How to be more Confident/Less Passive

Im sure there’s 1000 posts like this but I used to NEVER be passive or indifferent. Up until I was 21 I had not even the slightest hint of anxiety. However, I also used to have addiction problems and was generally a toxic male who got into a lot of fights. Keep in mind that this never affected my love life and I never had issues with finding female partners, just keeping them because I was such an ass. I was very confident in myself and was in great shape. Im now 28 and have been clean and sober for a very long time and have since turned my entire life around, however now I constantly second guessing what I say, have constant anxiety, and am indifferent to most thongs. It’s hard to keep a conversation and I’m adverse to asking requests at work for fear of bothering people even when to NOT ask that request is going to cause an issue. I dont necessarily feel helpless but even if im internally confident it doesn’t translate to the real world and I’m kind of at a loss. I have an amazing fiancee who reassures me that I’m awesome but I feel not so much almost daily and I dont know if its all in my head or what to do. It may just be trauma from when I caused so many issues to people around me in the past, but im not sure. Any ideas of what could help? I try to meditate daily and although I havent started working out again I plan to. But im still not sure if it will help.