Back to the AJ mailbag for today's question, an answer to which requires further details: (a) Which sort of Initiation do you mean?, and (b) Matter for what purpose? -- since the only way anything "matters" is by having a perceived value of some sort: for you, for your community, for the world, or however you care to define it. As always, some attempt to clarify terms might help, so let's try.*
At one level, "initiation" is unavoidable, just means focusing the mind toward some goal: anyone teaching anything at all is an "initiator," and anyone studying anything at all is being "initiated" into that subject. More formally, "initiation" has to do with unifying the contents of the mind, which is why "initiation" is something that deserves a lot of pondering on the part of those seeking it: around what, precisely, are you eager to unify the contents of your mind?...or for that matter, around what is someone else trying to unify your mind? The techniques of formal initiation -- indoctrination, disciplined practice, ceremony and so forth -- are pretty much universal among humans: take e.g. X years of school followed by a graduation ceremony and formal diploma, or the ritual solemnization of marriage; and formal initiation itself is common in non-"magical" circles (think fraternities, religious orders, police or military training and ranks, and even much corporate training). But since the inquirer is asking me, she probably means spiritual or magical initiation, of which there are four basic kinds: Self-Initiation; Outer Order; Inner Order; and Informal Instruction by an Initiate (or, alas, purported Initiate).**
One might expect me to define these terms, explain these roles, more formally here. (Then again, the reason I don't may well be obvious to those who look up the references in footnotes. ;) ) To clarify the possibly unfamiliar terms here -- and please note that I'm phrasing this next bit very precisely -- all group orders are "Outer Orders," all "Inner Orders" are one-on-one teaching orders, and "Informal Instruction" does not involve the awarding of degrees (Outer Order ranking) or formal recognition of grades (Inner Order ranking; though sometimes even experts (including AC) use the terms sloppily). Finally, those undergoing Self-Initiation can (and not infrequently do) attain the equivalent of Inner Order grades, but there is no self-initiating equivalent for an Outer Order degree: Outer Order degrees are largely about finding one's proper ranking in a group setting, and have no non-group analogue.
So "Does Initiation Matter?", now that we've clarified which sort we mean? Again, only you can answer that, by determining what purpose, if any, will be served in your life by your seeking it; and each form has dangers, and advantages, all its own. Fortunately the universe seems to have provided humans with a kind of self-sorting mechanism*** which tends to guide one, often over time, to one's proper place(s).
Hope that helps! :D
93 93/93 -- AJ
* Sorry for the repetition, for those of you who've read my C.'.G.'. Student Handbook: Mysticism, Magick, Thelema.
** Cf. CCXX I:49-53.
*** Cf. CCXX II:57-58.