Look, I'm going to be honest with you. When I downloaded a 14-hour theological autobiography from the 4th century, I was fully prepared to use it as a sleep aid. Ancient religious texts? On my 6AM Caltrain? That's basically asking for a nap.
I was wrong. Like, embarrassingly wrong.
When a 1,600-Year-Old Book Reads Like a Tech Confessional
Here's what nobody tells you about Augustine: the guy was basically writing the original "I was a mess before I figured it out" memoir. He's out here talking about stealing pears as a teenager just for the thrill of it, obsessing over his ex, struggling with addiction (to pleasure, to status, to being right), and having existential crises about what he actually wants from life. Sound familiar? Replace "pears" with "startup equity" and "Carthage" with "San Francisco" and this could be a Medium post from 2019.
The thing that got me—and I mean really got me, like I missed my stop got me—is how raw he is about his own contradictions. He wants to be good but doesn't want to want it yet. He prays "give me chastity... but not yet." That's not ancient wisdom. That's me with my screen time limits. That's every engineer who knows they should refactor the code but ships the hack anyway.
Richard Ferrone Earned His Paycheck
Okay, so the content surprised me. But what really made this work for commute listening was Ferrone's narration. The man has this way of making Augustine's philosophical tangents feel like actual thoughts instead of a lecture. When Augustine is wrestling with himself—and he does this constantly—Ferrone's delivery has this quality where you can hear the struggle. It's not performative. It's not dramatic. It's just... penetrating? That's the word that keeps coming to mind.
There are sections where Augustine goes deep into Neo-Platonic philosophy and honestly, those parts tested me. Around hour 8 or 9, there's this extended meditation on memory and time that I had to rewind twice. But even then, Ferrone keeps the pacing steady enough that you don't completely lose the thread. He's not rushing through the dense stuff, but he's not making it feel like homework either.
I couldn't find a ton about Ferrone's background, but based on this performance alone, I'd trust him with other classics. He's got that rare ability to sound eloquent without sounding pretentious—which is exactly what Augustine needs.
The ROI Question
So here's where I have to be real with you. This is not a 1.5x audiobook. I tried. It doesn't work. The sentences are too long, the ideas too layered. At 1.25x it's manageable, but honestly? Normal speed is the move here. Which means you're committing to almost 14 hours of your life.
Is it worth it? Depends on what you're optimizing for.
If you want productivity tips or life hacks, skip this. "Could've been a blog post" it is not. This is philosophy. This is someone genuinely trying to understand themselves and the universe, and documenting the process with brutal honesty.
But if you've ever laid awake at 2AM after fixing a production outage, wondering why you're building what you're building, or what you're actually chasing with all this optimization... yeah. This hits different. Falling Upward explores similar territory about what we're chasing and why, though with less ancient philosophy and more practical frameworks for the second half of life.
I finished it over about two weeks of commutes, and I kept finding myself thinking about it during standups. Not the religious parts specifically (I'm not particularly religious), but the parts about desire. About how we want things that aren't good for us, and we know it, and we want them anyway. Augustine's framework is theological, but the problem he's describing is just... human.
Queue It or Skip It?
Queue it for: Long commutes, flights, any situation where you want something substantial but not plot-dependent. You can zone out for a few minutes and pick it back up without being lost.
Skip it for: Gym sessions (too contemplative), anything requiring split attention, or if you're looking for something light. This is not light. Also maybe skip if religious content bothers you—it's literally called Confessions and he's a saint, so the God stuff is pretty central. But I'd argue even secular listeners can find value in the psychological self-examination. The guy basically invented the memoir format, and you can see why.
Still Thinking About Those Pears
Three weeks later, I am. There's something about Augustine's honesty—the way he refuses to let himself off the hook—that sticks with you. Not because he found all the answers, but because he was willing to sit in the questions long enough to actually see himself. That's rarer than it should be, in any century.
