Just to get the ball rolling.
There’s a concept known as SMART planning. When creating a workable action plan, one should come up with steps that are Specific, Measurable, Attainable or Actionable, Realistic, Time-based.
That’s just apropos of planning actions in general. You want to break a large goal down into steps that are right at the border between easy and challenging.
So you create a hierarchy of difficulty, 10 at the top down to 1 at the bottom.
Next to 10, you might put: standing my ground and actively pushing for my position in the face of a large group of dominant people in an unstructured situation. That’s probably as tough as it gets.
Then at 9, something slightly less challenging.
All the way down to 1, an act of assertiveness that feels easy and comfortable for you. Walking your dog, maybe? Or ordering your food from a friendly waiter in a restaurant. Something like that.
Then you push yourself to work out with actions at about level 3 or level 2 difficulty. As you practice, you’ll get better at it and what used to be level 5 will become a level 4 or level 3 difficulty.
Just like weight-training, don’t lift at your max. Workout at between 30% and 70% of your 1-rep max, to avoid injury and discouraging setbacks.
This is one approach to systematically attack it. There are other ways too.
Sold.