Enlisted to Airline: Overcoming Medical and Money Challenges

A Guide to Overcoming Medical and Financial Challenges in the Sometimes Overwhelming Journey from Enlisted to Airline (E2A)

Avgeekery is proud to partner with Erik Sabiston to share a series of articles on how to become a pilot in the aviation industry. Erik was founder of RTAG, an organization that has helped thousands of pilots and non-pilot military members turn their experiences into a professional career in aviation. He is also an airline pilot, founder of the highly successful Make the Donuts podcast, and has led multiple aviation-related businesses to success.

Stay tuned for a comprehensive reference series geared towards other specific groups, such as helicopter pilots, fixed-wing military aviators, and enlisted/non-aviator officers interested in transitioning to military flight school. For now, get ready to learn how to bankroll your wings without selling that deployment car you bought at 35% interest (We kid…)

Protect Your FAA Medical: Scrub Before You Soar

E2A folks, before you chase those wings, scrub your medical records like you should have scrubbed your first enlistment contract. Service members’ records can hide erroneous info (think “heart arrhythmia”) inadvertently entered under your name.

Catching mistakes now saves time and cash later by spotting conditions that could ground you. It also allows you to expunge errors or fix issues before they become disqualifying.

You’ll need someone with experience to review your medical history. Trying to decipher it yourself is like reading NOTAMS. I’d rather watch an apple core turn brown.

Veteran Service Organizations (VFW, American Legion, DAV, etc.) can actually help find all the stuff lurking on those pages before the FAA hears about it. Hotlines like the AOPA Medical Certification service (membership may apply) or experienced aviation medical examiners can provide quick, often free consults. Got a tricky medical issue?

Don’t wing it. Reach out to pros like Wingman Med for expert help navigating FAA red tape. If you need a special issuance, it’ll move through Oklahoma City about as fast as MRE cheese spread does through your lower intestine, but at least your military paycheck will keep the bills paid while you wait.

You good now? Then go get that Class 1 FAA medical ASAP

Too many folks on the journey from enlisted to airline pilot drop a fortune on training only to crash into a mountain of medical problems when it’s time to go get a job. Don’t be that guy who finds out post-ATP/CTP that the FAA doesn’t want you flying commercially if your PTSD diagnosis makes it sound like you’re still suffering from major issues. Start now, or you’ll be stuck on the ground, still watching others live the life that you wanted.

Below, I’ll walk through the three routes that you can take to arrive at your eventual goal…the cockpit. Feel free to read the details on all the options below. Or, if you already know your path, feel free to click ahead to read more info on how to achieve it.

Enlisted to Airline: Show Me the Money (Collegiate Route)

Flight training runs $80,000-$150,000, more than a military toilet seat (barely). But if you’ve endured a Med Cruise, you can handle this. Enlisted and non-aviator officers have access to benefits that civilians would kill to have if they weren’t so afraid of, well, killing. No, a four-year degree is no longer a requirement, but it’s still good to have. Let’s unpack this duffel bag and get you airborne.

Collegiate Route Funding Options for Veterans

• CREDENTIALING ASSISTANCE: Still in uniform? The Department of Defense Credentialing Assistance Program funds certifications, but flight training eligibility varies. The Army offers up to $2,000/year ($1,000 cap for pilot licenses) for Active Duty, National Guard, and Reserve through ArmyIgnitED, covering private pilot or instrument ratings at Part 141 schools. You might end up with a two-year service obligation, but the rules on this stuff change more often than a report time for a Division run. The Air Force provides up to $4,500/year for Active Duty, Guard, and Reserve via Air Force COOL, funding one flight training credential (e.g., private pilot) at a time with no additional obligation. The Navy, Marine Corps, and Coast Guard offer up to $4,500/year through Navy COOL, Marine Corps COOL, and Coast Guard COOL, but flight training is not covered, as credentials must align with MOS/AFSC/ratings (e.g., aviation maintenance, not piloting). Again, this program is constantly changing.
  
• GI BILL: Ignore the barracks lawyers, your private pilot certificate IS covered under the Post-9/11 GI Bill. In-residence college programs can fund your entire training, while VA-approved standalone schools cover a chunk. Use the “WEAMS” website to find your school. Funding resets every August 1, so time your courses like a precision approach from FAF to MAP. In 2024, over 5,000 veterans used GI Bill benefits for aviation, per VA data. The Post-9/11 GI Bill (Chapter 33) and Montgomery GI Bill (MGIB, Chapter 30 for Active Duty or Chapter 1606 for Selected Reserve) offer veterans distinct benefits for flight training, with differences in coverage, payment structure, and applicability to in-residence/online collegiate programs versus standalone Part 141 flight schools. Let’s break it down, Barney style, shall we?
  
• POST-9/11 GI BILL
  • Coverage: Covers 100% of in-state tuition and fees at public colleges or for veterans with 36+ months of Active Duty service post-10 September 2001 (prorated for less service). For private or out-of-state schools, it’s capped at $29,920.95 for the 2025-2026 academic year. You’ll also get a monthly housing allowance (based on E-5 BAH rates for the school’s ZIP code, averaging $1,934.80, less for online-only programs) and up to $1,000/year for books/supplies. Private pilot certificates are covered if part of an approved aviation degree program (e.g., Embry-Riddle’s Bachelor’s in Aeronautics).
  • Eligibility: Requires at least 90 days of Active Duty post-10 September 2001, or 30 days with a service-connected disability discharge. Benefits last indefinitely for those discharged on/after 1 January 2013 (Forever GI Bill).
  • Payment: It’s paid directly to the school for tuition/fees; housing and book stipends go to the veteran. This option requires monthly enrollment verification.
  • Example: At Embry-Riddle (a Yellow Ribbon participant), a veteran could get full tuition for a bachelor’s with flight training plus housing and books, maximizing benefits.
    
• MONTGOMERY (you are so old) GI Bill
  • Coverage: It pays up to $2,150/month (2025 rate) for 36 months, directly to the veteran, regardless of program type. This covers flight training within aviation degree programs but only up to 60% of approved charges for flight-specific costs (e.g., lab fees for PPL, IR, CPL). Veterans must cover any tuition/fees exceeding this amount out-of-pocket. No housing allowance or book stipend is given, and private pilot certificates are covered only as part of an approved degree program.
  • Eligibility: You must serve at least two years on Active Duty (MGIB-AD) or Reserve/Guard service (MGIB-SR). Benefits expire 10 years after separation (MGIB-AD) or when Reserve/Guard service ends (MGIB-SR).
  • Payment: Monthly payments are sent to the veteran, not the school, requiring careful budgeting for tuition-heavy programs.
  • Example: At a public college like Central Texas College, MGIB might cover $2,150/month for a 2-year aviation degree, but you’re on the hook for any shortfall, and no housing help means you’re couch surfing or hot bunking it like you’re on a submarine.
    
• YELLOW RIBBON PROGRAM
• Post-9/11 GI Bill: This applies to veterans with 100% eligibility at private or out-of-state colleges (not vocational schools). Participating schools (e.g., Liberty University, Embry-Riddle) waive a portion of tuition/fees exceeding the $29,920.95 cap, and the VA matches it dollar-for-dollar. For example, Liberty offers up to $13,100/year, matched by the VA for a total of $26,200 above the cap, covering most or all remaining costs. Active Duty members and spouses became eligible as of 1 August 2022.
• The Montgomery GI Bill is not eligible for Yellow Ribbon, as MGIB doesn’t cover tuition directly or offer additional funding for private/out-of-state schools. You’re stuck with the $2,150/month cap, like an outstanding DTS claim you get stuck with just for going to training during the Christmas holiday.
  
  Note: Finished with all your flight training, but still have money left over? Go get as much education as you can! Life happens, and you could end up furloughed or lose your medical. Prepare yourself for this possibility if life throws you a curveball. It’s a great way to spend your overnights as a new airline pilot. Slam-clicking to study in your hotel room gives you an excuse to skip the mandatory fun time at the bar with your boomer Captain, as he shows you 153 pics of his new home renovation on his flip phone. Plus, the extra money is nice to have during those first couple years of low pay!

Enlisted to Airline: Show Me the Money (Vocational Route)

What about Part 141 Flight Schools (Non-Degree Vocational Programs)? First off, if a school says to you, “We’re getting GI Bill any day now!” don’t walk away, run. If you’re on a track, lap them. This ranks right up there with, “If you enlist now, you can transfer to flight school as soon as you get out of basic training.” Don’t believe the hype. Getting approved for the GI Bill takes flight schools years, longer than some enlistments last. So, what do you get with these programs if you’re not excited about study groups with 18-year-old college students?

Vocational Route Funding Options for Veterans

• POST-9/11 GI BILL
  • Coverage: You can get up to $16,535.46/year (2025-2026) for vocational flight training at FAA-approved Part 141 schools (e.g., Pray Aviation, US Aviation Academy). Reimburses 100% of approved charges (tuition, flight instruction, simulator fees) up to this cap. For E2A and non-pilot officers, this option requires a private pilot license (PPL) and a second-class medical certificate (first-class for ATP) before starting. You’re not getting a housing allowance or book stipend for vocational training.
  • Eligibility: Same as above (90 days Active Duty post-10 September 2001 or 30 days with a disability discharge). Payments are issued after training completion, with schools submitting charges to the VA.
  • Payment: Veterans pay upfront and are reimbursed up to the cap, which can sting like that 19th round of Anthrax shots if your cash flow is tight.
  • Example: At a Part 141 school, the VA might reimburse $16,535.46 for a CPL course, but you’ll need to front the cost and pray the paperwork doesn’t get lost in the bureaucracy.
    
• MONTGOMERY GI BILL
  • Coverage: Reimburses 60% of approved charges for Part 141 vocational flight training, up to the $2,150/month cap for 36 months. Requires a PPL and second-class medical certificate (first-class for ATP). It does cover advanced ratings (IR, CPL, CFI, ATP). No housing or book stipends for you, and veterans must cover the remaining 40% out-of-pocket.
  • Eligibility: Same as above (two years Active Duty for MGIB-AD or Reserve/Guard service for MGIB-SR). This benefit expires 10 years post-separation (MGIB-AD).
  • Payment: Reimbursed to the veteran after training, based on submitted charges, with every $466 paid equating to one month of MGIB entitlement. Budget like you’re at JRTC and running out of TP.
  • Example: For a $20,000 CPL course at a Part 141 school, MGIB might cover $12,000 (60%), leaving you to scrounge $8,000, with no housing to soften the blow.
    
• YELLOW RIBBON PROGRAM
  • Post-9/11 GI Bill: Keep dreaming. Yellow Ribbon is exclusive to degree-granting institutions (colleges/universities). You’re capped at $16,535.46/year for vocational training, so choose your school wisely or risk a financial nosedive.
  • Montgomery GI Bill: No soup for you. You seeing a trend here? Here’s a couple more VA benefit updates: Last year’s Supreme Court ruling on Rudisill v. McDonough allows vets who’ve served multiple periods to combine their Montgomery and Post-9/11 bennies, giving them a new total of 48 months of eligibility! Going for a STEM degree? Get another $30,000 through the Edith Nourse Rogers Scholarship. Log in to VA.gov to learn more.

Enlisted to Airline: Show Me the Money (Mo Money!)

• Workforce Innovation and Opportunity Act (WIOA): This Department of Labor program paid for my commercial and instrument ratings! Open to those going from enlisted to airline, it’s free money if your flight school applies. Your school has to apply, so make them aware of what they’re missing out on. Expect intake tests and monthly check-ins for a year. States control the funds, so verify residency rules.
  
• VR&E (Vocational Rehabilitation): Don’t skip this! If you’ve got a VA disability rating of at least 10% with an employment handicap, VR&E retrains you for high-demand careers like piloting, often paired with a college degree through an approved program.
  
  You’ll typically need a private pilot license first, but for eligible E2A vets, it’s a golden ticket to advanced training without worsening your condition. In 2023, VR&E supported over 1,200 veterans in aviation programs, per VA stats. You really need to compile a stack of documents and evidence to counter the seemingly inevitable objections of some VA counselors. Even if you choose to get a degree in something more useful than aviation, do not let this benefit slip past you.
  
• DoD SkillBridge: Not funding, but a smart transition tool. This Department of Defense SkillBridge Program lets you work with industry partners for up to six months while drawing full military pay and benefits. Training must be free or low-cost, you can’t earn a paycheck during SkillBridge, and there needs to be a solid chance of a job if you perform well.
  
  You’ll also need to be allowed to return to your unit for out-processing. Smaller operators have embraced SkillBridge in the last few years, netting themselves cheap meat servos and mechanics. Use caution, though. Some SkillBridge companies charge these employers several thousand dollars per veteran to fill out a few sheets of paperwork and funnel you to their partners. What seems like a good deal isn’t always best for you; it’s best for them. Skip the middleman unless it’s your absolute dream gig, but look into it.
  
  According to DoD reports, over 3,000 service members used SkillBridge in 2024, and it beats doing PT. Not sure if your command will support you? Be respectful, but remind them that they’ll be paying for your unemployment benefits when you leave uniform if you don’t find work.
  
• Forces to Flyers and FAA Aviation Workforce Development Fund: The Forces to Flyers program connected vets with aviation training, but has since paused operations. Even if it doesn’t return, it helped many vets. I do know a regional pilot and former E2A who used it.
• The FAA Aviation Workforce Development Fund is also a lesser-known program that provides grants directly to schools and organizations that train pilots. In 2024, $10 million was awarded. According to FAA reports, AWDF often benefits veteran-focused programs. Research these; they’re like a headwind on takeoff.

Outstanding Scholarship Opportunities

Scholarships are a TOGA boost for E2A training. These are just a few of the most well-known organizations offering scholarship opportunities for those on the journey from enlisted to airline. I’ve listed them below from smallest to largest annual awards.

• National Air Transportation Foundation (NATF) provides $5,000-$10,000 annually in $1,000 scholarships for pilot training, focusing on safety and excellence.
• Arab American Aviation Professionals (AAAP) funds Arab American pilots with $5,000-$10,000 annually for certifications, promoting diversity in aviation.
• Sisters of the Skies awards $5,000-$10,000 annually for Black women pilots, supporting private and advanced ratings.
• TPNx (The Pilot Network Exchange) provides $5,000-$15,000 annually in scholarships through its networking events, connecting pilots with funding opportunities.
• Latino Pilots Association (LPA) awards $10,000-$20,000 annually for private, instrument, and commercial ratings. Active membership and enrollment in a U.S. flight school are required.
• Tuskegee Airmen Foundation funds minority pilots with $10,000-$20,000 annually, honoring the Tuskegee Airmen legacy.
• Experimental Aircraft Association (EAA) awarded $238,000 in 2024 for private pilot certificates and ratings, open to Young Eagles and members.
• RTAG awarded $250,000 in 2024 for veteran-focused flight training, emphasizing RTP (Rotor Transition Program) and E2A applicants.
• The Ninety-Nines offers $500,000-$600,000 annually via the Amelia Earhart Memorial Scholarship, helping about 50 women pilots in 2024.
• Professional Asian Pilots Association (PAPA) awarded more than any of the “Big 7”, around $1,000,000 in 2024 for certifications, supporting Asian American pilots.
• Aircraft Owners and Pilots Association (AOPA) awarded nearly 400 pilots $1,300,000 in 2024 for primary and advanced training.
  
  For more opportunities, check Pathways to Aviation for a curated scholarship list and join the Aviation Scholarships Facebook page for real-time updates and community tips. Start applying now. If you don’t, you’ll have zero excuses for why you can’t afford flight training, like landing with calm winds on a long runway. Begin yesterday, even if your DD-214 is years away.
  
  In Part 2, we’ll dive into building flight hours and balancing education to prep for your airline career so you can go from enlisted to airline.
  
  Need help? Reach out at sabistonconsulting.com or sabistonconsulting@gmail.com. Also, tune into the Make the Donuts podcast for insights from aviation experts and airline execs to fuel your E2A journey.
  
  I’ll see you in the terminals!
  – Sabby