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I feel pretty strongly that massage should not hurt. It is true that when you are first working ischemic muscle it may be a little tender but I would describe it as a "good hurt" in the sense of...if it were me I would be aware of the tender sensation and I would not want it to stop because it feels relieving and I can relax through it. I feel that if it just plain hurts and the client cannot relax then there is no reflexive benefit to the massage and the therapist is missing the mark.
Further, deep tissue does not necessarily mean heavy pressure. Deep tissue refers to the manipulation of deeper tissues which sometimes can be done with moderate, comfortable pressure. I think when it comes down to it the most wonderful thing we can give our clients is relaxation and a balance effect in the nervous and endocrine systems. When their muscles are re-oxygenated and ROM is improved that's a bonus :)