I don't regret it. But I do miss it some. I still have a passion for creating in general, but anything technology related is even better. In particular software. So I think that answers the last questions.
Though I want to make an extra point here. As I'm sure many will probably point out. At least most of my friends and family have. I know that I can find jobs as a remote employee. This is not my point. I chose to leave a good full time job, simply because I do not want this type of life anymore. Doing it remotely is not going to change the deadlines and working 40+ hours. The type of life I'm trying to set up is a life of more time to actually enjoy my life. Not spend it behind a computer or any other type of work. There are numerous other things I'm trying to do to make income. Blogs, Vlogs, affiliate marketing, etc. Those will all take time as well, yes. But when it is a result of capturing the content of my travels I am going to capture anyways. Why not make some money off of it. Also, you have to keep in mind, I have sold all of my belongings and have no debt (which I am very fortunate and thankful for) but my cost of living is significantly lower to where I do not have to make as much. Plus most other countries I'm visiting things are much cheaper than in the US. So in summary, need less income, lower my spending, find ways to make tiny fortunes off of results of things I am already doing.
It is a process, and still takes time upfront. My hope is that I can find a happy work life balance. It can work, I have already met many people that are doing these exact things and it is working for them. And if it does not work out for me, the IT industry is not going anywhere. There will be a slight adjustment getting back into the swing of things. But it is not an impossible task.