Survey the landscape first - get a hand-wavey high level understanding on the two primary schools today: analytic vs continental philosophy. Then study each one’s history and origins.
Read this book (also available as YouTube videos I think): https://www.amazon.com/Philosophy-Book-Ideas-Simply-Explaine...
This will give you high level introduction of the landscape across the various epochs, the big ideas and their main purveyors.
At the end of that you should have a good idea which philosopher/era/ideas interest you most. Only then consider diving deeper.
Specifically because you speak of mental models and “developing a personal philosophy” (and because you are on this website I am making some assumptions about your background ans familiarity with computer science/information theory) I also recommend Luciano Floridi. The Logic of Information: A Theory of Philosophy as Conceptual Design
https://www.amazon.com/Logic-Information-Theory-Philosophy-C...
> Starting with the slogan "proofs-as-programs," we now talk about "theories-as-systems."
But if you rewind history, you could also see the parallels to Peter Naur's "Programming as Theory building"
Or more recently: Luciano Floridi's "The Logic of Information: A Theory of Philosophy as Conceptual Design"
Different descriptions of the same thing. You could probably relate most of these ideas all the way back to the Greek classics. Democritus. Aristotle. Socrates. Plato.
Our tools are finally catching up...
(1) Floridi's multi-annual research project concerning information: http://www.philosophyofinformation.net/research/
The Logic of Information (vol. 3) follows Ethics of Information (vol. 2) follows Philosophy of Information (vol. 1), with one volume forthcoming The Politics of Information – what the entire research project is attempting to do is posit information as a basic term, an axiomatic or core concept in philosophy (like truth is, or beauty, or reason, etc.) and to add subject areas with information as their focus to the pantheon of philosophical subject areas …
This is not the same research project as
(2) which is readily apparent by perusing the list of researchers. Digital Philosophy flows from Digital Physics which posits that the structure of reality is discrete, essentially reducible to zeroes and ones; digital philosophy (in this sense) is the philosophical attitude that this view of reality is correct – confusingly there is another use of the term digital philosophy that is a sort of cognate of digital humanities and digital science insofar as those meta/mega-fields are related.
I am not sure (even though it is asserted there by Wikipedia) that digital philosophy (in the first sense) is a re-interpretation of
(3) Monadist metaphysics. NB: Monadist metaphysics is an example of a Monist metaphysics and shouldn't be conflated, any metaphysics which posits a supreme singular entity, another example is object-oriented ontology, or theologically the
(4) singular supreme being of the Abrahamic religions. Thing is, yes they're related – don't conflate, smudge, equate, or treat them as identical – they're not.
Lastly computational trinitarianism is a clever moniker for
(5) the idea that logic, category theory, and type theory are three sides of the same coin. the monads of category theory and type theory are not the monads of Leibnizean Monadism. Don't confuse these ideas.
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What have we learnt from all this? Things that have similar names are not necessarily similar. Philosophy is hard. The review of Floridi's work linked here is an okay jumping off point but there is nothing like reading the work for itself. I have read most of Floridi's 4th Revolution, his Very Short Introduction and most of his Philosophy of Information. I'd probably read them in the order he intended them to be read if I were you. Whether h has re-conceptualised much of philosophy is debatable but given we live in the information age he certainly is striking close to the bone in my opinion.