I have learned a lot about setting and enforcing boundaries with people. I believe that it’s much like a muscle — the more you practice it, the stronger you will become. And the more confident and comfortable you will be while doing it. One way to enforce strong boundaries is not to dilute your “no”. If you say you will not do something, stick to it. For example, I worked with a woman once (Kim) who claimed she does not work Tuesdays because that is the only day she had to spend with her son. He was a college student with a very busy class schedule who was also interning. Another coworker asked her to switch shifts and work Tuesday so that she could celebrate her wedding anniversary with her husband. Kim asked me for advice about whether she should make an exception just this once. I told her, if you agree to this, expect to be asked again. You will have diluted your “no” and shown that, despite your claims, you are in fact willing to work Tuesdays. After saying “yes” once, that boundary will be compromised and weakened, and it will be easier for others to ask you a second time. This principle can be applied to many situations, with coworkers, friends, and family. On the contrary, sticking to what you say and refusing to compromise that stance even once will more than likely result in your never being asked again. Saying “no” the first time will be uncomfortable and feel adversarial, but it will be much, much harder to say “no” after having already said “ yes”. Saying “no” the first time leads to less wiggle room for arguments. If you have said “yes” before, it will be much harder to justify saying “no” the second time you are asked. Also, if you never budge your boundaries and always stand by what you’ve said and don’t make exceptions, there is less chance of others getting their feelings hurt over perceived unfairness. Ultimately, you want your words to be taken seriously and at face-value by others. This will lead to a greater level of respect and understanding.