if the reason to study is for building future technology app that uses machine learning for some of its features- dont.
there enough 3rd party libraries that do that or people to hire that can do that for you.
if you aim to be entrepenuer focus on learning how to build succesful products, then do it
Thank you! very interesting advice!
How do i do that?
You can start by reading “the lean startup” of eric ries he explain the whole methodology
THank you once again!!
There is a lot of wisdom in this thread.
From what you’ve posted initially, I see self-doubt, legitimate concerns, and forgetfulness.
I think the first 2 are obvious so I’ll explain what I mean by forgetfulness.
Have you forgotten the times you’ve managed to do something great, yet you are still just like everyone else?
You may be one of the many IT people out there, but how is it you become great?
You become more skilled. More innovative. More determined. You also improve your ability to manifest outcomes of your own choosing, as well as develop more faith in yourself. You develop a network.
You have access to the power of your subconscious, which I think is even more powerful than being the smartest person. Inner Circle. Index Gate. All those manifesting modules. RICH. Power Can Corrupt. Manipulus. Quantum Limitless. How about healing modules?
From my perspective, I think the only option for you is success in what you choose.
Age is no barrier !! 27, 37, 47, 57 !
And remember that even if you personally don’t master it, you will still have an understanding what it can be used for.
Once you have a business that uses machine learning/AI/ whatever, you will be able to tell your staff better what to do. If you do not understand the topic at all, it’s difficult to lead them.
Even if you “fail”, you succeed 
Just throwing out this idea: offer to work a higher job you are not 'qualified for ’ for free for a trial period. You learn and get experience either way in the kind of work you’d want to be doing and you can get close to people there, build connections and potentially have an in if they like the work you do. Obviously you’d need to still have savings to do this but might be worth it.
Basically: If there is a will, there’s a way.
@mecharc I’m sure you can find a way to get a job when you put your mind into it. Think outside the box as @Azriel showed.
@mecharc Hoppa just pointed out an important point. Rather than you being the IT person, you can hire IT people. This is the difference in thinking like an employee or consultant, to thinking like a business owner.
This is who I am, the owner.
I’m not interested in mastering anything myself. Frankly, too much work and I will get bored too fast to do that anyway.
I just want to know enough, so that I can make other people and systems work for me.
I was talking about this topic with my wife on a video call a couple of weeks ago.
She said: Yes, you are the boss.
My answer to that was: Naah, I’m not a boss. I’m the owner who tells the bosses what they need to get done.