Is your definition of success missing this one thing?

By J. Douglas Holladay

Nothing strikes closer to the heart of what we truly value and believe than do our views of success and failure.

So, what is success? It can be difficult to get our minds around this elusive concept. Our thinking on this matter is deeply embedded in our subconscious mind, and at times it even surprises us. Many of us have a “number,” or amount of money, that seems to represent either security, success, or personal validation. It isn’t wrong to set a financial goal—but is it enough? What would success look like if we viewed it through a different lens, one that included other measures such as deepening friendships, reconciling with others, giving back, or learning to be better versions of ourselves through meditation and exercise?

Although the accumulation of wealth is certainly a prime motivator for many, success needs to be understood far more broadly. Those who see money and prestige as the primary measures of success are rarely happy and content. Quite the contrary. Sadly, many successful people who single-mindedly pursue those goals find they just don’t deliver where it matters most.

What’s missing in narrow definitions of success? When disconnected from meaning, success seen only as wealth accumulation is simply sterile and unsatisfying. The hallmark of a satisfying and well-lived life requires having and maintaining authentic bonds with others. Success should incorporate this larger purpose. It is not something we should put off till later. By the time we come to this realization, it is often too late. It has been deeply heartening throughout my journey to gather leaders to explore this very foreign territory of the heart and honestly look at the false gods our society so highly prizes.

I once chaired a panel with three individuals born into iconic American families, household names that are widely identified with great success: DuPont, Tyson, and Huizinga. All three panelists voiced a common sentiment: “Rather than advantaging me, my family name and history were at times paralyzing, as I tried to make my own way.” We may not face such overt expectations, but perhaps there are some implicit ones driving us as well—unconscious definitions of success we have absorbed that end up paralyzing us.

It takes real strength to resist those gale winds pushing us to certain destinations. Sober reflection and finding your grounding are perhaps the only ways to stake your claim to be truly you. What do you care about? What are your values—not your family’s or the broader culture’s, but your own? Is your life philosophy sufficient for the task of enabling you to resist such implicit messaging and to build a definition of success that will last your entire life?

The ancient Greeks had a very different idea of “success” than we do. For them, the “good life” was about living a meaningful life and contributing to the greater good. They knew intuitively what research confirms: “givers” are happier and more fulfilled, because they have a purpose beyond themselves. But what is that purpose?

Many leaders lack the tools, emotional intelligence, or courage to venture out into this messy emotional landscape. Spending time reflecting on a well-crafted question can create a pause, a moment to consider and recalibrate goals. At a salon I attended, the question was posed: What would your children say is most important to you?

After some initial discomfort, an electric evening resulted when those assembled shared some rather raw feelings and even some tears. They developed a different kind of relationship with each other, one that was more real, more true, more connected. The experience prompted many to rethink their lives.

How would you answer that question? In the journey toward becoming a better and more transparent person, half the battle is becoming comfortable enough to explore life’s big questions.

Often at the end of a gathering at which leaders have reflected on the big questions of their lives, we at PathNorth urge the participants to put pen to paper and craft a brief letter to themselves outlining their regrets and the changes they intend to make in the future. We collect these and then mail them individually to the participants a month later. The letter reminds them of an extraordinary moment when they touched on something truly important. After a time of major reflection “on the mountaintop,” so to speak, is over, people have a tendency to push back the big questions as they reenter their day-to-day worlds. Receiving a written copy of their reflections and promises from that time refreshes their memory and allows them to reengage and consider where they are in relation to the changes they wished to make.

Questions have a way of worming themselves into our hearts and minds. They prompt us to respond and struggle to be honest with ourselves. Here are additional questions you might use to pause and reflect upon:

    What fosters hope in you?
    How would you like to be remembered?
    How do you think you can get “unstuck” from a particular situation or behavior in your life?
    What would you shout from the mountaintop?
    What is the biggest obstacle keeping you from your personal greatness?
    Do you experience the “impostor syndrome”? How so?
    Whose life seems purposeful to you?

Becoming comfortable with thoughtful introspection is critically important if we are to rethink and reimagine ingrained notions of success and failure. In examining ourselves, it helps if we understand what factors shape our views and beliefs, particularly about what really matters.


From Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life by J. Douglas Holladay and reprinted with permission from HarperOne, an imprint of HarperCollins Publishers. Copyright 2020.

J. Douglas Holladay is the author of Rethinking Success. He is an adjunct professor at the Georgetown University School of Business, cofounder of Park Avenue Equity Partners, L.P., and founder of PathNorth, a networking organization for executives.


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