The winding path to success

It's a marathon, not a sprint

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I have been desperate to become successful for my entire life.

I grew up upper-middle class - my mother was a medical doctor. As an OB/GYN, she delivered thousands of babies throughout a 40-year career. She lived her passion and provided a stable income for my two brothers and me. My father was a lawyer by training, but he didn’t practice - instead, he devoted his life to raising his boys and running my mother’s medical practice.

My parents were ardent believers in education, and they happily paid for me to attend a private school in Baltimore called Gilman. Gilman provided me with an outstanding education and surrounded me with driven, hardworking, intelligent students. Due to the tuition requirements, most of my classmates were students from wealthier families.

Sadly, rising malpractice insurance premiums crippled my family’s financial security as I entered middle school. Simultaneously, my two older brothers attended private universities that my parents paid for in post-tax dollars. I had a front-row seat to see how quickly economic fortunes could turn at an early age.

Despite racking up a crushing debt load over those years, my family never suffered from food or shelter insecurity. I had the great fortune of being raised by two incredibly loving and committed parents. I was born in the United States of America during a period of unprecedented prosperity, peace, and tranquility - to say that I had an incredibly fortunate and privileged upbringing would be an understatement.

Despite my relative privilege compared to billions of people who have suffered from war, famine, plague, and dislocation over millennia of human existence, I chose to compare myself to my fellow private school students. Their families were far more financially stable.

Age brings perspective, but these formative years left a mark on my psyche and a burning desire to become “successful.”

Later in life, my parents split from one another. As I transitioned out of the military, my father’s physical and mental health rapidly deteriorated as he struggled with depression, alcohol addiction, and isolation. My father found it impossible to secure steady work due to his deteriorating health, and his financial outlook was incredibly bleak.

At 28 years old, I felt the tremendous weight of needing to provide for my father financially just as I departed a steady paying job to attend an MBA program. So, as I entered Wharton, I committed to making as much money as possible as quickly as possible to avoid this sort of situation. The thought of being 65 years old, unable to secure a job, with failing health and no savings, makes me physically ill.

In the fall of 2018, my father died suddenly during my first month at Wharton. I was devastated. Grief is a complicated emotion that I will dissect in a future post. Still, the worst part of this experience was the relief I felt about not needing to provide for him financially in the coming years - an emotion that haunts me today.

Do we all feel this way?

The Marine Corps allowed me to interact with people from every socioeconomic background. Attending Wharton exposed me to an equally broad range - I had a classmate who had grown up in a refugee camp in Africa, while others were the children of literal Billionaires. Most Wharton classmates fell between these extremes, but we all felt a deep desire to become “successful” in the eyes of the outside world.

On the lower end of the socioeconomic ladder, we want to become successful to avoid the pain and misery of poverty or to prove our worth to others. More money means more security, which means we can provide for the people we love.

The children of privilege are similarly motivated towards success to outgrow their parents’ shadows. They want to stand on their own two feet and achieve something for themselves.

This post is about success, the pursuit of success, and how we measure it. Financial prosperity is the most commonly used metric in America for measuring “success” for young professionals, but it’s a yardstick that is sure to leave us with a vacuous emptiness.

How we’re taught to think about success -

As children, our schools train us that we can measure success via a scoreboard - get good grades, score well on the SATs - accumulate enough points to gain acceptance to a university. The rules of life for externally validated success as a child are evident. The adults define success, give us boundaries and limits, then encourage us to push toward specific outcomes. For instance, this common path:

Graduate from college → a job → success.

By the time we reach adulthood, we believe that the game of life looks like this:

My former Goldman Sachs overlords would be proud of this graphic

On the X-axis, time marches forward. No matter what you do with your limited remaining days on this earth, you’ll continue to move from left to right across this graph until your death. We hope to also move up on the Y-axis over time through our efforts.

I’ve left the Y-axis deliberately vague for now - we’ll reconsider in a few paragraphs. You can feel free to substitute your subjective definition for “success” along the Y-axis.

We begin our journey young, but we haven’t accomplished anything noteworthy in our lives. Nevertheless, we know if we work hard, we’ll achieve success over time. This belief is a fundamental organizing principle of our society - the American dream. We organize and structure our lives around this principle - work hard, and you will succeed.

Truthfully, we’re all hoping for this:

The number of people who achieve wild success early in life is astronomically low. Yet, they occupy an outsized portion of our media attention, making it challenging to ignore these outliers. It is, however, effortless to overlook the role luck and timing play in these outcomes or the financial headstart many of these people have.

A quick thought experiment -

If the above graph depicts your existence, would you stop working? Would you sit back and bask in the glory of achieving what you initially set out to achieve, or would you set new, loftier goals? If you’re reading this, I suspect that you are the type who would continue working in some capacity, setting new goals, and comparing yourself to different strata of successful people.

For the rest of us, we expect the pursuit of success will be a straight line -

Our brains ignore the myriad successful people who talk about failures endured along the path. A linear journey to achieving our dreams is a myth.

The journey is always arduous. Failure is a guarantee, and ultimately success in one arena of life requires sacrifice in others.

More typically, the path to success looks like this -

The path from where we are today to where we will find ourselves later in life makes sense in retrospect. In school, we learn history as a cohesive narrative - X event led to Y outcome. Real-life is much more complicated.

If we were to take the place of a famous figure from history, their success would not appear obvious or guaranteed.

In the above graphic, we see a person who finds success later in life after repeated failure. What if this person had given up on their journey prematurely? Suffering another crushing defeat, this person decided not to continue learning, growing, and changing but rather crumbled under the agony of failure. We’d never see the final peak.

Regardless of whether you achieve success early in life or after repeated failure, you will likely continue working towards new goals and new heights over the span of a 40-year career. We don’t need to be in a rush to achieve success young in life - instead, we need to find contentment in the day-to-day struggle.

The journey is the destination.

This maxim is incredibly challenging to internalize but tremendously beneficial to remember. No matter what path you are pursuing, you’ll find struggles along the way.

In the pursuit of greatness, you will fail repeatedly. If you do not fail personally and professionally, you likely are not pushing yourself to achieve your full potential. This means that we will spend most of our lives outside of our comfort zones.

Spending our lives outside of our comfort zone makes it critical that we enjoy the ride. Unfortunately, there is no magical destination down the road that will render us happy. After all, your destination from 5 years ago is likely where you find yourself today.

What is success?

How do you define and measure success? I would pose a few variables that frequently arise:

1. Financially - income, net worth, homeownership, assets, 401k

2. Strength of relationships - romantic, family, and friendships

3. Work/life balance - hours of work per week, time off per year, ability to travel and take a vacation

The variables we choose to prioritize will affect how we measure successful outcomes. A breakneck pursuit of external validation is a surefire way to optimize for the wrong results.

Moreover, success in one arena requires sacrifice in others. It is never too late to reconsider our optimal outcomes and prioritize according to new metrics of success.

I hope you enjoyed this post. If it added value to your life, I would ask that you forward it to a friend who you think would benefit from reading it. As always, I look forward to your feedback.

- Brendan