I am going to say what sounds stupid. Get a list of classic fiction. Cross off anything still in copyright. Read.

There is an assumption today that everything can be known and expressed. Great authors know that isn't true. They lead you somewhere where you might catch a glimpse.

Out of copyright because even so they are still being sold. I am not suggesting a list because it would be mine, and contentious.

I'd say the typical recommendation is Viktor Frankl's "Man's Search for Meaning". I do recommend it, it's a great book. However, for me personally, the book that truly triggered my re-evaluation of life (my own and in general) was "The Selfish Gene" by Richard Dawkins. Lots of things instantly fell into place. It may not blow your mind the way it did for me, but read it anyway -- it's worth every second of your time.

Awareness by Anthony De Mello

I haven't been the same, in the best way possible, ever since reading it.

Anthony was well-read and traveled and his background as an Indian, Jesuit Priest and practicing psychologist put him at the perfect intersection of experience to deliver such a life-changing work that encompasses religion, science, relationships, your psyche, career, money, philosophy, spirituality, etc.

It's telling and (to me) validating of his mastery of life that, after his death, he was excommunicated from the church due to his 'blasphemous' works.

The ebook and audiobook are available for free here: https://archive.org/details/Awareness-AnthonyDeMello

Sounds like a classic existential philosophical question to me.

At some point in life we all end up asking ourselves "what is the meaning of life" and "who am I"?

In your particular situation I would look at the the "existential given" Meaning and Meaninglessness.

Are you Meaning Creating or Meaning Seeking?

There are 5 existential givens

1. Freedom, Responsibility and Agency 2. Death, Human Limitation and Finiteness 3. Isolation and Connectedness 4. Meaning vs Meaninglessness 5. Emotions, Experience and Embodiment

My own favourite existentialist philosophers are: Friedrich Nietzsche, Jean-Paul Sartre and Søren Kierkegaard.

My favourite existential psychotherapists are: Irvin Yalom, Emmy Van Deurzen and Rollo May.

Irvin D. Yalom "Love's Executioner & Other Tales of Psychotherapy" Basic Books (2012) Rollo May, "Man's Search for Himself" W. W. Norton & Company (2009) Professor Emmy van Deurzen, "Existential Counselling & Psychotherapy in Practice" Sage Publications Ltd (2002)

Seneca's "On the Shortness of Life" and his collected "Letters on Ethics", in that order, compelled me to re-evaluate. The results have been positive. I recommend the University of Chicago translations: a little pricey for paperbacks, but quite readable.

The purpose of life is to play.

Please read Johan Huizinga's Homo Ludens.[0]

[0]: https://en.wikipedia.org/wiki/Homo_Ludens

Mihaly Csikszentmihalyi, who coined the term ‘flow’, has a whole philosophy on life detailed in:

Flow

The Evolving Self

There’s the ‘awakening’ thing you can do, which might give a fresh perspective:

The Mind Illuminated - Culadasa

Seeing That Frees - Rob Burbea

Right Concentration - Leigh Brasington

"Early Retirement Extreme" by Jacob Lund Fisker. It's not your typical "rich dad/poor dad" financial advice book, but rather a systematic approach to seeing the economy aspect of your life in a new way. Interesting read just to see his perspective and have one or two takeaways from it, if nothing else.

[1] The author was a highly credentialed career physicist before abandoning that for thinking about alternative paths through life.

You don't go looking for an answer. The answer finds you. That may take years or decades, even. Just tough it out until then.

The problem with that is that it finds you (if ever) too late to be of any use.

Not the OP but in a similar situation.

Once you find the answer, you realize there was never any use to any of it.

There was never any use to it or you're not interested in using the answer?

This is what religious and philosophical books are for. I don't suggest reinventing the wheel; it was invented thousands of years ago. People go on about the benefits of meditation, but many religions emerged from it, and were subsequently built on top of those foundations.

I don't want to promote a specific religious book, but you could look into modern interpretations of past work. Rumi's poetry is built atop Sufism, atop Islam, which is atop the Abrahamic religions. Coleman Barks does the Rumi translations that many quote, but in doing so he morphed it to something no longer Rumi. If you find something that makes you uneasy, don't follow it, or look deeper into where the inspiration comes from.

James P Carse is also really good at digging deep and across multiple religions. I'd recommend that as another starting point. His most popular work is Finite and Infinite Games, which is well suited for modern society.

I've enjoyed reading books by James Hollis, a Jungian psychologist. These two are approachable. Read the description of each and check out whichever speaks most to you as they cover some similar territory.

- What Matters Most: Living a More Considered Life - Living an Examined Life: Wisdom for the Second Half of the Journey

Philip Su - Man’s Search for Baby Wipes, Pampers Sensitive Water Based Baby Diaper Wipes, Hypoallergenic and Unscented, 8 Refill Packs (Tub Not Included), 72 each, Pack of 8 (Packaging May Vary) in A/12/B/135

I thought this was some philosophical parody of Man's Search for Meaning

I generally recommend Thich Nhat Hahn's book fear, for pretty much all situations, it comes in useful for most situations relating to change.

I like Travels Michael Crichton for discussing the ups and downs of life.

Travelogues in general are a good source of new perspectives and are not usually heavy reading.

Courage to be Disliked Book by Fumitake Koga and Ichiro Kishimi

I read it sometime back. It questions the idea that our childhood events have formed our current personality and our behaviour. It asks us to reinterpret the past events from different perspective. It encourages everyone to live in the moment and form a mindset to change for better where we compare ourselves with our ideal self and look at each other as comrades and not as enemies in a zero sum game.

Thich Nhat Hanh wrote a book called "The Art of Living: Peace and Freedom in the Here and Now" which is pretty excellent. I listen to it every once in a while on audiobook and learn something every time.

https://www.amazon.com/Living-Godfrey-Robinson-Stephen-Winwa...

Jed Mckenna. It's possibly a hoax just like everything else.

David Graeber's "What's the point if we can't have fun": https://thebaffler.com/salvos/whats-the-point-if-we-cant-hav....

Graeber makes interesting points and also criticizes views that most people in tech will at least be familiar with by now, like Dawkins and Harari.

"The Magic of Thinking Big", by David J. Schwartz. It contains the secrets to getting the most out of your job and family life.

I can recommend Midnight library (https://www.goodreads.com/book/show/52578297-the-midnight-li...). It is about what path we choose in life and what other paths could have for us.

Take _any_ Stoicism philosopher, they are absolutely identical, and as far as I understood your request, any of them must be the perfect fit. Seneca, which is suggested in one of previous comment, worked great for me as a start of learning about Stoicism.

Democracy: The God That Failed by Hans-Hermann Hoppe

Typically read by anarchists and libertarians, I'm not recommending it to change your politics, but rather as a philosophical exercise. It does an amazing job at taking something so ingrained and obvious to us and then flipping it on its head and forcing you to use your own logical faculties to prove whether or not what you always believed is actually logically correct.

A paradigm shifting book regardless of your politics or philosophical belief system.

> Triggered by the thread on Philip Su

Sorry, but to which thread are you referring?

I am that by Nisargadatta Maharaj or Freedom from the known by J.Krishnamurti.

You may disagree with what they are saying, but these books will give you a new perspective.

Read some biographies.

If your idea of philosophy is Pirsig, try one of Plato's Socratic dialogs as a palate-cleanser. It shouldn't be toil.

Maybe not a book? Like go do something different and out of your comfort zone, New experiences will be new perspectives

Finite and Infinite Games by James Carse

Quran translations and tafseer.

If have more time, study Arabic and try to listen/read the Quran.

The Courage to be Disliked And The Courage to be Happy By Ichiro Kishimi and Fumitake Koga

Don't read philosophy...they are useless