I should have seen the handwriting on the wall in ... 1991. I should have pursued a new degree then.
You were in your 30s then? That seems to be a good time for a career change. Beyond that and it's more of an uphill battle.
Yes to the last question, your guess is correct. That's the last window of time in my life I could see that changing careers was feasible and possible with good results.
What prevented me from doing something like that in those days was geek self-image. I was committed to proving I could have made a go of things. The IT and SW dev field heated up for a few years after that and I did barely alright.
In the broader view I should have recognized at that time (1990-95ish) that the hot hiring I experienced fresh out of school wasn't coming back.
I got into IT via telecom in the early 90s just before the Internet exploded as a programmer. I was not even in it for 3 years and I wanted out. I freaking hated corporate America. And the field was not what I expected. I even contemplated going back to school to study what I had originally been interested in which was art/animation.
The problem was that I was making a lot of money at that time for my age. My parents would have been mortified, I just got out of school and wanted to quit. Coming from a poor background I sucked it up because of the $$.
As the late 90s were winding down I remember reading this article in Infoword about the H1B and what it was. It dawned on me that I was about to be competing with Inda and China for work. Needless to say I transitioned out of pure hands on IT work and focused on project management, business analysis and architecture.
So the dot com hit and salaries went bananas. Many people I knew left to work in the dot com. They made FAT, FAT money even by todays standards. I stayed put because in my poor brain - a bird in the hand was worth two in the bush. In the end not a single one became a millionaire. Many were made unemployed and had to scramble to find a job. Some got out of IT totally.
In 2001 I got laid off for the first time. Dot com had imploded and there were tons of IT people out on the street. I seriously thought about getting out of IT totally. I was late 30s at the time. But what? I thought about finance, accounting and marketing. But I realized those people were just as miserable as IT people. So I took some plumbing classes at the community college. I was seriously thinking about getting out of IT again.
I was only out about 3 months and found a job as a project manager on Wall Street. I have been doing project management ever since. My first job out of telecom was on Wall Street, boy was that a rude awakening. You know that movie Wall Street? It was real! Gordon Gecko was not a figment of someones imagination.
Than I got laid off from there and I was determined not to go back to telecom. I wanted to broaden my background in other industries to make myself more versatile. I ended up in a pharma company doing a variety of things as a contractor. That lasted for a while and the contract dried up.
Than I went back to telecom doing something totally different. I was doing IT cost reduction and IT procurement. I really liked that job as my focus was on saving money. Did that for about 3-4 years till the contract ran dry.
Than I went to an insurance company doing IT procurement. Did that for a few years and than transitioned back to a more hands on role. I was doing performance monitoring. Absolutely hated the work and the company. Than I got laid off just before I vested.
Job market was eh but I was offered two jobs from totally different industries - one was financial services, the other was pharma. Financial services paid more but I really wanted to get into pharma. I chose pharma as there are tons of drug companies here and its an extremely incestuous industry. Unless you have pharma experience they wont talk to you. . It worked out for me as I ended up working on some cutting edge stuff and still am in it.
Maybe because I came from a poor background but when things happened I always viewed it as an opportunity to make a change and take advantage of the situation. I guess thats the key - know when to kick and when to stick as they say in football.