Side Hustles, Part 2: Making Your Own Stars Align

I recently wrote a post aimed at helping baby pilots understand why experience is so important in our profession. ( I wrote that post because I’ve observed many young pilots trying to cut corners and rush their career development. Sorry, but it just doesn’t work that way. This post is geared toward those young pilots, but applicable to every TPNer interested in advancing their main career or setting up a fun side-hustle.

Some cynics complain that it takes a miraculous alignment of the stars for a person to get a job as a major airline pilot. I might be able to concede their point but only with the caveat that each of us has the ability to help nudge those stars into place. I feel bad for a pilot who can’t seem to get hired, but only after he or she has done everything possible to strengthen his or her application. (I wrote some suggestions here:

Some middle-eastern cultures have a saying and philosophy of “Inshallah,” or “If God wills it.” Though not representative of every person in that culture, this philosophy’s adherents have a tendency of just giving up when things get difficult, hoping that God will sort it out for them. (Before we get all high-and-mighty over this, I feel obligated to point out that the red-blooded American genre of country music has a well-known song promoting the exact same philosophy. A modern, American, translation for “Inshallah” could be “Jesus, take the wheel!”) There’s nothing wrong with praying for Divine help in your life, or hoping the stars will align, but you need to then go and do everything in your power to make things happen yourself.

When I mention my side-hustle instructing in the A5 for Icon Aircraft some people are very surprised. They can’t imagine how I, as a military pilot now flying big jets for the airlines, could feel qualified to teach GA at all, let alone in an amphibious light sport aircraft. Some can’t imagine how I could be qualified enough to get picked for the job. The answer is that I did the opposite of Inshallah…I made my own stars align.

I’m not writing this to kick those who are down…waiting with incredible patience for a major airline to call. My goal is to show you some practical ideas you can actively use to make your future look like you want it to.

Getting a job at Icon started 15 years ago for me, long before Kirk Hawkins had even mentioned the A5 to the world at large.

I earned my CFI (Glider) in college, and have kept it current almost continuously since then. I’ve continued to educate myself on General Aviation…including reading (and even writing) industry news/publications and flying GA aircraft. I’ve also taken advantage of opportunities to give civilian flight instruction. I’d always wanted to get a seaplane rating, so rather than just tell people about unfulfilled dreams for my whole life I went and did it. It took 2 days and $1200…not the smallest investment, but not insurmountable for a military pilot. I went with my father-in-law and my best friend and we had a great time!

I followed Icon Aircraft on social media and signed up for their email newsletter. I read, with sadness, about accidents that have killed three people and cost three aircraft. I learned everything I could about the A5 itself.

Over the years, I also wrote an aviation-focused resume. I had no intention of using it at the time, but figured it might come in handy in the future. (I was probably deployed somewhere or sitting at a desk during a pointless exercise at the time. Yes, writing a resume from scratch was a slightly less disagreeable alternative than gouging my eyes out with a rolled-up TPS report.)

When I finally saw a post announcing a part-time Icon flight instructor job in Tampa (,) all I had to do was update my resume and send it off. I think I spent a grand total of two hours on that process.


One of the first things you need to do to help your own stars align is to have a resume ready as I had. You may not need it today, but you will eventually.

Writing a resume is an important skill, and there’s no shortage of free and paid advice available. For a pilot it needs to be one page (one page only, Vasily!) You need to make sure you understand the organization you’re applying to, and tailor what you put on that page accordingly. Let’s look at some specific examples from resumes I’ve used in the past. (Please note that while this format has worked for me, I’m pretty sure there are better ones out there. Please focus on the content of what we’re talking about and look elsewhere for a better format. I’d consider if I needed professional resume help. I’m sure the esteemed Mr. Venema will be cringing as he looks at the examples appearing later in this post!)

I ended up applying to several jobs over the years. I applied to some USAF Reserve squadrons (and thankfully haven’t closed a deal with any of them yet.) I applied to be a contract pilot flying the Global Express for a company out of Asia. I submitted a package (including a resume) to renew my Master CFI accreditation with the National Association of Flight Instructors every two years. ( I work full-time for Delta and I fly the Icon A5 as my side-hustle.

Delta doesn’t use resumes in the application process. However, it’s a good idea to have one ready in case you go to a job fair, and to send people you ask for letters of recommendation. Here’s a section of the Delta resume that I had ready to go if needed:

Let’s contrast this example with the one I used for my most recent Master CFI update:

These two examples are pretty similar overall. You’ll notice that I didn’t mention my sUAS certificate or my medical on my Delta application…because they could care less about me being rated to fly baby drones for money. Part 107 drone flying is a big topic of discussion at NAFI though, and I mentioned some sUAS ground instruction in my MCFI application. I included many types of flight hours in both examples here because I wanted to illustrate breadth of experience. Now, let’s contrast these two examples with what I sent to Icon:

Big difference, huh? The Icon job involves flying a 1500 lb Light Sport Aircraft (LSA) and I could technically teach in it with a driver’s license in place of a medical certificate, so no need to mention that. Icon, like Delta, could care less about my drone-flying certificate as well. I ended up short on space, so I put my commercial certificate on the same line as my ATP. I saved space thereby not including some of the fancy details of my BBD-700 type rating. (The Icon A5 doesn’t have a HUD or EVS. Instead, it has gargantuan windows, which I prefer.)

Under hours, I figured Icon could care less about my SIC or night time. The A5 is a single-pilot mostly-day airplane. I lumped IP and EP time together, both because that’s what civilians do and because it saved space. The Icon A5 has a retractable nosewheel, so I figured tailwheel time wouldn’t be valuable in and of itself. However, their application materials make a big deal about tactical, low-level, and backcountry experience. Although I only accounted for military flying with that entry, I mentioned the backcountry nature of my tailwheel flying in a cover letter that accompanied my resume. I might not have included my combat hours for most civilian flight instruction jobs, but I knew a lot about the company. I knew that it was founded by an F-16 pilot, that many of the people who work there have military backgrounds, and that they’re looking for…uh…adrenaline junkies. (They mention things like motocross, wakeboarding, and contact sports in their application materials.) I enjoy rock climbing, boxing, and some other activities, but I figured that combat time (including some that is actually more meaningful than flying circles in the sky while reading a book) would fit that bill nicely.

Can you start to see how I started making my stars align for these opportunities long ago?

  • Delta wanted lots of flight hours and plenty of PIC and instructor time. I chose not to take the random job commanding a maintenance detachment as a Major, in favor of jobs that involve lots of flying. I’m sure I would have found that command job fulfilling, but it would have been detrimental to my ultimate goal of flying for an airline.
  • Major airlines want pilots with multi-engine turbine hours, and prefer PIC. I flew the U-28A and T-6A in the Air Force…both single-engine turboprops. I took a 6-month deployment flying the Global Express (E-11A) in part because it got me a boatload of PIC time in a 99,000 pound intercontinental bizjet.
  • Icon wanted instructor and low-level time. I not only made sure to get healthy helpings of these types of hours, but I kept track of them in my personal logbook. If I’d relied on an underpaid 18-year old video game addict to keep my logbook, I would have simply been unable to quantify my tactical/low-level hours when I applied to Icon.

Let’s look at the next sections of my resume:

On the work history, I prepared for Delta, I emphasized leadership and instructor positions, and volunteer work. It turns out that volunteer/charity work is something Delta puts a lot of effort into as a company. Noticing that about them, I feel like it helped me to show how my life reflected those values. This is another example of making my own stars align. I hadn’t necessarily done that volunteering with my future in mind, but it sure came in handy, didn’t it? If I were having trouble getting hired right now, I’d be doing something to serve those around me through an organization that people on an airline hiring board could recognize, or at least understand. (If I was trying to get to Delta, I’d be working at Habitat for Humanity every weekend.) Let’s contrast this with the work history I sent to NAFI:

My working for the USAF Academy doesn’t really do anything for Delta, so I didn’t bother telling them about it. Delta could also care less that I write about aviation online. However, the Master CFI accreditation has requirements for providing aviation-related education and mentoring. Both of these entries were applicable. These carried over differently for Icon:

I made sure to mention my writing to Icon because I’d been saying nice things about them for nearly a decade. ( I didn’t go into extreme detail though. I was pretty sure they also wouldn’t care about a TPN Podcast where I discuss airline applications and logbooks. (

You’ll notice I included a lot more detail about my time at Hurlburt Field because so much of what I did applied to the Icon instructor job. Yes, I took advantage of opportunities to work in Training, Safety, and Standards during that assignment. I could have applied to be the Wing Commander’s Executive officer instead. Time spent pouring coffee and managing a calendar would have been great for a long-term Air Force career, but useless for a future airline pilot or A5 CFI. (You’re almost lined up your stars, just move over this way a little more….)

I added an entry for “Freelance Flight Instruction” because that’s essentially what I’d be doing for Icon. However, Delta wasn’t going to be particularly interested in my flight instructing on the side and it would have been a waste of space for NAFI because it was implied in the fact that I was submitting a MCFI application in the first place. You may also notice that the entries for my volunteer flying don’t even appear on this version of the resume. This happened mostly because I was out of space, but I also wanted to elaborate on my Icon-applicable experience, more than I cared about showing breadth.

Have Something to Write About

Tailoring your resume is nice, but you can only do it if you have something to write about. I couldn’t have claimed credibility as a low level pilot if I hadn’t flown the B-1 or the T-6. I couldn’t have claimed credibility as an instructor if I hadn’t sought out instructor positions in the military and matched that experience in my own with civilian flying.

One of the most important parts of making your stars align is going out into the world and obtaining the experience needed to fill your resume.

Some of it will be flying you have to pay for. If I want a job flying a particular type of aircraft, step one for me is getting some time in it if at all possible. This may require paying for some flight time. However, sometimes there are opportunities to tag along or help. I have an hour logged flying an A-26. It’s not much, but if it’s down to you and me applying for an A-26 airshow copilot position, that hour could be what gets me the job. I’ve made a point of flying tailwheel airplanes because some of the most desirable airplanes in the world are made like that. (P-51, B-17, DC-3, PC-6, Helio Courier, DHC-3, An-2, for starters.) If I was going to be flying small aircraft anyway, I figured I might as well be logging tailwheel hours that would help make me a more qualified candidate if any of these opportunities ever came along.

If you’re a military pilot, you may have some ability to ask for assignments that give you valuable breadth. Ask to go to Advanced Instrument School and/or Safety School! If you’re an airlift pilot who gets an offer to fly little airplanes, go for it. If you’re a C-130 pilot who gets the chance to instruct in a multi-engine, turbojet T-1, take it!

(See this: and this: for more on that discussion.) If you think you might be interested in civilian aviation at any point in your life, seek out opportunities to fly with people who are involved in that world.

If you’re a military pilot who thinks you might want to do some civilian flying, go and get your civilian ratings! Nowadays, this is frequently nothing more than a paperwork drill. Just having the right ratings on your certificates can make all the difference. Showing up with ratings in hand makes you look a lot more serious and means you might be easier and cheaper to train.

The same principles apply for non-military pilots. What flying have you done that makes you look different from all the other people who have logged 50 hours in a PA-44 and 1450 in C-172s? This could be flying something unique, it could be education, and it could be aviation-related jobs other than just flying.

I’ve posted some ideas about things you can do to make yourself more attractive to airlines. ( I’ve received some feedback saying that some things in here just aren’t that useful. While I concede that point, I stand by what I wrote overall. If what you’re doing isn’t working you have two choices: sit around complaining (which guarantees that nothing will change,) or go out and try something else to get those stars aligned.

Positions of Strength

When you take charge of your career and start actively shaping your resume, something interesting starts happening: you’ll find that you’re better able to negotiate from a position of strength.

When I first started thinking about airline applications, I felt like my resume was pretty weak. I had a grand total of 300 multi-engine hours, of which fewer than 10 were PIC. I figured that the minimum number of multi-engine hours to be competitive at Delta would be 500, and that 1000 would be a lot better. Instead of whining and crying about how unfair it was that the Air Force never gave me the multi-engine hours I was entitled to, I just looked around for ways to fix my own problem. I found a 6-month deployment flying a multi-engine aircraft and volunteered. It wasn’t the easiest thing to do, but it ended up being a great time with great people and I’m confident that it was the key to me getting my airline job.

If I hadn’t been able do that multi-engine flying in the Air Force, I would have looked for ways to get some civilian multi-engine hours. I’d have searched for opportunities to moonlight flying a King Air. If nothing else, I would have planned to do a Regional Airline Touch & Go. (See this issue of TPNQ for a discussion on that concept.)

Once I had that multi-engine experience, I felt very little pressure applying to Delta. Sure, they might reject me, but I now knew that I was at least qualified and competitive. I knew there were several other companies hiring and figured I’d have a good chance at one of them. This decreased my stress significantly, improved my life, and probably improved my performance at my Delta interview itself.

I approached Icon from an even better position of strength. The best part was that I didn’t need the job – I was there for the pure fulfillment of it. I’d crafted a career that, while not perfectly aligned with their job specifications, fit very well with what they were looking for. I presented my credentials (in my probably less-than-optimal resume format) and let things ride. That interview was almost zero stress. Instead of having to worry about putting my family in a tough spot when I failed to bring home dinner that night, all I had to do was talk about my enthusiasm for the job and what I could do for the company. I’m not saying that I was a shoe-in, but I felt comfortably qualified.

Case Study

You can apply this to any flying opportunity, not just the airlines. Let’s do a quick case study: what if I decided I want to compete in the Red Bull Air Races?

Most important is: why? I’m not sure this could support my family, so it’d be a side-hustle for pure fun. (Though, I suspect the sponsorship contracts can be pretty lucrative.) This means I’m not under any undue pressure to get this job. If I achieve my goal, great. If not, oh well…but I’ll have gained a bunch of valuable experience and probably enjoyed the process of trying to get there.

Next for me is the aircraft. One of the more common planes on the circuit is the Zivko Edge 540. ( What do I need to do to be qualified to fly this in low altitude, aerobatic races? Well, I guess low-level experience would help. The B-1 and T-6 have me some there, but if I were a civilian I’d immediately be looking at some pipeline patrol, crop dusting, and firefighting opportunities. These all have side benefits of paying me to build hours, and potentially getting me some tailwheel time.

Tailwheel time matters, so I’d need to at least make sure that I have the proper endorsement and as many hours as I can get. Given the choice between teaching in a Piper Warrior and teaching in a Champ, I’d go with the Champ. I’d look for Edge 540 owners, and start asking around about people who might need someone to ferry their airplane between competitions or airshows. Not only is this a great way to build hours in this specific type of aircraft, it’s a way to start networking (see below.) While I’d look for an Edge to fly, I’d also try for jobs flying Extras or other high-performance aerobatic aircraft. Even ferrying a Citabria would be better than more instructing in a C-172 in this case.

I also need some aerobatic chops. As a former T-6 instructor pilot, I’m good to go. However, it wouldn’t hurt to get some civilian aerobatic experience. I’d actually consider buying a Pitts or a Decathlon to do some of that. You can get into either one for a surprisingly low price. (Again, this also lets me build total and tailwheel hours.) As a military pilot, I could accomplish the same goal by looking for a part-time job teaching civilian aerobatics. The employer would check me out and then just pay me to build the type of time that I need.

I’d improve my aerobatic credentials by joining the International Aerobatic Club ( and possibly enter some competitions. (I once got to hear Sean Tucker speak. [] He wanted to become an airshow pilot, and decided that the best way to get started would be to go win a world championship in aerobatics. It worked for him!)

Next would come networking. I’d be sure to go to some Red Bull Air Races and chat with anyone who would talk to me. I’d do the same with the pilots and teams themselves, and with their sponsors, at major airshows. Once I built some tailwheel or aerobatic chops, I’d consider posting videos on YouTube or and/or blogging about it. I’d tell flying stories, and give instructional tips. The key is to make yourself a valuable contributor to the community.

I could go on and on from here, but the point is: this is very different than sitting on the ground dreaming about the opportunity.

If you have a goal in mind, put yourself in the shoes of your future hiring department. What will they be looking for on your resume? Does your resume have all those items? If not, what can you do to get those items on there. Once you’ve identified those items, the pathway to success is obvious.

This doesn’t mean it’ll be easy or free of sacrifice. I can’t tell you how many times I’ve heard a pilot complain about not getting access to an opportunity because he or she lacked the right type of experience. Maybe that experience was expensive to obtain, maybe the opportunity required a large number of a particular type of hours, maybe family obligations or a day job prevented the pilot from getting the experience. I feel a little bit bad for those pilots, but I also want to smack them and ask, “What’s your problem?” We all have time and resources available to us. Each of us can choose to spend them pursuing a goal, or not. Many famous pilots (not to mention doctors, lawyers, entrepreneurs, athletes, musicians, actors, etc.) have achieved lofty goals in their professions, despite backgrounds of financial or other significant hardship. If you’re smart and diligent enough to have become some level of professional pilot, there is no reason you can’t achieve a lofty flying goal. It’s only a question of what you’re willing to sacrifice.

Don’t be that pilot who wastes a career complaining about how opportunities haven’t just fallen in your lap. (Especially don’t be the one who posts that whining on social media!) Go out there and make things happen. If your goal requires the stars to align, then go out there and start shoving!

If you don’t know where to start…check out Yep you guessed it. TPN is creating a Side Hustle that teaches you how to start a side hustle!

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BogiDope is a proud sponsor of The Pilot Network, and this post is republished from their site with permission. You can read the original post here. You can also get more great TPN content on the TPN Community Website, on their free TPN-Go app (iPhone or Android), in their quarterly TPNQ magazine, and on their Podcast.

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