A Structured Learning Path Into Philosophy, Focused on Existential Questions

TL;DR

The best beginner path is a three-stage scaffold: (1) two short overview books read in parallel — Thomas Nagel’s What Does It All Mean? and Simon Blackburn’s Think — alongside the free University of Edinburgh “Introduction to Philosophy” MOOC on Coursera; (2) two free, lecture-driven deep dives — Shelly Kagan’s “Death” (Open Yale Courses, 26 lectures) and Robert Solomon’s “No Excuses: Existentialism and the Meaning of Life” (24-lecture Great Courses set) — paired with Sarah Bakewell’s At the Existentialist Café as the narrative spine; (3) only then primary texts, in this order: Camus’s Myth of Sisyphus → Sartre’s Existentialism Is a Humanism → Kierkegaard (selections) → Nietzsche (selections) → Nagel’s Mortal Questions / Parfit excerpts → Heidegger’s Being and Time with a guide.
The single most central philosophers for the questions you care about (meaning, consciousness, free will, death, identity) are: Kierkegaard, Nietzsche, Heidegger, Sartre, Camus, and Beauvoir on the existentialist side, and Thomas Nagel, Derek Parfit, Bernard Williams, Shelly Kagan, David Chalmers, and Daniel Dennett on the analytic side. You should read both traditions — most beginners make the mistake of picking only one.
Structured courses beat self-study for you, but the best “courses” for these themes are not single MOOCs — they are combinations: Edinburgh’s Coursera MOOC for breadth, Kagan’s Yale lectures for death/identity, Solomon’s Great Courses set for existentialism, and Hubert Dreyfus’s free Berkeley Being and Time lectures (archive.org) for Heidegger. MIT’s 24.00x “God, Knowledge and Consciousness” is the best stand-alone course for the analytic side of mind and free will.

Key Findings

There is no single “best” course for existential philosophy. Existential questions sit at the intersection of four sub-fields — metaphysics, philosophy of mind, ethics, and the existentialist tradition itself — and no single introductory MOOC covers them all well. The right answer is a curated sequence of four or five free or low-cost courses.
Overviews-before-primary-texts is the right preference for these particular texts. Heidegger, Sartre’s Being and Nothingness, and Parfit’s Reasons and Persons are notoriously punishing without scaffolding; Camus, Nagel, and Kagan are unusually accessible and can be read early. The sequence below respects that asymmetry.
The best two overview books are Nagel’s What Does It All Mean? (1987, ~100 pages) and Blackburn’s Think (1999, ~300 pages). Nagel is the gentler first read: he covers free will, mind, death, meaning, and right/wrong in plain prose. Blackburn is the more substantive follow-on, with stronger chapters on the self, God, reasoning, and ethics. Read Nagel first, then Blackburn.
For the existentialist tradition specifically, Sarah Bakewell’s At the Existentialist Café is the consensus popular gateway. It was named one of the New York Times Ten Best Books of 2016, received starred reviews from Publishers Weekly and Kirkus, and Nigel Warburton chose it as the first of his Five Best Philosophy Books of 2016. It weaves Sartre, Beauvoir, Heidegger, Camus, Husserl, and Merleau-Ponty into a single narrative and does the structural work better than any single primary source.
Yale’s “Death” with Shelly Kagan (PHIL 176, Open Yale Courses) is the highest-leverage single course for your interests. It is free, complete (26 video lectures), and explicitly built around the questions of personal identity, the badness of death, immortality, and how mortality should shape life — exactly your existential cluster, framed in the analytic style.
Robert Solomon’s No Excuses: Existentialism and the Meaning of Life (The Great Courses, 24 lectures) is the best structured introduction to the existentialist tradition proper. Solomon (Quincy Lee Centennial Professor of Philosophy and Business at UT Austin, 1942–2007) authored more than 45 books and recorded seven philosophy courses for the Great Courses’ Superstar Teachers Series; his UT “Introduction to Philosophy” was famously oversubscribed. The course covers Camus, Kierkegaard, Nietzsche, Heidegger, and Sartre in that order and is widely considered the single best lecture series on the topic in English. Paid (Wondrium subscription or one-time purchase), but the most efficient way to get a curated, classroom-style sequence.

Details

1) Best introductory courses (structured, ranked for your stated goals)

Tier 1 — start here (free, broad foundation)

University of Edinburgh, “Introduction to Philosophy” (Coursera, free to audit). Seven modules, each taught by a different Edinburgh philosopher, covering: What is Philosophy? (Dave Ward), Epistemology (Duncan Pritchard), Political Philosophy (Guy Fletcher), Philosophy of Mind / “Minds, Brains and Computers” (Suilin Lavelle), Moral Philosophy (Matthew Chrisman), Philosophy of Science (Michela Massimi), and Metaphysics / Time Travel (Alasdair Richmond). Reviewers consistently describe it as “easy” but “well-structured” — exactly the right level for a first course. The official companion book is Philosophy for Everyone (Routledge). Use this as a survey to discover which sub-fields grip you.

Tier 2 — the existential core (do these next, in parallel)

Open Yale Courses, PHIL 176 “Death” with Shelly Kagan (free, no registration). 26 video lectures, freely streamed at oyc.yale.edu. Builds an entire philosophical worldview around mortality. Major assigned texts: Plato’s Phaedo, John Perry’s A Dialogue on Personal Identity and Immortality, and Tolstoy’s The Death of Ivan Ilych, plus Nagel, Williams, and Hume on death. The companion book, Kagan’s Death (Yale University Press, 2012), is itself excellent. Caveat: Kagan is upfront that his approach is analytic-physicalist and that he is arguing for specific conclusions (no souls, death is annihilation, suicide can be rational); critics note he largely ignores existentialism and non-Western perspectives. Treat him as one strong voice, not the final word.
The Great Courses / Wondrium, “No Excuses: Existentialism and the Meaning of Life” by Robert Solomon (paid; ~$50 one-time or via Wondrium subscription). 24 lectures of ~30 minutes each, covering Camus → Kierkegaard → Nietzsche → Husserl → Heidegger → Sartre, with a final lecture on existentialism and postmodernism. This is the single best structured course on existentialism proper.

Tier 3 — sub-field deep dives (pick based on interest after Tier 2)

MITx 24.00x, “Introduction to Philosophy: God, Knowledge and Consciousness” with Caspar Hare (MITx Online; free audit, paid verified track). Problem-oriented (not historical) introduction explicitly covering “Is there a God? What is knowledge? What is the place of our consciousness in the physical world? Do we have free will? How do we persist over time?” The verified track includes feedback from a professional philosopher on three written essays — a rare offering for a MOOC. Note: the legacy edX listing is archived; the live version is on MITx Online.
University of Copenhagen, “Søren Kierkegaard – Subjectivity, Irony and the Crisis of Modernity” with Jon Stewart (Coursera; free audit). Eight-week course on Kierkegaard as the godfather of existentialism, lectures filmed in Copenhagen. The live Coursera page shows 4.8★ with 725 reviews and 61,429 learners enrolled; 98% of learners said they liked the course. Take this only after Solomon’s lectures, since Kierkegaard’s idiom is dense.
Hubert Dreyfus, UC Berkeley Philosophy 185 and 189: Being and Time Divisions I and II (free, archived on Internet Archive at archive.org/details/Philosophy_185_Fall_2007_UC_Berkeley). Audio-only. Dreyfus is described by California Review as having been “considered the leading Heidegger scholar in this country for decades,” and his lecture course is by consensus the best way to enter Being and Time without drowning. Save this for last; do not start here.

2) Best introductory books / overviews (read first, before primary texts)

In order of recommended reading:

Thomas Nagel, What Does It All Mean? A Very Short Introduction to Philosophy (1987, ~100 pages). Covers free will, right and wrong, death, the meaning of life, mind, language, and knowledge in plain prose. Designed as a first book.
Simon Blackburn, Think: A Compelling Introduction to Philosophy (1999, ~300 pages). Eight chapters: Knowledge, Mind, Free Will, The Self, God, Reasoning, The World, What to Do. The standard recommendation on r/askphilosophy as a one-book intro to Western philosophy.
Sarah Bakewell, At the Existentialist Café: Freedom, Being, and Apricot Cocktails (2016, ~440 pages). The narrative spine for the existentialist tradition. Read this before attempting any existentialist primary text.
Shelly Kagan, Death (2012, ~400 pages). Read alongside the Yale “Death” course; same content in book form, with arguments more carefully laid out.
Walter Kaufmann (ed.), Existentialism from Dostoevsky to Sartre (1956). The standard anthology — short, well-chosen primary-text excerpts from Dostoevsky, Kierkegaard, Nietzsche, Jaspers, Heidegger, Sartre, and Camus, with Kaufmann’s superb introductions. The bridge from overviews to primary texts.
Susan Wolf, Meaning in Life and Why It Matters (2010, ~160 pages). A short analytic treatment of the meaning-of-life question (the famous “active engagement in projects of worth” account). The best contemporary entry to the question that does not require reading Camus or Sartre first.

Optional but excellent secondary guides for specific thinkers:

Michael Inwood, Heidegger: A Very Short Introduction (OUP) — recommended as the gentlest first read on Heidegger by virtually every reading list.
Stephen Mulhall, Heidegger and “Being and Time” (Routledge) — read just before tackling the primary text itself.
Andrea Sauchelli (ed.), Derek Parfit’s “Reasons and Persons”: An Introduction and Critical Inquiry (Routledge) — required if you ever attempt Parfit.

3) Recommended sequence (months, not weeks)

This is the path I would actually follow:

Phase 1 — Orientation (4–6 weeks). Read Nagel’s What Does It All Mean? cover-to-cover. Start the Edinburgh Coursera MOOC and complete one module per week. At the end of Phase 1 you should be able to name the main sub-fields of philosophy and explain in plain language what a thought experiment is, what dualism vs. physicalism are, and what the free-will debate is about.

Phase 2 — Foundations and the analytic side of your questions (8–10 weeks). Read Blackburn’s Think one chapter per week. In parallel, work through Open Yale’s “Death” with Kagan (2–3 lectures per week). Optionally, do MITx 24.00x for the mind/free-will/identity material if you want a second analytic voice. At the end of Phase 2 you should have a confident grip on the death, personal identity, consciousness, and free-will questions in their analytic framing.

Phase 3 — The existentialist tradition (8–10 weeks). Read Bakewell’s At the Existentialist Café in parallel with Solomon’s No Excuses Great Courses lectures. The two reinforce each other: Bakewell gives biography and narrative, Solomon gives the philosophical arguments lecture by lecture. End Phase 3 by reading Kaufmann’s anthology and Camus’s Myth of Sisyphus.

Phase 4 — Primary texts, in order (open-ended). See section 4.

Phase 5 — Going deeper, by sub-field. At this point pick your branch: Kierkegaard MOOC (Copenhagen) → Heidegger via Dreyfus’s Berkeley lectures, plus Inwood and Mulhall → Parfit on personal identity → Chalmers/Dennett on consciousness. By now you can choose for yourself.

4) Which primary texts to approach after the overviews, and in what order

Each entry below assumes you have done Phases 1–3.

Plato, Apology and Phaedo. Short, foundational. The Phaedo is the Socratic argument for the soul’s immortality and is directly engaged by Kagan. Read with Kagan’s lectures.
Albert Camus, The Myth of Sisyphus (essay, ~150 pages) followed by Camus, The Stranger (novel, ~120 pages). Camus is the most accessible existentialist primary author. The essay frames the question; the novel dramatizes it. Optionally finish with Camus, The Fall and/or Camus, The Plague.
Jean-Paul Sartre, Existentialism Is a Humanism (1945 public lecture, ~70 pages). Sartre’s own one-sentence summary of his position; a far better starting point than Being and Nothingness. Pair with Sartre, Nausea (novel) for the experiential side.
Søren Kierkegaard — selections. Do not start with a full Kierkegaard book. Read the relevant chapter from Kaufmann’s anthology, then either Walter Lowrie’s A Short Life of Kierkegaard or the Copenhagen Coursera MOOC, then Kierkegaard, Fear and Trembling (his most readable book).
Friedrich Nietzsche — selections. Start with Kaufmann’s The Portable Nietzsche anthology (preface and selections from Thus Spoke Zarathustra, Beyond Good and Evil, and The Gay Science). Avoid trying to read Zarathustra straight through as your first Nietzsche.
Thomas Nagel, Mortal Questions (1979). Contains the essays “Death,” “The Absurd,” and “What Is It Like to Be a Bat?” — three landmark short pieces that bridge analytic philosophy and your existential questions.
Simone de Beauvoir, The Ethics of Ambiguity (1947, ~160 pages) — the most concise existentialist ethics, and arguably more rigorous than Sartre on the same questions. Optionally The Second Sex for the social/feminist application of existentialist method.
Derek Parfit, Reasons and Persons (1984), Part III on personal identity. Do not attempt the whole book first. Read Part III, possibly with Sauchelli’s Introduction and Critical Inquiry alongside.
Martin Heidegger, Being and Time (1927). The hardest book on this list. Approach via Inwood’s Very Short Introduction first, then Mulhall’s guide, then Dreyfus’s Berkeley lecture course chapter-by-chapter. Most readers do Division I only on a first pass.
Optional further texts depending on direction: David Chalmers, The Conscious Mind or The Character of Consciousness (philosophy of mind); Daniel Dennett, Consciousness Explained (the opposing view); Bernard Williams, “The Makropulos Case” on the tedium of immortality; Viktor Frankl, Man’s Search for Meaning (lived-application of meaning-making).

5) Philosophers especially central to existential questions

The existentialist canon (read in roughly this order):

Søren Kierkegaard (1813–1855) — the “father” of existentialism. Subjectivity, anxiety, the three stages of life (aesthetic, ethical, religious), the leap of faith.
Friedrich Nietzsche (1844–1900) — the death of God, eternal recurrence, the Übermensch, the project of creating meaning.
Fyodor Dostoevsky (1821–1881) — Notes from Underground and The Brothers Karamazov are existential-novel foundations.
Edmund Husserl (1859–1938) — phenomenology, the methodological precondition for Heidegger and Sartre. Skip on first pass; come back via Bakewell.
Martin Heidegger (1889–1976) — being-toward-death, authenticity, Dasein, the question of Being. Hard but essential if you want to go deep.
Jean-Paul Sartre (1905–1980) — radical freedom, “existence precedes essence,” bad faith, the look of the Other.
Simone de Beauvoir (1908–1986) — ethics of ambiguity, situated freedom, the analysis of “otherness.”
Albert Camus (1913–1960) — absurdism (technically not existentialism in his own self-description), revolt, “one must imagine Sisyphus happy.”
Maurice Merleau-Ponty (1908–1961) — phenomenology of perception, the embodied mind. Increasingly relevant to cognitive science.

The analytic philosophers most central to your existential questions:

Thomas Nagel — “Death,” “The Absurd,” “What Is It Like to Be a Bat?” (mind), “Moral Luck.”
Derek Parfit — personal identity; the view that “identity is not what matters.”
Bernard Williams — the case against immortality (“The Makropulos Case”), integrity, moral luck.
Shelly Kagan — death, badness of death, well-being.
Susan Wolf — meaning in life.
David Chalmers — the “hard problem” of consciousness, panpsychism.
Daniel Dennett — the eliminativist / functionalist counter-view; consciousness as illusion.
Galen Strawson — free will, narrative self, panpsychism.
Harry Frankfurt — care, love, the structure of the will.

Recommendations

Start this week. Buy or borrow Nagel’s What Does It All Mean? and start the Edinburgh Coursera MOOC at the same time. Both can be done in about an hour a day for a month. If you cannot get through Nagel in two weeks, this whole path is too ambitious — switch to Blackburn’s Think read in shorter sittings and slow down.

Choose your Tier-2 pairing by where the Edinburgh MOOC’s Mind / Metaphysics / Moral Philosophy modules grip you most. If the death/identity/free will questions grip you, prioritize Kagan’s “Death” plus MITx 24.00x. If the freedom/authenticity/meaning questions grip you, prioritize Solomon’s No Excuses plus Bakewell.

Do not buy Being and Nothingness or Being and Time in the first six months. Both are widely abandoned by self-studiers within 50 pages. Wait until you have done Solomon, Bakewell, and the relevant secondary guide.

Set a benchmark to switch from overviews to primary texts. When you can, in one paragraph each, accurately describe (a) the mind-body problem, (b) compatibilism vs. libertarianism on free will, (c) the psychological-continuity vs. body view of personal identity, and (d) what Sartre means by “existence precedes essence,” you are ready for primary texts.

Set a benchmark to stop. If after Phase 3 you find yourself drawn far more to analytic than to existentialist authors (or vice versa), drop the side that does not grip you. Reading philosophy you find dead is the fastest way to quit philosophy entirely. The discipline rewards depth in one tradition far more than thin coverage of both.

One concrete budget number. If you do Coursera audits and Open Yale, the only money you need to spend in the first six months is roughly the cost of four paperbacks (Nagel, Blackburn, Bakewell, Kaufmann anthology) — under US $80. The Solomon Great Courses set is the one paid course I would actually recommend buying outright (~$50 on sale, or a Wondrium free trial).

Caveats

“Existentialism” is a contested label. Heidegger explicitly rejected it; Camus rejected it; Jaspers preferred “Existenzphilosophie.” When Solomon or Bakewell groups these thinkers together, they are doing useful pedagogical work, not reporting an agreed taxonomy. Your reading lists will sometimes contradict each other on who is “really” an existentialist.
There is no consensus on whether to start with Camus or Sartre. I have recommended Camus first (more accessible prose, less technical), but a serious minority view starts with Sartre’s “Existentialism Is a Humanism” because it sets the agenda the others react to. Either order works; do not agonize.
Kagan’s Yale “Death” course argues for specific conclusions (physicalism about persons, no afterlife, suicide can be rational, fear of death is irrational). It is not a neutral survey. Read it as a strong argumentative position to evaluate, not as the consensus view.
The MITx 24.00x course was originally on edX and is now on MITx Online; the older edX listing may appear archived in search results. The course is still offered, but verify the current enrollment window on the MITx Online catalog before committing.
Hubert Dreyfus’s lectures are audio-only and were never officially published. They were rescued to the Internet Archive after UC Berkeley took down its public podcast site. They are extremely good but lack the polish of a designed online course.
Most “best of” reading lists overweight the analytic tradition or the continental tradition depending on the recommender’s training. I have tried to balance both because your specific questions (meaning, consciousness, free will, death, identity) are the few questions where both traditions have produced first-rate work and serious reading requires both. If you find a single source confidently dismissing one tradition, treat that source’s recommendations with caution.
AI-assisted summaries are not a substitute for reading the texts. A real understanding of what Sartre, Heidegger, or Parfit are doing requires sustained engagement with the prose. Use overviews and lectures to scaffold the primary texts, not to replace them.