Well, yesterday was a weekday and I didn’t publish anything. I had something come up and I just wasn’t able to get it in.

That’s right, I’m only a few weeks into this experiment and I’ve already “failed”. But I’m not worried about it. In fact, I’m kind of glad.

When I’ve published daily in the past, one of the techniques that has allowed me to do so consistently is the concept of the “streak”. The goal is to build an unbroken chain of days that you’ve done your habit (publishing a post in this case) without fail. The longer the chain, the stronger the motivation to avoiding skipping and ruining your streak.

And it really works. Once I have a streak that is weeks or months long, it becomes an incredibly powerful motivator and I’ll do almost anything to avoid breaking the streak.

However, that same approach is also usually the cause of my downfall. On days when I want or need to take a break for some reason, there isn’t any slack in the system to allow that. So I push myself harder and harder to perform. Ultimately, it’s not sustainable and I always break the streak at some point.

What’s interesting to me is what happens next.

The logical thing would be to start a new streak the next day, right? But now I’m burned out, and the thing that was motivating me to continue most days is gone. If previously my streak was at 150 days, and I didn’t want to have to reset the clock, pushing myself to get something out today was worth it. But once I do reset the clock and start at 0, there’s no streak to keep me motivated. So I tend to have long gaps between streaks.

Honestly, I haven’t yet found a good way to combine the motivating and demotivating aspects of the streak. I suspect there’s a mental model shift in there somewhere. The problem with the streak is that it’s so black and white. Either you’ve kept it perfectly, or you’ve blown the streak and now you need to start at zero.

One approach might be to keep track of the number of perfect weeks. Almost like mini-streaks with limited duration. So for this newsletter, I’ve had three perfect weeks, but I missed yesterday, so this week won’t be perfect. But no worries, I can still have a perfect week next week (I’m taking Memorial Day off, btw).

Another approach would be to set a percentage-based goal that doesn’t require perfection. So rather than having a goal of publishing every day, your goal is to publish on 95% of days. Mentally, that works out to me as something like “Do it every day, but if you miss a day every month or so, it’s not the end of the world”.

If you’ve had any luck working with habit streaks over long periods of time without losing your mind, I’d love to hear from you!

Much love,
Ryan

The two news articles below were both written by a machine learning algorithm called GPT-2, released last year by OpenAI. What I’m doing here by generating these news articles isn’t remotely original, lots of people have done far more interesting versions, but GPT-2 just hit my radar a couple days ago because of this HN comment. I highly recommend you check out the /r/SubSimulatorGPT2 subreddit, in which all the posts and comments are bots running the GPT-2 algorithms and trained on different subreddits. It’s disturbingly close to reality.

For the articles below, I simply grabbed the text in bold from two random NYTimes articles and plugged them into this tool. From there, all I did was repeatedly request the next phrase and pick the one that sounded most interesting. Once I had enough length, I cleaned up the formatting a tiny bit (just removing some extra spaces and adding paragraph breaks), but the text below (other than the text in bold) is all AI-generated. More thoughts below after the articles:

Trump Does Bad Things: A Fake News Story

Bold text is the input I provided the algorithm, taken from here.

President Trump has embarked on an aggressive new drive to rewrite the narrative of the Russia investigation by making dark and unsubstantiated accusations that former President Barack Obama masterminded a sinister plot to bring him down.

Now the White House is considering a second round of investigations into Clinton, the Democratic presidential nominee and the Democratic National Committee.

"I think it's time we have a very vigorous investigation of Clinton. You know what? It was such an important year for Hillary Clinton. And, you know what? They're not going to find anything," Trump said during an interview with conservative radio host Laura Ingraham on Wednesday. "They're not going to find anything because they don't even want to look." Trump added that his former rival "couldn't win." He added that he thought the FBI should have pursued criminal charges against Clinton.

Trump's latest attack on Clinton and the Democrats comes as the president is facing mounting criticism over his comments, which some see as a thinly veiled warning about potential impeachment proceedings. The president's advisers have been debating whether to move the FBI investigation forward to determine whether there is any evidence of obstruction of justice. That has raised fears that Trump could be moving the nation into a dangerous constitutional crisis that could take months or even years to resolve. As Trump looks for ways to keep his supporters in the Trump coalition, he is likely to have to keep them up at night if they think the president is plotting against them.

On Tuesday, the Washington Post reported that the Trump campaign was told by a federal law enforcement official last month that an attorney for the Russian government had offered to provide the campaign with information that could be used against Clinton should she win the election.

According to the Post, the lawyer was described as a "source with direct knowledge of the situation." The newspaper reported that the official, who spoke on the condition of anonymity because of the sensitive nature of the relationship, said the offer occurred as Trump was leaving for his first foreign trip as president and that the campaign had not yet accepted the offer.

Trump has repeatedly denied that he has any financial ties to Russia or that Russia has tried to help his candidacy.

Virus Hurts Retailers: A Fake News Article

Bold text is the input I provided the algorithm, taken from here.

Even as stores reopen, some are not expected to survive the pandemic. The shutdowns across the United States devastated retailers in April, as retail sales plunged a record 16.4 percent, according to government data reported Friday.

While the number of stores that will remain closed this weekend is not known, the retailers who will be open have not yet announced what they will be operating.

Retailers have been scrambling to reopen their doors as quickly as possible after the outbreak hit. In the United States, which has had one of the worst cases of the disease, the National Retail Federation reports that nearly half of its retailers reported having closed stores during the most recent quarter, and another 30 percent have reported that sales have been hurt by the shutdown.

"There is a huge need to get the stores back open as soon as possible," said Bob D'Amico, executive vice president of retail for the NRF, who noted that there are about 7,000 retail stores in the United States. "We're very concerned about a number of retailers who are really struggling and have not been able to reopen," he said.

Some retailers are also warning customers to be extra cautious about shopping on the day after the outbreak. "I want to make sure you have all your essentials," said David Hickey, CEO of the Greater Boston Retail Association, which represents about 3,000 stores in the region. "You should do it in a place where it's safe, or at least not in a place where you're going to risk getting sick."

According to the CDC, the virus can be transmitted through contact with bodily fluids of someone infected with the virus or by sharing food and drinks. The CDC also advises people to avoid contact with sick or dead people or animals.

OK, Ryan here again. A few thoughts:

1. This is better writing than 99% of what I see on the Internet.

2. It’s still not that good, and if you read it with even half of your attention, it’s pretty obviously nonsense. But again, that’s true for almost everything online.

3. I put my thumb on the scale by providing inputs that I suspected would play well with this algorithm (though these two are the only ones I tried; you’re not just seeing the best examples produced), as well as picking the suggested word or phrase out of 3 that fit best into a cohesive narrative. However, the other suggestions provided were typically just as good. You should try the tool yourself.

4. This is a generalized machine learning model that has been trained a huge corpus of general text. If you train it with more narrow data sets, you can get really fun and interesting results, like some of these.

5. There are so many potential uses for this technology, some nefarious, some fun, and even some admirable. I wrote down a couple dozen this morning that I want to explore.

6. I think the fears about misuse of these kinds of technologies are overblown. People worry about a world where nefarious actors are using such tools to create massive amounts of nonsense and disinformation. To which I respond: “Have you even been on the Internet in the last decade?” We definitely don’t need robots to create huge quantities of nonsense and disinformation; we’re doing a great job of that on our own. Plus, maybe the arms race to combat AI-generated content will work out in our favor.

Anyway, I just thought this was interesting and worthy of sharing!

Much love,
Ryan

Well, this is my space, so I’m going to tell a little about my experience during this time. This is probably boring to everyone but me, but I think it’s cathartic to talk about this time, and useful to record the experience of going through what is easily the most pivotal moment of history that has happened in my lifetime.

At the outset, let me say that I have it much, much better than many. No one I know has died, and few have gotten seriously ill. Work is going OK so far, and we’re doing fine financially. We have a comfortable home to be quarantined in.

But the pandemic still sucks for us, just like everyone. Is anyone having a really good time right now?

For context, I’m 37 years old and I live in Manhattan with my wife and 5 year-old daughter. I’ve been a freelance software engineer and entrepreneur for many years, but I’m in a new phase of my career in 2020 that I’m not quite ready to talk about publicly yet.

The beginning for me

The coronavirus first hit my radar in late January, when Chinese authorities shut down Wuhan and Trump shut down travel from China. I stumbled on a tiny subreddit called /r/china_flu, and watched over the next two weeks with growing alarm. I brought it up to a few people, but no one was concerned. It struck me as obvious that if China thought it was worth such draconian measures, it was probably too late to contain this and it was only a matter of time before it went global. So in early February I started buying non-perishable food, cleaning supplies, protective equipment, and other things I thought we might need if the worst should happen.

I also did something I’ve never done in twenty years of investing: I moved my retirement fund almost entirely out of equities and into cash. I reasoned that if I was wrong and lost out on a month or two of growth, I could live with that, and it was worth it to avoid my retirement getting cut in half or worse.

I got very lucky there, and sold at the top of the market. Another piece of luck: I sold three small investment properties about six months ago that I’m really glad to not be dealing with during this time. I also got lucky again by buying some deeply OTM put options which seemed very underpriced in mid-February, and which subsequently went up in value by more than 100x when the market crashed. Sadly, my luck ran out and I failed to sell before the market recovered, losing six figures of potential gain. That one still hurts.

For the second half of February and the first week or two of March, I was just waiting for what I felt was inevitable. Almost no one around me thought this was a big deal, but writers and podcasters whom I respect were starting to take notice and sound the alarm. Then in early March companies started sending people to WFH and schools started closing.

The last day my daughter’s preschool was open was March 13th, but we had kept her home for a couple days prior to that. There was virtually no testing happening, so it was impossible to know where the virus was already spreading, and it was fairly obvious that schools were about to be cancelled, so a couple extra days at home didn’t seem like a big risk.

So the three of us have been at home for two months now. We don’t go anywhere except for the park next to our house. I haven’t been inside another building since this started, we get all groceries and other purchases delivered.

The daily pain

In addition to the stress and uncertainty of watching the whole world melt down around us with no end in sight, there are two specific things that are the root cause of 90% of my negative experiences during this time:

First, trying to “homeschool” a 5 year-old and get work done at the same time is a disaster, particularly if your work requires long periods of concentration. If there’s one thing I’m hoping will come back soon, it’s some form of school or childcare. I constantly feel like I’m failing at work, parenting, or both. This heavily contributes to a sense of being busier and more stressed out than ever, even while so many parts of my life have disappeared (like virtually all social activities, for example).

Second, I miss the gym! For the first time in my adult life, I had found a gym routine that worked for me in a sustainable way, and I was approaching a year of going religiously 4-5 times per week. I try to workout at home or go for runs, but it’s much more difficult and less enjoyable. Which is probably why I’ve gained some weight (well, that and the stress eating and increased alcohol intake).

The long-term pain

In addition to the above, there are some deeper stresses that aren’t necessarily a cause of daily friction, but are slowly grinding me down.

Friends

First, I’m a little introverted, but still I miss seeing friends. Just the normal rhythms of meeting people for lunches, drinks, dinner, playdates in the park, etc. Many of our friends have fled NYC to other parts of the country. Sadly, some of them will not return.

Marriage

Second, this hasn’t been amazing for my relationship with my wife. We’re doing OK, but after sixteen years of marriage and a rocky 2019, we were just getting into a good groove again. I miss going out to dinner with my wife, or our neighborhood cocktail bar. I miss going to Broadway shows with her.

My city

Speaking of Broadway, I’m terrified for NYC. I love this city, and the pandemic has hollowed out so much of what makes it such a vibrant place. I worry for the restaurants and shops in my neighborhood. I worry about Broadway and all the other cultural institutions here. I don’t understand how the subway will survive. I don’t understand how NYC and New York are going to stay afloat financially. I’m committed to this city, but I’m scared for her.

Travel

I love to travel, especially internationally travel, and I don’t know that I’ll be able to do it at all for the next couple years. I can’t see getting on an airplane or cruise ship until there’s a vaccine. I feel like my world has gotten much smaller.

Monotony

The most salient part of the pandemic for me is the monotony. March felt very chaotic, but for the last six weeks or so, I’ve gotten into a better daily routine. This helps in terms of energy, productivity, and not feeling like my world is spinning out of control, but it also means that the days and weeks pass in a jumbled blur.

Trump

Finally, there’s the psychological violence of watching your “leader” callously disregard the well-being of hundreds of millions of people and refuse to do the job that only he can do. And then worse, watching the members of his cult agree with him and revel in the nihilistic destruction of all we hold dear. It’s truly traumatic and makes me wonder if I simply don’t belong in this country. I may write more about this later, but I suspect this alone undergirds a large portion of the psychological and emotional difficulty of this time.

Some bright spots

I do want to highlight a few good things that I’m experiencing during this time.

Creativity

I’ve found myself coming up with a lot more ideas of things to make during this time. This newsletter is the most obvious example, but there are others. I’m finding myself having to be fairly judicious about which ideas I pursue because I have so many. I assume this is my brain’s coping strategy on some level.

No more autopilot

Something about this period has caused me to really rethink large chunks of my life and decisions I’ve made or values I’ve taken for granted. It’s making me reevaluate what’s important to me and how I want to spend my time. I thought about those things before, but doing so now feels more raw and open, more honest.

Meditation

I restarted my meditation practice a few weeks ago, using the Waking Up app by Sam Harris. It’s not magic, but I do find myself a little more calm and less reactive.

The park

The best part of my day is the time I spend outside. We’re fortunate to live across the street from Riverside park, and I typically spend almost two hours in the park, both alone and with my wife and daughter. Regardless of what happens next, I plan to keep up with my new practice of morning runs and walks in the park.

My prediction

I remain very pessimistic about both the pandemic and the economic fallout. My prediction is that the global economy won’t fully recover from this for 5-10 years.

I don’t think we’ll get the actual virus under control globally until we have a widely-available vaccine, which probably won’t be until 2022 at the earliest. The world’s economies will only barely limp along until then, while unemployment and desperation grows.

We’ll open things up partially, but people’s fear of the virus will mean that many industries will only see a fraction of the demand they did before, resulting in layoffs, bankruptcies, and damage to related or supporting industries.

Even once we have a vaccine and the economy can start to truly recover, that will take time. It took about four years to recover after the Great Recession. The recovery after the great depression took much longer.

So globally I think we’re in for a lot of economic and political turmoil, maybe even civil unrest. I don’t see any clear path out of this predicament currently, other than just going through it as best we can.

I hope I’m wrong.

What I’m looking forward to

Obviously, the most important thing to look forward to is the development of medical interventions, including a vaccine at some point. But those things are uncertain and out of my control, so I’ve been trying to come up with things to look forward to that I have reason to think might happen, or can influence.

Work projects

In addition to this bizarre little newsletter, I’m working on a couple other work projects that I’m excited about. Nothing I’m ready to talk about yet, but it’s been nice to have a little time and space to step back and think about my work and where I want it to go over the next few years.

Regional travel

Partly to flee the city in case we need to, we bought a car in March and I’m looking forward to use it to explore New York state this summer, from the beaches to the mountains and everything in between.

Workouts in the park

The gym I go to originally started as a group of people doing workouts in the park, and I think we’ll be returning to that model this summer when NYC starts to reopen and the weather gets a little nicer.

Childcare

I’m still hoping against hope that my daughter can start kindergarten in the fall. If not, and if the risk of doing so is acceptably low, we’ll likely try and hire someone to watch her part of the time. I have no idea how that will work logistically, but we’ll have to figure out something for this to be sustainable. We may even do that this summer if we can.

That’s it!

If you read all this, I applaud you. I told you this post would be mainly of interest to me, but I still felt it was important to talk through all this. I’d like to hear more accounts of others and how they’re dealing with this time too, so please share!

Much love,
Ryan

Love words, agonize over sentences. And pay attention to the world.
- Susan Sontag

Writing and publishing something every day is hard, even if you have some tricks up your sleeves. But that’s OK, because “easy” is not the point.

My goals with daily publishing: get better at paying attention to the world, noticing interesting things, capturing them in written form, and polishing what I’ve written so it’s more enjoyable to read.

That’s it. And some things that would make it easier would also interfere with those goals.

For example, one thing I’ve avoided so far is building up a backlog. Yes, it’d be nice to have a dozen pieces in the hopper, but I fear it might interfere with the daily practice of listening, of waiting, of “paying attention to the world”.

One of my tricks is jot down ideas of things to write about whenever they come to me. I’ve captured 70+ ideas in the last month, but curiously, I rarely go back and find something interesting and then write about it. The act of recording the note seems to be more helpful than referencing it later.

Probably, the act of jotting down an idea lodges it in my subconscious somehow, so that later if it resurfaces it’s easier to write about.

But that’s a boring way to think about it, so I prefer to imagine that me jotting down ideas is a way of giving them to my muse as an offering. And maybe if I’m lucky she’ll give them back to me later, in a better form, when the time is right.

This idea of a muse intrigues me. It conjures a sense that the creativity is not really coming from you, but rather you’re just letting it flow through you.

On the amazing podcast You Made It Weird with Pete Holmes, Zach Braff talks about having Bon Iver write a song for his film Wish I Was Here:

My music supervisor went up to Wisconsin where he works out of a farm. She showed him the movie, and he just stood up and went in his studio and wrote the song…the song was beautiful but it wasn’t exactly what I pictured for the moment…so I had the balls to reach out and say “Oh my god, thank you so much, this is an outstanding piece of music, but it doesn’t exactly fit where I was going to put it, is there any chance you’d do X, Y, and Z to it?” which I’m embarrassed to say I said, but I did say it.

And he just wrote back and said “Zach, I just have admit, that’s what came out of me.”

I love that idea, but sometimes it doesn’t feel like anything is going to come, or that I won’t like what does come.

However, with the muse model, I stress about it less. My goal shifts from “write something amazing”, which feels like a standard I will often fail to measure up to, and instead becomes “show up and record what you’re given”, which feels much more approachable. All I need to do is create some space and then show up and listen.

For example, the routine I’ve fallen into is to get up very early (4:30am), have coffee, do my morning pages (which I’ve been doing most days for 15+ years), meditate, and then go for a long walk in the park nearby. If I have something that’s really foremost in my mind, I’ll ruminate about that and usually end up writing about it later. If not, I try not to force it. I trust that something will be given to me.

This morning I left my apartment at 5:45am with nothing in mind to write about later. I scanned my list of ideas. A couple seemed mildly interesting, but nothing jumped out at me. I kept walking and thinking. I took this picture of a raccoon:

I kept trying to think of something to write about, but nothing was really jumping out at me, so I let go and just ambled. I let my mind wander for the next half hour. Eventually this post came to me, so I recorded a short voice memo with the elements, then kept walking. Then two more ideas came to me, which I dutifully jotted down. Maybe I’ll write about them next, or maybe the muse will give me something else. We’ll have to see.

But what if what comes isn’t good, or people don’t like it?

Ultimately if you view creativity as something that flows through you, then maybe don’t worry too much about it. Sure, you edit and polish, but you didn’t really create this thing, you were just given it, and then you conveyed it to the best of your abilities. Sometimes it’ll be good, sometimes it’ll suck. And trust that if you keep doing your best to convey what the muse tells you, she’ll tell you better and better things.

If you’re a writer or artist or otherwise creative, I’d love to hear about your process and how you think about your relationship with creativity!

Much love,
Ryan

PS - if you’re a Scrubs fan, I highly recommend the new podcast “Fake Doctors, Real Friends” where Scrubs co-stars and real-life best friends Zach Braff and Donald Faison watch the old episodes of Scrubs from 20 years ago and reminisce about what the experience of making it was like. It’s light and heartwarming, which I often need right now.

A man is rich in proportion to the number of things which he can afford to let alone.
- Henry David Thoreau

We’ve all experienced “inbox overload”, and there are a huge number of articles and strategies out there to deal with it, from inbox zero to elaborate filtering strategies to better tools to process email more quickly.

One solution to “inbox overload” that you don’t hear mentioned often is just deleting your email account. Not replacing it with a new one, but just…not using email anymore.

I know, it sounds crazy, especially if you’re an Important Person Who Needs To Get Things Done. It’s 2020, and email is as essential as electricity itself. Right?

Donald Knuth is a professor emeritus of computer science at Stanford, where he has been a member of the faculty for more than five decades. I’d like to draw your attention to this post on his Stanford faculty website, where he explains his relationship with email:

I have been a happy man ever since January 1, 1990, when I no longer had an email address. I'd used email since about 1975, and it seems to me that 15 years of email is plenty for one lifetime.

Email is a wonderful thing for people whose role in life is to be on top of things. But not for me; my role is to be on the bottom of things. What I do takes long hours of studying and uninterruptible concentration. I try to learn certain areas of computer science exhaustively; then I try to digest that knowledge into a form that is accessible to people who don't have time for such study.

On the other hand, I need to communicate with thousands of people all over the world as I write my books. I also want to be responsive to the people who read those books and have questions or comments. My goal is to do this communication efficiently, in batch mode --- like, one day every six months. So if you want to write to me about any topic, please use good ol' snail mail and send a letter to the following address:

The entire post is worth reading, but I’d like to focus on this question: if Donald Knuth is not filling his days with email like the rest of us, what has he been doing with all that free time?

A partial answer: he’s writing The Art of Computer Programming (TAOCP), a multi-volume work describing a variety of computer algorithms and their analysis. Knuth started it in 1962 (almost six decades ago!), and it still is not complete. It’s the work of a lifetime, and has been called one of the most important works of science of the twentieth century.

Now, I’m not anti-email, obviously. I’m writing these very words in preparation to send them out as an email newsletter.

And I don’t think that email is keeping most people from creating anything as valuable or enduring as TAOCP. I could have 1000 years of available time and I wouldn’t create anything so valuable.

What’s interesting is not the decision to give up email, but the ability to give up email. It’s a sign of having the freedom to focus deeply on something because it’s important or interesting, not because it’s immediately valuable to someone who is paying you for it. Those people tend to want you to check your email so they can keep tabs on you. The few people who can “go full Knuth” and give up email tend to be either wealthy, or so exceedingly talented that wealthy institutions or individuals become their patrons.

Everyone else has to try and carve out a little time and space to do their work while also paying for their bills.

And that’s really difficult for many types of work, which means we’re probably missing out on many Donald Knuth’s the world over. We’re missing people who have the capacity to create great works of art, science, philosophy, and more, who lack the free time and social support to think and create for the sake of doing so.

Now, going back to my post yesterday, why don’t we stop trying to identify the 1 in a million geniuses so we can give them time and space to do their work, and instead figure out a way to let everyone have that time and space, and see what happens?

There is virtually nothing about our lives today that wouldn’t have been absolutely crazy and impossible a few hundred years ago. So rather than constantly talking about how it’s impossible, let’s figure out a path towards a world where everyone is born with a birthright always having all of their basic needs taken care of.

What if we enabled everyone to devote their lives to whatever pursuits suited their fancy? How many more Donald Knuth’s would we get in return?

Much love,
Ryan

PS - mildly interesting: there’s a timestamp in the source code of the Knuth email page linked above that states it was last updated on more than two decades ago:

Changed by: Ursula N. Owen, 8-Mar-1999

I was curious about this “Ursula N. Owen”, thinking perhaps she was an assistant of Knuth’s back in the 90s. It turns out that it’s a pseudonym sometimes used by Knuth himself, and is a reference to “U.N. Owen”, a character from And Then There Were None, a best-selling Agatha Christie novel first published in 1939 and one of the best-selling books of all time. The name “UN Owen” itself is a play on “unknown”, and I like to think of Donald chuckling to himself whenever he used that pseudonym.

I told you, mildly interesting.

I know, I know, they’re animals. Of course they don’t have a bunch of leisure time, let alone some higher sense of meaning in their lives.

But are most of us so different?

We’re also reading Farmer Boy, the story of a boy who grew up on a farm in the 1860s. Again, it’s notable in the book just how much time and effort is expended every day just to stay alive. But at this point in our species development, there is a bit more time and space for leisure, education, and entertainment. Not a lot, but some.

Today, we’re doing a little better in terms of how much of our time we spend on “survival”, but I still think it’s shocking that so many of us are not that different from an animal who needs to constantly be striving for survival or they’ll starve or be eaten by a predator.

One of the most pernicious things about capitalism is that it leverages this sense of individual desperation. I read a story about how some politicians are advocating for ending the increased unemployment benefits as a way to force people back to work. Those workers don’t feel safe going back, but we need them to go back to work in order to get the economy running again. And they’re desperate, so if we take away their unemployment benefits, they’ll have no choice.

Why do we just accept this? Why can’t we have a post-scarcity economy? Why must the default be homelessness, starvation, and death?

I’m sure you’ve seen Maslow’s hierarchy of needs before:

For many people, making it halfway up this pyramid is the most they can hope for. When you’re fighting hard every day just to meet your most basic needs, the idea of ever reaching “self-actualization” is laughable.

Does it have to be this way? Why can’t we engineer a society that ensures that everyone starts partway up this pyramid, and doesn’t have to fear falling down it?

It’s true that if we look at nature, this is the way things work for all animals. So in that sense, it’s part of the natural order.

But many things are part of the natural order that we don’t accept. As a species, we’ve managed to develop written language, life-saving medical interventions, and incredible technological advances. The concepts of higher education, representative democracy, and the modern legal system are not found in nature. We invented those to rise above our nature.

And yet in 2020 we still have a system where each individual must either work or starve. In spite of our progress, most of us still must spend our lives as grist for the mill of human progress. Why? Is there really no better way? Is that too powerful a force of nature that we cannot surpass it as we have others?

To be clear, I’m not arguing that we should give up capitalism tomorrow, because I have yet to see a system that works better. I’m skeptical that basic income will get us there, but exploring it is a step in the right direction.

But regardless of how or when we get there, I don’t think we should be super proud of the fact that we’ve built an entire civilization on the back of individual desperation. We should probably be slightly ashamed of it, and be working hard to find a solution, rather than just accepting it as the natural order.

Much love,
Ryan

Last weekend, my wife and daughter and I all went to the park here in NYC. It was a beautiful day, clear, sunny, and breezy.

I was sitting on a grassy hill under a tree looking at a brilliant blue sky and green life everywhere and the Hudson River, and I found myself thinking this:

“Wow, this is such a nice day. I love this view and sitting here among the trees. I really want to enjoy this kind of thing more. Hmm, I wonder if I can find some forested land outside of the city so I could enjoy this all the time…”

And then I took out my phone and launched Zillow.

Maybe because I’ve been meditating more recently, some part of my brain interjected at this point to point out the obvious:

“Hey dummy! If you want to spend more time enjoying being outside in the grass and trees on a gorgeous day, you can do that right now. Put your phone away!”

I’ve realized that I do this constantly, almost reflexively. I’m always thinking about how I wish something was different, how I’d like to do X in the future, what would make this experience better, or even how I can avoid something bad happening later.

In Michael Gungor’s book THIS, he talks about the buddhist concept of suffering being related to desire, and to our belief that if only <blank>, we’d be happy.

This is never enough. If only we had that, then we’d be happy.

Not only does reaching those goals never satisfy us like we expect, it robs us of our enjoyment of so much of the journey along the way. And for what?

Gungor says it well:

How is it possible for a being who lives on a sparkling blue planet with penguins and palm trees and trampolines to be anything but constantly overwhelmed with gratitude, love, and laughter? Why do we let so much life pass us by because we are coasting through its miracles on autopilot looking for something other than what is right in front of us? And what is it we are looking for exactly? Something more interesting or wondrous than THIS? What could that possibly be? What do we think we would actually be satisfied with? Trees with blue leaves rather than green? Money? For what? Fame? For who? Power? To do what exactly? Power to breathe more air? Hear something other than sound?

So I put my phone away. I stopped thinking about the future I wanted, and stepped back into the present moment I had already been given.

And then I spent 15 minutes taking this photo of a bee:

No matter what’s going on in your life, I hope you find some time this weekend to let go of the regrets of the past and the anxieties of the future, and just enjoy the moment for the gift that it is.

Much love,
Ryan

PS - if you have any interest in the email newsletter space and you’d like some interesting things to read on the topic this weekend, the first edition of newsletter² is launching later today!

1. You need ~1000 true fans who will eagerly buy anything you produce.

2. You need to be able to earn ~$100 per year in profit from each true fan.

3. You need a direct relationship with your fans so you can keep 100% of the profit.

Sounds great, and much easier than “millions”, but finding 1000 true fans is still daunting. It’s hard to get people to type in their credit card number to buy something from a nobody online, and subscriptions are even harder. It takes some creators years to gather that many paying fans, and many more never get there at all.

It can be tempting to think about trying to find a way to make things that could get you there faster. After all, if there’s a big hungry audience, or you know that people are willing to pay a lot for a certain type of thing, why not create that and cut your risk?

It’s not that this kind of market-driven approach can’t work, but I think it’s usually the wrong question to ask, especially for creative things where you are trying to find fans who would eagerly fork over their money for anything you make.

Instead of trying to find something that you imagine would appeal to 1000 true fans, consider what would appeal to just one: you.

What would you eagerly pay for? What would you share with others?

It helps to start by separating out the question of whether you feel qualified or interested in actually producing that creative work. Just think about what you’d like to consume so badly that you’d be happy to pay for it.

Most of my successes have been things I would have paid for myself, and most of my failures have been things where I was chasing money. That’s not to say that anytime I’ve created something for myself it was successful. But it seems to make it more likely.

You might think that your interests or tastes are so esoteric that you could never find 1000 true fans out there, but you’re probably wrong. The internet is a big place, and you probably aren’t as unique as you think. Sorry.

There are several benefits to starting as your own first true fan:

It’s easier to stand out — yes, I mentioned above that you’re not as unique as you think, but your interest in “growing exotic culinary mushrooms” is a lot more unique than something like “travel” or “the latest fashion trends”. And even if your thing is travel, there’s probably specific aspects, areas, styles, trends, etc. within that segment that really interest you enough that you’d pay for anything related to them. Focus there.

It’s more sustainable — it’s really hard to create something good, especially if that thing is an ongoing creation like a podcast, newsletter, vlog, etc. If you pick something you’re super interested in, you won’t have to slog your way through it.

It’s more authentic — your audience isn’t stupid, and they know what true fandom looks like. It’ll be obvious if you’re creating stuff you don’t care about just to make a few bucks. But if you pick something you love and let your passion shine through, people will respond to that. Even people who didn’t previously have an interest in your thing may respond and get into it.

It’s more enjoyable, even if you fail — when you create something you love yourself, it’s more enjoyable, and it feels like less of a waste if it ultimately fails to get traction like you hoped. At least you had fun creating it along the way!

What would you eagerly pay for?

Much love,
Ryan

PS - if this topic interests you, you should definitely join newsletter². There are many ways to connect with your fans and have them support your work, but if the things you create can be delivered via email, I think it’s hard to beat the medium as a way to satisfy those criteria. Email is old and boring, but it’s also simple, reliable, and decentralized. Even if you gather and connect to your fans through other channels like social media, podcasting, vlogging, ecommerce stores, whatever, it’s still a good idea to make it a priority to connect via email as well, since that’s a channel you own completely.

In UX design terms, a dark pattern is a design choice that intentionally tries to mislead, deceive, trick, or annoy users into taking (or not taking) actions they wish to take (or not take).

For example, the New York Times is a great institution that I admire. I think they’re doing a lot of good in the world, which is why I subscribed in November 2016 (I shall leave it as an exercise to the reader as to why I was thusly motivated).

It’s easy to subscribe, but to cancel, you have to either jump into a painful live chat, or call them. On the phone. During certain hours only. In 2020.

(Note: I believe the chat option is relatively new. When I looked at this awhile back, a phone call was the only option as I recall.)

This is known as a “roach motel”, which means it’s easy to get into but difficult to get out of.

There is just no excuse for this kind of customer-hostility. Or bullshit like this, from some random online marketing blog:

Amusingly, that last example is both customer-hostile and broken. Neither button works.

There are so many of these on the web in 2020 that large swaths of it are becoming unusable. Here’s a Forbes link I clicked on while writing this post:

The actual “content” is a shitty slideshow with 1-sentence captions. You have to scroll down past the giant ad to even click the next and previous buttons on the slideshow. And every click reloads the page (to boost ad impressions) and scrolls you back up to the top to see the ad again. Yes, I have an adblocker but the page won’t even display if you have it enabled.

Everyone involved in creating this masterpiece of customer-hostility should be ashamed. You are making the world a darker place.

And this isn’t even the worst of it! I wasn’t assaulted with a half dozen popups asking me for my email address, for consent to be tracked, for browser notifications, etc.

For example:

Or this travesty:

I found all these examples in about 5 minutes. Now I need a drink, and it’s only 7:40am.

Dark patterns are a downward spiral

Stepping back from the horror show of modern web design, I would classify dark patterns more broadly as any action taken that is hostile to customers for the sake of financial gain.

The best companies focus on creating as much value as possible for customers, and capturing a relatively small slice of that value.

But companies that are dark-pattern-oriented flip that equation around and focus on capturing as much value as possible, regardless of how much value they create. Many bad companies capture far more value than they create, leaving the customer with a net loss of value.

The worst examples create negative value for their customers and the world at large. We’re all worse off because of their existence, and yet they still manage to extract money from us, usually due to some form of lobbying, regulatory capture, or other rent-seeking.

For example, a military industrial complex that spends trillions of dollars to first blow up and then rebuild infrastructure on the other side of the planet. Or giant unrealistic space exploration programs that are actually jobs programs in disguise and never actually launch anything. Or private prisons that lobby against criminal justice reform while steadily destroying the lives of hundreds of thousands of people.

Those are the examples that come to mind for me. Yours may be different, depending on your definition of “value”.

It’s a scarcity model that views all interactions as zero sum: for the company to win, customers need to lose.

Aside from the ethical question of whether you should rampage through the world capturing value for yourself at everyone else’s expense, the problem with dark patterns is that their effectiveness tends to drop over time. Indeed, one heuristic for whether something is a dark pattern is whether it becomes more or less effective over time. Another might be if it becomes more or less effective once customers are made aware of it.

As customers get more savvy and informed, they start to see these patterns for what they are, and avoid them. Trust and goodwill are eroded. And thus the dark-pattern-oriented business needs to put in place a new set of dark patterns to keep extracting the same amount of value. This pattern tends to be self-reinforcing, as the organization’s focus increasingly shifts to a cat-and-mouse game against their customers.

Enter…light patterns!

In contrast to the idea of dark patterns, I’ve been thinking about the concept of “light patterns”, or actions taken that are customer-friendly at an immediate cost to the business.

Two recent examples:

Free Memberships for the Making Sense Podcast

The Making Sense Podcast with Sam Harris is now listener-supported, and you can’t listen to all the episodes in their entirety unless you subscribe.

(By the way, I love this growing trend of content creators being compensated directly by their fans via subscriptions and memberships. See the PS block below for more.)

Sam opens every podcast episode with an announcement that you’ll need to subscribe to hear the entire episode, but then he says this:

I never want money to be the reason why someone can’t listen to the podcast, so if you can’t afford a subscription, there’s an option at SamHarris.org to request a free account, and we grant 100% of those requests, no questions asked.

This isn’t a theoretical benefit that’s actually impossible to find on the website either:

And its not onerous or invasive to actually submit the request:

Now, to be fair, I don’t know how well this is working for Sam. Maybe this guy is right and he’s not making much money from this overall strategy. But I believe he has taken a similar approach with the Waking Up meditation app, and as I recall that has a growing staff behind it. This site estimates revenue of $800k per month for the Waking Up app, which doesn’t seem that outlandish to me, given the amount meditation apps are making. Apparently giving away a few free memberships doesn’t mean you can’t build a meaningful business.

Easier ClassPass Cancellations

I recently saw a story about how ClassPass and other subscription services are making it easier to cancel. It used to be that you had to cancel with a human operator via live chat. I went through that flow myself last year, and it was super annoying. I had to just keep saying I want to cancel, over and over, while they threw various options and sweeteners and arguments at me to convince me to stay.

Now they’re doing away with that and letting members just cancel via automated methods:

“We know the ability to pause or make changes to a membership is something our members deeply value,” Ms. Cowher Hill said. “And this isn’t just true for ClassPass. Globally, there is a growing desire for a frictionless cancellation flow, especially for subscription services, and we’re proud to be making strides to deliver that.”

Reading between the lines of corporate bullshit speak here: the ability to easily pause or cancel a membership was always something that members deeply value, so why now?

Answer: because ClassPass was getting a reputation as a roach motel, and that was keeping members from signing up in the first place. Or if they went through the live chat cancellation option like I did, they might vow to never return and have to face that again.

But if ClassPass can change consumer perception to where they’re known as a service that makes it very easy to pause and cancel, customers will be less nervous to sign up and ClassPass will get more users over time.

(Side note: I suspect that’s also the reason you’re reading about this in the Wall Street Journal. ClassPass or someone else in the article probably pitched the story as part of a PR campaign to spread awareness of their new joyful experience of cancelling.)

I sound like I’m being critical of ClassPass, but I’m not. I wish they had done this from the start, but better late than never. Hopefully more companies choose light patterns over dark going forward.

With light patterns, everybody wins…eventually

Both of these policies positively affect everyone who is aware of them, not just those that take advantage of them. When I hear that Sam gives away free accounts to anyone who asks, I trust him more. The same is true for ClassPass making it easy to pause or cancel. I’m more likely to sign up in the first place because of that trust.

So while there might be a short-term cost (ClassPass having more cancellations and Sam giving away more free accounts), they create more overall value and more captured value for the business in the long run.

And unlike dark patterns, light patterns tend to become more effective over time and as consumers become aware of them, not less.

But since most of the benefit of light patterns comes in the form of increased trust, goodwill, and word of mouth marketing, the payoff can take time. This is perhaps one reason that light patterns are more rare than dark patterns. Making “costly” investments today in trust and goodwill that won’t pay off for a long time is not as tempting as something that will get immediate results.

Do you have any favorite examples of light patterns? I’d love to hear about them!

Much love,
Ryan

PS - as I mentioned above, I love the growing trend of people like Sam Harris asking their fans to directly support their work via subscriptions and memberships. One of my favorite examples of this is the explosion in paid email newsletters. It’s hard to get more simple and elegant than: “Pay me a few bucks every month, and I’ll send you valuable emails.” I like this model so much that I’m launching a paid email newsletter about paid email newsletters, called newsletter². It’s going to be free to start while I get my legs under me, and the first weekly edition will be out this coming Friday. If you have any interest in the space, I’d love your feedback!

Yesterday I wrote a little piece about a COVID-19 “research review” I read over the weekend and why I thought it wasn’t credible. It wasn’t my greatest piece of writing, but I was fairly pleased at the way it turned out, so I shared it on Hacker News.

Ten minutes later, it was rocketing up the homepage, gathering votes and comments quickly. The comments were fairly polarized, and enough people flagged it for the HN algorithm to kill the story and remove it. All in less than an hour.

Over the course of that hour, I got thousands of visits to the post. Here’s what my Substack dashboard looks like now:

(side note: all graphs should come with an option to exclude outliers)

Not my first experience hitting the HN homepage, but my first in many years. Just thought I’d share a few takeaways from this experience.

Headlines matter

I’ve been doing copywriting and email marketing for years, so I know this, but I also haven’t been in “marketer mode” with this newsletter, which I think is the right choice. My original headline yesterday was something like “Good vs. bad heuristics”.

Snooze.

On a whim, I changed it to the more eye-catching: No, I won’t read your COVID-19 “research paper”

Judging by the overall negative reaction to the post and how short-lived it was, I don’t think it would have gotten nearly as much play without the headline, and probably rightfully so.

People shouldn’t judge a book by the cover, but they do. I’ll put more time into headlines going forward.

Don’t sell what you can’t deliver

More importantly, I’m going to add some time in to put on my “editor hat” and review each day’s post with a critical eye. I don’t want readers who were hooked by the headline to feel let down by the post itself.

Some of the criticism of my post yesterday was fair, and in retrospect I wish I had taken a little more time to tighten up my arguments and think about common questions or objections from a reader. I don’t want to write too defensively, but I felt some commenters weren’t understanding my position because I hadn’t explained myself well enough in places.

Additionally, all that traffic did double my subscriber count…but that means we went from 3 to 6. About 0.1% of yesterday’s visitors subscribed, which is not ideal. Some of this is the nature of social media traffic spikes, which tend to be fleeting, but I suspect that some extra time spent on the post would have paid off in a bigger boost in subscribers.

I can do this

Overall, the experience yesterday was quite uplifting. I’ve had many posts hit the HN homepage, but not for almost a decade at this point. It’s encouraging to see that it’s still possible in 2020 for a nobody to write something that gets some attention. I’m optimistic that as my writing improves and my focus tightens, this newsletter will continue to grow.

Thanks for reading, have an awesome Tuesday!

Much love,
Ryan

PS - On Friday I’m launching newsletter² (pronounced “newsletter squared”), a new paid email newsletter about paid email newsletters. I’ve been making money from email for years now and I’m obsessed with this growing trend of independent writers launching paid newsletters. I’ll be sharing the most valuable articles, tools, and other resources that I’ve found for people who are interested in this space, and I’ve got a ton of ideas for where to go in the future (interviews, case studies, how to guides, etc). First edition goes out Friday, so you should sign up right now:

Visit newsletter²

EDIT: to be fair, the author did later go back and add a disclaimer that they lack any experience or credentials in any relevant fields.

It was only after exploring a bit that I realized that the author is a software engineer, not an economist, epidemiologist, etc.

(Side note: what is it about software engineers that we think we’re qualified to pontificate on anything remotely technical or complex?)

In the comments on Hacker News, the author took a lot of flak for having no experience or expertise in any relevant fields. His rejoinder was that calling him out for a lack of “credentials” was a form of ad hominem attack, and his work should be evaluated on its merits.

High-minded, but not really realistic. The idea that everything should be evaluated on its merits has a couple problems:

1. There isn’t enough time to evaluate everything on the merits. I’m sure there are millions of people out there with arguments and plans on how we should deal with COVID-19. We can’t take a close look at all of that chatter before deciding.

2. Most things can’t be evaluated on the merits by most people, because they lack the expertise to do so. In the case of this paper, the author linked to many research papers by experts, which is good, but then he wove an argument together out of all that research. And since I don’t have any expertise in any of those fields, I don’t know if he’s evaluating the data correctly, or if he’s ignoring other relevant data that doesn’t support his conclusion.

As a result, everyone relies on mental shortcuts or heuristics when evaluating ideas and arguments to decide how much credence to give them.

But some heuristics are better than others.

For example, when evaluating claims in a high-stakes, high-uncertainty, high-complexity area, like the public policy approach to COVID-19, a good heuristic might be “does this person have expertise or experience in a relevant field?”

A bad heuristic would be: “are the claims being made with very high confidence and in an authoritative style?”

Or the most common bad heuristic of all:

“Does this confirm my previously held beliefs?”

If I’m honest with myself, I have to acknowledge that I would have had much less of a problem with this paper if it agreed with what I already thought to be true. I likely would have just mentally filed it away as another piece of “evidence” supporting my position and moved on. In fact, I suspect that everyone who read that paper who was already persuaded to its conclusions did exactly that.

But that’s the problem: the paper might be built on good arguments, but it was presented in a format and context that encourages the use of bad heuristics. The tone was authoritative and confident, the author didn’t prominently disclose their lack of expertise, it’s fairly long and comprehensive, it’s well-organized, etc. The author even wrote the whole thing using “we” instead of “I”, which subtly gives the impression that a group of people collaborated to write this (which is probably a good heuristic for evaluation, if those people are experts).

At first glance, it looks like a comprehensive, evidence-driven report by a group of experts. As a result, the non-expert reader who can’t really evaluate the base claims is left with little in the way of good heuristics upon which to base their evaluation, which leads to them falling back on bad thinking.

This is exactly why the author wrote and presented the paper in such a format.

Doing so is a form of sophistry, where you care more about winning the argument than making your case in good faith. It’s pretty rich to be saying you want your claims evaluated on the merits while also going out of your way to encourage people to do the opposite.

If you are someone who has influence, who has an audience, who tries to persuade people that your ideas are true, you have a responsibility to not only make good arguments, but to provide them in a format and context that encourages the right kind of evaluation of those arguments.

And if you are reluctant to do so because it weakens your case, maybe you should rethink what you’re doing.

Much love,
Ryan

I started this newsletter a week ago as an experiment in creating a paid daily email publication. One of my principles that I try to live by is that doing the wrong thing is usually better than doing nothing at all, and the last week has been a perfect example of that. I’m pretty sure that I’ve already started off on the wrong track with this, but I also wouldn’t have realized it without just getting started.

What I thought this was

I had a few original goals with this newsletter:

1. Get back in the habit of writing and publishing daily, at least for awhile

2. Be able to write about whatever I want in the moment

3. Share some of my experience as a freelancer / entrepreneur / marketer

4. Build a paid email publication

It’s obvious in retrospect, but #2 and #4 are incompatible. As I said yesterday, once you take someone’s money, there’s an expectation that you’ll be delivering something of a certain quality on a certain timeline. That’s fine, but it does kind of put a crimp in my ability to feel free to write whatever I want.

So the plan that’s gradually emerging in my mind is to create two different newsletters, one free and one paid.

This newsletter will remain free

This email newsletter you’re reading now will remain free and published daily, and I’ll continuing exploring whatever ideas or topics I feel like writing about. If people don’t like it, that’s OK, because the goal is to cover the first two objectives above. It’s mainly for me.

In addition to having more freedom to write about what I want every day, there’s another benefit to keeping this publication free: every day’s writing has the potential to be shared more widely and bring in new readers. In my experience, it’s rare that a piece of writing catches fire, but when it does it can reach a huge number of people. It’s really hard to predict what’s going to snare people’s attention enough for them to share it widely, but putting your work behind a paywall guarantees it won’t go viral.

New paid publication

In addition to this free daily publication, I’ll be launching a new paid email publication that is specifically about freelancing. It’ll be released either biweekly or monthly, paid from day 1, long-form and actionable, and much more polished. In short, it’ll be the opposite of this.

I’m really excited about this plan. I’ve got a huge list of tens of thousands of freelancers to market this to already, and I’ve been wanting to write a book on freelancing for some time. With this approach, I’ll be researching and writing that book in serial fashion, with a topic being written and released periodically to a paying subscriber base. At some point, I’ll package those lessons up into a book, course(s), etc.

Next steps are to plan out the first year of topics, write editions #0 and #1 (edition #0 will be a free sample), pick a publication name, and do an early preview with a small group of readers. My current plan is to launch the first edition in early July, and I’ll continue to share the behind-the-scenes details here.

Much love,
Ryan

PS - a lot of my thinking on paid newsletters over the past few weeks has been influenced by conversations I’ve had at IndieMailer, things I’ve read in Not a Newsletter, and things linked to from this edition of trends.vc. I’m not sure if paid newsletters will continue rising in popularity, but as a writer the model is hard to beat if you can figure out how to make it work for you.

I talked yesterday about some of the tactics I’ve found helpful when going on a daily publishing spree. But I also said that in spite of those tools, it’s never really stuck for more than a few months.

Mostly, I think I’ve “failed” with daily publishing in the past because I was doing it for the wrong reason:

I was writing for my audience, not for me.

I know, that sounds like a good thing. And for many types of writing, it is!

But for the kind of daily publishing I’ve done in the past and am trying to return to, the biggest benefit I’ve gotten is how the act of writing and publishing daily affects me. It makes me a better writer, and ultimately, a better thinker.

But in order for that to be sustainable, I need to spend most of my attention and energy on what I want to write about, not what I think people want to read about. Because if I start thinking about that, the expectations go up. I feel like the writing needs to be sharper, more insightful, more interesting. My posts get longer and harder to write, or I worry that I’ve been writing about the same thing too long (or not long enough). Eventually it just becomes stressful and I stop.

It’s already happening with this list! I put that little disclaimer about navel-gazing at the top of this email out of self-doubt, because I’m thinking about my subscribers getting this email and thinking “🙄 he’s written another email about writing emails?”

And I have three subscribers.

Imagine my self-doubt when I have thousands! Or worse, when I have paying subscribers! I have to deliver good value for their money!

Obviously there’s nothing wrong with the mindset of wanting to deliver value to your audience, whether free or paid.

But needing to deliver value is fundamentally at odds with having an open space to play and explore with little expectation.

When someone subscribes to my newsletter, there’s a vague sense of a contract there. They’re signing up to get something, and I feel a responsibility to at least take that into consideration. If they actually pay me for that subscription, it’s even more true.

Related to the above, I started this “daily paid email publication” experiment with a few objectives , but I’m already rethinking the terms of the experiment. Not the “daily” part or the “email publication” part, but I’m now thinking that I have some competing objectives that would be better served with two different publications, one free and daily that I write mostly for myself, and one paid and delivered on a less frequent basis and with a much more clear benefit to the reader. I’ll probably explore this more tomorrow.

This kind of insight is exactly why I need to keep writing and publishing daily, even if I’m the only one getting value from it.

Much love,
Ryan

PS - Another reason my daily publishing has eventually failed is the same reason I initially succeeded: over-reliance on keeping an unbroken “streak” going. I’ll write about this soon.

One of the pieces of feedback I’ve gotten from the few people to whom I’ve mentioned this newsletter is that a daily posting schedule is “aggressive”. That’s a kinder way of saying “unsustainable”, or even “crazy”.

(Pedantic aside: when I say “daily”, I mean every weekday. Ain’t nobody got time for all my habits seven days a week.)

They’re not wrong. But I’ve gone through several periods of publishing daily in the past, and I’ve found a few tricks that help:

• Publish the right things. Most of what I’m writing doesn’t require a lot of prep time. I’m not doing interviews or heavy research, it’s mostly just sharing things I’ve learned or found useful.

• Record your post ideas. I use Evernote and each post idea gets its own note where I jot down everything I can think of that will help me write the post later. I’ve added 40 notes in the last 19 days.

• One idea per post. I’m still working on this one. Most things I write about could be an entire book on their own. It can be tough to find reasonable boundaries of a singular idea to make it both short and complete, but that’s the goal.

• Write early. I write early in the morning, when I’m freshest. It’s an amazing feeling to publish something awesome by 9a. I feel like I could do literally nothing else and that day was still productive.

• Reduce friction. I’m writing these posts directly into Substack. No copy-pasting, no formatting issues, no keeping track of what has been published and what hasn’t. Just write, edit, and hit publish. This also means that when I open the “New Post” editor here, my brain immediately jumps into “write and publish” mode.

• Listen to one thing on repeat. I know it sounds crazy, but this is some kind of weird superhack for me and many other writers (h/t Ryan Holiday). You can use a single song, a single album, a movie, whatever. I’ve been using the same song for years (no, I won’t tell you what it is) and I’ve racked up hundreds of plays, maybe even thousands.

• Write to someone specific. My favorite writing hack to get unstuck is to write to a specific person. Think of one person who needs what you’re trying to write, and then write “Dear {Name}” at the top. Tell them what they need to hear.

• Keep it short. Typically, my daily posts have fallen in the 500-1000 word range. I think that’s still probably too long (more later).

• Write fast. Write hard and fast straight through, without stopping to re-read or edit. It’ll be terrible (at first), but that’s OK. Just get it down and then revise.

• Be gracious with yourself. Accept that every post won’t be perfect, but that’s OK. You’ll get better with practice.

All that, and yet…

In spite of all the tricks above, publishing daily ultimately hasn’t stuck for me. I think the longest stretch was about six months, and there were some stressful days in there, as well as some posts that simply weren’t up to par that I published anyway to keep the streak going.

So why do this again? Aren’t I just setting myself up for failure?

Perhaps, but before we jump to that, it might be worth asking why it never seems to stick, and whether we can tweak something to fix that.

And in keeping with the spirit of “one idea per post”, I’ll tackle that tomorrow!

Much love,
Ryan

As I mentioned yesterday, I’ve been thinking about it in the context of an old Seth Godin post about sharing something with ten people who want or need it. If they don’t share it further on their own, it’s not ready.

Creating something that great is a tall order. The perfectionist in me immediately goes to this starry-eyed view of carefully crafting my creation until it’s perfect, refusing to be satisfied with mediocrity, refusing to compromise. And then I finally share it with ten friends who are so blown away by my creation that they make it their life’s work to spread the word of my genius to the entire world.

It’s a nice fantasy, but there are two huge problems with this approach:

1. Perfection is subjective, and unless you don’t care much about commercial value (which is completely fine!), there’s a lot to learn from your audience about what’s working and what’s not. You can’t get that feedback until you ship.

2. It’s risky. This kind of uncompromising perfectionism rarely results in “amazing creations that are lauded upon launching”, but mostly in “half-finished work that never launches at all.”

Because of these, I’ve always found better success with an approach heavily biased towards shipping early and often, usually before you think it’s ready:

“If you're not embarrassed by the first version of your product, you've launched too late.“
- Reid Hoffman (source)

This approach of “launch something as quickly as possible and iterate from there” is mostly great, both because it lets you start learning and iterating early (Reid’s point), and because it keeps you from dithering about endlessly and never launching at all.

But let’s be clear: it’s good for you. It’s usually not great for the customer.

Most people don’t really want to be on the receiving end of a “minimum viable product” that’s so half-baked that the creator is embarrassed with it. They’re probably not going to start sharing it because they just can’t help themselves. Seth will be so disappointed in us.

So where does that leave us? Reid tells us to launch early while we’re still embarrassed because it seems so crappy. Seth tells us it’s not ready unless ten people we show it to love it enough to start sharing it on their own.

I think there are two ways to think about this:

1. A few things are so innovative and useful and lovable out the door that they spread like wildfire, even if they’re far from perfect.

2. But most things require a lot of iteration after launch before they would pass Seth’s test.

The problem is that you can’t know in advance which bucket your thing falls into. We all want to be #1, but you just can’t know until you put it in front of people.

That’s why I decided to launch this newsletter before I felt remotely ready. I feel very embarrassed by this. But I’m forced to ship every single day, and I’m already getting better at it. I’m iterating in public on a daily basis, and I’m not asking anyone to subscribe unless they’re the kind of patient early-adopter that can look past the warts to get some value.

But effectively, if you’re going to launch early and then iterate until it’s so insanely great that people start sharing on their own, you’re usually signing up to work for awhile without a lot of feedback or validation. It just takes awhile to iterate (although shipping daily helps!), and then even if people start sharing it and it’s growing on its own, it still takes awhile to reach critical mass and really explode in popularity.

However, “toiling in obscurity” can be refreshing. As someone who has built products with many tens of thousands of users and a healthy income stream, successful things with a large audience have a life and momentum of their own. There’s an implicit contract there about what you’re going to deliver, and you can only venture so far from that without consequences.

For example, I couldn’t really just start writing daily posts about whatever is on my mind for my main email list of 20,000 people who signed up to get actionable articles about freelancing a few times a month.

So while I’m embarrassed with my launch, and thus Reid would be proud of me, the opportunity to explore and play and iterate while there are still few readers gives me the space to build something that will eventually pass Seth’s test.

That’s the theory anyway.

Much love,
Ryan

PS - I got my first two subscribers! Both came from IndieMailer.com, a great niche community for creators of paid newsletters, and I appreciate the curiosity and patience it takes to sign up for something as half-baked as this is. I also realized that yesterday’s email went out with the greeting “Happy Tuesday!” Yesterday was Monday. 🤷‍♂️

One of the principles I’m leaning on for this newsletter experiment is “product over promotion.” There’s often a tension between focusing on the product versus focusing on the promotion of the product, especially in the early days. For example, there’s a certain pride that many successful creators take in never spending any money on advertising or promotion, but instead relying solely on word of mouth. “Marketing”, “advertising”, and “promotion” are all dirty words to this type of creator.

I’ve been critical of this mindset. I’ve relied heavily on actively marketing my projects in the past, and that’s part of their success. I’ve gotten pretty good at it to. I can build out solid funnels and write sales copy that converts. It works, and I think many great products would benefit from being a little more open-minded about actively spreading the word.

But there’s a flipside to relying too heavily on promotion, especially in the early days. It’s not that you shouldn’t spread the word about a great product. It’s just harder to build a great product in the first place if you rely heavily on promotion too soon.

One of the things I’ve been thinking about recently is an old blog post from Seth Godin:

Find ten people. Ten people who trust you/respect you/need you/listen to you…

Those ten people need what you have to sell, or want it. And if they love it, you win. If they love it, they’ll each find you ten more people (or a hundred or a thousand or, perhaps, just three). Repeat.

If they don’t love it, you need a new product. Start over.

To be frank, most of the things I’ve built over the years would fail that test, even though they’ve been successful. Partly because of impatience, partly because of a lack of self-confidence in myself and my abilities, I’ve always jumped the gun and pushed things out to a wider audience when they’re 70% or 80% as good as they should be.

So why does it matter? If these projects made money and were successful, why should I care that they’re not so insanely great that people spread them without reservation?

Let’s take Freelance250k as an example. I’ve made several hundred thousand dollars in revenue from that product, after spending around $50k on promotion, plus a bunch more time writing content and appearing on podcasts. That’s a great ROI. I’m pretty happy with it.

And yet, it’s not so great that people will just share it spontaneously.

I think it could be. I think people need it to be.

There are literally millions of freelancers, solo consultants, independent contractors, and moonlighters just in the US alone. If you include people who want to do those things, the numbers get much higher. And there are tons of good resources out there for them, but few great ones.

The rewards for going from good to great are not linear, they’re exponential. You don’t reach 25% more people or make 25% more money by taking your quality from 80% to 100%. You reach 1000x more people. You make 1000x more money.

I’ve sold hundreds of slots in my course, and made hundreds of thousands of dollars. I think the right product in this category could sell hundreds of thousands of slots and make tens of millions of dollars. Just as importantly, I think it could help many more people than Freelance250k has.

(if you did any math looking at the above two paragraphs, you’re missing the point)

But it’s not just about money. I’m also not creatively satisfied with the product. Part of this is my perfectionism, I know. Since it launched, dozens of students have written me very nice emails about the course and how helpful they found it. But I’m still not happy with it, and it’s partly that I know it could be much better and help more people.

As I’m writing this, I’m also realizing that it’s not too late. I can remake this course into the kind of thing I know it should be. But that’s a separate discussion.

Promotion lets you paper over serious defects in your product, but only for awhile. Many truly great products spread virally, which exponential. But most promotion is linear.

If I spend $100 on ads and make $500 in revenue, spending $1000 on ads will probably make me around $5000 in revenue, and so on. That linear growth doesn’t go over forever though. You probably can’t go from $100 on ads to $100 million on ads and make $500 million in revenue. But a product where the average user shares it with a couple other people will be slow to get started, but over time the audience will explode far beyond what you can spend to promote it.

Also, most promotion is temporary, not evergreen. Once you stop promoting it, the sales will dry up. When I turn off the ads for Freelance250k, sales basically stop a few weeks later, unless I do another big blast to my list.

Going back to this newsletter, I do plan to do some light promotion just to get a few eyes on this in the early days, but that’s it. I won’t be spending any money on it for now, and I won’t share it with my network or existing audience until it starts growing on its own and I feel happy with it. Even at that point, I plan to share with a dozen or so friends that would be a good fit for it and see what happens from there.

And then once it’s growing organically and I feel really good about, I’ll consider pouring the gas on and actively growing the subscriber base with some more active promotion.

But not until it’s already so insanely great that people are sharing it on their own.

Much love,
Ryan

PS - There’s a really dangerous risk to this strategy of trying to build something so insanely great that people will share it on their own, and it’s partly why I’ve relied so heavily on early promotion in the past. Tomorrow I’ll tell you more about that danger and how I’m going to avoid it with this newsletter.

PPS - The photo at top is by Greg Rakozy on Unsplash

This is the very first email of this experiment of mine (read more here), and I’m breaking a bunch of rules for how you’re supposed to start a new venture.

• I don’t have any subscribers.

• I don’t really have a topic.

• I don’t have a target audience.

• I don’t have a name, tagline, elevator pitch, nothing.

• I don’t really have a marketing strategy.

• I’m talking too much about myself and not enough about you.

None of that matters though. This list is a space for me to play and I have low expectations, for now.

But the ultimate goal of this experiment is a lofty one:

I’m going to attempt to grow a sizable daily paid email newsletter from scratch.

Now, I know what you’re thinking.

“Come on, Ryan. No one wants more email. A weekly email newsletter in 2020 would be bad enough, but daily? And on top of that, you’re going to ask them to pay for the privilege? Delusional.”

First of all, let’s address the “2020” part. Implicit in the question is the idea that email is too outdated to build a business on top of. I’ve been hearing for the last twenty years about how email is dying. It’s all spam, it’s going to be replaced by Facebook / Twitter / Slack / etc. Remember Wave? It was going to kill email too.

But email just keeps trucking along. Nothing has been able to kill it so far, and it’s still my favorite way to keep in touch with people. It’s cheap, decentralized, and simple. And I’ve made hundreds of thousands of dollars from email with Everleads and Freelance250k.

Be honest with yourself: you don’t hate all email, right? You just hate most of it. But if you’re like me, there are emails that delight you as well. Whether they’re good news, great writing, or a funny forward from a friend, some emails are worth getting.

That’s my goal for these emails: something that makes you feel a little ping of joyful anticipation when you see it in your inbox each day.

As for “daily”, there’s just something about the daily discipline of writing that works for me. It’s stressful at times, but it’s a forcing function that results in a lot more quality in a shorter time frame. For example, I wouldn’t have written this email today if I hadn’t committed to publishing daily.

But there’s another reason to publish daily and to charge money: it sets a very high bar. No one is going to put up with crappy emails every day before they hit the unsubscribe button, and no one is going to pay on top of that. In order to get people to part with money for the privilege of getting an email every single day, that email had better be adding a lot of value to their life.

And that’s ultimately what I want for my writing, so this seems like the most elegant way to align everyone’s incentives and expectations. With a weekly or monthly free email newsletter, I can slack off and let the quality slide here and there, but you can’t get away with that for long on a paid daily email.

That’s the theory anyway.

To be totally transparent, here’s the rough “plan”:

• Publish every day for the next couple months while I figure out what this is. Really focus more on the product than promotion (more on this in a future email).

• During this time period, do very light promotion to get a few people signed up who don’t know me. See how they respond and if they share it. Iterate.

• Once I get a good rhythm with the writing and I have something that people are responding to, start sharing it more widely and deliberately, including with my existing audience.

• When I have several thousand subscribers, start charging for the daily emails. Keep 1-2 emails per week free.

Why start charging at several thousand subscribers? Well, I’m aiming for a 5% conversion rate of free-to-paid and $7 / month, which is about $5 / month after fees and refunds. So that’s about $750 / month in profit, which is about the point that it becomes worth it to me to start charging.

You might be thinking that no one is going to pay $7 / month for an email newsletter, but you’d be wrong. Sure, maybe no one will pay for my email newsletter, but there are a lot of people paying for email newsletters in 2020. Just check out the list of paid publications from Substack (the newsletter platform I use). And that ignores many thousands of other paid newsletters out there that aren’t using Substack (yet).

(For what it’s worth, I have no relationship with Substack whatsoever, other than being a user of their product. I just really like what they’ve built.)

The beauty of this “business model” (blech) is that it’s so simple and direct. I’m not going plaster ads or sponsors in my emails. I’m not going to sell your data. I’m not even going to use my free writing to hook you and then pitch you other paid products. My writing is the product, and you, the customer, are paying for it directly. Simple, clean, elegant.

Of course, all of this assumes that I can figure out what I’m writing about and execute well enough that you’ll want my daily emails enough to pay thirty-five cents each for them.

Guess we’ll see ¯\_(ツ)_/¯

Much love,
Ryan

PS - if you have things you’d like me to write about, let me know. Things I’m interested in writing about include creativity, mental models, habits, systems, psychology, freelancing & consulting, entrepreneurship, online marketing, software development, productivity, personal development, and investing. Most of all, I want to explore the good and bad sides of trying to live a life that isn’t ordinary or well-defined.