Lots of people ask: "I don’t want to go to grad school or become a professional philosopher, but I want more philosophy in my life. How can I get this?"
Here's how I think about this. Fundamental aspects of having philosophy in one's life include:
Taking these in turn:
First, how do you recognize philosophical questions? Life is full of them, but you'll be better off if you consume lots of high-quality stuff (any medium will do). When people ask me for philosophy recommendations, I more often want to encourage them to think about their intellectual consumption habits more broadly. (If you want lots of my opinions about this, just go to my home page and start reading; this site is full of them.)
The harder part is having the right receptive instincts. This is some combination of attention, energy, and a willingness not to fall back on broadly popular answers.
So, just last night I came across this passage:
"What had befallen him was most unkind: the bewildering illusion that he was now in love with the daughter of the only woman he’d ever loved! But who can distinguish between falling in love and imagining falling in love? Even genuinely falling in love is an act of the imagination." (Source.)
This is, I think, a perfectly good example of having philosophical questions dropped on your intellectual doorstep:
Here is the output of my last attempt to organize a bunch of philosophical questions (around a theme, and under other constraints).
Second: how do you gain and refine tools for addressing philosophical questions? Lots of practice is essential. Having really good models is also important. I'll always recommend Platonic dialogues here, but also consider great art and following philosophers on Twitter.
The best way to improve your tools is also the last item on my initial list, which is to discuss and test your ideas (or the ideas you've encountered, whether or not you take yourself to have originated them). I don't have any surprising or witty advice to give about this, but note that you don't always need a single interlocutor and it doesn't need to have the surface appearance of a prototypical philosophical discussion. My maintaining this Web site is largely motivated by my wanting to test myself in generating and explaining ideas that are, broadly, philosophical. I get plenty of feedback, and I feel more pressure to be rigorous in public writing than I do in idle thoughts (which often seem interesting only until I get around to actually formulating them in a disciplined way).
Finally, a note about academic philosophy. I adore a lot of academic philosophy, but I think most people who try to keep philosophy in their lives weight their consumption too heavily toward academic outputs. Academic philosophers have wonderful outputs, but a lot of their best work isn't what makes it into writing. I think the norms of (academic) philosophical writing have gone badly wrong.
There are plenty of great journal articles and books, but a good heuristic is to look for things that were commissioned but weren't as much at the mercy of peer reviewers. Introductions to anthologies and conference talks (check YouTube!) are often very good and have high philosophical value per word. (My favorite output of Terence Irwin is his "intellectual background" chapter in the Cambridge Companion to Plato.)