45f divorced 2022, one minor child graduating high school next year. Current job has no health insurance or retirement benefits. I recently started my own ROTH 401k and signed up for my own healthcare. I currently work two jobs one full time in an office (guaranteed but low dollar amount paycheck) and one as a fee for service (not guaranteed but high dollar amount paycheck). I currently reside in the rental home of the Low paying jobs owner, so the census is if I quit I am also looking for a place to reside with rent prices and availability this is quite challenging. The second job literally has the potential to make double for the same working hours allowing me more financial freedom and lifestyle freedom as I can make my own schedule. However it is not guaranteed income. I have no friends or family so I really struggle with this choice. Thanks for your input.

4 comments
  1. Personally, I’d be looking for a way to get a more secure housing option that wouldn’t be undermined by your boss and then keep the higher paying job (assuming you like that and can be successful at it.)

  2. I wouldn’t want a housing scenario where it’s tied to a boss. I would try to leave that as soon as possible, as that could go south at any time.

  3. You need to be looking for a good-paying guaranteed job with benefits. In the meanwhile you should milk both cows (including your boss’s housing situation) until they are dry, but not until they are dead

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