing what’s coming and on the internet today, you can find out the interview questions and all that.

I always joke an ILS, which is a, you know, precision instrument approach. Uh, usually the first couple you fly don’t go so good. You know, you’re all over the place because it, it takes a lot of knowledge and practice to get it. And then later on today, experience pilot, well, they nail it. And I always ask them, “What’s the difference?”

Well, the difference is practice, you know, knowledge and practice. So why would you practice at ILS and not practice your interview? That’s the key element to getting the job and you need some practice. So we go a three-hour training and practice session on Zoom, and I’d have to say for the last three years, the people we’ve prepared, we are 100% on a success rate.

It really makes a difference to practice a little bit and find out, you know, if you’ve got stressors, if you’ve got a, some, we call them disclosure items, accident, incident violation, training [00:34:00] failure, asked to resign. Whatever it is, you need to talk about it with somebody first before you talk about it with your potential employer, because the first time around it’s sort of fifty fifty on how it’s gonna go, and we don’t want those kind of odds on our career.

We have a book on interview questions, we review their resume and application, we spend at least three hours with them in practice, and we’re honest with them at the end. Occasionally, a, a few people need a little more. It’s very unusual to need more, but if we don’t think you’re there, we’ll tell you. 

[00:34:28] Tim: Well, I mean, that’s, you don’t wanna bust, right?

We’re, we’re all pilots. We’re used to check rides, so this is the check ride that’s gonna open the door to some of these numbers that we just looked at. Earlier, you mentioned that you also provide expert witness services. Tell us about that. 

[00:34:43] Kit: Hopefully he doesn’t need the expert witness services. The percentages are very small.

My market is extremely small, but if a pilot is delayed in his career, so let’s say you lose your medical due to somebody else’s fault, car accident, motorcycle, accident, whatever, and you [00:35:00] lose three years, five years out of your career, I can put a value on that. And your claim, your personal injury claim, which is primarily what it would be, you could lose your medical forever.

I mean, you can still work, but you lose your medical, can’t be a pilot, or you could be a fatality. And now we’re, we’re working for your estate where we build this model like the one, the, the results of, that we’re looking at now, and that is used in a claim. So the, the claim, if it’s someone else’s fault, the motorcycle, automobile accident, loss of medical, whatever, then that becomes a written report, a, a big spreadsheet initially and a written report, which I stand behind at deposition or trial to help you achieve, uh, your loss, either for your estate or for yourself if you’re still with us.

[00:35:45] Tim: I think it’s been really informative to hear about your background, to look at some of the compensation numbers. Again, on the Pilot Money Podcast, we’re financial planners for the professional pilot. We look a lot at the compensation and the money. And then you just shared with [00:36:00] us how you work with the individual pilot to help them grab the job that they’re shooting.

How can folks find your practice? How can they reach out to you for services? 

[00:36:09] Kit: KitDarby.com is the website. It has a store. I’m generally available by phone most of the time. 

[00:36:15] Tim: We will have kitdarby.com in the show notes. We’ll have the documents that you shared in the show notes as well. Kit, thank you so much for coming on the show.

[00:36:24] Kit: Yes, sir. Thank you for having me. 

[00:36:26] Tim: So as we bring this conversation back, there are three things that I want you to take away, right? So the first is that your career has a number attached to it, whether you’ve calculated that number or not. And as a professional pilot, that number is and can be, it can be quite large.

It can be enormous, right? It includes pay, it includes retirement contribution, benefits. Of course, the benefits that come with seniority, your aircraft, your seat, your longevity, the years that you have left in your profession, that’s what your career value is based off of, right? The second [00:37:00] takeaway is that high income should be converted into stability and then flexibility.

So what do I mean by that, right? So we use this income to create a great foundation, which our clients have done, right? They have no problem with that. And then we turn it into options. We turn into flexibility, right? So that means, hey, making sure that we have liquid assets, right? So that could be cash, that could be brokerage accounts, right?

Making sure we have investments that we can touch today, not everything is locked up in retirement accounts. That means making sure that we enjoy ourselves in a thoughtful way, right? You can think about avoiding inflation or lifestyle creep kind of thing. But look, you’re gonna go through phases and you’re gonna go through phases that, that you’re like, wow, this is, initially it’s gonna be uncomfortable because you’re like, well, this is more money than I’ve made in a while, right?

Or ever, and that’s okay. And when you’re in that phase, you’re gonna be able to do things, you’re gonna be able to plan to do things that maybe you’ve only dreamt about. All right, that’s cool. But we wanna do it in a thoughtful way, right? So meaning when [00:38:00] the cycle turns around that we’re not caught unaware because we plan very well, okay?

The third takeaway is that aviation is cyclical, right? It’s not theory, it’s cyclical. Pilots have lived through furloughs, you know, bankruptcies, mergers, shutdowns, pandemics, hiring boons, hiring slowdowns. The details can change, and it will, but the pattern remains the same. The goal is not to predict the next disruption perfectly, right?

Like if it’s gonna come from, you know, higher oil prices for longer and a global recession from there, and war if it’s gonna come from something else, right? The goal is just to be ready, to make sure that disruption does not derail the rest of your financial life. So as you think about what your career is worth, don’t stop at that big number, but ask yourself, “Am I protecting it?

Am I using it intentionally? Am I building a plan that gives me the life that I want and the options that I need, regardless of where the industry goes next?” Big [00:39:00] shout out to our sponsors, Beacon Relocation for supporting the show, helping you guys save money on your next real estate transaction, whether it’s locally or across the country.

Thank you to Beacon for your support. So thanks for joining this episode of Pilot’s portfolio. We’ll see you on the next one.

Thank you for joining this episode of Pilot’s portfolio. If you found this information helpful, spread the word and share it with a pilot button. Or if you have questions and there’s something that you would like to hear discussed on the show, send us an email. You can find the address in the show notes.

For those of you who are ready to learn how we help professional pilots with their financial planning needs, schedule an appointment. Until next time, keep the shiny side up and we’ll see you on the next episode.

Financial advisor and author of Pilot's Podcast, Tim Pope

Timothy P. Pope, CFP®

Timothy P. Pope, CFP®, is the Owner and Principal of 360 Aviation Advisors, a firm dedicated to helping professional pilots and their families achieve financial freedom. As a financial advisor for pilots with over 13 years of experience in personal finance and a Bachelor of Science from Wake Forest University, Timothy provides expert guidance on wealth management, retirement planning, and investment strategies tailored to aviation professionals.

An avid pilot himself, Timothy flies a Cirrus SR20 and loves exploring mountain biking trails with his kids, blending his passion for adventure with family time. Follow along for practical insights on financial planning, investing, and building wealth while living life to the fullest.

Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), registered investment adviser firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.

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