I don’t have first hand experience of the industry in the USA so the following is advice that I’d give to someone in your position starting out in Australia. It should be generally applicable anywhere though.
First of all you need to be clear on the minimum required to get you qualified. My goal, if I was you, would be to aim for the following progression, you can modify it along the way if it doesn’t work out.
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Private licence
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Commercial licence
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General aviation flying job (not instructing)
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Instrument rating / multi engine rating
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1500 hours / Air transport licence.
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First officer turbo prop.
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Entry level position with major airline.
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At this point you’ve made it and just need to follow the career progression for the company you are in.
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Private licence. Obviously the bare minimum to fly an aeroplane yourself with passengers. A worthy enough goal in itself and it’s quite possible you’ll get this far and be satisfied with a lifestyle of working a “normal” job and doing some flying in your spare time.
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Commercial licence. This is the very next thing you do and is necessary so you can be paid to fly. Between step one and step two you will need to do probably around 100 hours of flying just building hours. Check the rules in the US, but you may be able be able to do parachute flying and glider towing on just a private licence.
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A job but not instructing.
Why no instructing? Because I believe you should only instruct if you really want to do it. If you are instructing just to build your hours then you are doing yourself and your prospective students a disservice. Also in my opinion instructing is not the best way to develop your commercial decision making skills (weather avoidance, diversions, go / no go etc). If you want to instruct, then by all means do it, but try and find a flying school that does some charter work as well so you can get a broader range of experience.
The ideal first job is with a company that has some breadth to their services. A charter company that fly single and twin engine aircraft for example. The more progression you can get without changing jobs the better.
Note that getting a flying job has come close to the top of my list while you have it near the end of yours. This is where you are going to have to make some real sacrifices. You need to get a flying job as soon as you can. You will not get paid enough for it and you will probably have to work a second job (maybe your current employer can put you on part time) but the sooner you start flying for work the better.
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Instrument rating / multi engine. This is something you should aim to do once you have your first flying job. You are living and breathing flying at this point which will make the rating less of a challenge. This could be the last flying you ever pay for. I’ve lumped the IR and MER together because they tend to go together. Single engine flying is typically not IFR but multi engine flying is. If you find you need an instrument rating for a single engine job than do a multi engine instrument rating anyway, it saves having to go back and do it again.
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1500 hours / ATPL. The FAA recently introduced a regulation that requires US airline first officers to have an ATPL. To have an ATPL you need a minimum of 1500 hours. So the goal now is to get those hours so you can get the licence.
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First officer turbo prop. It is possible to skip this step but unlikely, so assume you have to do it. This will most likely be for a regional airline and the pay and conditions will probably be appalling.
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Entry level position with major airline. If you want to fly big jets then you need to fly for a major international airline. I don’t know how it works with airlines in the US, but in the airlines I’m vaguely familiar with, the entry level position is as a 2nd officer (“SO” also known as a cruise FO) on a big jet. So if you join Qantas for example, you’ll fly a B747 as your first type. Except you won’t fly it, you’ll monitor the flight path at 35000’ while your captain has gone back for a nap. You won’t land or take-off except in the simulator, you could be doing this for a loooong time (a friend of mine has been an SO with Qantas for 10 years.)
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From here you do whatever everyone else does in your company. From B747 SO you might go to being an FO on a B737 then an FO back on the B747 then maybe a captain on the B737.
I haven’t mentioned the theory side of things. You’d have to do that concurrently with everything else.
Don’t pay as you go. If you can spare a few thousand a year then see how much of a loan that can get you. If you can do your flying training in big chunks you will find it easier and there will be less revision which means you are more likely to gain your qualifications in the minimum flying time which means minimum dollars spent.
Be prepared to change the plan. Aim high but don’t get bitter if the best you can do is somewhat lower or if takes longer than expected. I hate to say it, because it is the mindset that has driven conditions down in the industry, but any flying job is better than no flying job. Everything I said about instructing? Well if instructing is all you can get, then do it!
Don’t be disheartened by the stories of people who haven’t made it. At every step in the aviation career path there are people who have gone as far as they think they can. This means that there will always be stories of failure and how the industry sucks. What you don’t hear so much of is the stories of success, that’s because the successful aviators have moved on already and aren’t around to tell you about it. The success you DO see will be disheartening as well because it will be your peers getting jobs before you do. Don’t worry about that, it just means it’s your turn next.
Be prepared to move. There’s a big wide world of aviation out there. If you’re prepared to move you can make the most of it. Places like South Africa are a popular for new pilots to build hours. If you can get out of the US in the long term then you will probably find aviation more rewarding. Better conditions, better pay, lower requirements etc. As your final goal you might look at companies like Emirates, Qatar, and Cathay.
Work out why you want to be an airline pilot. Find out what it is actually like to be one. Compare. Will achieving the assumed goal (being an airline pilot) satisfy the actual goal (why you want to be one.) For me, flying is definitely a job. It’s the best job for me and I’d rather do this than anything else, but I am not excited to go to work each day. There is generally something I’d rather be doing around the house than flying 100 miners to the gas fields. The best flying job I had, for the flying itself, was 20 years ago. Now it’s just a way to fund my non-work activities.
The most challenging time will probably be getting your first job. The problem you will have is that you can’t get a job without experience and you can’t get experience without a job.
With that in mind, don’t just show up to your flying school, have your lesson, then leave. Turn up in the morning and spend the whole day there. Chat to people, help out, hang around with the engineers, visit the control tower if you can. If you’d rather be doing something else, then flying is not for you. Gentle networking is key to getting work.
Here’s a perspective on it all from a US poster. I believe things have picked up for her since she posted this. http://boards.straightdope.com/sdmb/showpost.php?p=12137265&postcount=10
I disagree on not taking out a loan. If you don’t get a loan you can’t get it happening quickly enough.