Generation Screwed

We’ve all heard the statistics. More millennials live with their parents than with roommates. We are delaying partner-marrying and house-buying and kid-having for longer than any previous generation. And, according to The Olds, our problems are all our fault: We got the wrong degree. We spend money we don’t have on things we don’t need. We still haven’t learned to code. We killed cereal and department stores and golf and napkins and lunch. Mention “millennial” to anyone over 40 and the word “entitlement” will come back at you within seconds, our own intergenerational game of Marco Polo.


For decades, most of the job growth in America has been in low-wage, low-skilled, temporary and short-term jobs. The United States simply produces fewer and fewer of the kinds of jobs our parents had. This explains why the rates of “under-employment” among high school and college grads were rising steadily long before the recession. […] The decline of the job has its primary origins in the 1970s, with a million little changes the boomers barely noticed. The Federal Reserve cracked down on inflation. Companies started paying executives in stock options. Pension funds invested in riskier assets. The cumulative result was money pouring into the stock market like jet fuel. […] The pressure to deliver immediate returns became relentless. When stocks were long-term investments, shareholders let CEOs spend money on things like worker benefits because they contributed to the company’s long-term health. Once investors lost the ability to look beyond the next earnings report, however, any move that didn’t boost short-term profits was tantamount to treason.


In one of the most infuriating conversations I had for this article, my father breezily informed me that he bought his first house at 29. It was 1973, he had just moved to Seattle and his job as a university professor paid him (adjusted for inflation) around $76,000 a year. The house cost $124,000 — again, in today’s dollars. I am six years older now than my dad was then. I earn less than he did and the median home price in Seattle is around $730,000. My father’s first house cost him 20 months of his salary. My first house will cost more than 10 years of mine.


And the problem is only getting worse. That’s because all the urgency to build comes from people who need somewhere to live. But all the political power is held by people who already own homes. For homeowners, there is no such thing as a housing crisis. Why? Because when property values go up, so does their net worth. They have every reason to block new construction. And they do that by weaponizing environmental regulations and historical preservation rules.

Michael Hobbes — Generation Screwed

Open source is debt

An idea I'd like to throw in the wild.

Open source is software businesses use to shorten time to market and accelerate their product. Some businesses build and collaborate in public because it's a leverage strategy to get more from less. Most businesses maximize their use of open source software because they get it for "free".

Debt is the financial term, stolen for the sake of illustrating a concept.

Open source is debt because:

  • Open source software is not a sellable asset. It's both priceless and devoid of monetary value. What counts is the business value it enables.
  • The liability, and effort required to service this liability, grows as: 1) the software gains users, and 2) those users become more dependent the software. Support is a variable accelerant to the liability (e.g. it can grow the liability at an exponential rate).
  • Maintainers hold the debt liability. Their ongoing labor is required to service the debt. Typically, maintainers can only escape the obligation by declaring bankruptcy: "it's done" or "I'm done."

This idea could be helpful framing for:

  • Businesses to understand their dependency on open source in CFO-friendly terms.
  • Communities to understand the debt burden carried by maintainers, and general health of the project.

Another, possibly more correct, way of thinking about this is: "every line of source code, open or closed, is a liability." Businesses own 100% of their closed source liability. They like open source because they would rather own 0% the liability.

Specific challenges to hiring remote employees in India

A few interesting points that have come up in recent conversations:

  • Remote work has significant cultural stigma. It isn't yet a mainstream activity in India, so it's looked upon with negativity. For instance, the maid will come over and ask "why aren't you at the office? are you sick?"
  • Infrastructure isn't yet eventually distributed. Moderately reliable internet at the office costs 100x what most pay for internet at home. Even the most expensive home internet (5x baseline) can still be inconsistent.
  • Working from home has a space constraint. An entire family of five to six people could be living in 400 square feet.
  • Labor laws favor full-time employment over contracting. For instance, Indian law requires six months paid leave for mothers. Contractors aren't afforded similar benefits.

Remote work in India works best among the "intellectual elite", but this is still a small percentage of the total engineering talent.

Startup life

Two former Uber employees, both of whom left the company in 2016, told Quartz that Uber gave them just 30 days after departing to exercise their options. One of those former employees paid about $100,000 to exercise more than 20,000 incentive stock options (ISOs), plus a tax bill of over $200,000. The other paid about $70,000 to exercise about 5,000 ISOs, and then about $160,000 in taxes. Both former employees took out loans from family members to make the payments, and requested anonymity to discuss their personal financial situations.

The Bullet Hole Misconception

Computer technology has not yet come close to the printing press in its power to generate radical and substantive thoughts on a social, economical, political or even philosophical level. The printing press was the dominant force that transformed the middle ages into a scientific society. Not by just making books more available, but by changing the thought patterns of those who learned to read. The changes in our society brought about by the computer technology in the past 50 years look pale compared to that. We are making computers in all forms available, but we're far away from generating new thoughts or breaking up thought patterns.

Landing Gutenberg in WordPress 5.0

Some incomplete ideas I've been noodling on that I want to make public.

Ultimately, the goal is: the vast majority of WordPress users are excited and should be able to use Gutenberg on day one. Fundamentally, this breaks down into two objectives:

  1. Make the end-user experience is so good that WordPress users actively want to switch to it. We need to continue user testing as we have been, and iterate based on real user feedback. We also need to market Gutenberg — communicate what users should expect and get them appropriately excited.
  2. Mitigate WordPress plugin and theme incompatibilities, to minimize conflicts that would cause WordPress to fall back to the classic editor. Success is defined by the majority of WordPress users being able to use Gutenberg on day one. If too many can't use Gutenberg because of conflicts, then we've failed at launch.

I've been brainstorming some strategies for the latter, which really is two parts: identification and mitigation.

First, we need to identify the true extent of the problem: what plugins and themes are incompatible with Gutenberg, and in what ways are each incompatible? Some automated ways we can produce this data includes:

  • Manual/automated analysis of action and filters usage, etc.
  • Activate each in an isolated environment and take before/after screenshots of the editor screen.

But, I'm thinking good ol' fashioned crowd-sourcing might be most effective. What if WordPress users had an easy way to report whether a given plugin or theme was compatible with Gutenberg? We could collect this data in aggregate to get a good sense of what types of incompatibilities we should expect, and where we should focus our efforts.

Once we've identified the plugin and theme conflicts, we'll need to mitigate them. Doing so will require excellent documentation, so authors more easily understand the changes they'll need to make, and deputizing other developers to help with the outreach process.

AI is coming

A few recent podcasts that caught my interest:

"But Daniel, none of these links are conclusive proof that AI is coming."

No, the AI apocalypse hasn't happened yet. But, the pace of change is stunning and we can't reliably forecast more than six months out (if that).

Seeking hard problems

It's that time of year again (where my schedule empties out), so I find myself in search of a really hard problem to work on. Some problems that have piqued my interest:

  • Affordable housing. Did you know that affordable housing is defined as paying 30% of income or less on housing? And did you know that Washington County, where Tualatin is located, has a gap of ~14,500 houses and growing? I didn't either until about five months ago. Even if you can still afford your housing, this is a problem the entire socio-economic spectrum should be working on.
  • Government technology. The USDS is really cool and having an amazing impact. You should listen to Jennifer Pahlka's SALT talk, "Fixing Government: Bottom Up and Outside In". I wish there was a similar initiative in Oregon. Is there one?
  • Landing Gutenberg in WordPress 5.0. Gutenberg is a revolutionary editing interface. So revolutionary, in fact, that it's one of the worst-rated plugins in the directory. Getting from where we are now to happily shipped in core is going to be a challenging, multi-faceted initiative.

Let me know if you have any input on these problems, or whether there are others I should be considering!