I can give an anecdotal answer to this. One thing I despise is pushing people into "boxes" but for this answer I will have to do that. My older brother and I throughout our lives have always gotten into many fights (as children do) and one thing that I noticed as that he never apologizes, and never feels bad for me after our fight is over. I on the other hand immediately feel horrible, and apologize immediately. Similarly this has translated throughout much of my life. Whenever it comes to having tough conversations, by brother would always be able to and not feel sympathy and in the end get what he wants. Me on the other hand, always ends up compromising for the goal of the other person being happy.
Throughout my life the thing that I have learned, is that you have to be able to either feel that the thing you are saying will help the other person hence the need for no sympathy, or embrace the fact that you are difficult at being unsympathetic and cultivate an environment around you that appreciates sympathy, but also understands the requirement for understanding.
Checklists are both good and bad depending on how you look at it. They allow you to focus more on the task at hand as you are not focusing on the mulitple tasks required for you to do. Many productivity gurus speak about the reasons of success when it comes to checklists. Psychologically the main reason is that your brain delivers a boost of dopamine when you complete a task. Now as anything can, you can become addicted to this dopamine and hence when you complete a task without crossing something off of your checklist you won't feel as good as you would with one. Is it a serious addiction? Definitely not, but it is something to consider.
No matter how many software tools I bounce around for my whole life, nothing can beat Vim as my text editor and zsh (or even bash) as the terminal. Sadly enough, my life began on MacOS (now I mainly use Arch) but I still have almost every keyboard shortcut, a deep knowledge of AppleScript and all the other small quirks of the OS in the back of my mind. The best way to learn how to use an OS is to want to do something that you aren't allowed to do on it without doing a little bit of secret tinkering ;)
Throughout my life the thing that I have learned, is that you have to be able to either feel that the thing you are saying will help the other person hence the need for no sympathy, or embrace the fact that you are difficult at being unsympathetic and cultivate an environment around you that appreciates sympathy, but also understands the requirement for understanding.