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Home » I’m the First in My Family to Succeed — and I Feel Guilty
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I’m the First in My Family to Succeed — and I Feel Guilty

arthursheikin@gmail.comBy arthursheikin@gmail.comOctober 5, 2025No Comments4 Mins Read
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I was lying under a cabana in Playa del Carmen, Mexico, working on my computer. My two children were playing in the sand 10 feet away from me. It was at that moment that I realized that I had “made it.”

An overwhelming sense of pride swelled inside me, but almost immediately, it was followed by guilt. I was proud of everything that I had accomplished, but I felt guilty about surpassing my family.

Being the first in anything is a huge accomplishment, but it comes with responsibilities that are often invisible. I’m trying to move past these difficult feelings.

My education and entrepreneurial journey

Growing up as a first-generation American and as a daughter of an educator, college was a requirement. I started with an associate degree, but when I completed my master’s degree as a salutatorian, I felt a deeper sense of achievement.

Even while in school, I had an entrepreneurial spirit. I started a tutoring company, which laid the groundwork for what was to come next. After graduation, I founded Infusion Enterprises, a marketing agency, and today, I’m running a tech startup called 4kiddos.

As the daughter of a teacher and a hospital tech, I did not have a model for entrepreneurship. If you looked up trial and error in the dictionary, you would find my picture. Every milestone was built from scratch without a blueprint to follow.

The invisible weight of being first

Sometimes, I feel like I am the goal itself, setting the bar for what is possible in my family. But have I set the bar too high?

I’m also feeling the guilt of achieving more than all my family members. It feels like I’m leaving some of them behind — even though I know I’m not.

It’s tough to be a leader when there is no safety net. I wasn’t born into generational wealth or with a silver spoon. If I failed, there was nothing to fall back on.

I used to quietly grieve for what I did not have, such as a financial cushion, family business connections, and a road map. But that grief fueled my ambition. It made me driven, resourceful, and yes, sometimes a perfectionist.

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It doesn’t stop there. As a mom, I feel guilty about not spending enough time with my kids. As a daughter, I worry about creating a legacy for the family name. For myself, I constantly feel like I am neglecting my own self-care.

Motherhood and building a new blueprint

Now I am both a mother and a business owner. My children hear my calls, see me in meetings, and watch me work late nights. They know I am building something bigger than myself.

It inspires them. My son has told me he wants to start a business. I feel proud knowing I can provide them with the direction and support that I never received.

Still, the guilt lingers. I wonder if I’m doing enough for my kids. I often feel out of place in my family. They know I am always doing something different, and sometimes they think I am doing too much. But I cannot rest until I provide my kids with the foundation that wasn’t given to me.

Breaking cycles while healing

I want it to be clear that everything I do is bigger than me. It is not just for financial security. It is about breaking generational cycles and healing simultaneously.

I did not choose this journey; it feels like it chose me. But I am taking it stride by stride. Any time guilt resurfaces, I pause and reflect. I remind myself that I deserve everything I have worked for and more.

“Making it” has not erased the weight, but it has given me the strength to carry it.

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