We All Live Tied to the Mast
Why Modern Products Aren’t Designed for Freedom, but for Voluntary Confinement
we-all-live-tied-to-the-mast
Growth Constraint Engineering
Narrative Structures as Strategic Commitments
What makes commitment sacred?
Ulysses and the Sirens
Artist | |
|---|---|
Year | 1909 |
The strongest products do not persuade. They bind. And the user signs willingly, fearing their own future self more than any competitor.
I. The Founder’s Quiet Panic:
Your Users Know What They Want. They Just Can’t Make Themselves Do It.
You built a product to help people reach their goals. You did the research. The interviews showed strong intent. The surveys confirmed it. The user journeys were straightforward. The problem wasn’t ambiguity, users knew exactly what they wanted. They wanted to write more, spend less, stop scrolling late at night.
But even with clear goals, engagement stalled. Retention weakened. Nudges, reminders, and scheduled routines were implemented, but they didn’t move the needle. The issue wasn’t lack of motivation. It was fragmentation.
Your product isn’t dealing with a single, consistent user. It’s dealing with two competing versions of the same person. One sets the intention. The other overrides it. At 10pm, the self who planned ahead loses to the self who wants comfort, escape, or distraction.
Until your product architecture accounts for this internal conflict, until it gives the goal-setting self tools to constrain the impulsive one, it won’t solve the real problem. It will remain just another well-intentioned interface, quietly ignored when it matters most.
This is the real challenge:
You're not building for a user. You're building for a conflict between two selves inside the same user.Until your product can help one version of the user constrain the other, you’re just another suggestion box they’ll eventually ignore.
II. The Industrialization of the Ulysses Pact:
When Restraint Becomes a Market Category
The problem is ancient. So is the solution.
In Homer’s Odyssey, Ulysses knows he will be tempted by the Sirens, creatures whose song lures sailors to their deaths. He doesn’t try to resist in the moment. He doesn’t trust his future self to win that battle. Instead, he designs the situation. He orders his crew to tie him to the mast and plug their own ears with wax. That way, even if he begs to be freed, they won’t hear him. He will be powerless by design.
This is the original Ulysses Pact: a commitment made in a moment of clarity to constrain future behavior in a moment of weakness.
Today, this same logic isn’t just a metaphor. It’s a product strategy. In fact, it’s rapidly becoming a full-blown market category.
Great behavior-change products don’t just nudge. They bind. They let the motivated version of the user set constraints on their future, less disciplined self. Think of it as multi-self UX. You’re not optimizing for convenience. You’re creating intertemporal contracts, agreements between present intention and future impulse.
And most products avoid this. They default to polite encouragement. Light-touch motivation. Just-in-time notifications that hope the user still cares.
But users don’t need gentle reminders. They need masts to tie themselves to.
We’re watching the commodification of self-restraint.
Consider what users are now willing to pay for:
Calm sells temporary mental silence
Opal sells a voluntary ban on apps your future self can’t resist
Beeminder turns goal tracking into real financial penalties
Centered gamifies attention, rewarding your prefrontal cortex over your limbic system
These tools don’t promise freedom. They promise containment. A safehouse from your own future impulses.
And the market loves it.
Because once you admit that the biggest threat to your goals is you, products that help you constrain yourself become not just useful, but essential.
This isn’t about productivity anymore.
It’s a shift in consumer psychology - from desire optimization to desire governance.
The Industrialization of the Ulysses Pact:
When Restraint Becomes a Market Category
Most tech products sell ease. Fewer clicks. Faster checkout. Frictionless everything.
But somewhere along the way, restraint became a feature. Then a selling point. Then a category.
Think of Freedom, the app that blocks internet access. Or Opal, which limits screen time with a countdown and public commitment. Or YNAB (You Need A Budget), which forces users to assign every dollar a job, no room for vague optimism. These are not convenience tools. They are constraint engines. They are built to limit access, remove choices, and deliberately add friction.
And they work not because they’re sophisticated, but because they respect the underlying psychology: future-you will betray current-you. The only way around it is to embed that tension into the product itself.
Restraint is no longer an implicit benefit. It’s an explicit function. It’s why users seek these tools in the first place. Not to do more. But to be stopped from doing less.
This flips the usual product playbook. Instead of reducing steps, you add irreversible ones. Instead of personalizing freedom, you standardize guardrails.
Most software simplifies interactions - fewer taps, less friction, faster outcomes. Constraint products take a different approach. They insert irreversible steps, exchanging flexibility for structure and speed for accountability. Rather than prioritizing user autonomy, they enforce commitments that persist when motivation wanes.
UX design shifts focus from ease to endurance. The experience centers on creating barriers to abandonment, ensuring follow-through becomes the path of least resistance.
Self-binding as product onboarding
Self-binding as product onboarding
III. Case Study:
Duolingo Doesn’t Teach You language. It Trains You to Fear Breaking a Promise to Yourself.
Duolingo is a language-learning app in theory.
In practice, it’s a finely tuned behavioral constraint system, masquerading as a green owl with a push notification addiction.
Here’s what Duolingo gets right that most “habit” products don’t:
It doesn’t try to motivate you. It tries to trap you, in a feedback loop engineered to outlast your weaker self.
Let’s break it down:
Streaks aren’t just a visual. They’re a psychological contract. Missing one day triggers loss aversion so strong that some users pay to restore them. This is not learning. This is hostage negotiation with your own guilt.
Hearts limit how many mistakes you can make before being locked out. You’re not just learning a language, you’re navigating a punishment economy.
Pre-set daily goals create a subtle but powerful form of self-enforcement. You don’t want to do the lesson. You just don’t want to break the streak you chose.
It goes beyond education by serving as behavioral infrastructure.
Duolingo figured out that the core user need isn’t progress, it’s consistency.
And the only way to guarantee consistency is to help users bind themselves against future defection.
Which means Duolingo isn’t selling language learning.
It’s selling the illusion of rationality continuity.
And that’s exactly why it works.
IV. Ulysses Product Archetypes:
A Strategic Comparison Across Constraint Systems
Once you realize that the core value of certain products lies not in what they enable, but in what they prevent, you start to see the shape of a new product archetype:
The Self-Binding Tool.
These products don't just serve a function.
They operationalize restraint and they differ in how.
Let’s map the terrain across four major archetypes, each representing a different design philosophy for how to help users win a battle against their future selves:
Product | Constraint Type | Design Mechanism | Underlying Psychology |
|---|---|---|---|
Emotional Anchoring | Streak loss, push guilt, heart penalties | Loss aversion + routine attachment | |
Environmental Control | App blocks, scheduled focus sessions | Default reshaping + friction inflation | |
Monetary Penalty | Contractual bets, anti-charity donations | Precommitment + financial pain | |
System-Level Lock | Password-protected app limits | Executive override friction + parental framing |
Each of these products answers the same fundamental question -
"How do I prevent my irrational future self from sabotaging me?"
but answers it through a different layer of the stack:
Duolingo uses habitual shame and gamified guilt
Opal restructures your access environment
StickK turns failure into a literal financial loss
Apple gives your phone a second, stricter self with admin privileges
These products move beyond simple motivation. They create a space where conflicting selves within a person must come to terms. Rather than offering encouragement, they facilitate an internal negotiation, recognizing that users are not a single, unified entity but a collection of competing intentions. The value lies in managing that tension, not eliminating it.
And the more persuasive they are at enabling that negotiation, the more valuable they become, not just functionally, but commercially.
Because in a world where everyone is at war with their own attention span, products that help users win against themselves become category-defining.
Self-binding as product onboarding
Self-binding as product onboarding
Art by Barbara Kruger
Untitled (Never Perfect Enough), 2020
V. The Evolution of Self-Control Products:
From Willpower Tools to Incentive Infrastructure
Let’s rewind and trace the trajectory of this product class over time.
Because what looks like a scattered group of "focus apps" or "motivation hacks" is actually a slow industrialization of behavioral control, with each phase unlocking a deeper layer of user entanglement.
Phase | Era | Notable Products | Design Principle | Mechanism |
|---|---|---|---|---|
1 | Willpower as UX (2007–2014) | Nudging interface | Visual cues, gamification | |
2 | Infrastructure of Restraint (2015–2022) | OS-level enforcement | Precommitment, lockdown | |
3 | Incentive Engineering (2023–ongoing) | Contractual alignment | Money, social pressure, calendars |
Phase 1: Willpower as UX (2007–2014)
Era of Personal Apps and Atomic Habits
Notable tools: Forest, Habitica, RescueTime
Products in this era treated self-control as a UX challenge.
Interfaces were built to nudge, not restructure.
Willpower was still assumed; tech was just there to help remind, track, decorate.
Think of it as the Post-it Note phase.
Helpful, visual, but ultimately deferrable. The burden remained on you.
Phase 2: Infrastructure of Restraint (2015–2022)
Era of Systemic Precommitment
Notable tools: Freedom, Opal, OneSec, ScreenTime
The stack moved lower. Apps now interlocked with OS-level controls, browser permissions, VPNs.
Self-control became infrastructural. Not a behavior to be reminded of, but a rule to be enforced.
Tools shifted from nudging to automating resistance.
The user experience changed from “How can I help myself focus?”
to “How can I stop myself from cheating?”
This was the birth of the Ulysses pact as a product.
Constraint became the feature.
Phase 3: Incentive Engineering as Market Power (2023–ongoing)
Era of Psychological Contracting + Monetized Discipline
Notable tools: Reclaim.ai, StickK, Rise, Mindsera
These products don’t just block distractions.
They assign costs, bind contracts, and create synthetic accountability loops.
Some interface with calendars, others with your bank account, some with your coach or community.
In this phase, the product becomes a broker of incentives.
It doesn’t enforce your goals. It aligns your psychology, money, and social context so you do.
We’ve entered the age of Behavior-as-a-Service.
And like any service business, the most valuable ones aren’t the ones that offer features -
they’re the ones that reshape behavior at scale, reliably, and irreversibly.
Designing for the Self You Don't Trust
Every product decision lives inside a context: user expectations, platform distribution limits, incentive structures, and the competitive environment. Ulysses products aren’t just clever UX experiments, they’re a direct response to a shifting ecosystem where choice paralysis, user fatigue, and retention fragility are endemic.
In earlier product eras - especially during the late 2010s growth-hack boom - more was always better. More features, more control, more customization. Product teams were obsessed with dashboards, toggles, and “power user” affordances. But over time, it became obvious: users don’t want infinite optionality. They want relief from it.
Enter macro trend number one: Cognitive Load Saturation.
Across verticals, from finance apps to fitness trackers, attention is no longer the bottleneck - cognitive energy is. Even when users have time, they lack decision stamina. The average user doesn’t want to weigh ten ETF options. They want one portfolio they can stick to. That’s why apps like Wealthfront, Levels, and Noom began embedding behavioral constraints as a UX default. Not to limit capability, but to offload decision stress.
Macro trend number two: Algorithmic Intermediation.
In a world where distribution is platform-mediated (think: TikTok, X, YouTube), product-led growth depends on designing for engagement metrics you don’t control. Ulysses-style products - by engineering consistent behavior - generate more stable usage loops and cleaner data trails. Platforms reward that.
Look at Duolingo. Every interaction is structured, time-bound, streak-based. Its notifications are behavioral contracts disguised as encouragement. That kind of routine generates predictable outputs and repeatable engagement patterns. In a system trained to reward legibility, discipline becomes the new distribution hack.
Macro trend number three: Rebundling by Trust.
In the age of platform ecosystems, tools are no longer neutral utilities but extensions of the people and values behind them. The investor you follow, the trainer you trust, the writer whose newsletter you read - all rebundle products around identity. This creates systems that are not just functional, but deeply opinionated. They embed values directly into the constraints they impose.
This dynamic is inseparable from the concept of the Ulysses Pact. Originating from the myth of Odysseus who tied himself to the mast to resist the Sirens, a Ulysses-style product is one that helps your rational present self bind your future impulsive self. It’s a design pattern of self-imposed limits that cannot be easily reversed. These products do not merely remind you to do better; they engineer a path that closes off bad choices by default.
Rebundling by trust means you accept those constraints because they come from someone you believe understands you better than you do. The coach’s workout plan, the writer’s curated routine, the investor’s portfolio allocation - each acts as a proxy for discipline. You’re effectively saying, “I trust you to tie me to the mast.”
The power lies not in the features themselves but in what they refuse to let you do. Trust becomes the binding agent, turning products into commitment devices personalized by identity. The product is no longer just a tool; it is a trusted system that enforces discipline through alignment with your values and the people you respect.
Designing for the Pact: A Model for Multi-Self UX
To operationalize a Ulysses Pact, you need to stop thinking about one user. You’re building for two:
The planner, who sets goals and installs your app with conviction
The impulsive actor, who opens it at 11:47pm looking for a dopamine hit
Most products collapse these selves into one persona. That’s a mistake. What you need instead is a dynamic contract between the two. A UX that stages decisions in time.
This model has three critical phases:
Commitment Window
The product must recognize and amplify moments of clarity. When motivation peaks, constraints should be easy to set and hard to reverse. Think onboarding flows that lock in usage limits, or daily settings that can’t be changed mid-session.Fracture Point
The moment of temptation. The user wants to break their commitment. Here, your product becomes a gatekeeper. Delay friction, shame friction, or community friction can all be deployed. The goal isn’t punishment. It’s time dilation. Let intention catch up to impulse.Aftershock Layer
Once the moment passes, the product must reflect back the choice and its cost. Highlight streaks broken, goals postponed, or social accountability triggered. Over time, this builds narrative memory. The user starts to anticipate their own regret.
Done well, this structure doesn’t fight the user. It lets the best version of them win more often.
Why Most Products Don’t Go There and Why Some Should
Restraint is uncomfortable to build for. Most founders want to delight, not restrict. PMs are trained to remove friction, not add it. And investors rarely fund features that reduce usage on purpose. The incentives all point toward maximization, more engagement, longer sessions, higher frequency.
But if your product is meant to help people change - write more, spend less, focus longer - then usage maximization is often at odds with value creation.
This is where the market splits.
Entertainment products optimize for immersion. Their enemy is boredom. But transformation products optimize for integrity. Their enemy is inconsistency. If you mistake one for the other, your product will cannibalize its own purpose.
Action Painting (1981) by Mark Tansey.
From Hacks to Habits:
The Evolutionary Pressure Behind Ulysses Products
Ulysses products didn’t start as grand strategies. They started as panic. As stopgaps. As duct-taped answers to distribution leaks, retention drops, or viral threats. But the ones that survived, the ones we now recognize as strategic masterstrokes, were forged under evolutionary pressure.
Take calendar-first productivity tools. At first, they looked like glorified Google Calendar integrations. But under the weight of remote work, Zoom fatigue, and async chaos, they became a default operating system. Now, a “time-blocked” interface isn’t a gimmick. It’s a moat. Users lock themselves in, intentionally because the alternative is cognitive overload. Constraint becomes peace.
Or take multi-player collaboration tools. They weren't born from collaboration ideals. They were born because work stopped happening in the same room. Figma wasn’t just a better design tool. It was an anti-fragmentation protocol. Notion didn’t unify docs because of elegance. It did so because context-switching was killing team memory. In a chaotic ecosystem, only tools that imposed helpful constraints could scale.
Even AI writing tools are facing this same evolutionary demand.
The first wave said: “We'll write it for you.”
The next wave will say: “We'll make sure you don’t sabotage your own output.”
Expect to see Ulysses-style features like commitment layers, revision locks, and reputation-dependent publishing thresholds. The tools are becoming parents. Or parole officers.
Design alone does not explain it. In saturated ecosystems, survival depends on offering better defaults and creating friction that makes leaving difficult. Winning comes not from more freedom, but from carefully engineered constraints.
The Ulysses Product Stack:
A Three-Layer Trap That Users Thank You For
Ulysses products aren’t just sticky. They’re staged traps with narrative cover. Done well, they don’t feel like lock-in. They feel like relief. The secret? A three-layered product stack that slowly shifts power from user to platform, without triggering rebellion.
Layer 1: The Ritual Hook
Every Ulysses product begins with a habit scaffold. Daily check-ins. Scheduled sends. Timeboxed flows. These aren’t productivity tricks, they’re muscle memory architectures. The product doesn’t force you to come back. It just gives you one good reason every day not to leave.
Layer 2: The Constraint Engine
Once a user is “in,” the second layer kicks in: intentional limitations. The product reduces optionality, not because it can’t offer more, but because it knows you’ll do worse with it. Think Superhuman’s command palette. Linear’s ticket workflow. Figma’s multiplayer mode. Every interaction nudges users away from chaos toward a single optimal path - defined by the product, not the person.
Layer 3: The Strategic Inertia Layer
By now, switching isn’t just painful, it’s reputationally risky. The product begins storing not just data, but context. Shared docs, comment threads, custom workflows, team rituals. This is when users stop comparing you to alternatives. They start designing their life around you. In this phase, a calendar app isn’t a tool. It’s an identity.
Ulysses-style products carry an inherent risk. They are not designed simply to delight users but to create dependency. Once users become accustomed to these constraints, the cost of leaving rises dramatically. The challenge lies in maintaining a delicate balance: each added friction must deliver clear value. Without that, users feel trapped rather than supported. When the illusion of choice dissolves, trust evaporates, and the product’s foundation begins to crumble.
This is a design philosophy that demands rigorous discipline from makers. It requires anticipating where constraints empower and where they suffocate. Success depends on building systems that respect the user’s intelligence while guiding behavior. Otherwise, dependency turns into resentment, and control becomes a prison rather than a tool.
Ulysses vs. The Feed: The Next Ethical Battlefront
We’re entering a phase of product design where helping users “do what they want” means helping them resist themselves. That means building constraints, not just affordances. Friction, not just flow.
It’s a hard sell. Especially in a culture wired to equate freedom with optionality and growth with engagement. But the next generation of transformative products, especially in health, finance, learning, and time management won’t win by being frictionless. They’ll win by being loyal to the user's higher self, even when it hurts the metrics.
That’s the tension: between growth and restraint, between what the user clicks on and what they actually want.
And that’s the opportunity: building for the version of the user that can’t win on their own.
The products that survive in the pact era won’t just get used.
In a feed-driven world, attention is the constraint. But in the Ulysses universe, it's conviction. The conviction to build rituals that don’t optimize for virality. The courage to limit features so that behavior can harden. And the clarity to know when a product’s strength becomes its prison.
This model worked brilliantly for the last generation of SaaS. But it’s now colliding with a new set of user defaults - AI-native, feed-native, fluid-first. Products like Notion AI, Perplexity, or even iA Presenter assume that context isn’t sacred. It’s disposable. Shared knowledge is ephemeral. Switching isn’t a loss. It’s expected.
This creates a strategic fork. Founders can still build Ulysses-style products. They’ll attract power users, teams, builders who crave structure. But mass adoption will shift toward tools that degrade well, tools that lose less when abandoned.
What’s at stake isn’t control, but the tradeoff between stickiness and substitutability.
And the new question for every product founder isn’t How do I get users to stay?
It’s What does my product become when they leave?
In the Odyssey, Ulysses didn’t trust himself to resist the Sirens. So he asked to be tied to the mast. Today’s feed products are the Sirens. They win by seducing. But Ulysses-style products win by self-binding. They help users resist their lower impulses, so they can stay loyal to their goals—even after the app is gone.
Anchor Articles and Updates
Feed economy: How Each Platform Manufactures Dependency Loops — Why creators feel burned out, and what platforms don’t want you to understand about their invisible incentive systems
Crisis Is Not the End. It’s a Catalyst for Product Growth. — Reframing the Narrative of Windsurf, Astronomer, and Cluely
Building Products in the AI Era: The Deep Logic of Speed, Content, and Data Ownership — If you’re building a new product in 2025, you’re not competing on functionality.
You’re competing on attention loops, learning velocity, and data leverage.
How AI Platforms Reshape Innovation: Subordination, Risk, and Workflow Strategy — Rethinking Product Strategy Under Model Governance
How AI Understands User Intent Before They Search: Commercial Decision Loops and the Invisible Funnel — Why pre-intent behavior is becoming more legible and monetizable
Inspired by Lenny’s Growth Inflections: AI and Personal Brands Rewiring Startup Growth — AI automation and personal brands are redefining startup growth inspired by Lenny Rachitsky’s Growth Inflections.
Why Growth Marketing Is Not Digital Marketing and Why This Distinction Matters — It’s not that your marketing strategy is flawed. You might just be addressing the wrong problem.
When AI Products Can’t Find PMF, Build a Landing Client Instead — PMF isn’t always found in the product, Sometimes, it starts with one strategic client
Content as a Revenue Tool: Shortening Time-to-Close in Startup Sales — Content that shortens sales cycles, Not just builds traffic
Building Revenue Systems When Scale Isn’t an Option — Profitability First: How Startup Teams Can Drive Revenue in Constrained Markets
Case Studies
Mountain Gentleman — They knew they needed to go digital but had no idea how to start.So we saw things through the rider’s eyes.It wasn’t just about buying gear because it felt like building out your dream GTR.Every part of the journey was designed to match that thrill.
CoinRank — CoinRank needed a fresh way to stand out in crypto. We created a short video strategy that turns complex info into quick, engaging clips that grab attention fast.
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©2025
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©2025
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專案內容會包含什麼
02
價格是怎麼計算的
03
所有專案都是固定形式合作嗎
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在開始合作之後可以調整專案範圍嗎
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01
專案內容會包含什麼
02
價格是怎麼計算的
03
所有專案都是固定形式合作嗎
04
在開始合作之後可以調整專案範圍嗎
05
怎麼定義KPI
06
Do you offer ongoing support after project completion?
07
How long does a typical project last?
08
Is there a minimum commitment?
We All Live Tied to the Mast
Why Modern Products Aren’t Designed for Freedom, but for Voluntary Confinement
we-all-live-tied-to-the-mast
Growth Constraint Engineering
Narrative Structures as Strategic Commitments
What makes commitment sacred?
Ulysses and the Sirens
Artist | |
|---|---|
Year | 1909 |
The strongest products do not persuade. They bind. And the user signs willingly, fearing their own future self more than any competitor.
I. The Founder’s Quiet Panic:
Your Users Know What They Want. They Just Can’t Make Themselves Do It.
You built a product to help people reach their goals. You did the research. The interviews showed strong intent. The surveys confirmed it. The user journeys were straightforward. The problem wasn’t ambiguity, users knew exactly what they wanted. They wanted to write more, spend less, stop scrolling late at night.
But even with clear goals, engagement stalled. Retention weakened. Nudges, reminders, and scheduled routines were implemented, but they didn’t move the needle. The issue wasn’t lack of motivation. It was fragmentation.
Your product isn’t dealing with a single, consistent user. It’s dealing with two competing versions of the same person. One sets the intention. The other overrides it. At 10pm, the self who planned ahead loses to the self who wants comfort, escape, or distraction.
Until your product architecture accounts for this internal conflict, until it gives the goal-setting self tools to constrain the impulsive one, it won’t solve the real problem. It will remain just another well-intentioned interface, quietly ignored when it matters most.
This is the real challenge:
You're not building for a user. You're building for a conflict between two selves inside the same user.Until your product can help one version of the user constrain the other, you’re just another suggestion box they’ll eventually ignore.
II. The Industrialization of the Ulysses Pact:
When Restraint Becomes a Market Category
The problem is ancient. So is the solution.
In Homer’s Odyssey, Ulysses knows he will be tempted by the Sirens, creatures whose song lures sailors to their deaths. He doesn’t try to resist in the moment. He doesn’t trust his future self to win that battle. Instead, he designs the situation. He orders his crew to tie him to the mast and plug their own ears with wax. That way, even if he begs to be freed, they won’t hear him. He will be powerless by design.
This is the original Ulysses Pact: a commitment made in a moment of clarity to constrain future behavior in a moment of weakness.
Today, this same logic isn’t just a metaphor. It’s a product strategy. In fact, it’s rapidly becoming a full-blown market category.
Great behavior-change products don’t just nudge. They bind. They let the motivated version of the user set constraints on their future, less disciplined self. Think of it as multi-self UX. You’re not optimizing for convenience. You’re creating intertemporal contracts, agreements between present intention and future impulse.
And most products avoid this. They default to polite encouragement. Light-touch motivation. Just-in-time notifications that hope the user still cares.
But users don’t need gentle reminders. They need masts to tie themselves to.
We’re watching the commodification of self-restraint.
Consider what users are now willing to pay for:
Calm sells temporary mental silence
Opal sells a voluntary ban on apps your future self can’t resist
Beeminder turns goal tracking into real financial penalties
Centered gamifies attention, rewarding your prefrontal cortex over your limbic system
These tools don’t promise freedom. They promise containment. A safehouse from your own future impulses.
And the market loves it.
Because once you admit that the biggest threat to your goals is you, products that help you constrain yourself become not just useful, but essential.
This isn’t about productivity anymore.
It’s a shift in consumer psychology - from desire optimization to desire governance.
The Industrialization of the Ulysses Pact:
When Restraint Becomes a Market Category
Most tech products sell ease. Fewer clicks. Faster checkout. Frictionless everything.
But somewhere along the way, restraint became a feature. Then a selling point. Then a category.
Think of Freedom, the app that blocks internet access. Or Opal, which limits screen time with a countdown and public commitment. Or YNAB (You Need A Budget), which forces users to assign every dollar a job, no room for vague optimism. These are not convenience tools. They are constraint engines. They are built to limit access, remove choices, and deliberately add friction.
And they work not because they’re sophisticated, but because they respect the underlying psychology: future-you will betray current-you. The only way around it is to embed that tension into the product itself.
Restraint is no longer an implicit benefit. It’s an explicit function. It’s why users seek these tools in the first place. Not to do more. But to be stopped from doing less.
This flips the usual product playbook. Instead of reducing steps, you add irreversible ones. Instead of personalizing freedom, you standardize guardrails.
Most software simplifies interactions - fewer taps, less friction, faster outcomes. Constraint products take a different approach. They insert irreversible steps, exchanging flexibility for structure and speed for accountability. Rather than prioritizing user autonomy, they enforce commitments that persist when motivation wanes.
UX design shifts focus from ease to endurance. The experience centers on creating barriers to abandonment, ensuring follow-through becomes the path of least resistance.
Self-binding as product onboarding
III. Case Study:
Duolingo Doesn’t Teach You language. It Trains You to Fear Breaking a Promise to Yourself.
Duolingo is a language-learning app in theory.
In practice, it’s a finely tuned behavioral constraint system, masquerading as a green owl with a push notification addiction.
Here’s what Duolingo gets right that most “habit” products don’t:
It doesn’t try to motivate you. It tries to trap you, in a feedback loop engineered to outlast your weaker self.
Let’s break it down:
Streaks aren’t just a visual. They’re a psychological contract. Missing one day triggers loss aversion so strong that some users pay to restore them. This is not learning. This is hostage negotiation with your own guilt.
Hearts limit how many mistakes you can make before being locked out. You’re not just learning a language, you’re navigating a punishment economy.
Pre-set daily goals create a subtle but powerful form of self-enforcement. You don’t want to do the lesson. You just don’t want to break the streak you chose.
It goes beyond education by serving as behavioral infrastructure.
Duolingo figured out that the core user need isn’t progress, it’s consistency.
And the only way to guarantee consistency is to help users bind themselves against future defection.
Which means Duolingo isn’t selling language learning.
It’s selling the illusion of rationality continuity.
And that’s exactly why it works.
IV. Ulysses Product Archetypes:
A Strategic Comparison Across Constraint Systems
Once you realize that the core value of certain products lies not in what they enable, but in what they prevent, you start to see the shape of a new product archetype:
The Self-Binding Tool.
These products don't just serve a function.
They operationalize restraint and they differ in how.
Let’s map the terrain across four major archetypes, each representing a different design philosophy for how to help users win a battle against their future selves:
Product | Constraint Type | Design Mechanism | Underlying Psychology |
|---|---|---|---|
Emotional Anchoring | Streak loss, push guilt, heart penalties | Loss aversion + routine attachment | |
Environmental Control | App blocks, scheduled focus sessions | Default reshaping + friction inflation | |
Monetary Penalty | Contractual bets, anti-charity donations | Precommitment + financial pain | |
System-Level Lock | Password-protected app limits | Executive override friction + parental framing |
Each of these products answers the same fundamental question -
"How do I prevent my irrational future self from sabotaging me?"
but answers it through a different layer of the stack:
Duolingo uses habitual shame and gamified guilt
Opal restructures your access environment
StickK turns failure into a literal financial loss
Apple gives your phone a second, stricter self with admin privileges
These products move beyond simple motivation. They create a space where conflicting selves within a person must come to terms. Rather than offering encouragement, they facilitate an internal negotiation, recognizing that users are not a single, unified entity but a collection of competing intentions. The value lies in managing that tension, not eliminating it.
And the more persuasive they are at enabling that negotiation, the more valuable they become, not just functionally, but commercially.
Because in a world where everyone is at war with their own attention span, products that help users win against themselves become category-defining.
Self-binding as product onboarding
Art by Barbara Kruger
Untitled (Never Perfect Enough), 2020
V. The Evolution of Self-Control Products:
From Willpower Tools to Incentive Infrastructure
Let’s rewind and trace the trajectory of this product class over time.
Because what looks like a scattered group of "focus apps" or "motivation hacks" is actually a slow industrialization of behavioral control, with each phase unlocking a deeper layer of user entanglement.
Phase | Era | Notable Products | Design Principle | Mechanism |
|---|---|---|---|---|
1 | Willpower as UX (2007–2014) | Nudging interface | Visual cues, gamification | |
2 | Infrastructure of Restraint (2015–2022) | OS-level enforcement | Precommitment, lockdown | |
3 | Incentive Engineering (2023–ongoing) | Contractual alignment | Money, social pressure, calendars |
Phase 1: Willpower as UX (2007–2014)
Era of Personal Apps and Atomic Habits
Notable tools: Forest, Habitica, RescueTime
Products in this era treated self-control as a UX challenge.
Interfaces were built to nudge, not restructure.
Willpower was still assumed; tech was just there to help remind, track, decorate.
Think of it as the Post-it Note phase.
Helpful, visual, but ultimately deferrable. The burden remained on you.
Phase 2: Infrastructure of Restraint (2015–2022)
Era of Systemic Precommitment
Notable tools: Freedom, Opal, OneSec, ScreenTime
The stack moved lower. Apps now interlocked with OS-level controls, browser permissions, VPNs.
Self-control became infrastructural. Not a behavior to be reminded of, but a rule to be enforced.
Tools shifted from nudging to automating resistance.
The user experience changed from “How can I help myself focus?”
to “How can I stop myself from cheating?”
This was the birth of the Ulysses pact as a product.
Constraint became the feature.
Phase 3: Incentive Engineering as Market Power (2023–ongoing)
Era of Psychological Contracting + Monetized Discipline
Notable tools: Reclaim.ai, StickK, Rise, Mindsera
These products don’t just block distractions.
They assign costs, bind contracts, and create synthetic accountability loops.
Some interface with calendars, others with your bank account, some with your coach or community.
In this phase, the product becomes a broker of incentives.
It doesn’t enforce your goals. It aligns your psychology, money, and social context so you do.
We’ve entered the age of Behavior-as-a-Service.
And like any service business, the most valuable ones aren’t the ones that offer features -
they’re the ones that reshape behavior at scale, reliably, and irreversibly.
Designing for the Self You Don't Trust
Every product decision lives inside a context: user expectations, platform distribution limits, incentive structures, and the competitive environment. Ulysses products aren’t just clever UX experiments, they’re a direct response to a shifting ecosystem where choice paralysis, user fatigue, and retention fragility are endemic.
In earlier product eras - especially during the late 2010s growth-hack boom - more was always better. More features, more control, more customization. Product teams were obsessed with dashboards, toggles, and “power user” affordances. But over time, it became obvious: users don’t want infinite optionality. They want relief from it.
Enter macro trend number one: Cognitive Load Saturation.
Across verticals, from finance apps to fitness trackers, attention is no longer the bottleneck - cognitive energy is. Even when users have time, they lack decision stamina. The average user doesn’t want to weigh ten ETF options. They want one portfolio they can stick to. That’s why apps like Wealthfront, Levels, and Noom began embedding behavioral constraints as a UX default. Not to limit capability, but to offload decision stress.
Macro trend number two: Algorithmic Intermediation.
In a world where distribution is platform-mediated (think: TikTok, X, YouTube), product-led growth depends on designing for engagement metrics you don’t control. Ulysses-style products - by engineering consistent behavior - generate more stable usage loops and cleaner data trails. Platforms reward that.
Look at Duolingo. Every interaction is structured, time-bound, streak-based. Its notifications are behavioral contracts disguised as encouragement. That kind of routine generates predictable outputs and repeatable engagement patterns. In a system trained to reward legibility, discipline becomes the new distribution hack.
Macro trend number three: Rebundling by Trust.
In the age of platform ecosystems, tools are no longer neutral utilities but extensions of the people and values behind them. The investor you follow, the trainer you trust, the writer whose newsletter you read - all rebundle products around identity. This creates systems that are not just functional, but deeply opinionated. They embed values directly into the constraints they impose.
This dynamic is inseparable from the concept of the Ulysses Pact. Originating from the myth of Odysseus who tied himself to the mast to resist the Sirens, a Ulysses-style product is one that helps your rational present self bind your future impulsive self. It’s a design pattern of self-imposed limits that cannot be easily reversed. These products do not merely remind you to do better; they engineer a path that closes off bad choices by default.
Rebundling by trust means you accept those constraints because they come from someone you believe understands you better than you do. The coach’s workout plan, the writer’s curated routine, the investor’s portfolio allocation - each acts as a proxy for discipline. You’re effectively saying, “I trust you to tie me to the mast.”
The power lies not in the features themselves but in what they refuse to let you do. Trust becomes the binding agent, turning products into commitment devices personalized by identity. The product is no longer just a tool; it is a trusted system that enforces discipline through alignment with your values and the people you respect.
Designing for the Pact: A Model for Multi-Self UX
To operationalize a Ulysses Pact, you need to stop thinking about one user. You’re building for two:
The planner, who sets goals and installs your app with conviction
The impulsive actor, who opens it at 11:47pm looking for a dopamine hit
Most products collapse these selves into one persona. That’s a mistake. What you need instead is a dynamic contract between the two. A UX that stages decisions in time.
This model has three critical phases:
Commitment Window
The product must recognize and amplify moments of clarity. When motivation peaks, constraints should be easy to set and hard to reverse. Think onboarding flows that lock in usage limits, or daily settings that can’t be changed mid-session.Fracture Point
The moment of temptation. The user wants to break their commitment. Here, your product becomes a gatekeeper. Delay friction, shame friction, or community friction can all be deployed. The goal isn’t punishment. It’s time dilation. Let intention catch up to impulse.Aftershock Layer
Once the moment passes, the product must reflect back the choice and its cost. Highlight streaks broken, goals postponed, or social accountability triggered. Over time, this builds narrative memory. The user starts to anticipate their own regret.
Done well, this structure doesn’t fight the user. It lets the best version of them win more often.
Why Most Products Don’t Go There and Why Some Should
Restraint is uncomfortable to build for. Most founders want to delight, not restrict. PMs are trained to remove friction, not add it. And investors rarely fund features that reduce usage on purpose. The incentives all point toward maximization, more engagement, longer sessions, higher frequency.
But if your product is meant to help people change - write more, spend less, focus longer - then usage maximization is often at odds with value creation.
This is where the market splits.
Entertainment products optimize for immersion. Their enemy is boredom. But transformation products optimize for integrity. Their enemy is inconsistency. If you mistake one for the other, your product will cannibalize its own purpose.
Action Painting (1981) by Mark Tansey.
From Hacks to Habits:
The Evolutionary Pressure Behind Ulysses Products
Ulysses products didn’t start as grand strategies. They started as panic. As stopgaps. As duct-taped answers to distribution leaks, retention drops, or viral threats. But the ones that survived, the ones we now recognize as strategic masterstrokes, were forged under evolutionary pressure.
Take calendar-first productivity tools. At first, they looked like glorified Google Calendar integrations. But under the weight of remote work, Zoom fatigue, and async chaos, they became a default operating system. Now, a “time-blocked” interface isn’t a gimmick. It’s a moat. Users lock themselves in, intentionally because the alternative is cognitive overload. Constraint becomes peace.
Or take multi-player collaboration tools. They weren't born from collaboration ideals. They were born because work stopped happening in the same room. Figma wasn’t just a better design tool. It was an anti-fragmentation protocol. Notion didn’t unify docs because of elegance. It did so because context-switching was killing team memory. In a chaotic ecosystem, only tools that imposed helpful constraints could scale.
Even AI writing tools are facing this same evolutionary demand.
The first wave said: “We'll write it for you.”
The next wave will say: “We'll make sure you don’t sabotage your own output.”
Expect to see Ulysses-style features like commitment layers, revision locks, and reputation-dependent publishing thresholds. The tools are becoming parents. Or parole officers.
Design alone does not explain it. In saturated ecosystems, survival depends on offering better defaults and creating friction that makes leaving difficult. Winning comes not from more freedom, but from carefully engineered constraints.
The Ulysses Product Stack:
A Three-Layer Trap That Users Thank You For
Ulysses products aren’t just sticky. They’re staged traps with narrative cover. Done well, they don’t feel like lock-in. They feel like relief. The secret? A three-layered product stack that slowly shifts power from user to platform, without triggering rebellion.
Layer 1: The Ritual Hook
Every Ulysses product begins with a habit scaffold. Daily check-ins. Scheduled sends. Timeboxed flows. These aren’t productivity tricks, they’re muscle memory architectures. The product doesn’t force you to come back. It just gives you one good reason every day not to leave.
Layer 2: The Constraint Engine
Once a user is “in,” the second layer kicks in: intentional limitations. The product reduces optionality, not because it can’t offer more, but because it knows you’ll do worse with it. Think Superhuman’s command palette. Linear’s ticket workflow. Figma’s multiplayer mode. Every interaction nudges users away from chaos toward a single optimal path - defined by the product, not the person.
Layer 3: The Strategic Inertia Layer
By now, switching isn’t just painful, it’s reputationally risky. The product begins storing not just data, but context. Shared docs, comment threads, custom workflows, team rituals. This is when users stop comparing you to alternatives. They start designing their life around you. In this phase, a calendar app isn’t a tool. It’s an identity.
Ulysses-style products carry an inherent risk. They are not designed simply to delight users but to create dependency. Once users become accustomed to these constraints, the cost of leaving rises dramatically. The challenge lies in maintaining a delicate balance: each added friction must deliver clear value. Without that, users feel trapped rather than supported. When the illusion of choice dissolves, trust evaporates, and the product’s foundation begins to crumble.
This is a design philosophy that demands rigorous discipline from makers. It requires anticipating where constraints empower and where they suffocate. Success depends on building systems that respect the user’s intelligence while guiding behavior. Otherwise, dependency turns into resentment, and control becomes a prison rather than a tool.
Ulysses vs. The Feed: The Next Ethical Battlefront
We’re entering a phase of product design where helping users “do what they want” means helping them resist themselves. That means building constraints, not just affordances. Friction, not just flow.
It’s a hard sell. Especially in a culture wired to equate freedom with optionality and growth with engagement. But the next generation of transformative products, especially in health, finance, learning, and time management won’t win by being frictionless. They’ll win by being loyal to the user's higher self, even when it hurts the metrics.
That’s the tension: between growth and restraint, between what the user clicks on and what they actually want.
And that’s the opportunity: building for the version of the user that can’t win on their own.
The products that survive in the pact era won’t just get used.
In a feed-driven world, attention is the constraint. But in the Ulysses universe, it's conviction. The conviction to build rituals that don’t optimize for virality. The courage to limit features so that behavior can harden. And the clarity to know when a product’s strength becomes its prison.
This model worked brilliantly for the last generation of SaaS. But it’s now colliding with a new set of user defaults - AI-native, feed-native, fluid-first. Products like Notion AI, Perplexity, or even iA Presenter assume that context isn’t sacred. It’s disposable. Shared knowledge is ephemeral. Switching isn’t a loss. It’s expected.
This creates a strategic fork. Founders can still build Ulysses-style products. They’ll attract power users, teams, builders who crave structure. But mass adoption will shift toward tools that degrade well, tools that lose less when abandoned.
What’s at stake isn’t control, but the tradeoff between stickiness and substitutability.
And the new question for every product founder isn’t How do I get users to stay?
It’s What does my product become when they leave?
In the Odyssey, Ulysses didn’t trust himself to resist the Sirens. So he asked to be tied to the mast. Today’s feed products are the Sirens. They win by seducing. But Ulysses-style products win by self-binding. They help users resist their lower impulses, so they can stay loyal to their goals—even after the app is gone.
Anchor Articles and Updates
Feed economy: How Each Platform Manufactures Dependency Loops — Why creators feel burned out, and what platforms don’t want you to understand about their invisible incentive systems
Crisis Is Not the End. It’s a Catalyst for Product Growth. — Reframing the Narrative of Windsurf, Astronomer, and Cluely
Building Products in the AI Era: The Deep Logic of Speed, Content, and Data Ownership — If you’re building a new product in 2025, you’re not competing on functionality.
You’re competing on attention loops, learning velocity, and data leverage.
How AI Platforms Reshape Innovation: Subordination, Risk, and Workflow Strategy — Rethinking Product Strategy Under Model Governance
How AI Understands User Intent Before They Search: Commercial Decision Loops and the Invisible Funnel — Why pre-intent behavior is becoming more legible and monetizable
Inspired by Lenny’s Growth Inflections: AI and Personal Brands Rewiring Startup Growth — AI automation and personal brands are redefining startup growth inspired by Lenny Rachitsky’s Growth Inflections.
Why Growth Marketing Is Not Digital Marketing and Why This Distinction Matters — It’s not that your marketing strategy is flawed. You might just be addressing the wrong problem.
When AI Products Can’t Find PMF, Build a Landing Client Instead — PMF isn’t always found in the product, Sometimes, it starts with one strategic client
Content as a Revenue Tool: Shortening Time-to-Close in Startup Sales — Content that shortens sales cycles, Not just builds traffic
Building Revenue Systems When Scale Isn’t an Option — Profitability First: How Startup Teams Can Drive Revenue in Constrained Markets
Case Studies
Mountain Gentleman — They knew they needed to go digital but had no idea how to start.So we saw things through the rider’s eyes.It wasn’t just about buying gear because it felt like building out your dream GTR.Every part of the journey was designed to match that thrill.
CoinRank — CoinRank needed a fresh way to stand out in crypto. We created a short video strategy that turns complex info into quick, engaging clips that grab attention fast.
問答
01
專案內容會包含什麼
02
價格是怎麼計算的
03
所有專案都是固定形式合作嗎
04
在開始合作之後可以調整專案範圍嗎
05
怎麼定義KPI
06
Do you offer ongoing support after project completion?
07
How long does a typical project last?
08
Is there a minimum commitment?
We All Live Tied to the Mast
Why Modern Products Aren’t Designed for Freedom, but for Voluntary Confinement
we-all-live-tied-to-the-mast
Growth Constraint Engineering
Narrative Structures as Strategic Commitments
What makes commitment sacred?
Ulysses and the Sirens
Artist | |
|---|---|
Year | 1909 |
The strongest products do not persuade. They bind. And the user signs willingly, fearing their own future self more than any competitor.
I. The Founder’s Quiet Panic:
Your Users Know What They Want. They Just Can’t Make Themselves Do It.
You built a product to help people reach their goals. You did the research. The interviews showed strong intent. The surveys confirmed it. The user journeys were straightforward. The problem wasn’t ambiguity, users knew exactly what they wanted. They wanted to write more, spend less, stop scrolling late at night.
But even with clear goals, engagement stalled. Retention weakened. Nudges, reminders, and scheduled routines were implemented, but they didn’t move the needle. The issue wasn’t lack of motivation. It was fragmentation.
Your product isn’t dealing with a single, consistent user. It’s dealing with two competing versions of the same person. One sets the intention. The other overrides it. At 10pm, the self who planned ahead loses to the self who wants comfort, escape, or distraction.
Until your product architecture accounts for this internal conflict, until it gives the goal-setting self tools to constrain the impulsive one, it won’t solve the real problem. It will remain just another well-intentioned interface, quietly ignored when it matters most.
This is the real challenge:
You're not building for a user. You're building for a conflict between two selves inside the same user.Until your product can help one version of the user constrain the other, you’re just another suggestion box they’ll eventually ignore.
II. The Industrialization of the Ulysses Pact:
When Restraint Becomes a Market Category
The problem is ancient. So is the solution.
In Homer’s Odyssey, Ulysses knows he will be tempted by the Sirens, creatures whose song lures sailors to their deaths. He doesn’t try to resist in the moment. He doesn’t trust his future self to win that battle. Instead, he designs the situation. He orders his crew to tie him to the mast and plug their own ears with wax. That way, even if he begs to be freed, they won’t hear him. He will be powerless by design.
This is the original Ulysses Pact: a commitment made in a moment of clarity to constrain future behavior in a moment of weakness.
Today, this same logic isn’t just a metaphor. It’s a product strategy. In fact, it’s rapidly becoming a full-blown market category.
Great behavior-change products don’t just nudge. They bind. They let the motivated version of the user set constraints on their future, less disciplined self. Think of it as multi-self UX. You’re not optimizing for convenience. You’re creating intertemporal contracts, agreements between present intention and future impulse.
And most products avoid this. They default to polite encouragement. Light-touch motivation. Just-in-time notifications that hope the user still cares.
But users don’t need gentle reminders. They need masts to tie themselves to.
We’re watching the commodification of self-restraint.
Consider what users are now willing to pay for:
Calm sells temporary mental silence
Opal sells a voluntary ban on apps your future self can’t resist
Beeminder turns goal tracking into real financial penalties
Centered gamifies attention, rewarding your prefrontal cortex over your limbic system
These tools don’t promise freedom. They promise containment. A safehouse from your own future impulses.
And the market loves it.
Because once you admit that the biggest threat to your goals is you, products that help you constrain yourself become not just useful, but essential.
This isn’t about productivity anymore.
It’s a shift in consumer psychology - from desire optimization to desire governance.
The Industrialization of the Ulysses Pact:
When Restraint Becomes a Market Category
Most tech products sell ease. Fewer clicks. Faster checkout. Frictionless everything.
But somewhere along the way, restraint became a feature. Then a selling point. Then a category.
Think of Freedom, the app that blocks internet access. Or Opal, which limits screen time with a countdown and public commitment. Or YNAB (You Need A Budget), which forces users to assign every dollar a job, no room for vague optimism. These are not convenience tools. They are constraint engines. They are built to limit access, remove choices, and deliberately add friction.
And they work not because they’re sophisticated, but because they respect the underlying psychology: future-you will betray current-you. The only way around it is to embed that tension into the product itself.
Restraint is no longer an implicit benefit. It’s an explicit function. It’s why users seek these tools in the first place. Not to do more. But to be stopped from doing less.
This flips the usual product playbook. Instead of reducing steps, you add irreversible ones. Instead of personalizing freedom, you standardize guardrails.
Most software simplifies interactions - fewer taps, less friction, faster outcomes. Constraint products take a different approach. They insert irreversible steps, exchanging flexibility for structure and speed for accountability. Rather than prioritizing user autonomy, they enforce commitments that persist when motivation wanes.
UX design shifts focus from ease to endurance. The experience centers on creating barriers to abandonment, ensuring follow-through becomes the path of least resistance.
Self-binding as product onboarding
III. Case Study:
Duolingo Doesn’t Teach You language. It Trains You to Fear Breaking a Promise to Yourself.
Duolingo is a language-learning app in theory.
In practice, it’s a finely tuned behavioral constraint system, masquerading as a green owl with a push notification addiction.
Here’s what Duolingo gets right that most “habit” products don’t:
It doesn’t try to motivate you. It tries to trap you, in a feedback loop engineered to outlast your weaker self.
Let’s break it down:
Streaks aren’t just a visual. They’re a psychological contract. Missing one day triggers loss aversion so strong that some users pay to restore them. This is not learning. This is hostage negotiation with your own guilt.
Hearts limit how many mistakes you can make before being locked out. You’re not just learning a language, you’re navigating a punishment economy.
Pre-set daily goals create a subtle but powerful form of self-enforcement. You don’t want to do the lesson. You just don’t want to break the streak you chose.
It goes beyond education by serving as behavioral infrastructure.
Duolingo figured out that the core user need isn’t progress, it’s consistency.
And the only way to guarantee consistency is to help users bind themselves against future defection.
Which means Duolingo isn’t selling language learning.
It’s selling the illusion of rationality continuity.
And that’s exactly why it works.
IV. Ulysses Product Archetypes:
A Strategic Comparison Across Constraint Systems
Once you realize that the core value of certain products lies not in what they enable, but in what they prevent, you start to see the shape of a new product archetype:
The Self-Binding Tool.
These products don't just serve a function.
They operationalize restraint and they differ in how.
Let’s map the terrain across four major archetypes, each representing a different design philosophy for how to help users win a battle against their future selves:
Product | Constraint Type | Design Mechanism | Underlying Psychology |
|---|---|---|---|
Emotional Anchoring | Streak loss, push guilt, heart penalties | Loss aversion + routine attachment | |
Environmental Control | App blocks, scheduled focus sessions | Default reshaping + friction inflation | |
Monetary Penalty | Contractual bets, anti-charity donations | Precommitment + financial pain | |
System-Level Lock | Password-protected app limits | Executive override friction + parental framing |
Each of these products answers the same fundamental question -
"How do I prevent my irrational future self from sabotaging me?"
but answers it through a different layer of the stack:
Duolingo uses habitual shame and gamified guilt
Opal restructures your access environment
StickK turns failure into a literal financial loss
Apple gives your phone a second, stricter self with admin privileges
These products move beyond simple motivation. They create a space where conflicting selves within a person must come to terms. Rather than offering encouragement, they facilitate an internal negotiation, recognizing that users are not a single, unified entity but a collection of competing intentions. The value lies in managing that tension, not eliminating it.
And the more persuasive they are at enabling that negotiation, the more valuable they become, not just functionally, but commercially.
Because in a world where everyone is at war with their own attention span, products that help users win against themselves become category-defining.
Self-binding as product onboarding
Art by Barbara Kruger
Untitled (Never Perfect Enough), 2020
V. The Evolution of Self-Control Products:
From Willpower Tools to Incentive Infrastructure
Let’s rewind and trace the trajectory of this product class over time.
Because what looks like a scattered group of "focus apps" or "motivation hacks" is actually a slow industrialization of behavioral control, with each phase unlocking a deeper layer of user entanglement.
Phase | Era | Notable Products | Design Principle | Mechanism |
|---|---|---|---|---|
1 | Willpower as UX (2007–2014) | Nudging interface | Visual cues, gamification | |
2 | Infrastructure of Restraint (2015–2022) | OS-level enforcement | Precommitment, lockdown | |
3 | Incentive Engineering (2023–ongoing) | Contractual alignment | Money, social pressure, calendars |
Phase 1: Willpower as UX (2007–2014)
Era of Personal Apps and Atomic Habits
Notable tools: Forest, Habitica, RescueTime
Products in this era treated self-control as a UX challenge.
Interfaces were built to nudge, not restructure.
Willpower was still assumed; tech was just there to help remind, track, decorate.
Think of it as the Post-it Note phase.
Helpful, visual, but ultimately deferrable. The burden remained on you.
Phase 2: Infrastructure of Restraint (2015–2022)
Era of Systemic Precommitment
Notable tools: Freedom, Opal, OneSec, ScreenTime
The stack moved lower. Apps now interlocked with OS-level controls, browser permissions, VPNs.
Self-control became infrastructural. Not a behavior to be reminded of, but a rule to be enforced.
Tools shifted from nudging to automating resistance.
The user experience changed from “How can I help myself focus?”
to “How can I stop myself from cheating?”
This was the birth of the Ulysses pact as a product.
Constraint became the feature.
Phase 3: Incentive Engineering as Market Power (2023–ongoing)
Era of Psychological Contracting + Monetized Discipline
Notable tools: Reclaim.ai, StickK, Rise, Mindsera
These products don’t just block distractions.
They assign costs, bind contracts, and create synthetic accountability loops.
Some interface with calendars, others with your bank account, some with your coach or community.
In this phase, the product becomes a broker of incentives.
It doesn’t enforce your goals. It aligns your psychology, money, and social context so you do.
We’ve entered the age of Behavior-as-a-Service.
And like any service business, the most valuable ones aren’t the ones that offer features -
they’re the ones that reshape behavior at scale, reliably, and irreversibly.
Designing for the Self You Don't Trust
Every product decision lives inside a context: user expectations, platform distribution limits, incentive structures, and the competitive environment. Ulysses products aren’t just clever UX experiments, they’re a direct response to a shifting ecosystem where choice paralysis, user fatigue, and retention fragility are endemic.
In earlier product eras - especially during the late 2010s growth-hack boom - more was always better. More features, more control, more customization. Product teams were obsessed with dashboards, toggles, and “power user” affordances. But over time, it became obvious: users don’t want infinite optionality. They want relief from it.
Enter macro trend number one: Cognitive Load Saturation.
Across verticals, from finance apps to fitness trackers, attention is no longer the bottleneck - cognitive energy is. Even when users have time, they lack decision stamina. The average user doesn’t want to weigh ten ETF options. They want one portfolio they can stick to. That’s why apps like Wealthfront, Levels, and Noom began embedding behavioral constraints as a UX default. Not to limit capability, but to offload decision stress.
Macro trend number two: Algorithmic Intermediation.
In a world where distribution is platform-mediated (think: TikTok, X, YouTube), product-led growth depends on designing for engagement metrics you don’t control. Ulysses-style products - by engineering consistent behavior - generate more stable usage loops and cleaner data trails. Platforms reward that.
Look at Duolingo. Every interaction is structured, time-bound, streak-based. Its notifications are behavioral contracts disguised as encouragement. That kind of routine generates predictable outputs and repeatable engagement patterns. In a system trained to reward legibility, discipline becomes the new distribution hack.
Macro trend number three: Rebundling by Trust.
In the age of platform ecosystems, tools are no longer neutral utilities but extensions of the people and values behind them. The investor you follow, the trainer you trust, the writer whose newsletter you read - all rebundle products around identity. This creates systems that are not just functional, but deeply opinionated. They embed values directly into the constraints they impose.
This dynamic is inseparable from the concept of the Ulysses Pact. Originating from the myth of Odysseus who tied himself to the mast to resist the Sirens, a Ulysses-style product is one that helps your rational present self bind your future impulsive self. It’s a design pattern of self-imposed limits that cannot be easily reversed. These products do not merely remind you to do better; they engineer a path that closes off bad choices by default.
Rebundling by trust means you accept those constraints because they come from someone you believe understands you better than you do. The coach’s workout plan, the writer’s curated routine, the investor’s portfolio allocation - each acts as a proxy for discipline. You’re effectively saying, “I trust you to tie me to the mast.”
The power lies not in the features themselves but in what they refuse to let you do. Trust becomes the binding agent, turning products into commitment devices personalized by identity. The product is no longer just a tool; it is a trusted system that enforces discipline through alignment with your values and the people you respect.
Designing for the Pact: A Model for Multi-Self UX
To operationalize a Ulysses Pact, you need to stop thinking about one user. You’re building for two:
The planner, who sets goals and installs your app with conviction
The impulsive actor, who opens it at 11:47pm looking for a dopamine hit
Most products collapse these selves into one persona. That’s a mistake. What you need instead is a dynamic contract between the two. A UX that stages decisions in time.
This model has three critical phases:
Commitment Window
The product must recognize and amplify moments of clarity. When motivation peaks, constraints should be easy to set and hard to reverse. Think onboarding flows that lock in usage limits, or daily settings that can’t be changed mid-session.Fracture Point
The moment of temptation. The user wants to break their commitment. Here, your product becomes a gatekeeper. Delay friction, shame friction, or community friction can all be deployed. The goal isn’t punishment. It’s time dilation. Let intention catch up to impulse.Aftershock Layer
Once the moment passes, the product must reflect back the choice and its cost. Highlight streaks broken, goals postponed, or social accountability triggered. Over time, this builds narrative memory. The user starts to anticipate their own regret.
Done well, this structure doesn’t fight the user. It lets the best version of them win more often.
Why Most Products Don’t Go There and Why Some Should
Restraint is uncomfortable to build for. Most founders want to delight, not restrict. PMs are trained to remove friction, not add it. And investors rarely fund features that reduce usage on purpose. The incentives all point toward maximization, more engagement, longer sessions, higher frequency.
But if your product is meant to help people change - write more, spend less, focus longer - then usage maximization is often at odds with value creation.
This is where the market splits.
Entertainment products optimize for immersion. Their enemy is boredom. But transformation products optimize for integrity. Their enemy is inconsistency. If you mistake one for the other, your product will cannibalize its own purpose.
Action Painting (1981) by Mark Tansey.
From Hacks to Habits:
The Evolutionary Pressure Behind Ulysses Products
Ulysses products didn’t start as grand strategies. They started as panic. As stopgaps. As duct-taped answers to distribution leaks, retention drops, or viral threats. But the ones that survived, the ones we now recognize as strategic masterstrokes, were forged under evolutionary pressure.
Take calendar-first productivity tools. At first, they looked like glorified Google Calendar integrations. But under the weight of remote work, Zoom fatigue, and async chaos, they became a default operating system. Now, a “time-blocked” interface isn’t a gimmick. It’s a moat. Users lock themselves in, intentionally because the alternative is cognitive overload. Constraint becomes peace.
Or take multi-player collaboration tools. They weren't born from collaboration ideals. They were born because work stopped happening in the same room. Figma wasn’t just a better design tool. It was an anti-fragmentation protocol. Notion didn’t unify docs because of elegance. It did so because context-switching was killing team memory. In a chaotic ecosystem, only tools that imposed helpful constraints could scale.
Even AI writing tools are facing this same evolutionary demand.
The first wave said: “We'll write it for you.”
The next wave will say: “We'll make sure you don’t sabotage your own output.”
Expect to see Ulysses-style features like commitment layers, revision locks, and reputation-dependent publishing thresholds. The tools are becoming parents. Or parole officers.
Design alone does not explain it. In saturated ecosystems, survival depends on offering better defaults and creating friction that makes leaving difficult. Winning comes not from more freedom, but from carefully engineered constraints.
The Ulysses Product Stack:
A Three-Layer Trap That Users Thank You For
Ulysses products aren’t just sticky. They’re staged traps with narrative cover. Done well, they don’t feel like lock-in. They feel like relief. The secret? A three-layered product stack that slowly shifts power from user to platform, without triggering rebellion.
Layer 1: The Ritual Hook
Every Ulysses product begins with a habit scaffold. Daily check-ins. Scheduled sends. Timeboxed flows. These aren’t productivity tricks, they’re muscle memory architectures. The product doesn’t force you to come back. It just gives you one good reason every day not to leave.
Layer 2: The Constraint Engine
Once a user is “in,” the second layer kicks in: intentional limitations. The product reduces optionality, not because it can’t offer more, but because it knows you’ll do worse with it. Think Superhuman’s command palette. Linear’s ticket workflow. Figma’s multiplayer mode. Every interaction nudges users away from chaos toward a single optimal path - defined by the product, not the person.
Layer 3: The Strategic Inertia Layer
By now, switching isn’t just painful, it’s reputationally risky. The product begins storing not just data, but context. Shared docs, comment threads, custom workflows, team rituals. This is when users stop comparing you to alternatives. They start designing their life around you. In this phase, a calendar app isn’t a tool. It’s an identity.
Ulysses-style products carry an inherent risk. They are not designed simply to delight users but to create dependency. Once users become accustomed to these constraints, the cost of leaving rises dramatically. The challenge lies in maintaining a delicate balance: each added friction must deliver clear value. Without that, users feel trapped rather than supported. When the illusion of choice dissolves, trust evaporates, and the product’s foundation begins to crumble.
This is a design philosophy that demands rigorous discipline from makers. It requires anticipating where constraints empower and where they suffocate. Success depends on building systems that respect the user’s intelligence while guiding behavior. Otherwise, dependency turns into resentment, and control becomes a prison rather than a tool.
Ulysses vs. The Feed: The Next Ethical Battlefront
We’re entering a phase of product design where helping users “do what they want” means helping them resist themselves. That means building constraints, not just affordances. Friction, not just flow.
It’s a hard sell. Especially in a culture wired to equate freedom with optionality and growth with engagement. But the next generation of transformative products, especially in health, finance, learning, and time management won’t win by being frictionless. They’ll win by being loyal to the user's higher self, even when it hurts the metrics.
That’s the tension: between growth and restraint, between what the user clicks on and what they actually want.
And that’s the opportunity: building for the version of the user that can’t win on their own.
The products that survive in the pact era won’t just get used.
In a feed-driven world, attention is the constraint. But in the Ulysses universe, it's conviction. The conviction to build rituals that don’t optimize for virality. The courage to limit features so that behavior can harden. And the clarity to know when a product’s strength becomes its prison.
This model worked brilliantly for the last generation of SaaS. But it’s now colliding with a new set of user defaults - AI-native, feed-native, fluid-first. Products like Notion AI, Perplexity, or even iA Presenter assume that context isn’t sacred. It’s disposable. Shared knowledge is ephemeral. Switching isn’t a loss. It’s expected.
This creates a strategic fork. Founders can still build Ulysses-style products. They’ll attract power users, teams, builders who crave structure. But mass adoption will shift toward tools that degrade well, tools that lose less when abandoned.
What’s at stake isn’t control, but the tradeoff between stickiness and substitutability.
And the new question for every product founder isn’t How do I get users to stay?
It’s What does my product become when they leave?
In the Odyssey, Ulysses didn’t trust himself to resist the Sirens. So he asked to be tied to the mast. Today’s feed products are the Sirens. They win by seducing. But Ulysses-style products win by self-binding. They help users resist their lower impulses, so they can stay loyal to their goals—even after the app is gone.
Anchor Articles and Updates
Feed economy: How Each Platform Manufactures Dependency Loops — Why creators feel burned out, and what platforms don’t want you to understand about their invisible incentive systems
Crisis Is Not the End. It’s a Catalyst for Product Growth. — Reframing the Narrative of Windsurf, Astronomer, and Cluely
Building Products in the AI Era: The Deep Logic of Speed, Content, and Data Ownership — If you’re building a new product in 2025, you’re not competing on functionality.
You’re competing on attention loops, learning velocity, and data leverage.
How AI Platforms Reshape Innovation: Subordination, Risk, and Workflow Strategy — Rethinking Product Strategy Under Model Governance
How AI Understands User Intent Before They Search: Commercial Decision Loops and the Invisible Funnel — Why pre-intent behavior is becoming more legible and monetizable
Inspired by Lenny’s Growth Inflections: AI and Personal Brands Rewiring Startup Growth — AI automation and personal brands are redefining startup growth inspired by Lenny Rachitsky’s Growth Inflections.
Why Growth Marketing Is Not Digital Marketing and Why This Distinction Matters — It’s not that your marketing strategy is flawed. You might just be addressing the wrong problem.
When AI Products Can’t Find PMF, Build a Landing Client Instead — PMF isn’t always found in the product, Sometimes, it starts with one strategic client
Content as a Revenue Tool: Shortening Time-to-Close in Startup Sales — Content that shortens sales cycles, Not just builds traffic
Building Revenue Systems When Scale Isn’t an Option — Profitability First: How Startup Teams Can Drive Revenue in Constrained Markets
Case Studies
Mountain Gentleman — They knew they needed to go digital but had no idea how to start.So we saw things through the rider’s eyes.It wasn’t just about buying gear because it felt like building out your dream GTR.Every part of the journey was designed to match that thrill.
CoinRank — CoinRank needed a fresh way to stand out in crypto. We created a short video strategy that turns complex info into quick, engaging clips that grab attention fast.
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