I don't like to think about it, but I've really had bad professional timing for practically all of my adult life:
1) In college, internships were becoming mandatory, but paid internships weren't yet a thing and so you couldn't afford them unless your family could.
(The work-around then was trying for a handful of national fellowships to fund your internship -- good luck with that.)
2) When I chose between law school and graduate school -- I had actually taken the LSAT -- I decided to go for graduate school if I could get my MA funded, and then after that, I decided to only do a Ph.D. if it was at a top program, because otherwise chances weren't good enough, however:
a) My Ph.D. became very dysfunctional *when* I was there, unnecessarily prolonging degree completion to just an insane degree, even as expenses drastically leapt up in the city that I used to live in;
b) At the time of embarking on that path, you'd have been dumb to plan on an academic job -- that was too uncertain even then -- but there were a number of "off-ramps" to attractive enough industries (academic admin, certain writing teaching jobs, non-profits, editing), but those worsened as possible "Plans B, C, D, E, and F" *while* I was in graduate school, in part of stuff like "rise of the internet" and independent contractor misclassification and stagnancy/depression of wages;
c) My Ph.D. program actively refused to provide internships when it was becoming clear that they were necessary, depriving me of an internship again (I would have done one in comms): and
d) As I was applying around for jobs, corporations began using resume-screening software but no-one knew that they were doing that yet or the work-arounds of super closely matching your language to the job description (here again, they also probably screened me out because I didn't have a recent internship with a super-applicable job title).
3) During the various unionization drives that I was a part of, the major one failed, in part because of a turf war and competing drives that arose between major unions, when I was already in the middle of trying to unionize that vital workplace.
4) When neighbors etc. encouraged me to run for office, the cost estimates that I got through candidate trainings were just on the edge of plausibility, but it turns out that costs like were **doubling** that cycle, and plus a major political actor had pre-determined to push a divisive issue that put me in a hardspot in my district and deprived me of the ability to fundraise from the most motivated parties (since to do that, I'd have to adopt an unpopular issue stance).
5) With choosing to focus on popular writing, venues were slowly decaying, but that went downhill rapidly, and the situation quickly developed where you needed a formal academic affiliation to get the traction that I used to get without one. Also, the book market decayed, where now you need a huge social media presence and to deliver a ready-made audience to a publisher in order to get a contract (a huge job in itself).
6) With eldercare, I was just at the point where I'd put my time in and ready to credential and move up, when the pandemic hit and kept me in low-level lower-wage jobs. Then, when I began to credential after the pandemic, wage inflation destabilized the sector, so I was never able to establish myself or move into higher-paying jobs.
7) With the one EU country where I had a good chance at dual citizenship, their processing times massively slowed down after my application had been submitted, and then their requirements massively changed right in the middle of that, necessitating waiting and then maybe re-applying in the future and in any case hugely reducing my chances and pushing any potential positive response off for like 3-5 years.
. . .
When I've mentioned this just vaguely to people -- for example, my mother -- she says stuff like, "Oh, I went to college for teaching, and then I got out and they didn't need any teachers."
Older generations don't just understand the sheer amount of instability, and the recurring vast time-energy sinks that you put it, for very uncertain and negligible gains.
People also blame you, a lot of times, that you set out on paths blithely or somehow didn't have back-up plans or do due diligence on what was needed and you chances.
As I've increasingly said to or thought about those sorts of people, "I'd like to see you alive now, and giving it a whirl."
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