The main problem for the aspiring professional pilot, in both airplanes and in rotorcraft, appears to be this simple catch 22: no one wants to hire an inexperienced pilot, and no pilot can gain enough experience without a job. But really, it's a slightly deeper problem. Commercial Pilot certification alone does not fulfill the insurance requirements of most aviation businesses. Also, most aircraft used for profitable purposes are larger, more complex, and much more expensive than the training aircraft most pilots use to build their initial flight hours. Then, on top of those reasons you won't get hired, there are literally hundreds of qualified applicants seeking each available piloting position announced by a company. All of which leads to the new professional pilot's conundrum: how do I get that first job when everyone is lowballing each other? And how low am I willing to go to get it?
Because a pilot's first job is likely to be in the same small aircraft they did their training in, one of the most common ways to seek employment at the start is by becoming a Certified Flight Instructor. Some people call it a pyramid scheme, because each CFI essentially needs to train 4 or 5 other people up to the CFI level in order to build enough hours to start applying for commercial jobs. That leaves, of course, 4 or 5 more CFI's who each need to find jobs recruiting and training 4 or 5 more people before their careers can move forward. But regardless of that, there's simply the problem that more people want their first piloting job than there are jobs available, by a large margin. And with so much demand from fresh, certified pilots and such a limited supply of employers, competition is fierce.
All too often, employers are ready to abuse desperate new pilots by offering them low paid (or unpaid) positions that require them to do an assortment of other tasks beyond piloting, from answering phones to cleaning the office and aircraft to running errands 6 or 7 days a week. The actual flying may be limited, strenuous, or even hazardous, and some disreputable businesses may even want the pilot to take part in unethical or 'less-than-legal' practices. Some will make promises that aren't fulfilled, and some will require that the new employee PAY for additional training at their school before getting hired. And these are all the same businesses that get hundreds of resumes fighting over every job opening.
There is no easy answer to this conundrum, but each pilot who reaches it must choose for him or herself how they want to deal with it. The secret to overcoming the hurdle seems to be a combination of adjusting one's expectations, remaining positive while networking with others in the industry, and remaining open to unexpected opportunities. Undeniably, though, it is daunting to reach the limits of your financing, and to step off into the dark unknown of the professional aviation industry.

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