Mandatory warning that I’ve used this system for exactly 3 days:

How to use systems: #ADHD edition

1) get excited about system
2) set system up instead of doing whatever it is you’d planned on doing
3) use it for 3 days
4) recommend to everyone you know
5) get busy
6) abandon system
7) feel guilty about abandoning system & avoid forever

— Jessica McCabe (@HowtoADHD) August 4, 2020

And secondary mandatory warning that nearly all advice is bad.

In Part I, I proposed a short list of solutions to working independently after quitting your job. Here’s the long version with details fleshed out.

Accept that you max out at 4 hours a day, and make sure you actually hit it every day.
The major caveat here is that it is incredibly difficult to consistently work 4 hours a day. Nearly no one can pull this off, and even people with stressful full time jobs are often just faking it by spending 8 hours on Slack and in meetings.

So while 4 hours a day sounds downright leisurely, you can’t get tricked into complacency.

If 20 hours a week sounds like easy mode, the easiest way to become dramatically more productive is not to “hustle harder”, but to add weekends. This puts your total weekly hours at 28, a 40% increase over only working weekdays, but still keeps you at 30% under a normal 40 hour workweek.

Also note that you’re still “on” the remaining 140 hours a week. That time is for making sure you’re healthy and energetic enough to do 4 hours work very consistently. Most people don’t actually know how to relax, just how to “blow off steam”. If you go out to a bar after work, you don’t feel more motivated the next day, you just feel more able to handle another 8 hours in an office.

Find sources of lasting intrinsic motivation that aren’t based around feelings of inadequacy.
If you’re a smart person, you’ve spent your whole life winning competitions, getting praise from authority figures, checking boxes and gaining prestige.

Understand that there is no difference between a superiority and inferiority complex. The feeling of being great just means you value your ego, and will fear losing it even more.

I don’t have any concrete advice here, other than to take it seriously, give it time, and hope that after years of education and employment you still have any genuine interests remaining.

Measure yourself by what you’ve done, not how many hours you’ve put it
This is a bit misleading. If you’re working independently, you likely won’t have any “accomplishments” in a conventional sense for many months.

The real advice is Scott Adams’, which is to follow a system instead of a goal. If you want to learn a new language, don’t try to measure progress towards fluency, just set up a simple system (study flash cards 1 hour a day, watch 30 minutes of content, write 10 sentences in your journal using the new words you learned) and measure progress by how consistently you’re able to follow the system.

A month in, you can see how the system is going and try to establish progress on external goals, but that can’t be the first step. Day to day, progress is never going to be linear, so winning has to be about behaving the right way, not achieving the right results.

If you’re like me and love abstraction, not hyper-optimizing the system at every opportunity feels incredibly wasteful. But the truth is for most pursuits, a very simple system will get you 80% of the way there, and much much further than an optimal system poorly followed.

More deeply, goals and systems are two parts of the same coin, and you can’t fully design the system without spending time engaged in practice. You might discover after a month that you derive way more joy from conversation than from writing, and decide to shift your language learning focus, but that insight won’t happen from taking the bird’s eye view.

Enjoy your newfound freedom, but in ways that don’t directly compete with your real aims.
I banned myself from video games throughout my last job, which means that as soon as I quit, I binged everything I had been denying myself.

Some hobbies just feel all-consuming like this. If I get deeply involved in a TV show or game, I basically just have to give up on the entire week and try to get work done later.

In other cases, the activity might not be time consuming, but will still impede efforts elsewhere. The most obvious examples are drinking, sleep deprivation, and having a poor diet. You can stop taking shots at midnight, but still feel horrible at noon the next day.

The only thing I’ve found effective for quitting addictive habits is binging to the point of self-hatred. I will stay up all night playing video games, and then hate myself enough to stop for the next 3 months. This might not sound particularly healthy, but outside of alcohol, I don’t actually think it’s a serious harm.

Create psychological distance by choosing a particular time and place to work, if necessary, inform everyone you live with of your “official work hours”.
This is fairly straightforward. The only caveat is that it might be embarrassing to tell your parents or housemates that you’re “writing a blog on the internet” or “doing independent research” or “starting a startup” and can’t be interrupted.

I’m even more embarrassed to write about this publicly, but I literally solved this problem by becoming nocturnal, and doing all my writing after my housemates have gone to bed.

Conclusion.
This isn’t meant to be generic productivity advice. I’ve read so much of those posts, and gotten basically no value from them. This won’t solve all your problems, but hopefully it will at least make you feel less alone if you’re struggling with similar issues, or give you a jumping off point to figure out your own system.

Recently, there’s been headway in adopting Ranked-Choice Voting, used by several states in the 2020 US Democratic presidential primaries and to be adopted by New York City in 2021.

For all its virtues, Ranked Choice Voting contains a number of risks, largely due to tactical voting and democratic illegitimacy.

First, a quick primer on existing systems.

The one we’re used to is called Plurality Voting, and is by far the simplest: Each voter casts a vote for one candidate, and the candidate with the most votes wins.

Though clear and intuitive, there are several problems best illustrated by example:

Tactical Voting for “Realistic Candidates”
Say public polls report:

• 45% of voters prefer Alice
• 45% of voters prefer Bob
• 10% of voters prefer Carol

No matter how strongly voters support Carol, on election day, they would rather vote for Alice or Bob than “waste” a vote on a candidate who won’t win.

It’s worth asking why Carol was polling so low in the first place, but a common explanation is perpetuation through a party system. If Alice and Bob’s parties have won historically, the electorate may be locked into a perpetual two-party system, no matter how compelling a particular third-party candidate happens to be.

Loss of Popular Moderate Candidates
In another race, voters have real preferences such that:

• 50% of voters prefer Alice > Carol > Dave > Bob
• 50% of voters prefer Bob > Carol > Dave > Alice

Alice and Bob are both despised by half the population, yet one of them is guaranteed to win. Meanwhile, Carol has universal appeal, but would receive 0 votes in a plurality election, no matter how polarizing the other candidates are.

In a more extreme case, we might have:

• 25% of voters prefer Alice > Bob > Carol > Dave
• 25% of voters prefer Bob > Alice > Carol > Dave
• 30% of voters prefer Dave > Alice > Carol > Bob
• 20% of voters prefer Carol > Alice > Bob > Dave

Alice is the clear intuitive choice, but according to plurality rules, Dave ends up winning despite being despised by 70% of the electorate.

Tactics in Ranked Choice Voting
In theory, these are precisely the problems solved by RCV, but the general form I’ve outlined above can still apply.

Given real preferences:

• 33% of voters prefer Alice > Bob > Dave > Carol
• 33% of voters prefer Bob > Alice > Dave > Carol
• 34% of voters prefer Dave > Alice > Bob > Carol

Each cohort knows that Carol is not a realistic threat to their preferred candidate, and will thus rank her second, while ranking their true second choice last. For any individual, this is a good strategy to maximizing the odds of their preferred candidate, but in aggregate, it leads to:

• 33% of voters prefer Alice > Carol >  Bob > Dave
• 33% of voters prefer Bob > Carol > Dave > Alice
• 33% of voters prefer Dave > Carol > Alice > Bob

Leading to a victory for Carol, even though she was universally despised.

What’s Wrong with Tactics?
At some point, we might bite the bullet and say that all voting is tactical, in the sense that it incorporates outside information rather than merely expressing one’s preferences.

But as we saw in the last case, tactical voting doesn’t just skew results, it can have arbitrarily bad outcomes, like the election of a universally despised candidate, or the failure to elect a universally liked candidate.

Self-defeating Tactics Over Time
It is also worth introducing the concept of self-fulfilling and self-defeating tactics.

Self-fulfilling manipulation is what we’re used to. A candidate attempts to portray themselves as having a real chance of winning that is not yet guaranteed, thus giving voters the impression that their vote is likely to matter.

Self-defeating manipulation is weirder, and possibly much worse. Take our RCV scenarios again with equally sized cohorts:

• Cohort 1 prefers: Alice > Bob > Carol
• Cohort 2 prefers Bob > Alice > Carol

2 weeks before the election, a polling organization correctly reports these  preferences, thus creating the perverse reaction described earlier, and a shift to:

• Cohort 1 states a preference for Alice > Carol > Bob
• Cohort 2 states a preference for Bob > Carol > Alice

1 week before the election, the polling organization reports these new stated preferences. Voters see that their preferred candidate is no longer at risk of losing to their second favorite, and shifts back to to their real preferences:

• Cohort 1 prefers: Alice > Bob > Carol
• Cohort 2 prefers Bob > Alice > Carol

Thus restarting the cycle of polling > new tactics > new polling up until election day.

At this point, each voter is confused and uncertain, and votes according to tactical necessity rather than actual preferences. In this scenario, Alice, Bob or Carol could win, and it just depends on the particular rhythm of polling, speed of reporting, date of the election, and other factors largely incidental to voter preferences.

Condorcet Paradox of Circular Preferences
Finally, consider the case where ranked choice voting is simply incoherent:

• 33% of voters prefer Alice > Bob > Carol
• 33% of voters prefer Bob > Carol > Alice
• 33% of voters prefer Carol > Alice > Bob

No matter which candidate is elected, there is an alternative preferred by 66% of the population, such that there appears to be no stable solution. If Alice is elected, the majority of voters would prefer that Carol be elected instead.

Note that this is not a coincidental feature of perfectly balanced distributions, we can just as easily have:

• Cohort 1 (20%) prefers Alice > Bob > Carol
• Cohort 2 (35%) prefers Bob > Carol > Alice
• Cohort 3 (45%) prefers Carol > Alice > Bob

Where in the best case scenario, Carol wins, but 55% of voters would prefer Bob.

(In general, the worst case scenario depends on the number of candidates, such that in a 5 candidate race, an alternative could be prefered by up to 80% of voters.)

One might object that this is simply unrealistic. Are such circular preferences coherent?

We can generate intuition using a simple model where candidates and voters are mapped on 2-dimensional space, and rank candidates based on proximity. In the above example:

The key thing to note is that circularity exists across cohorts, but not within them. Each voter or cohort has a simple linear ranked order, it is only in aggregate that the paradox appears.

To be clear, this paradox exists equally in Plurality Voting, it just remains invisible. Even without stated preferences, real preferences could contain the same circular result.

But since voting serves as a coordination mechanism, this invisibility is a feature. With a single vote per person, simple plurality feels like a fair result. In contrast, Ranked Voice Voting risks the instability of a majority-preferred alternative, and undermines democratic legitimacy.

There’s a persistent myth among unhappily employed people that “if I could just quit my day job and pursue my passion full time, I would finally be satisfied”.

It’s me, I’m the unhappy person.

The unfortunate truth is that many people become dramatically less productive after going independent. After quitting her job and becoming a “full-time writer”, Nadia describes her life as just being “pretty crappy”. Several close friends have experienced the same effect, becoming less productive on side projects after quitting their day jobs.

How is this possible? Why doesn’t alleviating a 40 hour a week burden change things dramatically for the better?

Opportunity cost skyrockets
With a day job, you’re more or less tied down. If you’re only free from 6pm-10pm every day, there’s not too much to do other than eat dinner, exercise, and work on your side project.

But once you quit, anything is possible. You could be traveling, parting, learning a new skill, visiting relatives, hiking in the middle of the work week while everyone else is stuck inside, or visiting great restaurants at 2pm when there’s no crowd.

Rather than hit a satisfactory limit, many of these activities actually take up more time the more you get into them. You can watch TV for 2 hours a night and not have an urge to do it at work, but if you get deeply excited about a new hobby, it can engulf your life.

You can only do 4 hours of real work a day
As reported by Cal Newport, famed mathematician Henri Poincaré could only work 4 hours a day. In an interview, Newport writes of his own life:

I think if you’re able to do three, maybe four hours of this sort of deep work in a typical day, you’re hitting basically the mental speed limit, the amount of concentration your brain is actually able to give.

With a day job, you were working 6pm-10pm, now you’re working 10am-2pm instead, but your total output hasn’t increased.

The exception is day jobs that take up hours of deep concentration. But if you’re already fantasizing about quitting, this probably isn’t the case.

Having a boring job is motivating
Einstein famously worked as a patent examiner, Kafka worked assessing personal injury claims for insurance companies.

Having a boring day job provides freedom (your mind can wander), but also a feeling of being underappreciated that borders on resentment. You know you’re being underutilized, you know you’re capable of more, and you’re desperate to prove it.

Lack of psychological distance
With a job, you go to a particular location, on a highly regular schedule, surrounded by a cohort of colleagues and environment. This creates a kind of psychological distance between work and the rest of life. When you’re at the office, you’re in work mode.

On a side project, you’re working alone, often from home, and without any kind of defined schedule. This means that any time could be work time, any place could be a workplace, and accordingly, any time and place could be for leisure. It’s easy to sit on the couch working, and then lapse into a nap when there aren’t clear boundaries.

There’s no more shallow work
It’s easy to spend 12 hours a day being “productive” at a day job, if all you’re doing is sitting in meetings, reading memos and replying to emails.

In contrast, personal projects are often chosen specifically because there is no busy work. You have no colleagues to waste time with, you are working solely on the difficult and interesting things that you want to do.

Conclusion
Hopefully, at this point, the steps to resolve these issues stem intuitively:

• Accept that you max out at 4 hours a day, and make sure you’re actually hitting it every day
• Find sources of lasting intrinsic motivation that aren’t based around feelings of inadequacy
• Measure yourself by what you’ve done, not how many hours you’ve put it
• Enjoy your newfound freedom, but in ways that don’t directly compete with your real aims
• Create psychological distance by choosing a particular time and place to work, and if necessary, inform who could distract you of your “official work hours”

For details on implementation, read Unemployment Part II