Why am I passionate about this?

As a philosopher, I’m not just interested in solving ‘academic’ problems that arise from philosophical inquiry. I also think philosophy should return to the role it often had in the ancient world, as a tool for helping us navigate the perennial challenges that being human presents us. Much of my own philosophical work has sought to help us figure out how to relate to arguably the biggest challenge we face: that we inevitably die. The books on this list are powerful examples of how philosophy can provide us with an emotional compass!


I wrote

Grief: A Philosophical Guide

By Michael Cholbi,

Book cover of Grief: A Philosophical Guide

What is my book about?

In Grief, Michael Cholbi presents a groundbreaking philosophical exploration of this complex emotion, offering valuable new insights about what…

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of On Anger (De Ira)

Michael Cholbi Why did I love this book?

Anger is a seemingly recalcitrant emotion – hard to avoid and difficult to manage. De Ira is the Stoic philosopher Seneca’s attempt to show us otherwise. To Seneca, anger is a wicked emotion. Yet a life free both of the turmoil of anger and of the desire for vengeance that Seneca thought defined anger is possible, he argued. Not only does anger lead us to lash out at others, it corrodes us from the inside – in Seneca’s image, like vinegar stored in a clay pot. While I find Seneca’s conclusion that we should eliminate all anger hard to swallow, his description of the dangers of anger, both to ourselves and to others, never fails to impress.

By Seneca, Aubrey Stewart (translator),

Why should I read it?

1 author picked On Anger (De Ira) as one of their favorite books, and they share why you should read it.

What is this book about?

De Ira or “On Anger” is an essay on anger by Seneca the Younger. The work offers advice on controlling anger and to make it subject to reason. This essay contains an active table of contents for easy maneuverability throughout the eBook.

It is not clear to scholars who wrote the first work on the subject of passions or emotions (the terms are thought interchangeable), but while Xenocrates (396/5–314/3 BCE) and Aristotle (384–322 BCE) were students at Plato's Academy, a discussion on emotions took place which provided likely the impetus for all later work on the subject. The Stoic Posidonius…


Book cover of The Anxious Mind: An Investigation Into the Varieties and Virtues of Anxiety

Michael Cholbi Why did I love this book?

I enjoy being surprised by philosophical work on emotions. Kurth’s The Anxious Mind is full of unexpected insights into anxiety, an emotion that seems to have little to recommend it. But Kurth manages to persuade readers that we should actually be glad for the presence of anxiety in our lives. He explains how anxiety can enhance our performance and contribute to moral progress both individually and collectively. 

By Charlie Kurth,

Why should I read it?

1 author picked The Anxious Mind as one of their favorite books, and they share why you should read it.

What is this book about?

An empirically informed, philosophical account of the nature of anxiety and its value for agency, virtue, and decision making.

In The Anxious Mind, Charlie Kurth offers a philosophical account of anxiety in its various forms, investigating its nature and arguing for its value in agency, virtue, and decision making. Folk wisdom tells us that anxiety is unpleasant and painful, and scholarly research seems to provide empirical and philosophical confirmation of this. But Kurth points to anxiety's positive effects: enhancing performance, facilitating social interaction, and even contributing to moral thought and action.

Kurth argues that an empirically informed philosophical account of…


Book cover of Naked: The Dark Side of Shame and Moral Life

Michael Cholbi Why did I love this book?

Like many emotions, shame seems like a double-edged sword. Shame seems to notify us that we haven’t lived up to our own ideals – that we’re not the people we thought or hoped we were. But shame has, as Thomason carefully delineates, a dark side: Shame can lead us to withdraw from the world in order not to be seen, and too often shame is a precursor to self-destructive behaviors. Naked ultimately argues that we need shame despite these drawbacks. Thomason’s book is also among the very best of recent books to use philosophical tools to investigate social media; her discussion of online shaming should not be missed.

By Krista K. Thomason,

Why should I read it?

1 author picked Naked as one of their favorite books, and they share why you should read it.

What is this book about?

We know shame can be a morally valuable emotion that helps us to realize when we fail to be the kinds of people we aspire to be. We feel shame when we fail to live up to the norms, standards, and ideals that we value as part of a virtuous life.
But the lived reality of shame is far more complex and far darker than this - the gut-level experience of shame that has little to do with failing to reach our ideals. We feel shame viscerally about nudity, sex, our bodies, and weaknesses or flaws that we can't control.…


Book cover of A Grief Observed

Michael Cholbi Why did I love this book?

A Grief Observed falls into a rare genre: a philosophical memoir on grief. Lewis, the well-known defender of Christianity and author of the children’s book series The Chronicles of Narnia, recounts the days after the death of his wife, Joy Davidman. Lewis seems to be drowning in an emotional tidal wave in the book’s opening pages, facing an array of emotions he did not expect to undergo in grief: sadness of course, but also fear, disorientation, and anomie. I find Lewis’ nuanced and vivid picture of grief more compelling than his theological tribulations, but the power of A Grief Observed is undeniable. (And it’s hard not to speculate on why Lewis did not publish this under his own name during his lifetime: Was the great C.S. Lewis embarrassed by his grief?)

By C. S. Lewis,

Why should I read it?

6 authors picked A Grief Observed as one of their favorite books, and they share why you should read it.

What is this book about?

The perennial classic: this intimate journal chronicling the Narnia author's experience of grief after his wife's death has consoled readers for half a century with its 'sensitive and eloquent' magic (Hilary Mantel)

'An intimate, anguished account of a man grappling with the mysteries of faith and love ... Elegant and raw ... A powerful record of thought and emotion experienced in real time.' Guardian

'Raw and modern ... This unsentimental, even bracing, account of one man's dialogue with despair becomes both compelling and consoling ... A contemporary classic.' Observer

'A source of great consolation ... Lewis deploys his genius for…


Book cover of Political Loneliness: Modern Liberal Subjects in Hiding

Michael Cholbi Why did I love this book?

We live in a very interconnected world, and yet loneliness is rampant. How can that be? Gaffney’s Political Loneliness helps us see that today’s loneliness is the byproduct of our specific political moment. Modern political life, she argues, alienates us from one other and fosters anonymity while also priming us to value belonging and inclusion. Gaffney’s purpose is less to offer us advice about how we can overcome this ‘political loneliness’ on an individual level. Rather, her uncomfortable message is that, with respect to loneliness at least, the personal is indeed the political, and she warns us that many will find totalitarianism an appealing antidote to the loneliness endemic to contemporary life.

By Jennifer Gaffney,

Why should I read it?

1 author picked Political Loneliness as one of their favorite books, and they share why you should read it.

What is this book about?

Political Loneliness: Modern Liberal Subjects in Hiding examines the political significance of the experience of loneliness. The book conceives of loneliness as a symptom of the political alienation of modern life. Its central claim is that neoliberal subjectivity has rendered us lonely. That is, that the political structures we have inherited from the liberal tradition-such as the anonymity of the vote, or the emphasis on representation rather than deliberation-have left us hidden from one another, unable to appear as members of a common world. In view of this, the author suggests that it is precisely this experience of loneliness that…


Explore my book 😀

Grief: A Philosophical Guide

By Michael Cholbi,

Book cover of Grief: A Philosophical Guide

What is my book about?

In Grief, Michael Cholbi presents a groundbreaking philosophical exploration of this complex emotion, offering valuable new insights about what grief is, whom we grieve, and how grief can ultimately lead us to a richer self-understanding. Drawing on psychology, social science, and literature as well as philosophy, Cholbi explains that we grieve for the loss of those in whom our identities are invested, Their deaths not only deprive us of worthwhile experiences; they also disrupt our commitments and values. Yet grief is something we should embrace rather than avoid, an important part of a good and meaningful life. Although grief can be tumultuous and disorienting, it also reflects our distinctly human capacity to rationally adapt as the relationships we depend on evolve.

You might also like...

The Open Road

By M.M. Holaday,

Book cover of The Open Road

M.M. Holaday Author Of The Open Road

New book alert!

Why am I passionate about this?

I grew up a fan of an evening news segment called “On the Road with Charles Kuralt.” Kuralt spotlighted upbeat, affirmative, sometimes nostalgic stories of people and places he discovered as he traveled across the American landscape. The charming stories he told were only part of the appeal; the freedom and adventure of being on the open road ignited a spark that continues to smolder. Some of my fondest memories from childhood are our annual family road trips, and I still jump at the chance to drive across the country.

M.M.'s book list on following the open road to discover America

What is my book about?

Head West in 1865 with two life-long friends looking for adventure and who want to see the wilderness before it disappears. One is a wanderer; the other seeks a home he lost. The people they meet on their journey reflect the diverse events of this time period–settlers, adventure seekers, scientific expeditions, and Indigenous peoples–all of whom shape their lives in significant ways.

This is a story of friendship that casts a different look on a time period which often focuses only on wagon trains or gunslingers.

The Open Road

By M.M. Holaday,

What is this book about?

After four years of adventure in the frontier, Win Avery returns to his hometown on the edge of the prairie and tracks down his childhood friend, Jeb Dawson. Jeb has just lost his parents, and, in his efforts to console him, Win convinces his friend to travel west with him―to see the frontier before it is settled, while it is still unspoiled wilderness.

They embark on a free-spirited adventure, but their journey sidetracks when they befriend Meg Jameson, an accomplished horsewoman, lost on the Nebraska prairie. Traveling together through the Rocky Mountain foothills, they run into Gray Wolf, an Arapaho…


5 book lists we think you will like!

Interested in philosophy, life satisfaction, and anxiety?

Philosophy 1,751 books
Life Satisfaction 224 books
Anxiety 209 books