Plato’s dialogues are mostly accessible and deal with basic philosophical questions. He was not the first philosopher, but his works are a great starting point to understanding the foundations of western philosophy. I forget the names of each one, but the series of dialogues involving Socrates’s trial and imprisonment are quick to read and thought-provoking. The best part of Plato is that he doesn’t just tell you what he thinks, he teaches you how to think critically and philosophically.

Once you’ve finished Plato, you can move onto Aristotle, particularly his Ethics.

As for “how to deal with bad things,” the Stoics are very popular now. Also check out the Epicureans. I think you should balance out these views with alternate approaches, maybe from Laozi.

After that, you may be interested in the rationalist-empiricist debate. (I’m skipping over a lot of medieval work that laid the foundations for this.) Descartes and Hume are the most readable of each group, respectively, in my experience.

If you are interested, you can move onto questions of “the meaning of life” or however you want to phrase it. A lot of this work rests on the very difficult works of Hegel and Kant, which would take a ton of time and effort to read and are probably not worth it for a non-academic. Kierkegaard is wonderful but also difficult to read. Fortunately at this stage, there are novelists who have read this stuff and put it into novels. Dostoyevsky and Camus provide a good synthesis of existential thought, coming to very different conclusions.

Everything I’ve mentioned in this comment can be read in a year or less, assuming you read at least the major one or two works from each author I’ve mentioned. At that point you won’t have an academic understanding of the field, but you’ll have a solid practical philosophical foundation for your daily life.