I am experiencing feeling depressed (quality: feelings of despair, feelings of worthlessness, feeling smothered), trouble sleeping (worsened by: psychological stress, varying sleep schedule) (quality: difficulty staying asleep, difficulty falling asleep

Evaluation. You are describing trypical symptoms of depression, which is a fairly miserable state, but which usually can be helped significantly. It is unclear which kind of help would be most useful for you: options are various kinds of psychtherapy, and medications, assuming your feeling persists and is not just a temporary reaction to something. It would be prudent to seek a full professional evaluation.