I'd like to get opinions on whether going back to programming as a career in my late 30s is a good idea or not.
I was a web programmer in the first four years of my career; however then I thought I could make more money doing things like project management and spent the next ten years pushing paper.
I've done a couple of side projects in the meantime as the thought of going back to programming has kept coming back. I even attempted to do a SaaS startup but failed to get any traction.
Anyways, at this point I'm sick of pushing paper and want to go programming full-time. A few things are holding me back though:
* I can't leverage the last 10 years of my career; it would basically become a lost decade for me
* my technical skills are rusty; I'd have to most likely get a huge pay cut and start at a junior-level position
* I think recruiters are going to give me a weird look, meaning I'd most likely have to overcome additional barriers when seeking a job
So far all of the above is speculation on my part as I really don't know what I would be getting into. I'd appreciate honest opinions going either way as I have to choose my moves wisely, having a family and all.
What do you want, to make a lot of money or to write code?
Then you wrote: "I can't leverage the last 10 years of my career; it would basically become a lost decade for me."
What have you lost (other than time?) are you concerned again that its the money that you're not going to make?
The point I'm trying to get to here is that you are at a pretty critical point in your life. You've got a solid 20 years of 'job' ahead of you, and you're about to turn 40. You are looking back at your previous 10 years as a "lost decade" which suggests you've made some internal value judgement that those years were wasted? (or only wasted with respect to getting a programming job now?)
Here is the thing, you made that choice 10 years ago because you wanted more money. It does not seem like it worked out for you. Consider using a different algorithm for making the next choice. Maybe spend time figuring out what you want to do, leaving money out of the picture for now, and see what answer pops out?
Is it programming? You can test that while in your current 'day job' by doing it in the evenings and on weekends. There are projects from operating systems to data bases to web infrastructure out there, pretty much any programming 'task' can be done in the open source world.
Now after doing that for six months, are you racing home to work on your project? Or are you sad because its your "second job, the one without pay" that you do after you leave your main job? That is a good litmus test for what the next 10 years might feel like.
Of course if you have steady work, and you want to change, I suggest you try a number of things until you find the one that you want to do even if they don't pay you.
The "1%" are called that because they aren't most of us. Most of us spend our lives living and working and then eventually dying. We cannot escape death, but we can choose how we live. You're going to spend a lot of time doing what ever it is you choose to do for "work", and so when you look back at that if it was "good times" you will be happy, if it was "a treadmill" you will be sad. Choice is up to you.