Rich or Driven: Who Would You Choose to Work With?

My father always told me, “Don’t look at someone’s wealth; look at their goals and actions.” Lately, as I’ve worked with a few very wealthy people, I’ve thought about his advice more and more.

It’s easy to be impressed by luxury—fancy cars, expensive clothes, and well-regarded degrees. But when someone is born into wealth, receives the finest education, and seamlessly steps into the family business, they might never truly challenge themselves. As my father put it, “If someone isn’t willing to step out and create something on their own, they may lack the hunger needed to achieve real success.”

This lesson became very personal for me. After graduating with a prestigious degree, my family made a bold and unexpected decision: they completely cut off my financial support. While I had always known this day would come, the reality of it was still a shock. Throughout my six years at university, I had been preparing for this moment. I saved every extra dollar my parents gave me and worked multiple jobs from my first year to my last. I wanted to ensure I could cover rent and bills while job hunting, knowing that most fresh graduates start with unpaid or low-paying internships to build the experience needed for stable careers.

It was hard. Deep down, I still hoped to be the “favorite” child and receive some kind of support, but I was learning one of life’s most valuable lessons: independence. From graduation onward, not a single dollar came from my family, nor did any job offers arrive through family connections. But, looking back, I realize that it was my father’s way of teaching me resilience and independence early on. The experience showed me what it’s like to be resourceful and creative—skills I might never have gained if I’d had a financial safety net.

The simple truth is that if someone with a great education chooses to stay within their family’s empire, they often lack the skills and drive to handle real challenges. When you work with them, it can be disappointing. Promises go unmet, deadlines are missed, and they can act more entitled than accountable. People like this may never have experienced the reality of building something on their own, so they don’t fully understand what it takes.

When you’re deciding whom to work with, don’t be distracted by designer clothes, high-end possessions, or the comfort of a wealthy background. Especially now, when people can create an image on Instagram that looks like success, appearances can be misleading. “People show you their highlight reel, not their reality.” Focus instead on their actions and what they’ve achieved independently.

There’s a big difference between someone who simply joins their family’s business and someone who has had to work hard to create success. Imagine a young person who graduates from a top university and joins their father’s company immediately in a senior role. They’ve had minimal work experience outside the family business, and while they have good grades, they’ve never had to work their way up. When they face setbacks, they aren’t used to handling pressure and tend to rely on their family’s resources to cover mistakes.

On the other hand, think about someone who worked several low-level jobs to pay their way through school, taking on internships and small freelance gigs to gain real-world experience. They may not have had the luxury of choosing any job they wanted, but they’ve learned through hard work and determination. In their role, they are dependable, don’t shy away from responsibility, and understand what it means to keep their promises to clients and coworkers.

While the first person might be flashy and appear accomplished on paper, it’s the second person’s real-world experience and accountability that often make them a stronger and more reliable partner.

There’s something special about working with people who have built their success from the ground up.
These people tend to be more reliable because they’ve had to fight for every step. They understand the ups and downs, and that experience makes them more responsible and grounded. As they say, “Turned dust into diamonds.”

If you work with clients, take the time to really get to know them before you sign any contract. Look for the signs that they’ll keep their word and be reliable. Notice if their actions line up with what they say. Doing this can save you from future stress and disappointment.

Of course, the economy isn’t great, and it can be tempting to take on clients quickly. But doing your research is worth it. Even if it feels hard to be selective, you’ll thank yourself later for choosing clients who are dependable and respectful of your work. “It takes years to build a good reputation and just moments to ruin it,” said Warren Buffet. Picking your clients carefully is one of the best ways to protect your business and your peace of mind.

In the end, wealth isn’t what makes someone a valuable business partner. It’s their drive, actions, and what they’ve achieved by themselves. So look closely at who they are and what they’ve built, and let that guide your choice.

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