You and I have had very similar career experiences.
I started working in high school and built a reputation for being a reliable and capable employee. I was able to work my way up through promotions. I'm in my mid-forties and can count on one hand the number of jobs I've had in my life. I've always made well above minimum wage. I have never been at a job for less than a year. I also, with the exception of 1, have never been turned down for a job for which I have applied.
My first big hit financially was student loans and credit cards. I was too young to be given that temptation and ran up debt pretty early in college. Looking back on it now, it doesn't seem that bad, but it set me up for some not-so-good habits/susceptibility to temptation. Once you start using credit cards it's easier to continue.
The second hit I took, and I would never place the blame completely on another person, was getting married. It's a whole lot easier to manage your own finances without needing to consider the feelings, opinions and needs of other people. Then the kids come and the expenses of a full blown family. I've been simmering in debt and expense for a while and need to get a handle on it. I think the family is finally on board with the austerity needs to happen. It was a long time coming.
So, now that we feel like we can move forward we're planning out the paying off of debt and reducing expenses. But I know that's not enough especially this late in the game of life. There has to be more investment and the lottery is too hit or miss.... mostly miss.
My real interest is in what strategies with saving and investing you used and possibly what investment vehicles worked best for you. My dad did something similar to what we're talking about but he had some avenues available to him that are no longer good options. So, I try to get lots of different perspectives and strategies. It sounds macabre, but our current best realistic chance for financial security are the deaths of our parents and the inheritance we'll get from that which will be helpful in the short term, but will still fall short. :-/