That's an excellent question. My road to philosophy was a long one. It took me a while to realize that the kinds of questions I was asking or preoccupied with—often having to do with basic presuppositions and what reality must be like for the facts as we know or accept them to obtain, questions of identity, etc—were ultimately philosophical in nature.

I would first distinguish between history of philosophy from philosophy itself. Sometimes these two things are confused, much like people will sometimes confuse being a philosophy professor with being a philosopher (these two can coincide, naturally, but the former does not necessarily entail the latter). Some history is edifying, of course, because philosophical arguments and discussion occur in time, and indeed, history will incidentally enter the picture on its own as a way of presenting the dialectical refinement of some position (for example, the typical way Aristotle's theory of act and potency is presented is by beginning with Parmenides, followed by a somewhat idealized version of Heraclitus and then by showing how Aristotle's theory resolves the resulting aporia).

In retrospect, I would recommend something in the Aristotelian vein. It not only serves as a strong and sound foundation, as well as a good base from which to examine other positions, but it will save you a lot of grief later (even here, it took me a long time to overcome ingrained biases and habits of mind that were insinuated by the modern education system). I would highly recommend some of Edward Feser's books. He's well known for writing in a lucid style that dispenses with some of the the needless jargon that some philosophers are known for. On the introductory side, "Aquinas" [0] is probably a good starting point. A follow up, or if you can handle something a bit more substantive to begin with, would be his "Scholastic Metaphysics" [1]. I emphasize metaphysics first because the most basic philosophical questions are metaphysical; everything else benefits greatly from a clear understanding of metaphysical issues. Avoid any philosophical approach that begins with methodological doubt. It will destroy your capacity to know or to reason and may actually succeed in driving you mad (no joke). Groarke [5] wonderfully argues how such doubt is ultimately unresolvable through reason because it isn't a rational doubt—something that arises when we are met with, say, conflicting evidence—but a _willed_ doubt.

I'll leave it at that, partly because I would have to take some time to think about what additional recommendations I should make so that they would be most helpful to you, and partly because I think the recommendations I've made above will occupy you for some time and lead you in a direction of inquiry all on their own.

(Some honorable mentions: David Oderberg's "Real Essentialism" is a nice complement to [1]. Etienne Gilson's "Being and Some philosophers" [2] is also a nice trek through metaphysics. His "Methodical Realism" [3] is also a nice quick read in which he argues against idealism, while "The Unity of Philosophical Experience" [4] is a historical tour of how various major philosophers in history have failed.)

[0] https://www.goodreads.com/book/show/6963088-aquinas

[1] https://www.goodreads.com/book/show/19160503-scholastic-meta...

[2] https://www.goodreads.com/book/show/2479290.Being_and_Some_P...

[3] https://www.goodreads.com/book/show/12409190-methodical-real...

[4] https://www.goodreads.com/book/show/232542.The_Unity_of_Phil...

[5] https://ndpr.nd.edu/news/an-aristotelian-account-of-inductio...