In his new book, Ego is the Enemy, Ryan Holiday recounts the story of Howard Hughes, Jr. inheriting his father’s company at the age of 18.
Hughes is a legendary figure, his craziness often romanticized (as in The Aviator), but Holiday shows that the reality is that he was a horrible businessman who used profits from the one successful company that he inherited to fund his increasingly crazy ideas and strange lifestyle until he ultimately lived in a gilded, self-made asylum.
It’s a cautionary tale filled with numerous moments in which Hughes’s life could have taken a turn for the better.
The thing is, if I had been in the same situation, I’m not sure I would have done anything differently.
I have a career, family, and a house and, despite my very best efforts, I still make dumb money mistakes, think short-term, or simply act like an entitled, immature asshole.
And I’m 36. I am twice the age I was when I graduated high school, the same age as Hughes when he succeeded his father. It is now the halfway mark of my life. Half of my time on this Earth took place before that moment; half of it after.
But it certainly doesn’t feel that way. I don’t feel like I’m as far away from 18 as when I was born, but it’s the truth and, more importantly, it is illuminating into how much more growth and maturity we have to do even after we become legal adults.
As I was writing this, Holiday published a piece that contained this sentence: “All of us have been 18 years old, and all of us know the ways in which our youthful arrogance held us back.” He used it to make a boarder point, but that sentence hit me hard.
I look back at myself at 18 and I cringe hard. I was fun and funny, interesting and energetic, but also goofy, insecure, and self-conscious, all of which I covered up with incredible arrogance. I thought I knew more than most, knew better than everyone else, and had the best taste around.
And I was petrified of growing up.
I worked four jobs in college and had very little disposable income, but after tuition and books, all of my cash went to partying. While in the dorms as a freshman and sophomore, my nights out were mostly constrained to the usual long weekend – Thursday night through Sunday afternoon – but once I moved into an apartment, it was lights out.
For our senior year, we moved into an apartment with three balconies and little university supervision, in a building that was condemned only a few years prior, so all bets were off. As such, I spent the next nine months coasting through school, drinking with friends every single night, and trying to squeeze every last ounce of fun out of my existence.
Looking back, I had an incredible amount of fun, but I wasted so much time.
When faced with the inevitable end of carefree youth and the onset of adulthood, I responded not by applying for internships or plotting a career path, but rather drinking and partying with my friends every single night (and often days), casually expecting that someone would just magically drop a job opportunity into my lap. Talk about entitled. I was twenty-two at that point, yet in many ways I had regressed. I was dangerously close to sounding like this guy.
Even beyond college, I moved into the city for a variety of reasons, but the biggest was that I didn’t want to become the boring suburban dad when I was still single and was still in denial that it was time to grow up. I saw my father go to work, come home, eat dinner, watch some TV, go to bed, and repeat the same exact process five days a week before spending the weekends like an early American settler, maintaining four acres and everything that went with it. I didn’t want that. I wanted late nights in bars and clubs followed by outdoor brunch and a visit to a coffee shop. #Millennial
And I had very little cash with which to do it all.
I worked at a non-profit, had student loans, and, before long, a mortgage. Soon after came business school, even more bills, and other obligations to worry about. Being close to insolvent probably saved my life. If I had been wealthy, there is no doubt I would’ve become a textbook alcoholic, treating every day like the last day of vacation, trying to ensure the party never ended by any means necessary. It most likely would have killed me.
So who am I to judge?
One of America’s favorite pastimes is watching people richer than us spend – and often squander – their money. From Lifestyles of the Rich and Famous to Cribs to Rich Kids of Instagram.
Many of us hate-watch these shows. We enjoy belittling and mocking children born into wealth because we know that if we ever had that much money we’d be smarter and more reserved than they are. We’re positive of this despite the fact that, when given even a fraction of what they have, we act just as douchey.
Money permeates everything else we consume as well.
We watch House Hunters and simultaneously marvel and scoff at people with budgets we can only dream of demand things that have little or no basis in reality. The best part of Behind the Music was always when the career began to nosedive and the money vanished. We envy Walter White’s pallet of cash.
Every time the NBA and NFL drafts come around, we’re reminded of the washouts and failures that were given huge contracts with fat signing bonuses: Ryan Leaf. Kwame Brown. JaMarcus Russell. Anthony Bennett.
Allen Iverson pretty much grew up without any adult supervision and began drinking early in his life, so why should it surprise us that he’s an alcoholic who pissed away his money? Who was going to teach him right from wrong? Do you think anyone in his family ever thought about an IRA, let alone generational planning, foundations, and international tax shelters?
Still, pundits and fans alike grab their torches and pitchforks and attack these athletes for being wasteful and immature with money. These are adults chastising teenagers, some of whom were raised in poverty, for not being financially savvy.
I was taught all of the correct things from early on. I work in corporate finance. I read and study personal finance. And I still make dumb financial choices. What’s my excuse?
If there had been a Rich Kids of Black & White Instagram in 1923, Howard Hughes would have been in it. And, if put in the same circumstance, so would I.