My father always wanted to be in the Navy. He joined the ROTC in college, and went to Officers Training School after he graduated. By that time he and my mom were married, and they moved to Norfolk, Virginia, where she endured long months alone while he was at sea.

Dad had always loved the water. He grew up in New Orleans near Lake Pontchartrain, and spent a good bit of his time on the family vessel. His father was captain of the local U.S. Power Squadron, and took his wife and kids on frequent trips to explore the Gulf Coast. For Dad, the Navy was a natural extension of those days; he relished the adventure on the high seas, and the camaraderie inherent in ship life.

In the meantime, his father had started a drilling company to serve the exploding business of Gulf Coast oil production. Daddy Booker, as we called him, had learned the business by working for other companies; now he was ready to go out on his own.

And there was business to be had. Daddy Booker soon found himself overwhelmed with work, and he called on his second son to come home and help. My father, who earned a civil engineering degree from the University of Notre Dame, reluctantly agreed. After two years of service, he received an honorable discharge from the Navy he loved, and brought his wife and baby – a tiny red-haired girl version of the baby he had been – back home to New Orleans. That baby was me.

The first house they rented was a little 2-bedroom place where they rode out the deadly winds and flooding of Hurricane Betsy. My younger sister was born 17 days later.

In the meantime, my grandfather’s business was slowly digging in its heels. The company now owned a couple of rigs that were constantly in demand by major oil companies, including Shell and Esso. Remember Esso? My parents bought a 2-story suburban home in Metairie, Louisiana for $35,000. My mother, who had been raised by her grandparents in a public housing apartment, thought it was a mansion.

In 1966, just before the birth of my second sister, my grandfather, Harry Hamilton Booker, died after a short but devastating illness, and my father became president of Booker Drilling Company. He was 25 years old.

Soon afterwards, Booker Drilling Company – partly because it was the oil-obsessed 1970s and partly because of my father’s leadership, the company surged, building rig after rig to suck more and more oil from the depths of the Gulf of Mexico. Many weeks of my childhood summers were spent in Grand Isle, Louisiana, where the company’s main warehouse was located. Grand Isle was then a tiny dot of a community with a single grocery store and nothing to do but play in the surf and fish. Our beachfront camp was a simple clapboard house up on stilts, and we spent evenings underneath it, boiling crabs we had just caught and learning how to suck the meat out of the claws.

We all had old shoes for swimming and romping because tar balls dotted the sand like enormous black gumdrops, and adhered to feet just as stickily. Inevitably, though, we wandered around shoeless at times, and sported dark stains on the soles of our feet for days.

My third sister was born in 1970, and our family was complete – four girls, a dog, a hard-working dad and a stay-at-home mom.

The oil boom of the 1970s was good to our family. My father worked hard, traveled often, and before long Booker Drilling Company was one of the largest privately-owned employers in the state. I loved to take rides to south Louisiana with my dad, and say hello to men I had come to know as family – longtime Cajuns living on the bayou who had been with Booker Drilling since its inception. Dad felt indebted to his men – other than office workers, all of his employers were men – and worried constantly about their safety on the rigs. Each year during hurricane season, if a storm threatened our region, he sent us north, usually to Jackson, Mississippi, so that he could focus on getting everyone out of the Gulf.

By the late 1970s, my father – and his five siblings, who were equal shareholders – were doing very well. So when the mammoth W.R. Grace came calling with interest in buying Booker Drilling, people thought Dad was crazy for even entertaining the notion. Why sell the cow when the milk was still flowing?

But Dad, in one of the most prescient decisions of his life, foresaw the bust. He convinced his siblings to sell the company he had built from a single rig or two into an economic force employing hundreds of people.

The company was sold, and for the Bookers, that was a very good deal.

My father wasn’t yet 40.

Explicit in the sale’s contract was a provision for my dad to continue to serve as company president for seven more years. He did. And then he bowed out. That was over 25 years ago. He has never held another job.

I’ve spent a lot of time lamenting that fact. My father has a brilliant mind; he always loved to read and follow politics. He was a leader in his youth, and people loved to be around him. He was inspiring.

He could have achieved greatness, I always thought. Instead, he quit.

But then last week I watched a documentary that shook me to my core, and it made me question nearly every goal I’ve had in my life. It also made me re-evaluate my father’s life. All of my What Ifs have been condensed in a single question:

What if Greatness is not what I thought it was?