If your W suffers from self-esteem, just make a note of it. The only person who can work out her self-esteem issues is herself.
If she wants to get a job, then be encouraging, but don't go overboard with the help. The problem is that she will cycle through waves in which she'll be excited about something one minute, then look for something else the next.
AND THAT is the point you have to understand. Self-esteem is being happy and content with who you are on the inside and not looking for an external stimulus to make you happy. It's why your W went looking for another man. If she wants to increase her self-esteem, she needs to realize (on her own) that nothing and no one will make her "feel" happy but herself.
That's why it's not your job to make her happy. Don't tell her what she should or shouldn't be doing or what she should look for, etc. Just encourage and validate. Let her do the talking.
M-43 W-40 2D - 9 and 5
Emotion, yet peace. Ignorance, yet knowledge. Passion, yet serenity. Chaos, yet harmony. Death, yet a new life.