I have difficulty saying no sometimes... for those who are attributing having trouble saying no only to being a coward and/or a liar, maybe I can present a different perspective.
I have trouble saying no in people-situations primarily because I get enjoyment out of making others happy, and feel displeased when others are disappointed for what I see as legitimate reasons. So it often comes down to choosing between taking care of myself, which potentially involves boring maintenance tasks, or contributing to someone else's happiness, which is fun and pleasing. Sp-last probs.
I also feel responsibility for not ditching commitments I have made, or leaving others in a lurch. For example, I recently have gotten a new standard-hours job, and am leaving the job where I used to work non-standard shifts with a sweet disabled man and his generous family. I could have left them after two weeks, but instead opted to stay on for longer, because I know that it is a long and sometimes difficult process to find a new caregiver who is both skilled and whose personality meshes well with the man and his family's. I had not intended to leave the job so soon, and had voiced to the family when I was hired that I was planning to stay on for at least a year. I still took the other job out of respecting my own needs, but I felt better about doing more than the minimum because the man and his family are good, kind people who have been respectful and affectionate towards me. So, in this case, while it would have been nice to have less than a 62-hour workweek, I would rather help the family have an easy transition than to be sitting at home relaxing but knowing that I might have contributed to a difficult time in their lives.
It often just comes down to having a choice between two pleasing options. Being guilt-tripped just makes me avoidant of that person, so it's not like I'm constantly caving against my own will. I just get a large amount of genuine enjoyment out of contributing to others' wellbeing.
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Complexity, what I hear out of reading your posts is that you place high value on your relationships and you desire to make those people feel good and you're wanting to live up to their expectations. I assume you probably get enjoyment, as do I, out of making others proud of you. If that's true, it's not necessarily a bad thing. It sounds like you're a a loyal friend and daughter, and you probably do a lot to make them feel fulfilled.
For a long time, I wanted to become a physician, not just because female doctors were my role models growing up, but also because I wanted a way to make my parents, especially my dad (who is sometimes hard to relate with), proud. Recently I had a realization and change of heart and decided to walk a different career path, and to my surprise, my dad found common ground with me there, and I've realized that my parents are basically always proud of anything I succeed at, even if it's not what they'd envisioned or planned.
I think that it's hard sometimes to go outside of the expectations of the people who are most important to us, but I think deep down, they just want us to be happy and healthy. I think people tend to get set notions of what would make for a happy and healthy life - like marriage or avoiding entrepreneurship- and discourage us, because they care about us, from other paths. But to some extent it will be an unhappy prison if you don't allow yourself to blossom outside of others' expectations, and I think you will find that, if you are able to craft a happy and healthy life, that your parents will adjust to understanding what it is that makes a good life
for you, even if that means rethinking their visions of what your life "should" be like.