Redefining Success: What Are We Really Chasing?

Throughout my life, I’ve met scores of highly “successful” people—doctors, lawyers, engineers, business owners, many of them incredibly wealthy. And yet, beneath the polished surface, so many of them are quietly miserable.

This isn’t a coincidence. It’s because the metrics of success in our culture—status, wealth, and achievement—have very little to do with what actually makes us feel alive. These external markers rarely reflect the deeper human needs for love, connection, joy, awe, and purpose.

I learned this early in life.

When I was a child, my father re-entered my life after years of absence. He petitioned for split custody, not because he wanted a deeper relationship with me, but to stop paying child support. I began alternating a week at a time between his house and my mother's. For a brief period, when I was around six, he made small efforts to connect. It was the closest we ever were.

But it didn’t last. As his obsession with wealth deepened, so did his disconnection from me. He met and married a woman who seemed to care about money as much as he did. There was no space for me and I was discarded like a broken toy. Their relationship ended in a costly divorce—she took half his wealth and more—but the greater loss was that he continued to choose work, money, and possessions over me. Relationships to him were something you could buy.

We never recovered.

That experience taught me something I’ve seen echoed in so many others’ lives: you can be rich, accomplished, and admired—and still feel empty, alone, or unlovable.

As I grew up, I paid attention. I watched people chase money and power at the expense of their relationships, their health, even their lives. I started to question what we’re really chasing when we seek “success.”

This is a question I now explore in my work with clients. What are we truly hoping to feel when we seek status, admiration, or wealth?

• What does being important to people who don’t truly know you actually give you?

• What fear are you trying to soothe by building financial security at the cost of your well-being?

• What are you sacrificing in order to feel like you matter?

  
  

I once worked with a client who was pouring his energy into climbing the ladder at work. As his son prepared to leave for college, he started renovating part of their house—hoping the project would strengthen their bond. But in our work together, he realized the renovation wouldn’t bring them closer. The real renovation wasn’t on the house—it was on their relationship. So he stopped the project immediately and began investing his time directly into building connection with his son.

In our society, success is often glorified in the form of numbers in a bank account, closets full of things we don’t need, or titles that earn us respect—but what are these trophies giving us beneath the surface?

Real thriving isn’t found in accumulation. It’s found in connection. In being seen, accepted, and loved—not for what you do or what you have, but for who you are when all the roles fall away.

Even those who achieve the pinnacle of status often carry a quiet question in their hearts:“If I stop doing this, will anyone still care about me?”

Until we reckon with that question, we’re just building castles on sand.

But it doesn’t have to be that way. We can remember what truly matters: The experience of awe. The moments of real thriving.

The time spent building deep, meaningful connections.

The top five regrets of the dying, according to Bronnie Ware, are:

• I wish I’d had the courage to live a life true to myself, not the life others expected of me.

• I wish I hadn’t worked so hard.

• I wish I’d had the courage to express my feelings

• I wish I had stayed in touch with my friends.

• I wish I had let myself be happier.

We don’t have to wait until we’re dying to acknowledge and begin to transform these regrets.If you’re ready to begin that transformation—and want someone to walk with you—sign up for a free call.