A TEDx, a Podcast, and a Book Walk Into a Newsletter
This article first appeared on Substack at https://jacoporomei.substack.com/p/a-tedx-a-podcast-and-a-book-walk.
A few weeks ago I published a ten-episode English-language podcast entirely produced with AI assistance. It’s not perfect—I’d say it’s about 90% there. A year ago I would have waited to finish the remaining 10%. But waiting for perfection is exactly the kind of trap I’ve been arguing against for twenty years—in contracts, in products, in how we think about work. Ship the value. Validate. Iterate.
This newsletter is about that principle, applied to everything from pricing to negotiation.
Over the next few minutes, I’ll make a few points:
-
Selling your time is the most fragile business model a knowledge worker can adopt—and one day it will be considered scandalous.
-
AI just removed a bottleneck that kept me from sharing this message with you—which, as it turns out, is the message itself.
-
There is a concrete, field-tested alternative to hourly billing, and I’ve spent twenty years refining it.
-
I’ll give you a TEDx talk and an accompanying ten-episode podcast about the topic discussed today. Neither will ask you to track your time. 😝
The bottleneck
I gave a TEDx talk three years ago, in Italian, called “Chi vende il proprio tempo vende la libertà”—To Sell Your Time Is To Sell Your Freedom.
It’s about fifteen minutes long; it contains the sharpest version of an argument I’ve been refining for twenty years and articulating publicly since 2012, and for years I couldn’t share it directly with the majority of my audience because it was locked behind a language barrier.
That barrier is now gone. I used AI to translate and dub the talk into English, and I used AI to produce a ten-episode English-language podcast that expands on the same ideas and on the principles from my book on the same topic, Extreme Contracts.
There’s an irony here that I don’t want you to miss. The entire argument I’m about to make is that value doesn’t live in the effort—it lives in the outcome. And the AI that translated my talk didn’t sweat, didn’t bill me by the hour, and didn’t ask for overtime. It simply removed a bottleneck that was preventing value from reaching the people who needed it. Which is, as it happens, the best possible introduction to what follows.
The problem with selling time
Here’s the thesis, stated plainly: selling your time is a terrible deal, and one day people will look back at it the way we look back at other forms of human commodification—with disbelief that it was ever considered normal.
I don’t say this lightly. I know it sounds extreme, but the argument is not emotional. It’s structural, and it holds up under scrutiny. Let me walk you through it.
The first problem is arithmetic. If you sell your time, your income has a hard ceiling: there are only so many hours in a day, you need to sleep, eat, and live, and no amount of ambition will add a twenty-fifth hour. But the real damage isn’t only in the ceiling—it’s the asymmetry beneath it. If you deliver a project late, you get punished: penalties, lost trust, damaged reputation. If you deliver it early, you don’t get rewarded—you get paid less, because you billed fewer hours. The person who solves the problem in three hours instead of six doesn’t earn twice as much for being twice as good; they earn half as much for being twice as fast. The incentive structure is pointing in exactly the wrong direction.
The second problem is psychological. Living on an hourly rate generates a constant, low-grade anxiety about unbooked time. Daniel Kahneman’s work on loss aversion explains why: we feel the pain of an empty calendar slot far more intensely than the pleasure of a full one. This leads to a paradox that anyone who’s freelanced for more than a year will recognize—you start fearing new clients, because your time is already scarce and every new commitment competes with existing ones. You’ve built a business model in which success—having too much demand—becomes a source of stress rather than opportunity.
The third problem is spatio-temporal. Selling time almost always implies selling presence, whether physical or digital. You sit at a desk, you appear online, you demonstrate that you are working. But as Alan Weiss has argued for decades, the most valuable resource a knowledge worker has is discretionary time—the freedom to allocate your hours to whatever creates the most value, including thinking, reading, walking, or doing absolutely nothing productive in the conventional sense. Forcing a knowledge worker to sit in front of a screen to prove they’re earning their keep is like paying a musician only for the minutes they spend on stage, ignoring the years of practice, the hours of composition, and the fact that the best melody of their career might arrive in the shower on a Sunday morning.
Which brings me to the fourth problem, and the one I find most damning: intellectual work doesn’t happen on a schedule. I have solved programming problems in my sleep—literally dreamed the solution and woken up knowing exactly what to write. It has happened three times that I can remember.
Should I invoice that nap?
The question sounds absurd, but it exposes the absurdity of the entire model. If you pay me for my hours at a desk, you are paying for the wrong thing. You don’t want my time. You want the result of my thinking, and my thinking needs time, yes, but doesn’t punch a clock.
The core distinction is this: we want the gold, not the mining. If you could have the solution without the effort, you’d take it in a second—and you’d be right to. We romanticize effort, but it’s not the sweat that carries value—it’s the outcome.
And before someone objects that “the value of intellectual work can’t be measured”—it can. Easily. You ask the person who receives it. When you buy a house for 350,000 euros, you don’t audit the construction costs; you pay for the value you perceive. When a consultant saves your company two million euros a year by restructuring a single process, the fact that it took her three meetings or thirty is irrelevant. If I generate value worth 100 and charge you 80, I’m not taking 80 from you—I’m giving you 20.
“Yes, but there’s no alternative”
This is the response I hear most often, and I heard it again just recently from a potential partner—someone who agreed completely with the diagnosis but couldn’t see a way out. “The problem is real,” they said, “but what’s the operational solution?”
The alternative exists. I’ve been building it for twenty years, testing it with real clients, refining it through failure and success, and it now has a name, a book, and a body of principles that any knowledge worker can adopt. It’s called Extreme Contracts.
What Extreme Contracts are
The purpose of Extreme Contracts is to create the conditions under which knowledge work can happen at its best—generating real value, without impediments of any kind: economic, commercial, relational, or emotional.
This is not a method for filling in contract templates. It’s not a legal framework. It’s a set of principles for negotiating agreements that lead to genuine collaboration—centered on value, not on time. The foundational idea is simple: instead of designing contracts that protect you when things go wrong, design contracts that make it easy to build trust quickly—because once trust is established, collaboration follows, and collaboration is where value is created.
The traditional contract—whether fixed-price or time-and-materials—is essentially a life raft: it exists for when the collaboration is already sinking. An Extreme Contract is designed for sailing. It assumes that if you validate frequently, keep the stakes small enough to survive failure, and align incentives so that everyone’s skin is in the game, you won’t need the life raft.
I distilled these ideas into a podcast—ten episodes, each built around one operational principle. Here they are, with the core idea of each.
Ten episodes
01 — In Their Shoes: win by giving them nothing to lose. The most effective negotiation starts when you understand the other side’s problem better than they do—and design an offer they’d be foolish to refuse, not because it’s cheap, but because it eliminates their risk.
02 — Talk to the Grinder: stop negotiating with the monkey. If you’re negotiating with someone who can’t make the final decision, you’re not negotiating—you’re performing. Find the person who can actually say yes, and talk to them directly.
03 — Customer Channel: your contract is a customer channel. The contract you propose communicates who you are before you write a single line of code or deliver a single report. A rigid, hundred-page contract says one thing about your culture; a three-rule agreement that lets the client walk away at any point says something very different.
04 — Chaos in Small Doses: negotiating with small bits of chaos. The hundred-page contract you signed to protect your business might be the very thing that kills it. In complex environments, the safest move is to break the collaboration into pieces small enough that even total failure is survivable—and then iterate.
05 — Ethics Over Rules: stop selling fatigue, start selling impact. Rules can be gamed, circumvented, and exploited through technicalities. Ethics can’t. An Extreme Contract is deliberately simple—not because the situation is simple, but because a few clear rules validated frequently are more robust than a mountain of clauses that nobody reads twice.
06 — Skin in the Game: stop selling hours, share the risk. If the project fails and you lose nothing, you’re not a partner—you’re a vendor. Extreme Contracts require that all parties have something real at stake, because shared risk is the only honest foundation for shared reward.
07 — Value-Centered: stop selling hours, start selling outcomes. The best idea of your week might arrive in the shower on Sunday morning, and your current pricing model says it’s worth exactly zero. Value-centered agreements detach the price from the effort and attach it to what actually matters: the problem you solved and the benefit you delivered.
08 — Optionality: why your projects need save points. The smartest move in any negotiation isn’t committing to a plan—it’s deliberately keeping your options open. If you have optionality, you don’t need to be right that often; you just need the wisdom not to lock yourself into decisions you can’t reverse.
09 — BATNA: a debate. Your negotiation power doesn’t come from being smart, experienced, or charming. It comes from how good your alternatives are if the deal falls through. Developing your Best Alternative to a Negotiated Agreement before you sit at the table is the single most important thing you can do to negotiate well.
10 — B*llshit Jobs and Bureaucracy: why your job feels so pointless. A UK poll found that nearly 40% of full-time workers feel their job doesn’t need to exist. This episode connects that feeling to everything we’ve discussed—contracts that celebrate effort over value, organizations that measure presence over impact, and the quiet desperation of knowing that the system is broken but not seeing a way out.
Each episode is self-contained—you can start with whichever principle resonates most.
You’ll find the full podcast on different platforms:
☞ Spotify
☞ Spreaker
☞ Audible
Where to go from here
If the TEDx convinced you that selling time is the problem, and the podcast gave you principles for doing things differently, and you want the full picture—the stories, the theory, the negotiation frameworks, and real-world contract examples you can adapt—there’s a book.
It’s called Extreme Contracts: Knowledge Work from Negotiation to Collaboration. The first edition came out in Italian in 2017. The second edition—and the first in English—is a work in progress: I’m releasing it through Lean Publishing, chapter by chapter, as I write it.
Here’s the deal: buy the in-progress edition today and you get everything published so far, plus every future update at no extra cost—including the chapters I’m still writing. When the book is complete, the price goes up. Grab it here.
But here’s what I’d really like you to do, even if you don’t plan to spend a cent: pick one principle from the list above—just one—and think about how it applies to your next agreement. Not your whole business model, not your career strategy. Just your next conversation with a client or a partner. See what happens when you stop negotiating over hours and start negotiating over value. See what happens when you put some skin in the game and invite the other side to do the same.
Best,
Jacopo
Thanks for reading Jacopo Romei // The Sweep! Subscribe for free to receive new posts and support my work.