When You’re Successful, But Still Feel Like You’re Disappointing Your Parents

You did what you were supposed to do: You worked hard, you went to school, you built a career, you became independent. Maybe you bought the house, got married, had the kids, started the business, earned the degree. Perhaps you’ve even built a life that looks very different from the one your parents had at your age.

By most measures, you’re doing well.

And yet, when you talk to your parents about your life, you can sometimes feel like you’re still waiting for them to tell you that you’re doing it right. Maybe they don’t actually say they’re disappointed. They may love you deeply, be proud of you, and have sacrificed enormously for you. But you still find yourself second-guessing decisions because you know they wouldn’t make the same ones. (Or, if you’re like me, you come from a culture where parents, especially those who immigrated, don’t make it a habit to tell you they’re proud of you or express much verbal affection at all. But that’s a different story.)

You hesitate before telling them about a relationship, a career decision, a move, or a choice that doesn't fit the life they imagined for you. You hear yourself saying, “I know they just want what’s best for me,” while simultaneously feeling frustrated that what they think is best doesn’t always feel best to you. For adult daughters of immigrants, this can create a particularly complicated relationship with achievement, responsibility, guilt, and independence.

Sometimes the hardest part of becoming your own person isn't figuring out what you want. It's tolerating the possibility that the people you love most may not understand it.

For many children of immigrants, achievement isn't just achievement. It can carry the weight of a family story, of countless generations’ suffering and resilience. Your parents may have left behind familiarity, extended family, language, financial security, professional status, or an entire way of life. They may have worked jobs they were overqualified for. They may have started over. They may have made sacrifices you understood only much later.

You grew up knowing, explicitly or implicitly, that your opportunities mattered. You were expected to do something with them. And I feel I must state, there is nothing inherently unhealthy about that message. Hard work, education, responsibility, and ambition can be meaningful values. The complication comes when achievement becomes intertwined with love, loyalty, and worth, and when succeeding feels like a way of repaying a debt you could never quite finish paying.

Sometimes, making a different choice feels less like making an adult decision and more like disappointing the people who sacrificed for you. This is one reason a woman can be objectively successful and still carry a persistent feeling that she isn't doing enough. The goalpost keeps moving. The degree wasn't enough because now you need the career. The career isn't enough because now you need the promotion. The promotion isn't enough because now you need to buy the house. The house isn't enough because now there's the question of marriage, children, family, or what comes next.

At some point, you may realize that you have become extremely accomplished at answering the question: “What should I do next?”

But you haven't spent nearly as much time asking: “What do I actually want?”

Here lies the conflict between choosing and complying, and the distinction can be surprisingly difficult to recognize. You may genuinely want the career you're in. You may genuinely value family. You may genuinely want a committed relationship. You may genuinely want children. You may genuinely enjoy being successful. The fact that your family also values those things doesn't automatically make your choices inauthentic. The question is what happens when what you want and what is expected of you begin to diverge.

Can you tolerate choosing differently? Can you disappoint someone without immediately assuming you've done something wrong? Can you make a decision that your parents don't understand without spending weeks trying to convince yourself that they're right (or convince them)? Can you say, “This is what works for me,” without needing everyone to agree?

That is where autonomy becomes complicated. Becoming an adult isn't simply about becoming independent. It's about developing the ability to remain connected to the people you love without allowing their approval to determine every decision you make. And that is much harder than it sounds. I’ve been there. And I’m still there in ways!

One of the things that can be confusing about setting boundaries or making independent decisions is the guilt that follows. You tell your mother you can't come home this weekend. You decline a family obligation. You choose a partner your parents wouldn't have chosen for you. You take a job they don't understand. You move farther away. You decide not to have children—or you want children sooner than they think you should. You spend money differently. You prioritize your mental health. Nothing catastrophic has happened. You’re not a bad person, and yet you feel guilty.

It's tempting to assume the guilt means you've crossed a line. But (and you know what’s coming if you know me at all): guilt isn't always an indication that you've done something wrong. Sometimes guilt is the emotional consequence of doing something that conflicts with a role you've occupied for a very long time. If you've learned that being a good daughter means being available, accommodating, grateful, successful, and considerate of everyone else's feelings, then acting differently can feel wrong even when it isn't. This is one reason boundaries can be so difficult.

The boundary itself may be relatively simple. The emotional aftermath isn't. And there is often a lot of competence hiding inside this pattern. You know how to manage things. You know how to anticipate problems. You know how to keep everyone happy. You know how to work hard without complaining. You know how to take care of yourself (typically only literally, not emotionally). And you know how to take care of everyone else, too.

People may describe you as independent. They may not realize how much effort that independence requires. You may have become so accustomed to handling things yourself that asking for help feels uncomfortable. You may have become so good at reading other people's emotions that you notice someone's disappointment before they say anything. Perhaps you automatically adjust your behavior to prevent conflict, throwing yourself into instant self-abandonment. You may find yourself explaining your decisions excessively — not because you need permission, but because you need the other person to understand why you're making them. And you may not realize how much mental energy this takes until you begin to stop doing it.

That's often when the real work begins. Not when you learn how to say no more, but when you learn how to let someone be unhappy with your “no.”

You don't have to reject your family to become your own person. This is where I think the conversation around boundaries can sometimes become too simplistic. You don't necessarily need to cut people off. You don't need to stop caring what your parents think. You don't need to reject your culture or decide that everything you learned growing up was wrong. And you don't need to become someone who never considers anyone else's needs. For many adult daughters of immigrants (or eldest daughters and our other over-functioning sisters who are always welcome in this club), that kind of advice doesn't feel liberating. It feels like another false choice.

The work can be much more subtle. It can mean deciding which parts of your upbringing you genuinely value and which parts you have outgrown. It can mean staying close to your family while allowing yourself to have opinions they don't share. It can mean respecting your parents without treating them as the final authority on your adult life. It can mean understanding that gratitude does not require obedience. And perhaps most importantly, it can mean learning that connection and autonomy are not opposites. You can have both.

What if your parents are disappointed?

This may be the hardest question. Because, I’m holding your hand as I say this, sometimes they will be. Sometimes people we love will genuinely disagree with our choices. They may worry about us. They may criticize us. They may express disappointment. They may need time to adjust to a decision they wouldn't have made themselves. You cannot always prevent that. What you can work on is your relationship with their reaction.

Can you hear their disappointment without immediately abandoning your own position? Can you listen without automatically defending yourself? Can you recognize their fears without making those fears your responsibility? Can you allow them to have their feelings without taking those feelings on as evidence that you've failed?

This doesn't mean becoming cold or dismissive. It means developing enough internal stability to stay connected to yourself when someone else is unhappy with you. That is a very different kind of strength from simply being the person who can handle everything.

I don't think most women in this position actually want to stop caring. They want to stop feeling responsible for everyone else's happiness and stop-second guessing every decision they make. They want to be able to have a different opinion without feeling like a bad daughter. They want to know whether a decision is truly theirs or whether they are still trying to earn approval. They want to be successful because success is meaningful to them, not because it proves they were worth all the sacrifices made on their behalf. And they want to feel like adults in their relationships with their parents.

That can take time. Sometimes it involves grieving the fact that your parents may never completely understand certain parts of your life. Sometimes it involves recognizing that the version of you who was rewarded for being easy, successful, responsible, or accommodating is not the only version of you that deserves a place in your life. And sometimes it means figuring out what you want when nobody else is answering the question for you.

Becoming yourself doesn't have to mean turning your back on where you came from. You can carry your family's values forward while changing the way you live them. You can value hard work without working yourself into the ground. You can value family without being available for everything. You can be grateful without feeling indebted. You can respect your parents without surrendering your adulthood. You can be a loving daughter without making yourself responsible for everyone's feelings. And you can build a life that your parents didn't necessarily envision for you.

For some women, that process begins with a very uncomfortable realization: your life does not have to be a repayment plan.

Your parents' sacrifices can be honored without your entire life being organized around proving that they were worth it. You get to ask what makes your life meaningful. Not what looks impressive or makes everyone comfortable or makes you the person everyone can count on.

What actually feels like yours? That question can be harder to answer than it sounds. But it may be one of the most important questions you ever give yourself permission to ask.

If you're an adult daughter of immigrants who has built a successful life but still finds yourself struggling with guilt, perfectionism, people-pleasing, family expectations, or the difficulty of setting boundaries, therapy can be a place to explore what's underneath those patterns. Therapy can’t make you care less or tell you what decisions to make, but it can certainly help you understand yourself well enough to make those decisions without losing yourself in the process.

With love and hummus, always,
Rosette