I've also had immense luck - I've been a computer nerd for a very long time and I was programming a lot in my field (neuroscience). So all it took was a word from one guy I knew at a big software company and I was hired. I also have to say, that a PhD, or better said, a Dr. in my country still means something, especially if you have customer contact.
But I've seen things... bright people in their 40s who have to drop out in their 40s to be hired as a labor assistent at pharma. Associate professors who would run out of money and that's the end of the career. Doing a PhD was easily the dumbest and most risky decision of my life and I was extremely lucky to get away with only some mental scars. The only positive things I can think is the friendship with other PhD students (because you went through hell together!) and the confidence in my abitity to process and dissect huge piles of information. In the end, the latter is sole reason companies are willing to give you a shot. Dont undervalue it and sell it accordingly. If you have a PhD you most likely are very persistant and very capable of self-learning.
I met one person at my Master's degree lab who went on to PhD, he said his childhood dream was to be a professor (and his father was a professor). I also have a father that is a professor (and have been very curious about PhD - although that window is getting narrower as I'm getting closer to 30:s) but he have multiple times told me that "it's not worth it", "it's a waste of time, the opportunity cost lost is too high", yet in my field I often see job post that requires a PhD, so I get mixed signals.
Going from PhD to Prof though, is a difficult, unlikely path of awkward postings: for every 100 PhDs expect ~1 successful academic. Oh, and once you are a professor, expect a salary....less than that you'd get in a starting job straight out of your PhD.
Bluntly, if your goal is to become a professor, don't. With 99.99% certainty, you will not become a professor and the opportunity cost is extremely high.
Almost nobody with a PhD who dreams of being a professor ever actually gets to be. Most quit or only ever become adjuncts, and, in the US at least, adjuncts earn less than minimum wage and get zero respect from anyone. Most likely you will be abused by institution after institution who will keep telling you how important your dream is while stringing you along and paying you next to nothing. Or you will quit. Or you will have a mental breakdown.
If you can see yourself being happy doing literally anything else, do literally anything else. If you can't see yourself being happy doing literally anything else, spend some more time thinking about it.
If you're independently wealthy and don't really need to succeed at the goal to live a happy life of luxury, then definitely go for it.
I can relate, as this basically describes me - though I've been lucky enough to find bare programing jobs that I quite like doing.
One of the toughest things about leaving academia is discovering that (i) no-one who doesn't have a PhD has any clue what a PhD is and (ii) everyone who has a PhD has a healthy disregard for the intellectual capacities of their fellow doctors.
Last month we helped clean the room of a colleague after he "passed away" after 10 years of post doc.
Another colleague got a job at 36 as a bare programmer after a very successful PhD where he wrote books and was invited to conferences. At 40 he rage quit this job after a bout of frustration and we haven't heard from him since.
Luckily they didn't have kids. Wouldn't I have kids I would definitely follow their path.