Contracting: A Great Career Option for the Professional Pilot

As much as one may love flying, it can be a tough career choice. Many pilots struggle through the food chain only to end up discouraged, if not downright hating their job. We’re all aware of the reasons: low pay, long days, little respect, too much time away from home, difficult working conditions, commuting, regulatory hassles, bankruptcies, furloughs, and ruinously expensive training.

Quite a list, isn’t it?

Ours is a small community; word gets around, and it begs the question, how many have bypassed a flying career altogether because of it? I once read a survey suggesting that most pilots would not recommend the field to their children. Of course, many vocations are in this rickety boat. Even formerly high-flying professions like physician and attorney have lost their luster. The message: “it ain’t what it used to be”.

On the other hand, life is often what we make of it. From bush flying to firefighting, there are many different gigs out there for those willing to take Frost’s road-less-traveled. For the past three years, for example, I’ve been flying as a “contract pilot” and truly enjoy it.

The Contractor

Ready to Ride

It’s kind of a generic term, since anyone who flies as an independent contractor rather than a traditional, W-2 employee fits the definition, but I’ll focus on Part 91 and 135 corporate/charter flying because that’s what I know best.

Contract pilots function as a kind of overflow labor. Operators might need temporary help in the cockpit for a variety of reasons: a full-timer is sick, on vacation, leaves the company, times out due to regulatory limitations, or is unavailable for some other reason. God forbid, maybe they ran into trouble with a checkride or medical exam. Perhaps a trip requires multiple pilots due to length or logistics.

Some companies find it advantageous to run tight on full-time labor and supplement with contract pilots since there are no annual costs for training or benefits. They only have to pay contractors when they’re actually used, so as the flight schedule ebbs and flows, they can gracefully scale their workforce up or down without the inefficiency of, say, leaving full-time, salaried pilots sitting at home for an extended period.

For the pilot, there are both pros and cons to life as a contractor.

The Pros

  • You’ve got some control over your schedule and can decline trips. I really hate doing that, because a) I don’t want the company to stop calling me, and b) you never know when things will slow down, so it’s smart to sock away some acorns for the winter. But if you’ve got a big vacation planned or your best friend is getting married? You’re ultimately in control.
  • We can work for multiple operators, which can provide a bit of protection if the flying slows down at one company.
  • You aren’t tied to a seniority system. If you’re an experienced captain at company A, you needn’t start over as the lowest-paid right seater at company B.
  • Contractors earn far more per day than full-time employees, and therefore needn’t work as many days to reach a given income level. That means better quality of life, especially if you’re married and/or have kids.
  • Contract pilots are typically paid by the day. I might have a five day trip consisting of a flight to Hawaii followed by three days on the island before flying home. That’s five days “on the clock”. It can be a more lucrative system than one where you are compensated based on flight hours. Operators are essentially purchasing your time.
  • You’ll travel the country, if not the world. Instead of a few major airports, on larger aircraft like the Gulfstream, you’ll see places you’d never dream of. Though I haven’t been there — yet — North Korea and the South Pole have both been on the table. (Random note: Jeppesen does publish charts and procedures for Pyonyang!)
  • I always get an honest sense of gratitude from the operators for whom I fly, because by definition I’m helping them out when they really need a pilot. For example, I recently got a call from a Part 91 Gulfstream operator whose pilot broke his arm in the middle of a trip. I airlined out the same day and flew that evening’s leg to Las Vegas, keeping the aircraft on schedule.

The Cons

You knew there had to be a few, right?

  • Contractors inherit all the hassles of being your own boss. Does anyone work harder? From providing your own benefits (don’t get me started about healthcare) to paying self-employment taxes, it’s not always the carefree work-and-go-home experience of a full-time employee.
  • You pay for your own training. On a jet, the annual recurrent training costs run in the thousands. I currently allot $15,000/year for recurrent training and associated costs (airfare, hotels, food, incidentals) on my airplane. The expenses are deductible, which helps a bit, but I figure my first month’s work each year is spent digging my way back to financial “zero”.
  • You can’t control when the phone rings. That can mean short-notice trips and/or weird hours.
  • It can be hard to plan your life out when you never know what days you’ll be working. I average about 10 days a month away, so my philosophy has been to just plan my social life as usual, and make sure people know I sometimes have to reschedule or cancel.
  • Work can conflict with itself. I’ve had three operators call me for a trip on the same day. I can only be in one place at at time, so I “missed out” on two of them.
  • No guarantee of work. But then, history has shown that there are no guarantees in life or aviation for anyone, are there?
  • It can be tough getting started. As with many careers, the best entrée is knowing someone who can get you in the door. Initial start-up costs of obtaining a type rating can be a major barrier.


I like contracting because when a trip is offered I know it’s because the operator wants to use me rather than has to use me. Contracting represents some of the best that flying has to offer: adventure, interesting destinations and passengers, phenomenal aircraft, and decent pay for the work I do.

So why don’t more people jump into contracting? Awareness, for starters. Not everyone knows about this little niche. Also, it can be tough to break in to the business. You don’t have to know someone on the inside, but it certainly helps.

The initial expense is probably the largest impediment. The best compensation is found on the larger aircraft, and that means an expensive type rating funded solely by the contractor. Some pilots speculate on their ability to get work by obtaining the type before they have a job to use it on. Unless you’re well-heeled, that’s a big financial risk, but it works out for some people.

There is a rather circuitous way around the type rating burden: start off as a salaried employee and switch to contracting after a couple of years. That way the operator pays for your training and in exchange you accumulate a significant body of experience on the airplane.

FAA to the Rescue! Not.

I should note that contracting in the Part 135 world is a bit harder than it used to be. In the old days, if you were typed and current on an aircraft, you could fly for any charter company that operated that kind of plane. It wasn’t uncommon for a contract pilot to fly for several operators. A few years ago — for reasons no one has been able to adequately explain — the FAA essentially did away with that capability.

Today, a five-figure recurrent only entitles you to work for the certificate holder under whom you trained. It doesn’t matter if you’re a veteran of ten years and 10,000 hours in a Gulfstream IV; if you went to recurrent on Company A’s OpSpec, as far as the FAA is concerned, when you move to Company B you are completely unqualified to operate a G-IV on any Part 135 flight until you’ve been through another recurrent… at your own expense, of course.

At first, this seemed like a potential deal-breaker for contract pilots, but it can help as much as it hurts. Just as the change make it harder for a contractor to work for multiple operators, it also makes it more challenging for that operator to replace a contract pilot since a successor wouldn’t be legal to fly until they went back for recurrent training.

Walking the Aviation Tightrope

Contracting does have something in common with scheduled airlines: it’s not right for everyone. If you’re the type that wants a fixed schedule or has to know exactly how much your bi-weekly paycheck is going to be, this ain’t the place. In addition to all the attributes of a good corporate or charter pilot, contracting requires the ability to run a business and cope with uneven income. Some months will be fantastic. Others, not so much. Even when business is slow, though, I get something valuable: more time at home with friends and family. Like I said at the top, life is what you make of it.

But the ability to earn a six figure income right off the bat while working a relatively small number of days? For me at least, it’s more than worth it. What I want in my flying carer is sustainability, the capacity to survive on this aviation tightrope, and ironically that’s what contracting provides. I want to fly without hating it, and that means avoiding the soul-crushing schedule and monotony of many professional flying jobs.

Ron Rapp is a Southern California-based charter pilot, aerobatic CFI, and aircraft owner whose 9,000+ hours have encompassed everything from homebuilts to business jets. He’s written mile-long messages in the air as a Skytyper, crop-dusted with ex-military King Airs, flown across oceans in a Gulfstream IV, and tumbled through the air in his Pitts S-2B. Visit Ron’s website.


  1. Unless it would cause Anti-Trust issues, the Pt 135 issue non-transferrable recurrency might be solved by an agreement something like “Open Airplane”. I wonder if the local FSDO and the climate in general would allow “collusion” between 135 operators to make similar enough op-specs so that recurrency with company A = recurrency with company B, C, D?

    • It is possible to do that. Much of the corporate/charter
      jet training is done at CAE Simuflite or FlightSafety International, so
      many of the syllabi are similar since they’re based on the respective
      Part 142 training provider’s material. So if they both use Simuflite,
      for example, Company A and Company B probably have very similar

      I know Simuflite is willing to compare training programs and ensure
      that any differences are covered during a recurrent. Not sure if
      FlightSafety does that. But at the very least, a second checkride will
      be required to ensure all the proper boxes are checked. It costs a
      little more, but it can get you onto two company’s certificates
      simultaneously. It’s basically a paperwork exercise. The only
      differences you’ll typically find between such programs are the OpSpec
      approvals for certain operations. For example, Company A might be
      approved for VNAV approaches whereas Company B is LNAV only.

  2. Mark Jeffrey Congco-Antoine

    April 16, 2014 at 9:15 pm

    The timing of this article couldn’t be any better.

    I’ve been up against the wall about going to full-time contract flying and instructing and quitting my job. I’ve had to turn down quite a bit of flying and could have made a decent chunk of change. Networking networking and more networking has given me the opportunities for these clients to call. Personally, I’m uneasy about the “down” times mentioned in this article, but I’m slowly but surely mustering up the strength to contract full time.

    • Yes, the slow periods are what give many pilots pause when
      considering contracting. If you do other things — instructing, for
      example, which I do as well — it can help fill in the gaps. I try to
      soak up as much work as I can and put some money away for those slow
      times. Then I can hang out by the pool without stressing (too much)
      about money.

      As they say, the grass is always greener on the other side, right?
      When the money is rolling in, contracting looks brilliant. On the othe
      hand, when it comes time to fork over thousands and thousands of dollars
      for recurrent training while the full-time employees are doing it on
      the company dime, it doesn’t seem quite as attractive.

      But as with all things in life, there are pros and cons. I know some
      pilots who contracted and later moved back to full-time W-2 status.
      Just because it’s the right thing for this stage of your life doesn’t
      mean it will always be that way. But it’s nice to have the option!

  3. Where are you finding Gulfstream recurrent training for 15k? My full service training contract is SIGNIFICANTLY more than that. If I could find training for 15K contract flying would be a viable alternative. When training costs the equivelant of 6 months salary, it takes a bit of the shine off the apple.

    • Ah, mine is not a full-service contract. Yes, it adds up quickly and if your training costs equate six months salary, it’s going to be a lot less attractive. Gulfstream training is expensive, even by jet standards.

      • Interesting. I would have guessed that training with less than a full service contract would be cost prohibitive. As most large cabin operators are complying with, or at least trying to comply with IS-BAO standards and recommendations, how are you handling the additional training requirements like emergency procedures, international ops, cold weather ops, SMS, etc?

        • That training is provided in-house rather than at the 142’s facility.

          • Having found an operator who is willing to provide that type of in-house training to their contractors must be a real advantage for you. Contracting is also an excellent way to gain experience with a company that you might consider for permanent employment. As an employer, it’s a great way to vet prospective employees who may be turn out to be “posers”. Everybody wins.

  4. Outstanding article.

  5. How much time does a new contracting pilot need? I contract in my current job (marketing consulting for wireless companies), and instruct flying when I can. But while instructing in single engine land airplanes helps build the hours at someone else’s expense, what would realistically be needed to make the leap from a Cessna to a Gulfstream or Learjet (or even a King Air) right seat?

    • That’s difficult to answer. I had nearly 6,000 hours when I started doing it, with about 2,000 multi-turbine time.

      The experience requirement seems to vary depending on the job. If you know the right person, you might get into a Part 91 King Air with pretty low time. Some of the minimums seem to be driven by insurance requirements.

  6. Sterling RaShad Brown

    April 21, 2014 at 10:30 pm

    So is contract flying similar to Air Force Reserves? I have a cell Bio and biotech degree and I plan to work in a lab during the week and spend weekends on reserve and on deployments if my eyes let me as a transport, recon, and support pilot. Will contract flying let you hold two careers?

    • No, it’s quite a bit different than the Reserves. If you have another full time job, it would be difficult to accept any contract work since your schedule would be so full. I do know someone who is a full-time commercial real estate broker who works an occasional trip in a Citation, but that’s more of a minor side job than a second career.

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