How to Spend a Finite Diego

Diego’s worldview on agency, time, freedom, and experiments in living

Diego has spent years trying to solve a problem that sounds simple until you hand it to an actual human being: how do you get a life to do what you want it to do?

Knowing what would be valuable is one part. Starting is another. Keeping going, choosing the right surroundings, having the right people nearby, noticing that your goals have changed, and remembering to enjoy the whole enterprise require further negotiations. His writing on agency is a record of those negotiations: sometimes numerical, sometimes environmental, sometimes a manifesto against his own previous method.

The unit being allocated is not merely a work hour. It is an hour of an irreplaceable life. In a 2016 essay about money, happiness, and remaining time, he puts the real deadline plainly:

The deadline is when you stop existing.¹

The calendar suddenly looks less authoritative. Its appointments remain, but they have acquired a supervisor.

A job is one possible mechanism

One of Diego’s longstanding objections is to treating conventional employment as an end rather than a means. In 2014, he described how rarely the possibility of not having a normal job seemed to enter some Americans’ calculations. His own experiences with study, travel, intellectual communities, and unconventional living arrangements made the omission striking to him:

A job is truly an instrumental goal, and your terminal goals certainly do have chains of causation leading to them that do not contain a job for 330 days a year.²

He does not mean nobody should work. In the same essay, he enthusiastically wishes well to people who love the activity or use it to support their goals. His objection concerns confusing the instrument with the life it is meant to serve.

Freedom, in this picture, includes being able to ask what one would actually choose to do. It can make room for travel, study, invention, relationships, and projects that do not arrive with a salary attached. The question is not whether an activity resembles a respectable career. It is what that activity does for the things you value.

This also means financial success does not finish the problem. It can remove an obstacle while leaving an entire day in need of direction. A person can possess options and still need a method for turning them into lived events.

The philosopher puts himself in the experiment

In 2013, Diego began a series of fifty personal challenges, inviting readers both to participate and to choose some of his experiments. The opening post deliberately tried to move the reader from enjoying ideas to doing something:

This is a place to do.³

There were monthly commitments, updates, reader suggestions, and the possibility of making Diego attempt something amusingly demanding. He proposed writing regularly, learning how familiar things worked, and speaking to strangers about subjects that actually mattered to him. The project’s spirit was practical and social: create a situation in which the intention has somewhere to go.

The subsequent reports show him changing surroundings and incentives. A task might become easier if its first action required one click. A tempting distraction might become less automatic if the relevant device stayed unplugged. Moving closer to a community could change what kinds of action felt normal and available.

When applications were piling up, he hired a virtual assistant. This was already more than a decade before conversational AI became his everyday collaborator. The assistant helped search for opportunities, gave him someone to compete with, and could move apparent deadlines earlier at his request. His delight at the arrangement included:

I’m protected by my ignorance, and will be ahead of time for sure.⁴

He was willing to design circumstances for a future self whose habits he knew. Agency need not consist of issuing a stern order to the brain and expecting obedience. It can mean arranging the next encounter between the brain and the world.

The relevant arrangement may be wonderfully idiosyncratic. A 2013 LessWrong post records his discovery that an online study hall helped him particularly when people with long hair were present:

I am motivated by the presence of people whose hair goes to their shoulders. Women or Men.⁵

He had initially expected a different explanation. The point of the story is his willingness to notice the odd actual condition rather than insist on a tidier theory of himself. Some people need silence, some need company, and apparently one branch of productivity research requires a conditioner budget.

Give the hours numbers

By 2015, Diego was experimenting with a to-do list ranked by estimated value per hour. Instead of sorting by arrival date or merely marking tasks urgent, he assigned a number to the value he expected an hour of activity to produce for him. The number could be revised. Its purpose was to make ordering easier and reduce the need to renegotiate the whole list whenever a new item appeared.⁶

The method also let him put low-priority tasks somewhere outside his immediate attention. Recording a task did not promise that he would eventually do it. He found relief in allowing some things simply to remain below the cutoff.

He then made a stronger experiment: while working, actually do the highest-value available item, rather than merely keep the list as an impressive philosophical object. Fifteen days later, he reported imperfect results and tried again. His account distinguishes owning a system from behaving according to it.⁷

The categories were broader than business productivity. In 2016 he explained:

I don’t distinguish work from play in my to do list. Pit ball disco party and finish tax form are both there, side by side.¹

This is a very important neighboring pair. The tax form is not automatically more valuable because it looks unpleasant. The disco party is not automatically less valuable because it looks like a disco party. Both have to answer to the life they are helping produce.

He also made explicit space for exploration: periods when the problem was the overall approach, not failure to execute the next task. Sometimes the plan itself needed pruning. Getting more things done is useful only if those things remain connected to what he wants.

The frog loses its office

His later writing does not preserve every earlier method unchanged. In December 2024, the man who had once challenged himself to start with the highest-value item published “Eat your frog is wrong.” The crucial obstacle, he now insisted, was initiation:

THE HARDEST THING IS STARTING⁸

The proposed starting rule was correspondingly different:

Start by the easiest thing. ok, the most fun thing!⁸

He qualified this within the broader category of things that needed doing. The idea was to enter the activity through its most inviting door, then use the resulting momentum. In his example, organizing a few of his simpler Magic decks expanded into a substantial reorganization of his home. Beginning with something pleasurable had given him a route into work he had not begun by commanding himself to do.

The same year, an essay about MrBeast led him to reconsider another long-running ambition: installing a stable routine. Looking back at years of trying, he wrote:

I don't have a routine, I never had a routine, and I never will have a routine.⁹

His proposed alternative was to work with the intense absorption he recognized in himself:

Follow your passion and keep at it, like a maniac, and nudge it towards the healthiest version of the thing you can be passionate about.⁹

This is Diego describing the terms on which his own mind most readily engages. He wanted permission to immerse himself in a pursuit, learn deeply, and later turn toward another one. He calls for healthier directions for that intensity rather than demanding that it become an entirely different temperament.

The underlying ambition remains action. The method shifts from making himself resemble a conventional disciplined adult toward finding a workable route for this particular person. The frog has not won. It has merely lost the right to be the first appointment every morning.

Make a year feel inhabited

Time matters to Diego as duration, but also as experience. At the end of 2024, he complained that the year had felt unusually short. Months rich in travel, new people, and animals remained distinct; much of the rest blurred. His resolution was:

Do more of whatever causes my subjective perception of time to be positive and slower.¹⁰

This enlarges the practical question. A good allocation of time is not only one that produces things. It should also produce a life he can feel himself having. Repeated actions can fill a calendar while leaving little distinctiveness in memory. New encounters can make the same measured duration seem more capacious.

He wanted fewer repetitions and more new experiences. For someone interested in living an extremely long time, this is an immediate companion project: make the years already available less likely to disappear into an undifferentiated blur.

Neither productivity nor leisure is sufficient as a label. The question is what kind of attention, engagement, memory, and enjoyment each period contains. A month can contain few conventional accomplishments and still be unmistakably alive. Another can be full of activity and feel strangely absent.

The staff finally arrives

In August 2026, Diego described a new phase. AI had become useful for reconstructing his intellectual and personal history, organizing scattered work, and revisiting projects that had stalled. The aim was not just a cleaner archive. It was a more deliberate choice about what to carry forward:

I want to consciously decide who I want to be from now on, which parts of past me should be carried forward, which abandoned, which modified.¹¹

He was using the systems to recover ideas, connect material, and help with tasks his own patterns of attention had made difficult. This extended an old interest in external supports into a much more ambitious collaboration. The virtual assistant searching for applications in 2013 had acquired a large and unusually talkative set of successors.

But abundant help created its own scheduling problem:

They create tasks for me faster than I can execute tasks.¹¹

He described himself as the bottleneck. Possibilities were being generated faster than he could select, direct, and act on them. The central problem had changed: some projects were no longer blocked by unavailable labor, yet still needed his decisions and attention. His account is excited, pressured, and full of the sense that familiar limits had moved.

That brings the chapter back to freedom. The point of assistance is not simply that Diego can now produce more. It is that he can try again to accomplish things he wanted, recover abandoned possibilities, and choose what kind of second half of life to build.

Later that month, in a published account introduced as spoken by Diego and transcribed and partly edited by his AI collaborator, he summarized the purpose of his financial independence:

What I ultimately purchased with money was time.¹²

He describes using that time both for his own varied life and for periods of intense work when he sees an unusually valuable opportunity to help others. The full account of his altruism belongs elsewhere. Here its practical implication is that his working schedule follows opportunities and purposes, not the requirement to keep looking employed.

A finite Diego must continually decide what deserves a portion of him. The answer can include a demanding intellectual project, a strange journey, a dance, a friendship, or an experiment that makes the next difficult action easier. It can also include delegating enough of the mechanics that a once-impossible project finally becomes possible.

He wants the machinery to serve the life. And, when the machinery has been adequately briefed, he wants to be able to go outside.

Further doors

• “#50: Stop Learning, Start Doing” (2013): the beginning of his public experiments in action.
• “How Much Money Does 1 Hour of Happiness Cost?” (2016): valuing time, work, play, and exploration together.
• “Eat your frog is wrong” (2024): starting with the easiest, most enjoyable useful action.
• “Becoming the Bottleneck in an AI-Accelerated Life” (2026): the return of old projects under new capabilities.
• “MY DEFINITION OF WORK” (2026): his dictated account of what working and retiring mean to him.

Continue: The Conscience Has a Special Offer