Imagine spending decades working toward a goal, pouring your heart and soul into it, and then finally achieving it—only to realize it was never what you truly wanted. This isn't the fear of failure; it's the fear of succeeding at the wrong thing. It's the fear of waking up one day, surrounded by accomplishments that don’t resonate with your inner self.
This is a story about a friend of mine. By all external metrics, he’s the most successful person I know: a graduate of the best schools, an incredible athlete, financially secure, and blessed with a loving, expansive family. Yet, in his mid-40s, he came to a sobering realization: his accomplishments were largely shaped by what others wanted for him, not what he genuinely desired. For years, he had lived striving to make his parents proud, chasing the validation of others, and neglecting the hard work of asking himself, What do I really want?
His story hit me hard. As a parent, I can’t shake the fear of unintentionally steering my daughter down the same path—one where she spends years working toward something only to discover it wasn’t hers to pursue.
My friend’s life seems like a dream from the outside. He has checked off every box on the “success list.” But that very checklist was the problem: it wasn’t his. His well-meaning parents, like many of us, had created a roadmap they believed would lead to a good life, and he followed it diligently.
In conversations with him, I learned the issue for him came not from a lack of achievement but from the realization that he’d been living someone else’s dream. For all the success, he felt disconnected. He admitted he never took the time to figure out what made him happy because he was too busy making others happy.
That story left me with a nagging worry. As a parent, how do I ensure I’m not unknowingly nudging my daughter toward a life where she feels obligated to live for me or my expectations?
One day, while driving with her, this fear surfaced in an unexpected way. She casually said, “I have to swim because you and Mommy were swimmers.” My heart sank. I immediately stopped her: “You don’t have to do anything because of us. This is your life, not ours.”
She looked at me, puzzled. I explained that swimming was something her mom and I chose for our lives because we loved it. But she wasn’t here to fulfill our dreams. Her job wasn’t to make us happy; it was to find what she loved and pursue that.
It was a pivotal moment, but it didn’t stop there. I realized the conversation couldn’t end with, Do what makes you happy. I had to guide her to the next level: Why do you want it?
The truth is, even with good intentions, it’s easy to get caught up in pursuing what we think we want—only to find out later it was driven by external expectations. This is why I’m trying to teach my daughter, even at nine years old, to ask why. Why does she want to do X? Why does she want to excel in school or any other activity?
At her age, it’s unlikely she’ll have all the answers. But the practice of asking why is essential. It’s a skill that can prevent her from chasing someone else’s dreams and help her build a life that feels authentic.
As adults, many of us never learned this skill. We don’t stop to ask why until we’re already well down a path that doesn’t feel quite right. And while it’s never too late to course-correct, the earlier we start this work, the better.
My friend’s story is a cautionary tale. He’s a living example of what happens when you don’t do the internal work to figure out what you truly want. Instead, you default to living for external validation, whether from parents, society, or peers. The longer you defer this self-discovery, the harder it becomes to disentangle your own desires from those imposed by others.
As I reflect on his experience, I can’t help but think about how easily this could happen to my daughter—or to me. It’s not enough to set goals or define success. We have to continuously ask ourselves if those goals are aligned with our values and passions.
The good news is that it’s never too late—or too early—to start this process. The best time to discover your true desires and motivations might have been when you were nine, but the second-best time is now. Whether you’re guiding a child or reflecting on your own path, here are some steps to start:
1. Ask the Hard Questions:
Regularly pause to ask yourself (or your child), Why do I want this? What do I hope it will bring me? These questions help clarify whether the pursuit is driven by genuine desire or external pressures.
2. Embrace Iterative Discovery:
Finding your path is not a one-time event; it’s an ongoing process. Encourage curiosity and the courage to change course when something doesn’t feel right.
3. Let Go of External Validation:
It’s natural to want approval from loved ones, but fulfillment comes from aligning your actions with your own values—not theirs.
4. Model the Journey for Others:
As parents, mentors, or friends, the best way to help others find their path is to show them what it looks like to walk yours authentically.
The tragedy isn’t failing to reach your goals. The true tragedy is spending years climbing a mountain, only to find it wasn’t the right one. My friend’s story serves as a powerful reminder that success without alignment to one’s true self is hollow.
Whether you’re nine or ninety, the journey of self-discovery is always worth taking. As parents, partners, or individuals, our responsibility is to build lives that feel honest and fulfilling—not to chase someone else’s version of success. Start today, ask yourself why, and never stop exploring the answers. Your life—and your happiness—depend on it.