You're thinking too narrowly
First of all, read my post in response to a resume advice question located in the following thread:
http://forums.flightinfo.com/showthread.php?s=&threadid=3926
One thing you can be certain of is that the subject of your career change will take center stage in any interview you might take. Your resume is NOT the place to delineate everything there is to know about your career change. The place to put those particulars on the table is in a cover letter. More on that in just a bit.
Generally speaking, you should try to keep your resume down to one page. If you can do it, put ten years' worth of employment history in it, but not at the expense of the one page maximum. Resumes are reviewed very rapidly - often in under a minute. You will need to capture someone's attention in that time. Too much clutter will work against you. As I said there are other places (like on the application and the background check forms) where you will be able to direct their attention to what you've been doing with yourself.
In your case, I think I would recommend that you simply put five years' worth of history down and let other information channels carry the rest of your message. If you're changing careers you probably have an entry have aviation job. Lead your resume's work experience section with this and just go back five years.
Returning now to the issue of clutter on a resume, you need to be careful of some of the formats out there. Many of them contain WAY more information than a Chief Pilot ever sees as he breezes through. All he needs to see is qualification. They'll look at the particulars later in an interview. Getting in THAT door is your primary concern right now. Keep the appearance of your resume neat and concise. Demonstrate qualification and let them ASK for more if they want it.
It is for this reason that I suggest caution in summarily accepting the advice of self-proclaimed experts in the field of aviation employment like Cheryl Cage or Judy Tarver. Please do not misunderstand what I am saying here. Both of these women, as well as many other individuals have a great deal of value to put forth in this arena. You must however, temper what you hear with the nature of YOUR requirements as defined by YOUR job search criteria because their advice and opinion is colored by certain biases that each has.
These people ARE indeed experts because of their experience and an accompanying reputation that engenders acceptance but they didn't start out that way. Ms. Cage isn't even a professional pilot and as far as I'm concerned that leaves her out in the cold in terms of having a visceral understanding of a pilot's drive and motivation. Again, not a slam. Just an observation of a fact.
I DO NOT exclude myself from this advice. Don't listen to me if you don't like what I have to say, or if my advice is not applicable to your situation. I think the key is to take in all that you can and use what works for you.
Now here's why I titled my response the way I did. You seem to be thinking exclusively about how to cover things in your resume but you should be thinking in terms of the whole story. As, I said, the story of your career change will be at the core of many of the questions you will be asked in an interview. Even in the event that such questions don't come up I think you should prepare your presentation so that it DOES come up.
In making your career change you have discovered a desire, formulated a plan, executed the various parts of the plan and made financial, social and lifestyle sacrifices. All of this was done in the name of making aviation your career. If proof of that level of dedication to career and professionalism isn't one of the best reasons to hire an individual, I don’t know what is! It is a point that you NEED to plan to make very clear. It should be a major component of both your written and personal presentations.
I will conclude with another excerpt from my book. It emphasizes the point that you should NEVER underestimate the power of your written presentation.
Excerpt:
Your Cover Letter
At its simplest, a cover letter is a letter of introduction addressed to the person who will be reviewing your resume. It is also a very powerful way to convey information about yourself that is important for a prospective employer to have without congesting the body of your resume. Failure to take full advantage of this additional channel of communication would be a big mistake.
As we discussed previously, before you write your resume you should take some time for a little introspection, prepare some notes about yourself, and establish a list of your personal selling points. With this exercise, you will come up with a great deal of information that might fit into the story you want to tell the interviewer. In writing your resume, some of that information will be used to portray the professional side of your story and perhaps a small part of your personal story. But what about the information that does not fit the standard format for a professional resume? What should be done with it? How and where does it fit in?
At the beginning of our discussion on bringing your job search to the interview stage, it was suggested that your life story and how you came to be where you are today might make for a lively discussion if crafted properly. Everyone has such a story and almost as universally, an aversion to boring others with idle chit-chat about themselves. However, what many people either do not recognize or fail to keep in mind, is that an interview is an open invitation to talk about yourself. That's the whole point! Doing so eloquently is how you will gain your advantage and earn a place in the memory of the interviewer.
You will want to organize the information in your notes about yourself into a coherent story of how you came to be where you are today. If you were liberal in making your notes, you should have plenty of points to work with. Now you must decide how to tell your story. Is there something unusual about the path you've taken to get where you are? Have you met some unique challenges along the way? Which facts will make your story a standout when compared with your likely competition? Once you have decided on the scheme of your story you will be ready to write your cover letter.
Because the cover letter should be viewed as a written portion of the job interview, there are three things to keep in mind. First, remember that you are trying to take advantage of the law of primacy in the way people learn. What you say in your first encounter should be among the things they remember best so be careful what you say and how you say it. Recall from the beginning of this chapter that a good educational presentation will always contain applicable and appropriate information. don’t allow your thoughts to wander on paper. Present information in the letter that you want the interviewer to have in mind when they meet with you. Your cover letter affords you the advantage of having total control over the information and how it is presented which may not be the case in a face-to-face interview.
Second, a cover letter provides you with a well-organized, written reference about yourself, which can be invaluable when you are actually in the face-to-face interview. Opportunities may arise for you to take advantage of the law of exercise by referring to your letter to bring up certain points about yourself that you want to repeat for emphasis. Often, a question will come up whose answer lies partly or completely in the cover letter. As you begin your answer you might say, "As you might recall from my cover letter..." This allows you to reiterate a point that you wanted to make clear to the prospective employer and it allows you to do it by "reminding" the interviewer of information they already know about you. By applying the law of exercise in this way, you will focus their attention and increase the educational impact of what you have to say making your point more memorable as a consequence. In addition, your ability to cite concepts from your cover letter contributes to an overall impression of organization and clear thinking skills while under pressure, both of which are desirable in a pilot.
Third, the manner in which you present the information in the cover letter should leave the same impression on the reader as you would leave if you spoke to the person directly. Your letter should be free of error, as clear and concise as possible, and its writing style should match your speaking manner. If it ventures too far from your natural speech patterns, the person conducting the interview will have a hard time connecting the letter with the personality he or she encounters in the interview.
When you write your cover letter, include the points that you want to stand out in the interviewer's mind. Organize your thoughts and structure your letter so key points are easily remembered. This will allow you to use your letter as a kind of "cheat sheet," both for yourself and for the interviewer. Finally, once you think your letter is complete, have someone who knows you well read it through. If your reader can imagine your voice speaking the words you have written, you've got your cover letter!
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Hope this helps!
TIS