Design Changes for Ambition, Coming Out Jan. 2018

I’ve figured out how to fix a few of the design flaws remaining in my card game, Ambition.

If anyone’s interested in beta-testing the game over the holidays, please let me know; I’ll send a link to the proposed changes.


Why I Didn’t Do It

Forgive me if I don’t find the best order to use in telling this story. Life is chaos; chronological order may dissatisfy. And, since this narrative continues into the future, I have no idea how it ends.

I left a high-paying job in finance, early in 2008, to work at a startup. I had, one could say, a naive, rosy view of technology and the nobility of its place in society. I believed that if I became a great programmer, I’d both have a positive effect on the world, and earn my own reward. I wrote code, I wrote words, I read a lot, and I worked my ass off. That hasn’t changed.

My first taste of what one could call “fame” came in March 2011. A now-deleted essay hit Reddit and got 30,000 views in two days. In July 2012, I wrote “Don’t waste your time in crappy startup jobs.” At the time, I wasn’t advising people to avoid startups– only to be selective about which ones to work for. That post received 135,000 views in one day, and about 250,000 over its entire life.

Through this, I made some enemies. Advising tech employees to negotiate with employers does not earn love from all corners.

I removed those “hit” essays in February 2016, after receiving a few not-credible but disturbing physical threats. I intended to restore them, but a technical mistake (partly mine) led to their permanent deletion.

If one wants to find them, the Internet Archive (“Wayback Machine”) is what I’d recommend. The problem with my earlier writing on technology is that it has diverged from my interests and, to a lesser extent, from my values. I spent years trying to inject efficiency and integrity into venture-funded, private-sector technology. I no longer have faith that I, or anyone, can improve it. My aim in 2012 was to save it; in 2017, my goal is to minimize harm (especially, to myself) from its inevitable Untergang.

I experienced an aggressive public attack, starting in the fall of 2015. I was “de-platformed.” To wit, I was banned from Hacker News and Quora on false, defamatory pretenses. Why was I banned? It had nothing to do with my conduct on either site. First, I suggested that, instead of enduring the creep of micromanagement and surveillance, software engineers might consider collective bargaining. Second, I wrote a blog post that Paul Graham thought was about him– it wasn’t. Third, Y Combinator abused its power as an investor in Quora to force a ban on my account. It would have shut the company down, costing 120 innocents their jobs, had it not complied.

It must seem bizarre that I’m still upset about website bans from two years ago. In fact, I’m glad those sites banned me; they were monstrous wastes of time. I’m disgusted by the defamatory pretenses they used to do so, and the public statements they made. Their goal wasn’t to get me off the sites (I was a top contributor) but to damage my reputation. In a normal industry, such things would have no effect. How many industries or careers are there where a website ban could be used as a reason not to offer someone a contract or job? I can’t think of any, but one: venture-funded technology– that is, startups and ex-startups like Google and Facebook.

Leaving finance for a startup, in 2008, was a failure of career planning. That’s on me, and me alone. By doing so, I locked myself for a time in an incestuous weird industry where petty gossip drives careers. It is also an industry whose values and mine have diverged.

In early 2016, I was informed that I had been turned down for a job because of these bans. The perception was that I’d been humiliated by Dan Gackle and Marc Bodnick and failed to strike back. This petty gangster shit ought to be beneath me.

I don’t want to “strike back”. I don’t want a damn thing to do with those sick fucks. Revenge keeps you involved. Life’s too short.

I spoke to a public relations specialist about that experience. She asked me what money I would have made if I had gotten the job. I told her. She laughed.

“As smart as you are, you’re concerned about a startup job making $XXX,000?”

It amused her that, the stakes being so low, I’d even care to consult a PR coach at all. Here’s what I had to explain to her: the rest of the economy doesn’t want people from the startup world. (There are good reasons for this; most of us are sociopaths.) Often, we get stuck in it. In the tech industry– startups and ex-startups– it’s usual that one has to change jobs every 18 months to have a career, because those companies don’t invest in their people or promote from within. In real careers, that’s a sociopath’s résumé.

There are many undisclosed dangers of private-sector technology. Yes, it pays well, relative to most other careers, in the first 5 years. Still, it maroons almost all of them by middle age– and “middle age” in tech means 30. The job-hopping résumé that’s necessary in private-sector technology looks terrible anywhere else. Silicon Valley may think that it’s the future, but the rest of the country looks at five jobs in 6 years and says, “Nope.” Those who enter the startup scene often ignore the high probability of being stuck there. They think they’re younger and more invincible than they really are.

I ought to admit that I’ve never been great at processing the bizarre adversity that started with my first attempts to improve the tech industry. I have nightmares and panic attacks. I Google phone numbers I don’t recognize. I watch my back, especially in large cities.

The anonymous threats, the unjustifiable closing of doors, the necessary vigilance… that took a toll on me in 2015 and ’16. For an example of what I was going through, a homeless person in San Francisco chased me, brandishing a stick. He told me not to “fuck with” certain people, whom he named.

I hit rock bottom around March of that year. It wasn’t that I gave credibility to the death threats. Those came from high-placed people in Silicon Valley who had too much to lose, and I lived in Chicago, so I perceived myself as out of their way. Looking back on it, their objective wasn’t physical harm. Their work was incompetent and that was intentional. Rather, they wanted me to speak up. They knew I would, and I played into it. Why? Because it sounds utterly fucking nuts. If I stand up and say that, one time in San Francisco, a person associated with Y Combinator sent a homeless man to harass me, I sound insane. It seems bizarre and unreasonable, because it is. However, it happened. I wish I were making it all up.

Even I have trouble integrating these experiences, years later. I’ll confess to this: the other-than-real aura of certain events in the 2010s has led me to seek professional assistance in their processing. The normal reaction to abnormal occurrences, sometimes, requires that.

At that rock-bottom point in March, I was considering my own exit. Why? When I wrote about open allocation, or organizational dynamics, or programming languages, I held a certain opinion. Namely, that private-sector technology was a well-intended but wayward industry. There were bad guys, sure, but good guys as well, and the good guys could win.

Quora seemed to be the good guys. (Ha!) Even Y Combinator seemed, at one time, to operate with moral decency. I had this sense of computer programming as this noble activity; we were automating away worlds’ worth of undesirable work. I learned, abruptly, that I was wrong about almost everything. I realized that I’d invested in almost 10 years in an immoral career.

Our other favored debates seem so small, in comparison. One can argue about the merits of Haskell versus Python, or Bayesian models versus maximum likelihood, but to what point? These technical matters are hills of sand compared to the shit mountain that is our industry’s ethical failure.

I had a hard time accepting the role I had played. Yes, I experienced death threats and attempted blacklisting. From an objective external perspective, I’m not a sympathetic party. First, I chose to work in the tech industry. Second, by revealing unethical and illegal activities to the public, press, and authorities, I “bit the hand”. Third, my experiences raise questions but don’t answer them. I’ve proven corruption in Silicon Valley; do I have a fix for it? I don’t. Fourth, I must confess to my immaturity while the worst fights (2011 to ’15) were going down. In one case, my revelations of illegal practices led to numerous successful lawsuits against the company. Am I a hero? Nah; I did it to settle a grudge. I did a good thing, but my intentions were pedestrian. If I represent my story with honesty, I must admit this.

So, there I was, in March 2016, doubting whether I wanted to consider existing. Harassment and defamation from people who are powerful in one’s industry has that effect. Believing you’ll never get a decent job again (false, proved later) because a Quora ban (tech is petty; it’s plausible) has that effect. Spoiler alert: I’m still alive. As a general rule, I’m not suicidal, for two reasons.

First, while I don’t ascribe to literal religion, I find it plausible-to-likely that (A) there’s more to consciousness than we see on the surface, and (B) that my conduct in this life matters. So, I see no upside in self-violence, even when it tempts. There’s no guarantee, in any event, that it provides the cessation of existence that, in darker moments, I might desire. Whereas there’s a certainty of emotional harm to people who remain.

Second, when I get to that point, I often pretend I am dead or dying, just for the exercise. “I’m dead already; what do I do now?” We’re all terminally ill, after all; we just don’t know the timeframe.

Usually, I can come up with something worth doing. Perhaps it’s as pedestrian as cleaning the cat’s litter box. I ask myself how much life, in the current state, I can tolerate… and then figure out what I can do in that amount of time. Let’s say I decide that I can tolerate 6 more months. If I rushed and left editing to posterity– I have too much pride to do that, unless necessary; but it’s what I’d do if diagnosed with a terminal illness– I could finish my novel, Farisa’s Crossing, in half that time. That’d give me a valid reason to kick around for a few months, right? I find that, once I get to work on something I care about, that wish for a long sleep (which may or may not be what death is) dissipates.

It was at this bottom of night that I started writing Farisa’s Crossing. I figured it’d be a 60,000-word book. After several rounds of revision, and several to go, I’m on target for 175,000. That’s only the first book. I expected the amount of work involved in writing a significant (as opposed to merely publishable) novel to be high. It’s much more than I expected, but it’s fun work. As Camus said of Sisyphus, “One must imagine [him] happy”.

I found that I enjoy fiction more than I enjoyed tech writing. I’ll be publishing it in a year or so. There’s a lot to figure out, on that front. We live in a time where some of the best work is self-published and where any celebrity could get a prestigious house to print garbage. So, I view the process as unpredictable. My job, though, is to write significant work– and maybe, for once, give some value to what I’ve experienced.

Over 2016, for reasons mixing protest and privacy, I accelerated my own de-platforming. It was bad for my reputation to be banned from Hacker News and Quora on the defamatory pretenses that were chosen, but it was good to be banned from them.

What I realized, that year, was that the addiction to internet microapprovals had damaged my focus. It became hard to read, much less write, significant work. Ten thousand words became “too long” to read. In online magazines, even for excellent, enjoyable articles, I’d find myself checking that side cursor for total length. “Are we there yet?” “Are we there yet?” Social media feeds the monkey mind. It leads to a loss of discipline.

I quit Twitter in November 2016. Like I said, there was an element of protest, and this may have been rash. When you’re publishing a book, you need “platform”. I burned mine down. I had 2,600 followers. If I joined again, I’d start at zero.

Now, I am facing the question of whether and how to “re-platform”, as I want Farisa’s Crossing to succeed. Should I rejoin the world of 140-character insights and @-mentions? Should I start batting out 750-word blog posts that say the same thing as one from three years ago, but might “go viral” this time?

I know I can “re-platform”. I could get 10 times the attention I had at my peak. But at what cost? When I used social media, I developed unhealthy obsessions: famous followers, page view counts, blue fucking checkmarks. Do I want that in my life again? My sense is that I don’t.

It might be my age, but I enjoy books more than websites these days. Some promises of technology have been fulfilled. Most have not. The industry sucks, and it’s not getting better.

What ought to have been the first sign of broad-based moral corruption was this: in 2011, I remember someone saying she wanted to “demolish” a competitor. Not “we’d like to build a better product” but “we want to end them.” (They’re still around.) See, it’s valid and usually moral in business to compete. If another firm suffers because one offers a superior product, that’s not something to be ashamed of. However, taking job in the other’s destruction– or, in today’s language, “disruption”– seems perverse. Why wish for another’s failure, as opposed to pursuing one’s own excellence?

It’s a sad fact, but most of what we do in technology is destructive. Very few of us make new things under the sun. Most of us make business processes cheaper. There’s nothing wrong with that; we might think, naively, that the value we create would be invested into research and development. That’s not what happens. Businessmen lay people off to pay their own bonuses. We’re the ones who make that possible. Society gets worse with each iteration, and it’s our fault.

Then, is it a surprise that we fail to arouse public sympathy when we can’t afford houses in the Bay Area? Or when we suffer age discrimination at 30?

I don’t know what life’s ultimate purposes is. Though I don’t ascribe to literal religion, I tend toward anti-nihilism, like Farisa. There must be a purpose, I can’t help but feel. What is it? It’s not to destroy.

Life’s purpose is not to code people out of jobs. It’s not to wreck the reputations of innocents on social media. It’s not to get people addicted to meaningless social microapprovals. Whatever imperative I can find, in the moments when the darkness goes away, points in the opposite direction.



There’s a game called Universal Paperclips in which one plays the villain: a paperclip maximizer, or an AI whose purpose is to make as many paperclips as possible, at any expense. The result of this, should the thought experiment become real, would be our own quick death; the machine would want our matter for its own work.

Paperclip maximizers come to mind often, as someone who’s worked in the tech industry for more than a decade, and has nothing to show for it. I didn’t get rich. I didn’t change the world. I know approximately 47 programming languages, but who cares? I’m 34 years old and the vast majority of my time in this industry has been pure waste and an embarrassment.

There’s one thing I got from the tech industry. Although I developed the illness beforehand, my panic disorder really came into its own thanks to open-plan offices and startup health insurance. It didn’t help that, when I was finally on the mend in 2011, I joined Google and had a manager who provoked attacks for his own amusement. That was fun.

If I hadn’t gotten myself stuck in the tech industry, the condition would have fully remitted by now, if not several years ago. Instead, the fight has gone on for a decade, and I’m not fully out just yet.

So, my souvenir from the tech industry is, rather than some neat futuristic bauble, a defect in an ancient part of my brain, the amygdala.

When I grew up, in the 1980s, we learned about what technology might do one day: holiday lunar trips, robot servants, an end to illness, certainly an end to work except for the most rewarding kinds of it. And what have we actually achieved? Fucking Bitcoin. A 140-character President. Literal fake news. That’s what we have to show for ourselves.

As private-sector programmers, we’ve unemployed a lot of people: we’ve annihilated hundreds of millions of jobs. Some of these people got better jobs; many didn’t. We never cared when it was happening to other people, but now we have “Agile Scrum” and Jira and open-plan offices and the surveillance system we built… sits over us, its passive-management eye always watching.

In what we do, as private-sector programmers, where is the honor? There’s none. We are a failed tribe that has made rich people richer– even at our own expense. If we’re lucky, our work will be erased and we will be forgotten.

This may explain the Fermi Paradox. Perhaps there is a plateau of mediocrity at which, though a civilization could continue to innovate, it chooses not to. Perhaps it does not go the way of violence, but bored purposelessness. Perhaps we are not totally alone in the universe, but all those other supposedly intelligent civilizations are mired in thousands of years of user stories and TPS reports. Seems unlikely, right? Sure. But it’s even more absurd, if we could send a man to the Moon using 1969 computers, that we’re using supercomputers to run Jira and do “user stories” in 2017.

A Middle Manager Learns Zen

For a short break from my work on Farisa’s Crossing, I wrote this parable.

Zen and the Art of Middle Management

A middle manager went to a Zen master.

He said, “I suffer from anxiety. It’s holding me back in my career. With this problem, I’ll never become a True Executive.”

The Zen master said, “I’ll teach you how to overcome your anxieties.”

He studied under the master for a week, and learned how to control his fears and reduce his worry.

A year later, he returned to his mentor to thank him.

“You’ve helped me cut my anxieties to 25 percent. I’m smoother than silk in meetings. I’m Assistant Director now.”

The mentor smiled.

“May I study with you, for another week?”

The mentor nodded.

The manager studied. He meditated. He learned how to calm his own nerves and mute the darker bits of his mind.

He returned, a year later, with more thanks.

“You’ve helped me cut my anxieties to 10 percent. I’m a Vice President now. Almost a True Executive.”

The mentor smiled.

“May I study with you, for another week?”

The mentor nodded.

So the manager studied more. He meditated, from five in the morning to eleven at night, every day for a week.

After much work, he learned how to extinguish his anxieties, to tap into the universal calm, to pull the mind back to its sky-like nature.

A year later, the (ex-)manager returned– with a lawsuit.

“What’s this for?” the mentor asked.

“You ruined my career!”

“I don’t see how–”

“You’ve helped me cut my anxieties to 0.1 percent.”

“That’s good. You are learning to overcome samsara and its poisons.”

“No, it’s not! The job of a True Executive is not to overcome his anxieties, but to offload them to other people. How can I do that now?”

At that moment, the mentor was (dis)enlightened.