I've struggled in the area of assertiveness even after 28 yrs sobriety! For me I had to learn some hard lessons in being assertive in that when I was assertive and thought I was being assertive in getting what I want and thought it was only right for standing up for myself, I only discovered later on that I was only doing self-will, which in turn led to some unhappiness!
Now if it's for standing up for an unjust situation, then yes, I will be assertive! Such as there were a handful of times where my employers were jipping me out of pay; such as not paying me for the hours that I worked! Yes I went to the supervisor and addressed it! But then they just make the next chess move and cut my hours by a few hours! So its back to square one! I'm not making any more anyways! That's when I realized the world really has the power to kill and that everyone else has a self-will and is also assertive!
Another time I had conflict with my son! It was about me being assertive and telling him to lock the doors after he comes in the house! I would check the doors at night in the house and they were unlocked! I figured, 'I'll be assertive and tell him, son, please lock these doors after you come into the house!" Only to that leading to a big argument and my other son calling the police and making me look like the bad guy!
Another time before my mom died I had a close relationship with her! We talked everyday and told each other we loved each other as mother and son! Many times she would call me and tell me how much she loved me and that she knew she doesn't have much time to live cause she was really sick in her last days! Only to have my two vicious sisters not liking that and putting her cell phone to block my calls! And when I became assertive and told my mom how cruel that was, by that time it was too late! My sisters had brainwashed my mom into going against me cause she was too weak to stand up for herself!
Just a few examples! I've been through some hellish moments on jobs, relationships, finances....about every area in life! All while being sober for 28 yrs! That's when I realized how cruel life can be - even when I'm sober!
I think the only thing that saves me and my sobriety during these moments where I'm assertive and it still seems like it's a mess is saying: I'm an alcoholic, and I'm putting this situation in your hands God! It's the only way I've found that gets me through!