I think that you might want to re-think and/or get in touch with the bolded because either
A) you are lying to yourself and the need to do better, prevent problems, and/or be seen as the one with the answers. I get where you are coming from, and sometimes think I'd just like a no-stress job like that, but I suspect that I would need to figure out a way to do better at janitoring and how to make the janitoring better for the company and before I know it, I'd be back in the same place
OR
B) you are more beholden to the money and feel the need to validate that (through expensive purchases as alluded to above) and that compulsion is what drives you and as you move up, I assume it is harder to obtain marginal increases in lifestyle that create absolute pleasure. Kind of like that graph that shows the correlation between happiness and income rises to a certain point and then flattens or drops.
I get what it is like to be worrying. I think I used to be a victim of catastrophic thinking, continually strategizing to prevent problems everywhere (at home, at work, maximizing free time, maximizing outcomes of hobbies). I needed to prevent terrible things from happening and I also would re-live prior decisions to determine if they were optimal. In the end again, the marginal impact that can be had by this continual strategizing and re-calibration is minimal. Good things will happen, bad things will happen. The amount of control that we have over when and how they happen them is really quite small. I guess about 4 or 5 years ago, I read The Black Swan, and Taleb's example of the turkey before thanksgiving got me to start shifting my thinking (which has been a long process).
“Consider a turkey that is fed every day,” Taleb writes. “Every single feeding will firm up the bird’s belief that it is the general rule of life to be fed every day by friendly members of the human race ‘looking out for its best interests,’ as a politician would say. “On the afternoon of the Wednesday before Thanksgiving, something unexpected will happen to the turkey. It will incur a revision of belief.”
https://hedgenordic.com/2015/11/the-thanksgiving-turkey-black-swan-dilemma/
Today could be good or today could be bad. A future day could be good and a future day could be bad. I would say that bigbottom's idea of compartmentalizing and djmich's idea of being present are sort of 2 sides of the same coin. I would say be here now and eat it all (as Ram Dass says). I think that compartmentalizing is an operational strategy, while being present is more of a guiding life force. Be here now and stay focused on what is happening in the moment. Eat it all and recognize that there is good and bad and that we will all experience all of those things, and without one, we couldn't have the other and it is all part of the life experience.
I also think that what kutta said about working hard to provide for your family should and can be a source of joy. Feel happy and proud for what you can give them. Remind yourself that your actions can translate to goodness for them. But don't lose sight of the fact that what they probably what most is for you to be present and respond to their needs as they change and arise. They would probably be a lot happier overall with a hug or a compliment than a new pair of shoes (even though I know in the moment they will even say otherwise, especially the kids)
I didn't mean for this to get to preachy or new age-y. I guess I'm just seeing the places where these issues have intersected in my own life and the way that I have tried to deal with that.