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When considering a career in high school as a band nerd I thought "man, I love music AND I love helicopters." So my reasoning went: if I become a professional musician or a band director MAYBE I'll be able to afford to fly helicopters one day. But if I become a professional pilot I should DEFINITELY be able to afford to play music (professionally, career, for fun, assist local bands). Verdict: VERY glad I chose to be a professional pilot. Definitely been able to afford to pursue music on the side. Now in retrospect, I wish someone would have challenged me about flying planes. I could have afforded to pursue helicopters on the side if I'd have chosen to fly fixed wing as the career entry... because it's extremely hard (expensive) to do that the other way around. I'm mid-40's and considering other life options to reach retirement as a result; a place you don't want to be. Served my country, loved all the military and civilian flying I've done in the US and overseas (both mil/civ), have some really cool stories, experiences, and pics to prove it, but I'm not where I thought I'd be financially at this stage of life and it's taken a toll on the family. As a helicopter pilot your physical locations of job options are extremely limited compared to airplanes and the pay disparity is pretty wide. Get your fixed wing and build a lot of instrument and multi-time early... those are the most valuable things on the resume; anything you choose after that will be easy career-wise (helicopters, singles, floats, tail-wheel, EMS, etc.). Also, consider the Guard/Reserves to get your helicopter ratings/experience on the side. That's a great way to do it if you're not sure you want to wait to do helicopters later but jump on the airplane bandwagon early.