It seems like you'll never be a female boss enough till you've given birth to kids. At least that's how my family makes me feel, even though I've made a lot of things happen for them that they could have never imagined for themselves. It's so heartbreaking when you're always made to feel like you haven't done enough just because you haven't married someone and started a family with them. And sadly, I'm the kind of person who attaches my own happiness to my parents', and to think they're unhappy with me even after everything I've done is a lot to deal with. Any words of encouragement or a fresh perspective is greatly appreciated!

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What you’re feeling is incredibly valid, and you’re not alone in experiencing this kind of pressure. It’s really unfair when your achievements and the ways you’ve supported your family are overshadowed by expectations that have nothing to do with your worth or success. Being a “boss", in any sense just means leading your own life with strength, compassion, and resilience, and you’ve clearly done that in ways your family may not fully see right now. Remember, your value isn’t defined by marital status or motherhood, but by the impact you make, the kindness you show, and the courage it takes to live authentically. It’s natural to want your parents’ approval, but your happiness and fulfillment matter just as much.

I have never felt this way - I've worked hard, accomplished many impressive things in my personal and professional life, and I'm very proud of what I've achieved. I am a female boss regardless of whether I have kids or not, which I don't. I think this is about your perception of yourself, and internalizing harmful views of what some people expect from you as a woman. If *you* want to get married and have kids, and *you* see that as your biggest life goal and achievement, that's great and you should pursue it. If you have other goals that you feel are as or more important to you, work to be able to separate how others view you and how you view yourself. Your opinion of yourself is more important, and that's what will make you feel whole.

Single, no kids here. My parents haven’t pushed for marriage and kids even though I’m 40 now. (Gulp). But I do know the pain to want to please your parents/happiness is attached to the parents.

So, single female to single female - have they told you are unhappy with you because you aren’t married and have babies? Or are you assuming they are unhappy with you?

While you were growing up, how did they show that they like you and are proud of you? Can you still see that element in your conversations with them now?

Our brains are wired to keep us safe. They aren’t wired for happiness. We have to think about the thoughts we have to see if they are telling us the truth of the situation.

What stands out is how you’ve already accomplished things they could never imagine that speaks volumes about your capability and drive. Yet it’s exhausting when the goalposts keep moving, isn’t it?

I wonder if there’s space to gently separate their definition of fulfillment from yours. Your worth isn’t transactional you don’t owe life milestones to earn their pride. Easier said than done, I know, especially when your happiness feels tied to theirs. But consider: what if honoring your path is honoring them, even if they don’t see it yet?

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