Book Update: Two Stabs at “So What?”

Well, I ended up typing my notebook up much faster than I had anticipated. Circumstances ended up making it convenient for me to do a weekend-long marathon to just get it out of the way.

I couldn’t resist putting out some pieces of it into the world.

Putting that last one out, in particular, has been valuable in terms of drawing feedback. I have a pretty good idea how I’m going to revise it now, though I think some of people’s critiques apply less when the piece is situated within the context of the rest of the book, where it acts more as a balance than as a euphoric ode to consumption.

Anyway, going through everything all at once to type it up was a nice exercise. I’m feeling quite good about this project right now, which probably just means I’m in for another humbling.

At the end of the day, though I can describe what I’m aiming for with the book, it’s important not to lose sight of the “so what?

Below are two fragmentary, somewhat redundant stabs at that. There will only end up being one of them in the end, probably something much longer and drawing on elements of each, but show your work, right? These fragments were produced as part of the process.

Continue reading Book Update: Two Stabs at “So What?”

Book Update: My Notebook Against the Dark Night of the Soul

Well, it’s been quite a while since I’ve done a book update, hasn’t it?

The subtitle of this post should be: Austin Kleon was right.

He was doubly right. There are two specific things mentioned in Show Your Work which I crashed into in the past six months.

The first was the dark night of the soul, a concept he got from the novelist Maureen McHugh.


In my last update, I laid out a cursory outline for the book. It’s a bit embarrassing, but simply sketching the outline gave me far more confidence than it should have. I looked at it and thought to myself, “this will be easy! I could write this book in my sleep! After all, I write lengthy posts all the time, sometimes needing only a couple of hours to do so.”

In other words, I thought I’d have this “dark night of the soul” stuff licked. Maybe normal authors struggle with that, but I, clearly some sort of super-author, won’t have to worry.

It did not take long for that soaring hubris to be brought crashing back down to Earth.

Let me emphasize this in public, less because I think other people are unaware than because I clearly need to admit it to myself in a place where people can see the confession—writing a book is hard. The outline, if anything, made the whole process harder. As I sat to write a section, I felt like I was caging myself in with the structure of the outline. The creative spark was completely killed, and I had to really work at writing in a way that I am not used to.

It was not for nothing—I got out a few decent draft chapters, and integrated some previous writing in a way that I think will work well.

But it didn’t take long for me to hit a wall. As of a couple of months ago, my progress was crawling.

Which brings me to the second thing from Austin’s corpus (I actually can’t remember now whether it was in Show Your Work or Steal Like an Artist) that came through for me: the power of writing with an actual pen (or pencil) and paper. This one I really scoffed at to begin with. I’m a child of the PC revolution! I grew up with word processors! Who needs paper?

Well, we took a trip to Scotland in August. Including travel time, we were gone for about 10 days. I bought a notebook and brought it with me, and wrote during much of our downtime. When we returned, I brought the notebook with me on my commute, a time I usually reserve for reading. I decided I wouldn’t read during my commute until I’d filled the notebook up with material I could potentially use in my book.

The Notebook

This was extremely helpful, and I made a lot of progress. It wasn’t exactly linear, however.

I have terrible handwriting

The whole point of this was to give myself the freedom to just write, even if it ended up being irrelevant. And to begin with, I wrote a lot of stuff I couldn’t use. It’s possible some of it can be adapted, but a lot of it will just have to be thrown away (though I’ve already turned some if it into posts at Sweet Talk).

Moreover, almost from the start I began to rethink the structure of the book, and even its central idea. I started drifting far, far away from where I had planned to be.


At certain points I seriously considered going with an entirely different angle on the whole thing.


Thankfully, sanity prevailed. And I think it was healthy to explore other possibilities.

In the end, I did decide to revise my initial plan for the book, but nothing too radical. Rather than simply having seven section on the virtues, I’m going to have two sections:

  • Part 1 will discuss the virtues, explaining each one with examples from business settings.
  • Part 2 will be application—stories from the business (as well as nonprofit) world.

The idea of Part 2 is to show how an understanding of the virtues can enrich our understanding of business. It is also to show how business and commerce can and are noble activities, and there is dignity in participating in them. Making this second case means acknowledging the many ways people in business and commerce also fall into vice. I was interested to see Joseph Heath talking about industry specific patterns of criminality, because in the book I discuss how companies and whole industries have a character of their own, just as individuals do. But of course, Heath doesn’t believe that individuals do.

No backspace button here
No backspace button here

I finished filling in the notebook a couple of weeks ago. There’s a lot of work left to be done, but I’m happy with how this has turned out. The next step will be to type it all up. Then, I’ll have to make a judgment call. Do I have enough to simply edit, organize, and perhaps supplement a bit, to create a viable first draft? Or should I get myself another notebook and get to producing more material with an eye to quantity?

I’m giving myself a little break before I get to typing it all up, but I expect I’ll do it sometime this month. We’ll see how it plays out from there!

All in all, I’m feeling pretty positive about the whole project at the moment. At least, better than I was feeling before I caved and got the notebook!



This is not book related, but it does impact my timeline, so I thought I should mention it.

Earlier this year I decided I wanted to do what it took to move into a career in data science. I have an education in statistics, but have never practiced it, so those skills (such as they ever were) have atrophied. But I figured I could relearn, and if my current employer was open to it, I could start putting what I learned to use, and thus developing those skills with real experience.

I asked for advice from our (now former, as he has left to travel the world with his wife for a year) head of data science, and he gave me some very valuable advice. First and foremost: learning Python. Then brushing up on statistics and matrix algebra. After that, if I wanted to get really deep into it, I should take a course on machine learning. Also, it couldn’t hurt to take a basic intro to computer science course that focuses on Java or C, because learning those makes it easier to learn other languages later.

So I started on Python. At first I attempted Data Science from Scratch, which is all done in Python. But though it said you didn’t need much in the way of programming experience, I found that it wasn’t really working for me. So I’ve been doing Learn Python the Hard Way instead, and it’s been extremely helpful.

Why do I bring this up? Well, obviously, time I spend investing in becoming a data scientist is time I’m not working on the book. And then there’s the small matter of having a full time job and also wanting to have something like a life! I worked on Python the Hard Way for a few weekends, meaning I did basically no writing those weekends. But it was hard to get into a good learning routine just on the weekends. Trips, and visits, and special occasions disrupted whatever routine I had managed.

Now, I’ve got a good routine going, thanks to my boss, who lets me work on learning Python during the last hour or so of my day if I don’t have anything pressing. Between that, and writing during my commute, it has felt like I’ve struck a good balance between these projects.

But I’m not naive—there are only so many hours in the day. Working on becoming a data scientist will inevitably slow down my progress on the book. It already has, to an extent.

But I’m determined to do both. We’ll see how it goes once I’ve moved out of the notebook phase of the book—that is, when I can no longer really work on it during my commute. I’m not sure I’m there yet, as I said above. But I’m going to write this book, even if it takes me another two years. I’d prefer it to take no more than one—but I’ve had my butt kicked by trying to do too much too soon on this book once already, so I’m trying to be realistic.

However long it takes though, I’m committed to it. This new routine with work is very fresh, and I’ve only just filled in my notebook. In a month or two I’ll check back in and we’ll see where I am. Hopefully making tons of progress on both ends! But we’ll see.

As always, thanks for taking an interest in this little project of mine.

The Basic Structure of the Book

I have only gone through perhaps a quarter of the big list of business and self-help books I set out to read before beginning to work on my own. However, because of a few other things going on in my life right now, I’ve decided the time has come to get to work. I’m going to continue reading books from my list as I write, but at this point I’m also feeling quite confident about the range of styles and formulas within the genre. I am also very glad that I chose business books rather than self-help books; my samples of each so far confirm that this was the correct choice.

I spent some time this weekend working on the structure of the books as well as a few notes for how to flesh out each section. I thought about just putting the chapter titles here, but decided to stick with Austin Kleon’s mantra and really show my work here, even though (or perhaps especially because) it’s pretty rough at the moment. In particular, my “central story” is a paragraph when it should be a sentence. I’m definitely going to boil that down.

You’ll notice it isn’t the structure that I mentioned in the only post I touched on structure at all. My friend Sam Hammond quickly convinced me that that wasn’t going to work. Instead, I went with something more straightforward: seven sections, one for each virtue. Each has an introduction and then 1-3 chapters. I based the maximum word count on the list in this post but would definitely appreciate feedback, on that or anything. Keeping the book concise is, I think, going to be the hardest part for me.

Again, any feedback or criticism will be hugely appreciated.

Without further delay, here’s the plan of the book as it stands (apologies for weird formatting, I’m copying this straight from a Word doc):

Basic Plan of the Book

Structure: an introduction and then seven sections representing each virtue, with at most two or three chapters per section.

Central Story: How you make a living is an important part of your life as a whole. Having a good life requires that you deal with the place of work in your life. In order to do that, you need to figure out what a good life even looks like to begin with. The specifics will change based on the person and also the circumstances, but in general being a good person just is what it means to have a good life. The seven virtues provide a useful way of thinking about what it means to be a good person, and just why that would add up to a life worth living.

Desired Word Count: 80,000 or less.



  • Don’t Be Steve Jobs/imposing a theme on your life/virtue as the ingredients to a good life

Part 1: Prudence

  1. Introduction: Prudence, Prudentia, Phronesis
    1. The contemporary version of prudence will be called things like due diligence, thrift, etc. I may refer to something as being or not being prudent in this sense, but I will try to make it clear from the context what I mean. Also “narrow prudence” vs “broader prudence”.
  2. Beyond Work-Life Balance
    1. Work is not compartmentalized; it is a significant part of your life.
      1. If it is not healthy, your life will not be healthy, no matter whether you’re working closer to 40 hours a week than to 80 or 100.
    2. Balance is good, but balance should be among the virtues.
      1. Prudence is the virtue of finding the balance among the virtues.
        1. How courage is not truly a virtue without charity, without justice, without due diligence. The prudent person will have the wisdom to find this balance.
        2. A skill that can only be developed by doing, by living.
      2. First, ask: why are you even doing this? What life are you trying to support materially, and with whom? Is your job primarily a means of supporting that, or is it also something more to you, a craft that is an important part of your identity?
      3. Then explore your options.
        1. Really explore all the extreme possibilities; making drastically less money to have a much lower stress job, moving a great distance in order to live in a lower cost of living area, changing industries, going back to school, taking professional development courses; all of them.
        2. You will probably not go for the extreme options. But knowing they are there is very comforting. It is much easier to renegotiate your circumstances—with your employer or simply with yourself, in terms of what your priorities should be—when you are concretely aware that you are not trapped in them.
  1. The Ingredients to a Good Life
    1. Socrates thought that the formula for the good life involved a simple scale of value
    2. Economists have tried to bring this about
    3. Milton Friedman’s social responsibility of business to increase its profit is in this vein.
      1. The vulgarized version of it is Gordon Gekko’s “Greed is Good”, meant to be a caricature but now often taught as truth.
    4. Being prudent is good, but greed is not
      1. The narrower version of prudence involving due diligence, looking after your interests, saving for a rainy day, and so on, involve the other virtues—temperance, or restraint, in delaying gratification; courage in making decisive trade-offs, charity in building up your resources so you can be in a better position to help your loved ones should they call upon you in an hour of need, and so on.
      2. Greed is myopic, material gain for its own sake; contra Milton Friedman and vulgarizations of his argument, the economy needs ethical behavior in order to function. It needs people who have faith in one another, who have hope that they can add more to the world than they take from it, who treat each other fairly and don’t seek to break the rules out of short-sighted opportunism.
    5. There is no single scale of values on which to measure a good life. A good life is more like a recipe with many different types of ingredients. There are many recipe books, but anyone who has attempted to cook from the instructions in such books knows that they are no substitute for true experience. Particular fruits may have greater than average intensity in flavor; your oven may be more temperamental than the one used by the book’s author. Prudence, true prudence in the broad sense of practical wisdom, is the skill of determining the right mixture of ingredients in any given situation, so that one day you can look back on your life as a whole and say that you truly lived well.
    6. The virtues are the ingredients used for coming up with such a life.

Part 2: Justice

  1. Introduction: The Virtue of Always Giving What is Due
  2. Work to be Trustworthy Rather Than Trusted (use the Bogart quote from Sabrina)
    1. Networking is ascendant as the top prudent strategy among the most pragmatic people.
      1. But networking as it is recommended today often breaks down to trying to win people’s trust.
      2. What if we focused first on being worthy of trust, rather than trying to gain it?
    2. Working on becoming reliable, rather than being relied upon.
      1. Being relied upon should be seen as validation in the eyes of others that you are, in fact, reliable, rather than as the end goal in itself.
    3. Being worthy of trust, being reliable, this is what you owe to the people you work with.
      1. The impossibility of specifying every possible contingency in a contract
      2. Honoring the spirit of a contract, thus making yourself an honorable and reliable business partner. Something you should be striving after for its own sake, because you want to be the kind of person who can be relied on, because the world needs people like that if we’re to continue feeding and delighting each other on the scale we currently do, and hopefully for the poorer countries, on an even greater scale in the future.

Part 3: Charity

  1. Introduction: Giving more than is due/helping for the sake of helping/seeing others as human beings.
  2. Networks of Uncalculated Giving
    1. Alasdair MacIntyre’s formulation, the parents whose kid has special needs example
    2. Adam Grant/Give and Take, what these networks looks like in practice.
    3. These networks can turn out to serve your interests, as Grant shows.
      1. But if your goal is to serve your interests, then you aren’t doing it right.
      2. And they may not end up serving your interests, they may end up costing you and primarily benefitting others.
      3. But if you can help build or maintain or grow such a network, you will have done something truly worthy.
      4. Forging meaningful connections between human beings.
      5. Return to theme of not being Steve Jobs.
  1. Seeing People as People
    1. How we numb ourselves to others because we believe it will make it easier to look after our interests in dealing with them.
    2. How cognitive biases play into this.
    3. Arbinger Society’s message; people are more amendable to our requests if we do the hard work of seeing them as human beings with needs, dreams, beliefs, desires, just like us.
    4. William Ury and the power of a positive “no”. There is prudence here.
    5. But a good person works on seeing others as people even when it isn’t convenient, even when it might be a hindrance. Basic human decency demands it.

Part 4: Temperance

  1. Introduction: Temperance as self-control, restraint, discipline.
  2. Willpower, Habit, and Support
    1. Your basic Baumeister stuff on what we know about willpower, how it can be trained.
    2. Better than strengthening your willpower, however, is building habits that economize on it.
    3. Heath and Anderson on social support.

Part 5: Courage

  1. Introduction: the martial virtue, popular among people who believe the lessons of Machiavelli and Sun Tzu are the most applicable to the world of business. But courage in business is very different from courage in war.
  2. Everyday Courage
    1. Back to the positive “no”
    2. Commitment
      1. In a way, commitment is what is owed, therefore about justice, and also about going above and beyond, and therefore about charity.
      2. But truly, it’s about vulnerability. It’s about caring about the quality of your work and whether you’ve really made an effort to work with the people you need to be working with, and being able to own up to it when you haven’t. Voluntarily making yourself vulnerable, whatever the degree, is an act of courage. (cite Daring Greatly here)
    3. Uncertainty and Entrepreneurship
      1. Explain the difference between risk and Knightian uncertainty
      2. A lot of finance and insurance is about trying to reduce more and more areas of uncertainty into quantifiable risk.
      3. That’s a worthy endeavor, but most of the material gains we’ve made since the onset of the Industrial Revolution have come from people boldly charging into unexplored and poorly understood areas.
        1. Henry Ford and Frederick Smith of FedEx, creating whole new markets.
        2. McCloskey and Taleb on tinkerers, and people who “knew how” before they “knew why” (such as the blast furnace and the jet engine).
      4. This is the true courage of the marketplace, not the courage of warfare.

Part 6: Hope

  1. Introduction: A confident expectation, a way of approaching the world. It cannot bend reality (briefly criticize The Secret) but it does clear aside self-fulfilling pessimism.
  2. Your Career
    1. The people who are most miserable in their jobs are the ones who have lost hope. They have no hope in the trajectory of their career, or no hope that they could get by without clinging to this one job that they hate, or no hope that they could make a living at all if they let go of this job or made a drastic career change.
    2. The prudent exercise of thinking imaginatively about your options should help to remind you that you are not really trapped. Among the options you should consider are those that challenge you; going back to school, going into a more technical field.
    3. The Option Value of Satisfying Work; setting your expectations low in terms of material gains or audience size, but always having the next project to look forward to adds an element of hope to your life.
  3. The Great Enrichment (if the book gets too long, this will be the section to cut)
    1. McCloskey on how the emboldening of entrepreneurs created the Great Enrichment.
    2. Not a hypothesis, not a guess, but a firm belief in the possibility of improvement. Improving production processes, improving business models, improving morality itself.
    3. When we talk about disruption, or innovation, or dynamism, what we’re talking about is a firm belief that we can sweep away today’s problems and build a better future.
    4. This confidence can sometimes go too far, especially when we become too forward-gazing and forget all we have to learn from the past.
    5. But properly balanced with the other virtues, hope is the great uplifting force in the world as well as in our lives.

Part 7: Faith

  1. Introduction: the foundation you stand on, your source of strength, who you are.
  2. Trust
    1. While trustworthiness is an aspect of justice, of giving people what they deserve, trust is an act of faith in others.
    2. Robert Soloman and Fernando Flores; trust creates possibilities.
    3. “High Trust” societies much wealthier than the opposite.
    4. Trust has allowed ethnic minorities in exile to flourish in spite of hardship and prejudice; dig up a few examples.
    5. Everything bureaucratic about large corporations is a response to the trust that is lost when you scale up beyond a level where everyone knows everyone else.
    6. But bureaucratic processes do not get rid of the need for trust, they merely economize on them.
    7. Management without trust is not possible. (cite HBR article on inability to delegate)
  3. Who You Are
    1. What are you doing this for? What keeps you from walking away from your life?
      1. Perhaps your life has reached a stage where walking away sounds very tempting, once considered.
      2. If you aren’t sticking around out of simple fear of the unknown, then what is it?
    2. Discuss what grounds me.


  • Those of us who work for a living have a lot to be proud of.
    • Whether we are employees, employers, entrepreneurs, sole proprietors, freelancers, or civil servants.
  • The way we talk about this matters. It influences how we think about the enterprise and how we think about ourselves.
  • Arguing that private greed produces public wealth is no defense at all, and it’s largely untrue.
  • Private virtue plays a huge, central role in the production of public wealth, and in creating communities and individual lives that are rich beyond measure.
  • A great example of how to talk about these things can be found in The Alliance, by Reid Hoffman, Ben Casnocha, and Chris Yeh. It’s about how to fix the mismatched expectations created by a shifting marketplace by changing our rhetoric to better fit the situation, and making it easier to make ethical commitments in that environment. Hoffman and his co-authors assume they are dealing with moral adults capable of making such commitments, not the maximally opportunistic homo economicus.
  • We need to demand a fairer assessment from our culture’s intellectuals. We need to get better at defending ourselves. And in order to do that, we need to start by believing we are worth defending.
  • I believe it, and I hope this book has helped you believe it as well.

Time to Dive in: Self-Help and Business Book Reading List

I’ve been tip-toeing around an important part of my research because it is less appealing to me. I’m trying very hard not to be a snob, but my continuing resistance to really diving into the self-help and business book segment of my research is beginning to make me feel that I probably am one.

In addition to the books listed at the bottom of this post, I’ve read Daring Greatly, which I knew would be good because I had read The Gift of Imperfection, another book by the same author. Earlier in the year I had also read Austin Kleon’s great books on creativity, Steal Like an Artist and Show Your Work. And that’s the sort of tip-toeing I’ve been doing; piecemeal forays into the genre from authors (or reviewers) that I already trust.

It all came to a head a week ago when I tried to defend self-help books in general to my dad, who called bullshit. “Go to a best seller list and read those books,” he said. He assumed that what I would find would be garbage, and probably exploitative garbage at that.

So I did what he said, and assembled a list of both self-help and business books, based on current best seller lists as well as some lists of all-time best sellers.

This is what I’m committing to read by the end of the year, at which point I plan to begin drafting the book:


I’m not looking forward to it. But I imagine it will be quick reading.

The business book part I’m less concerned with, though there are certainly some that look less than appealing:

Business Books

I’m going to read more than just what’s on these lists, though probably not more self-help and business books. I’m going to read Lecky, for instance. And the last book in Deirdre McCloskey’s Bourgeois trilogy is set to come out sometime this year; I will definitely read that. The above is basically market research for me: I want to see what sells in the category I intend to write in. It doesn’t mean I’m going to mimic what I find there, but you don’t have to mimic something in order to learn from it.

There are a few books that I read last year that I also intend to re-read. The Morality of HappinessHappiness for Humans, and of course, The Bourgeois Virtues come to mind. That may be a bit ambitious for my timeline; and I won’t let them stall that. I may end up opting for more selective rereads of specific parts of various books—in fact that’s quite likely either way.

Anyway, that’s after the…market research.

See you on the other side.