I am in my 60’s and took a contract position with a woman I have known for over 20 years at her marketing agency. I had hoped this would be my last job prior to retirement. The work and money for the first year were great. As time went on, it became clear why her 10+ year company had not grown. Her strengths are in her initial sales ability and creativity, not in her business acumen.
To make a long story short, it’s been three years now. She made some poor business decisions and lost some significant money. While my work has reduced significantly my last six-figure project was very profitable. At a team meeting in early January, she informed everyone she was pivoting her business away from my preferred work. I followed up with her, suggesting I continue it, assuming more business risk. (She has many ins with corporate procurement teams which often takes years to set up.) I provided her with some initial terms to which she countered with an unrealistic proposal. The next thing I know, she shuts down my email (on her domain) and is accusing me of lying and hiding a new proposal. (Not true I had cc’d her on it.)
Here’s my big dilemma. She owes me approximately $20,000. She has never severed our relationship but continues to pretend to want to negotiate an agreement. She is moving ahead with the proposal I negotiated. I know she has some income, but I also know she owes a lot. Small claims court is only $10k, do I give up half my income and take her to court? If I win it still doesn’t guarantee I get paid. Do I threaten to expose her to her corporate clients? I wouldn’t actually do that, I would just look bitter, but should I threaten it? If it’s even possible to get an interview for a “real job” what do I say to prospective employers about the last three years, especially if they ask for a reference? Any advice would be appreciated!