It is very unusual for 18-year-olds to accurately plan for what they will when they are 33.
Most people don't plan their lives out like you are suggesting. They take opportunities as they come, and build their life as it comes along. He attended Yale, liked America, stayed, worked and built a life for 15 years. I find this reasonable, and consider it unrealistic to expect him to, at any point during that time, to just abandon his current life because he might not be able to stay.
Right, but what happened between 18 and 33. At some point the author must have realized "the system is fucked" but decided (for multiple reasons) to risk continuing to work and live with the US.
It's one thing to attend university for 4 years, get a job and then head home. Quite another thing to base/commit your entire life/career in the US without a clear path to citizenship.
I'm not saying the author should "suck it up" but rather it seems many take this risk, knowing the dangers and therefore shouldn't be surprised or shocked to eventually have to leave (given a gap in employment)
I should add, sad because it is very hard to build and plan a life where you do not know where you will be in 3 or 6 years. For example, why would you try to buy a house if you don't know what will happen? Because of all this I am probably considering to not even bother with H1B.
The GC application should follow the H1B immediately. Don't accept an offer from an employer that cannot promise you that they will do that. Either they don't know what they are doing or they can't imagine you still working there several years later.
Basically, the rule is that your first job after college should be with an employer that will sponsor your green card application. I knew that when I graduated and it was my number one criterion when looking for a job. Most of my foreign-born friends knew it too and they did the same. Most, but not all. The ones who didn't due to naivete, carelessness, or limited job opportunities ran into problems later. You have only 6 years on an H1B and time flies quickly. US society is in general very welcoming to immigrants, especially highly-skilled ones, so it's easy to forget that you are just a guest here subject to the vagaries of the system. Getting the green card should be the absolute priority when selecting an employer, no compromise.
The problem is that you generally don't realize "the system is fucked" until you've spent several years in the system and you suddenly drop into a kafka-esque black hole because someone put one wrong date on a 50 pages filing.
Also due to the duration of time involved changes in the law can both screw you up or make it possible. Can you predict what the legal system will be like 6 years down the road ?
Most people don't plan their lives out like you are suggesting. They take opportunities as they come, and build their life as it comes along. He attended Yale, liked America, stayed, worked and built a life for 15 years. I find this reasonable, and consider it unrealistic to expect him to, at any point during that time, to just abandon his current life because he might not be able to stay.