[scobar]

Thanks for mentioning your post. I really enjoyed it. I have a couple questions that, to my understanding, weren't covered in your blogpost, and I'd like to learn your opinion.

I'm guilty of having contacted someone I greatly respect and asking "Will you mentor me?". While I honestly believe that particular individual understood the naivete in the format of my request as shown by the kind response, I would like to improve the manner in which I seek mentorship in the future.

In your examples, you offered to help improve a project of a prospective mentor with work you had already completed. If you don't know what work may help that person, would you ask directly how you may provide a benefit to him/her?

My next question is about the type of advice I seek. You suggest "[...] have gone as far as you can by yourself" before seeking mentorship. I'm not stuck, but there are a few paths I might choose. Each is a considerable time investment, and making the wrong choice would be a setback I'd really like to avoid. The conventional advice I have sought online hasn't provided a clear answer to my specific situation. What is the best way to ask someone if he/she has the time to offer advice? I don't want to start by presenting the questions and making them feel obligated to answer something that may take more time than they have available to consider.

[plinkplonk]

(a) If you don't know what work may help that person, why do you presume he/she would be a good mentor for you? You have to research/know what your prospective mentor is doing, has done, is interested in etc before seeking mentorship.And you get this knowledge by actually doing some work in whatever area your prospective mentor is an expert in and coming across his work in that field. (vs choosing someone famous first and then deciding to seek his mentorship)

"If you don't know what work may help that person, would you ask directly how you may provide a benefit to him/her?"

No I wouldn't. I get these sort of emails myself,though I am just a programmer and have no world class expertise even in programming, and I know what timewasters they can be.

More importantly I let my work lead to potential mentors than the other way round. In other words, I'll work on what interests me/I think is important even if no mentors are available. Mentors are an occasional aid, not a dependency, to doing good work. Which leads me to

(b) The desire to take the "optimal path" (no such thing exists for most realworld situations) can in itself be a paralyzing factor. Taking some paths, realizing they are not right for you and then backtracking is part of the learning process. This time is not "wasted". Seeing it thus only shows you are at a certain stage in learning how to learn, and need to move a little further.

Doing this exploration and backtracking improves your skill in choosing and walking paths. Sure, too much of it can be debilitating, but knowing when to stop and when to continue is itself a valuable skill, which can be acquired only by gaining experience and reflecting on it, not by someone else trying to guess the 'right path' for you.

If you completely avoid these situations, waiting for someone else to give you an "optimal" path, you end up (in the best case) as someone who can take a path only when someone else lays out all the pros and cons of each path. And that is not a good place to be, even if such a situation were possible (which is usually not the case, though in some highly structured environments like studying for an academic degree, it might be possible)

[scobar]

Thank you for your thorough response. I agree that only after sufficient research (not only about the person, but about the subject of focus as well) does one get a good idea of who may be a good mentor. The research does provide insight about the interests and attitude of the prospective mentor, but doesn't always clarify how that person may want help. Perhaps after more time and research, I'll prove myself wrong.

I agree that one should not be dependent upon a mentor's guidance. I think, based on your response to my second question, I may have inadvertently implied that I was seeking a mentor to enlighten me with the 'right path' or that I wouldn't start until I had received the advice. In fact, when I considered the circumstance prompting my second question before I had written it, my thoughts were very similar to your answer.

The guidance I expect a mentor can provide is similar to the reading list provided by tptacek for those who wish to learn more about security (http://www.amazon.com/lm/R2EN4JTQOCHNBA/ref=cm_lm_pthnk_view...). Someone who wants to learn who blindly chooses the first few resources may eventually come across the same books or learn the information elsewhere, but may take far longer than necessary, pick up some bad habits, and not gain more expertise for the extra time spent stumbling along tangent resources that turn out to provide little or no benefit.

I think your strategy of delving into the work and in turn the community surrounding it is a great way to promote the serendipitous mentor-like relationships that will naturally form as a result.

My only disagreement is that you seem to find little value in seeking out those who aren't necessarily 'famous' but definitely are experts in a particular subject, researching more about them, and asking for mentorship if the research suggests it would be a good decision and could provide mutual benefit. There's likely a very low chance of success, but that person (who may have been a great mentor) may not have noticed you otherwise. I've decided that I'll do what I can to avoid any more reasons to think to my future self "I wish I had tried." A single mentor who I may not have been acquainted with otherwise would be worth all of the rejections to me.

Thank you again for taking the time to respond with such a well-thought-out comment.