I feel like I've been along for the ride for a reasonable amount of that journey.
I've always stayed for the long term in roles I've had.
First job out of uni 6 years. Second job, 8 years. Third 7 years.
Then I worked with / for my wife in the family business for 8 years.
And now back in software for almost 2, with no plans to move on.
Each role - including our family business - has had pluses and minuses.
I've generally been able to carve out a place that suited me, worked with good people (only 2 I can think of I did not like), had interesting projects including building a full service credit card platform that connected directly to MasterCard. Nearly all my "bosses" were either good people, good managers, left me to do what I was good at, or a combination of all 3.
I'm not the greatest IT worker, by any stretch. But I am able to solve problems others often can't, with solutions that are as simple as possible.
When I think about my career, I consider myself lucky. But was that all there was to it?
Did I end up working for good people because they connected with me well in interviews & early in my tenure at a company?
Was it that the interviewers were able to see my ability to both think and stick with a problem until it was solved / completed?
I'm on the fence right now, but maybe it's time to ask the questions?
I only have maybe 15 years left in my career. It may be time to find out a little more about why & what other people think.