This is a good question, because in the modern world, we mostly create benefit by using our minds, and most people cannot simply become immersed in traditional mindfulness practices and retreat situations most of the time. We need to discover the "one mind" in our little minds, while minding what we do, without minding what happens along the way. Mind you, this is a lot to ask.
I was a programmer for 12 years, creating complex things that got used commercially. I am familiar with frustration, and elation. Now I teach programming to adults making a career change, and I tell that that programming is frustrating! But, as my Guru says, "There is no 'problem'. We are the problem." You are frustrated. As you say, there is observation of this fact. With observation and reflection come the possibility of awareness and knowledge. So you are on the right track.
It might seem that using the mind to create mental models and concepts (such as in programming) is somehow more ensnaring than other types of work. Perhaps. But if your observer sits with you and helps you remain connected inwardly, then this gets better. There is no fundamental obstacle to conceptual work being also mindful. Eventually, your observer has done a good enough job and dissolves. Then there is no one to get ensnared, frustrated, or wonder if it is being done correctly. (This is nonduality.)
For your other question, deciding what is best to do, how to balance work, practice, rest, etc: that is more practice. Make a decision, observe what happens, reflect. There is no way out of this, it is how life is. Good luck!
ADDITION: Whew, this is a thicket if I ever saw one. Related questions about Mindfulness and so on swirling like a storm of words... Here is how I experience all of this, if it does not clear it up for you, perhaps your mind simply functions differently than mine.
My consciousness is a collection of points of view. I see the functioning of the mind as a bunch of "bubbles of awareness" of varying sizes, more or less known to me at any given time. In an alpha state, or perhaps a nondual state, it feels as though my entire consciousness is a single, silent point of view, but of course small bubbles are constantly arising below awareness and causing small effects, which might grow and distract me again. One cannot live one's life in an alpha state! My model of multiple points of awareness in the mind has scientific backing, but I came to it from my own experience.
My mind includes 4 past life personalities (which I no longer have a view on whether they are "true" or not, they are relics of earlier in my life). A few years ago, I created about 5 "personality facets", based on my understanding of the Archetypes, in an attempt to develop more areas of my abilities. I have other experiences of "voices" and things going on inside that I will not attempt to categorize. To me, all of this is just the simple functioning of a creative mind. We can model other minds, so it is obvious that we can model and construct personalities in our own minds. This is the basis for part of Transpersonal Psychology. (I found out about that long after I created my facets.) Also, I have one "Accompanying Voice" which I do not see as part of myself at all. I learned what it was once, but the understanding was so powerful that my mind halted and rejected it. (So I can't tell you what it is.) My facets and past lives comment on my life, have emotional reactions (often two or more of them at once), converse with each other, paint, write books and do other things. It is like living in a busy household. This is my normal state. Everyone I have described it to understands and finds me sane, although different from themselves. I call it, being a Creative Person.
I have long thought of my mind as my "experimental laboratory": I get to try things out and see how they work. When we come to questions like "who is watching the watcher" etc, I see these as just silly. Consciousness is "whatever it does" and does not need a definition from us. However, it did not come with an Owner's Manual, so we need to discover how it works as best we can and learn how not to fall in to error. Some ideas are approximations, some are tools, some are crutches, and many are crippling.
Krishnamurti's Master when he was a boy said: "You are not your mind, but it is yours to use." Have fun!