Books that have changed my life

The 2am answer

Epistemic status: Personal and retrospective, filtered through hindsight and some dramatisation.

4 July 2026
3950 words - 18 min read
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The books that shaped me, one per life stage: my definitive answer to "What books have changed your life?"

Every time I've been asked, "What books have changed your life?" it was late at night, we were in a remote place, most people were drunk, and I didn't have the mental capacity to answer with the depth required.
Not exactly the right situation to consult Obsidian (containing the information needed) since it lived on a turned off PC in my (typically) faraway room.

This post serves to definitively answer the question and provide a Source of Truth to refer to when I'm asked.

Soyjak meme pointing excitedly at an Obsidian vault
POV: you just asked me what books have changed my life

■ One, No One and One Hundred Thousand (age 12–13)

At the end of elementary school, we started saying swear words when the adults couldn't hear us, knowing they said them too.
I began wondering why it worked this way: couldn't we all just openly swear, all the time?

The summer after elementary school, I decided to move on from Goosebumps to "grown-up books," and "Pirandello" was a name lofty enough to suit the purpose.

I barely understood it (I was 12...) but I grabbed the one thread I could get: we have multiple behaviors (or identities) that we adopt depending on the situation.
Understanding this helped me make peace with the whole "social conventions" thing: every place and every situation has a behavior (and if you don't know what it is, watch the others).

Hence I finally understood why you couldn't swear at school.
And that maybe it was "normal" to do it when our parents couldn't hear us...

■ Alcatraz: A DJ on Death Row (age 13–15)

What's better, at 14, than reading the transcripts of a radio show by an Italian on death row in the US?

It was the school period where we started addressing teachers formally, who suddenly turned stricter and more demanding.
What drove students crazy was that the teachers' approach shifted from the nurturing style of elementary school to "Start taking responsibility for your actions" which in reality masked the dictatorial "These are the rules I'm imposing on you and you must follow them" (different from teacher to teacher, or rather from one personal pet peeve to another...).

While school was trying to funnel this "dictatorial hypocrisy", the book talked about the freedom to decide which actions to take: the practice of actually thinking before acting (so even before taking responsibility).
It concealed, under the concept of freewill, the concept of critical thinking.

This is definitely the book that gave birth to my hyper-rational streak.
And to my doubts about the unjustified authority of teachers and the arbitrariness of parental authority[this is how Bill Gates put it in a documentary], in what I would now describe as the beginning of my (involuntary) Sartrean phase against deontological ethics.
Which of course led to Nietzsche (damn you moustached-man, you're so irresistible to teenagers!)
But don't worry folks: I converted to utilitarianism now.
I think.

NOTE: as enlightening as it was for a 14-year-old, at 20 I found it... adolescent. It was some sort of rite of passage for me more than something I'd recommend. It's not necessarily "wrong": if this post has a lesson it's "a mediocre book at the right time does more than a masterpiece at the wrong one".

■ The Flowers of Evil (age 18)

At 10 I was a smug little nerd who loved math and figured poems were just "a normal bunch of words" (I literally told this to the teacher), certainly not worth studying at school.

Fast forward: in high school we studied Baudelaire.
As the passionate reader I was, I read the full edition of The Flowers of Evil.
And damn, I had to take that back: indeed a bunch of words, if chosen well, can become something magical.

From that moment on, I started paying attention to situations where the choice of words, syllables, and timing is everything: stand-up comedy, rap, public speeches.
The best performances were the ones where everything was in sync, where I forgot I was even watching.
The way I understood this was through the bad ones: one missed comic beat, one syllable out of place, and not only do you remember you're an audience member, you wish you weren't...

I was starting to understand that how you say something changes what you're saying, the all-time classic:

The medium is the message

— Marshall McLuhan


I manifested this obsession in the only way available to a student: meticulous attention (calibrated to subject and professor) to writing style, visual structure, font choice, and layout of essays, project documentation, and theses.
Basically: increasing the perceived value of my work.
And look at me now: capitalizing on my obsession through marketing and copywriting.
(Well, kinda...)
Turns out obsessing over fonts at 18 was foreshadowing.

Here are 3 poems that struck me:

NOTE: thinking back, I'm amazed I reached this conclusion through a translation. Reading more poetry, I noticed no non-Italian poet survives translation as well as Baudelaire does!

■ 80,000 Hours (during bachelor's degree)

Bachelor's degree is a blissful time when you think you know what you're doing with your life ("Not like my high school classmates").
Then it ends and the void returns.
It's the same Vietnam-style flashback from the last year of high school: "Shall I get a job or keep studying?"

Turns out there's a book for that.
Reading it, I concluded that I wanted to help science solve the #1 cause of death worldwide: cardiovascular diseases.
The book goes something like:

Proudly, I applied to a master's degree in biomedical applications of mathematics, convinced that this was the career I wanted ("A book told me so!").
The two years went well... and then came the research year.

When you think you've found your raison d'être, when you think you know what you'll do with your life and that it will bring you money, happiness, and meaning... and then you find out it won't... well, no bueno.

My impression of this research field is that it's moving at an extraordinarily slow pace.
Partly because of European regulations (privacy, compliance...), partly because of funding... But what REALLY bothered me was the ivory-tower academic attitude of the researchers.
They don't want to deal with companies (you know, those things that bring products to hospitals) nor do they want to build products (like founding startups, who cares, right?)
What they want to do is to test their newly developed methods, publish a paper, boost their h-index, collaborate with other professors who want the same thing, and then brag about having collaborated with professors whose h-index is slightly higher than theirs.
Nobody is working on the real problems in this field[see Hamming question], namely making models regulation-compliant, i.e. actually bringing products into hospitals, i.e. EXACTLY WHAT I WANTED TO DO.

Aella (@Aella_Girl) on X, after her first academic conference: she loved the conversations — 'curious people who understood clearly what I was doing, asked great questions and wanted to work with my data. In absolute heaven.' — but found the structure inefficient, and the researchers' timelines 'SO LONG': 'all the conversations felt like they were being choked by the invisible hand of academia. I am used to just doing everything I want immediately.' She notes 'zero conception of methods of getting survey respondents outside of academic discipline. Absolutely no concept of marketing', and that a world outside academia didn't seem real to them: 'people would be like I don't like my job and I'd be like have you thought about other ways to do research and make money, and it didn't seem accessible whatsoever.'

News-flash everybody: I am not a Molochian bitch.
Let me tell you what you want to do when you don't want to become a Molochian bitch: you read 80,000 Hours.
So I read it again (harder this time), I reapplied the framework, and jumped ship.

Luckily, a couple of degrees in mathematics help with the LinkedIn grind: I found a job relatively quickly in process improvement at a corporate.
The only problem was an unwanted check:
Getting your soul sucked? Check.
And then I became self-employed, but that's another story.

So yeah, the lesson of that period of my life is: "Don't become a Molochian Bitch".
I've seen too many people choose to keep studying "because I don't know what else to do", or take a corporate job "because I couldn't find anything better."
Don't do that, it's a bad life (you dirty anti-socratic hedonist).

Don't become a Molochian Bitch.
NEVER become a Molochian Bitch.

(BTW the book is free, even in print)

■ Docs for Developers + Every Page is Page One (end of my master's)

Ever since a friend of mine introduced me to the world of PKM, I've become an Obsidian nerd.
When I came across these books I immediately thought they'd be applicable to PKM: IT documentation is Knowledge Management, add 'Personal' in front and the same rules apply.
The only mental leap you need to make is to identify the 'product' as the notes and the 'client' as your future self.

EPPO's core idea is that every note must be self-sufficient and answer one specific need, while also routing the reader to the related information.

We are all children of the Web, and we come to any information system (...) expecting every search to work like Google.
There is no first, last, previous, next, up, or back anymore.
Every Page is Page One.

— Every Page is Page One

The catch is: those two demands (self-sufficient + linked) pull against each other:

What helped me achieve PKM-inner-peace was realising that a good PKM lives within this tension and doesn't try to resolve it.
A note is never 'too self-sufficient', and a note is never 'too connected'.
If it responds correctly to a specific need and links appropriately to any related information within the PKM, it is perfect as it is.
As new notes get added and the user (you) needs change, the PKM needs maintenance.
But it's always about the same thing: adjusting the balance between these two pulls.

The other book, Docs for Developers, attacks the problem from the user's side.

It teaches to always think about the user (future you), whose goal is to find a specific piece of information when they need it: the quality of a PKM is its ability to surface the right information at the right moment.
Too much useless information makes the useful kind harder to find; badly managed information makes it impossible.
After this book I got pickier about what to add and stricter about how to file it, updating the system (tagging, name convention...) every time I failed to find a note.
NOTE: I use the CGP Grey approach.

To write effectively for users, you need to understand who they are and what they want to achieve.
(...)
Determine your goal for users of your product, write it down.
Later, you can measure the success of your documentation by how well it meets your goal.

— Docs for Developers


Anyway, just nerdy PKM things for a nerdy PKM guy.

■ The Power of Business Process Improvement (two months before quitting academia)

After 5 years studying math you know a lot about linear isomorphisms and... that's pretty much it.
Which doesn't help when you're looking for a job outside academia.

When I was brainstorming, the first thing that sprang to mind was project/product management: I enjoy organising projects (both at university and in my personal life) and events (I helped organise the Pride event in BZ).
But it didn't take long to realise that being a PM is an 'Asana simulator', so not quite what I was looking for.

Then, in a few podcasts, I heard people talking about processes and operations, and I wanted to look into it further.
I picked up this book at random, just to understand how the whole process side of things worked.
AND MY GOD, I FELL IN LOVE WITH IT.

I don't know if it's the similarity between processes and algorithms, or if it's the extreme methodicalness, but this stuff really clicked with my brain.
The book walks you through a full BPI case: study the problem, analyse the steps, optimise, test.
Which is basically how my brain works.

The first thing I did right after reading the book was apply it to my weekly meal prepping, cutting it from 3 hours to just over 1.
Then I tried applying it to small university situations: the time-off request process (which involves 3 people besides the requester, a nonsensical amount of time, and something like $50K a year just for approvals, entirely avoidable) and the conference organised by my research office (which had exactly the problems I'd identified).
Of course, all my suggestions were ignored because "we have 10 years of research experience."
Good.
Amazing even.

But beyond the how, this book has shown me that there are people who solve 'organisational' problems for a living.
In other words, it's made me realize that my way of thinking has a whole market.
And the good news is: I know how to solve those problems!
Heck, I'm even good at it!
Better yet: I love it!

That was the moment when I put 80,000 Hours to good use again to work out what to do.
What I like most about 80,000 Hours is that it warns against falling in love with a career based on vibes alone: it suggests talking to people who actually do the job to find the downsides.
Problem was, I didn't know anyone doing BPI and I couldn't find much online.
So there was only one way to find out if it was right for me: applying for as many roles as possible on LinkedIn.

It turned out the way it did, but I managed to discover that my supervisor hired me because I explained to him my passion for it and... because in the interview I explained how I applied it to my weekly meal prepping.

Anyhow, this book opened up an important perspective on work:

Money = solving problems

— an important lesson


And that's a big deal especially when you become self-employed.

NOTE: This book then guided me through the early stages of my self-employment, during which I worked as a consultant on AI automation for businesses, solving and optimising problems using AI tools.

■ What I Wish I Knew When I Was 20 (while quitting my new job)

Once I understood what I didn't want to do and the direction I wanted, I applied to roles that matched what I was looking for: process improvement, process optimization, some that were "show us what you can do and we'll let you do it".
I wasn't expecting to find the job of my life on the first try, but to understand whether the department was right, get familiar with adjacent roles, and figure out what actually worked for me.

As I've already written, I was hired in an operational excellence team and after one month I fled corporate hell.

In that moment of doubt and lostness, I started reading blogs, listening to podcasts, watching interviews... Looking for something to pull me out of it.
And this was what I needed:

A couple of years ago I arrived at class a few minutes early and found one of my students listening to her new iPod nano.
I hadn't seen one before and asked to take a look.
She handed it to me and turned it over.
The back was engraved with the words, "Never miss an opportunity to be fabulous!"
(...)
I've been remarkably surprised by the stickiness of this message.
It's as though students are just waiting to get this instruction.
They're hungry for permission to do their very best, to hit the ball out of the park and to shine their brightest.
Unfortunately, in most situations this doesn't happen.
We're encouraged to "satisfice."
That is, we're subtly or not so subtly encouraged to do the least amount we can to satisfy the requirements.

— What I Wish I Knew When I Was 20

I'd always been one of those students desperately hunting for the right professor and the right project.
I always found that projects were too trivial, or gave students too little room to dig deeper and build something genuinely interesting.
They were too much "homework assignment".

Work hadn't changed that: I was still looking for a chance to do something fabulous.
I remember that during the interview I asked for more details about the job specifically to avoid ending up in corporate hell... only to let myself be swayed by corporate buzzwords...
Big mistake: I ended up making slides, measuring tables, and translating English to Italian.

Despite all that, during that month I was naturally drawn to problems I actually wanted to solve:

This, for me, was the fabulous: the serendipity of finding solutions from unexpected angles, sometimes as a software person, sometimes as a workflow enthusiast.
In other words, as Rory Sutherland puts it, leveraging the magic of the explore-exploit trade-off.
Solutions that... nobody wanted to hear, despite them being the team's responsibility.
The business-as-usual approach was to send support tickets (for 4 years on the data problem!) and suggest that production managers reorganize shifts to waste less time replacing the part (without actually solving the problem).

It was hell.
But again: useful for understanding what I want.
So I built a heuristic for picking a job: "Does it give me the opportunity to be fabulous? To do fabulous things?"
The point of interviews now is to understand how the job answers that question.
If "no", it's not the right opportunity.

The problem with this requirement is that no single person in a company can answer it: it depends on the company culture, on every person in the hierarchy, on the company's situation... It seemed unlikely that a "normal" job would reliably give me that opportunity.
At that point it became clear that the best move wasn't to hope someone would hand me that opportunity, but to create it myself: become self-employed.

So I started working for free for a solopreneur friend, knowing that if his project worked we could do great things.
Fabulous things.

■ The Gervais Principle (shortly after quitting)

I clearly remember this line from Dr. House to an arrogant little chess prodigy:

You know, it's a real thin line between tortured genius and awkward kid who can't get girls because he's creepy.

— Dr. House


As usual after important decisions, after I quit I started having doubts.
Specifically, they took the form of this line from a fictional Dr. House:

You know, it's a real thin line between startup founder wannabe and awkward kid who has problems with authority.

— Fictional Dr. House


That's because during my time as a researcher I had already been told that: when I shared my strategy to improve a process at UniGraz, my office mates answered... "I think you have a problem with authority."
Got that?
Business process improvement happens when you have problems with authority, not when you want to optimize processes!

Anyway, I read this book right after quitting my job to understand how corporates work: maybe I'd really missed out on an opportunity because of my hatred of authority!
And... nope, they are hell.
The hellish nature of the corporate world is something employees can only sense, they perceive it out of the corner of their eye, like the "shadow in the alley."
They're too immersed in it, which is why after a couple of weeks on the job it loses its shape and blends into everyday life, permanently corrupting their personalities.
It would be like asking fish to explain what water is.

Venkatesh, on the other hand, has understood it perfectly: he lays out all the details, all the hidden dynamics that underpin the great power game.
The hidden politics, the secret language, the sacrificial victims: the corporate world is a grand circus of power.
One in which I don't want to participate, neither as a cringing spectator nor as a dancing clown.
(NOTE TO MYSELF: "Dancing clown" is a great name for a song about corporate life.)

The real insight this book gave me is awareness: a conscious hatred of every aspect of corporate life.
I don't have "problems with authority": I'm opposed to the corporate concept of "work," I find corporate hierarchical rules senseless, and I believe those political games are a farce that slows down work for the benefit of the idiot losers who participate in them.
The system isn't right for me, so I made the best decision: to build one myself that was right for me.

Winning this fictional exchange with the fictional Dr. House was a relief that gave me the energy to keep going despite my doubts.
(NOTE: The "real" Dr. House is "fictional" too.)

■ The Last Lecture (start of self-employment)

The first thing that comes to mind when you become self-employed is: "What now?" There's no boss to tell you what to do, no paycheck at the end of the month.
It's just you and the rest of the world.
Want to make money?
Well, go ahead, find a way, try selling something to someone: there are no rules.

What I quickly realized is that the big difference between employee and self-employed is one: the emotion that drives your days.

An employee is constantly at odds with their boss, the office rules, their coworkers...
Frustration is what drives their life.
But it's a "reassuring" frustration because they know the rules of the game, and they know it's limited to that office, that boss, and those coworkers.
Sure: at the end of the day, they only want to vent about work and complain that things will never change.
But deep down, they're glad that things will never change, because predictability is the perk of being an employee.

For the self-employed it's the opposite.
Every day is different, you have to manage your own schedule, and you can choose where to work and who to work with.
But the trade-off is total uncertainty about everything.
You don't know if clients will come, you don't know if the project will work out, you don't know how much you'll pay in taxes (shoutout to Italy as the most nightmarish country for that).
It's just you and everything else, the game has no rules.

This book, besides being the autobiography of a great man, is also about the determination that this sort of situation demands.
Did I want my independence?
Well, there's no such thing as a free lunch, mate.

The brick walls are there to stop the people who don't want it badly enough.
They're there to stop the other people.

— The Last Lecture


Do I want it badly enough?
Damn, yeah.

■ Conclusion

So here it is, now you know the books that have changed my life.
Next time, don't ask me at 2am.