The True Definition of Success


Success: it’s a word that we are obsessed with as a society, yet is vague. Guidance counselors, motivational speakers, LinkedInfluencers (barf) and their cohorts will acknowledge this as they urge young people and nearly anybody who’ll listen to find your definition of success. While the advice of find your own meaning of success isn’t wrong, it is unfortunately not pursued very often. Since I’ve been elected to solve all of your problems for you, I’m going to supply you with a solidly workable definition; I won’t even charge you for this one!

First, we need to eliminate one of the chief answers; prestige. Having a cool job title is not a definition of success to optimize for. regardless of if it makes your folks proud of you. One famous line of mild-right Conservatives during the Trump era was the office is more important than the man who occupies it. If it is true for the literal most important job on Earth, then it rings true for becoming the Executive Vice President of Who the Fuck Cares at Goldman Sachs or Facebook that millions of people are gunning for. Similarly, the make and model of vehicles is also not something to optimize for (unless you’ve always lusted for a Jeep, Harley-Davidson, Volkswagen, etc). When a pedestrian or fellow driver see you in an impressive set of wheels, they don’t think that you are cool; they’re thinking about how cool they would be if they had that car. In case you forgot, most people are thinking about themselves and not you.

“Well Dan, is it money?” Well, yes and no. I won’t stand here and pretend that it doesn’t play a factor because it absolutely does. For instance, few would refer to a homeless person as a success or something to shoot for; however, there is a limit. As much as I’m not trying to sound like Captain Minimalist (despite how frequently others have called me that) but money is not for flexing or materialism. Few guests will care that you poured wine for them into no-name brand wine glasses; they’ll remember the good times with good company (and if they don’t, then it’s best to cut ties). Money is best used for buying freedom.

Essentially, what I mean by freedom is that the true definition of success is completely controlling your time. What do I mean by that? I mean that there is no external force that can leverage you to be at a certain place at a certain time. It also means that one is free to eat, sleep, workout, or pursue hobbies whenever they so choose to do so. There isn’t a boss, committee, or shareholders that orders their presence somewhere, nor are there bullshit meetings to show up for or call into.

To drive this point home, let’s look at Bill Gates at two different points in his life. Late 1990’s Bill Gates was by far the richest man on the planet, and it wasn’t close. He was the CEO of Microsoft at the time, and while his net worth was through the stratosphere, he didn’t truly control his time. As I’ve mentioned earlier; there’s no such thing as the perfect job and being a Fortune 500 CEO is no exception. His daily life was filled with meetings from Wall St analysts (glorified pundits), interviews with media personnel with an obvious slant, nosey intrusions from Drunk Uncle Sam and meetings with investors. Yes, the richest man in the world was still beholden to investors; he was legally required to keep them in the loop regarding the health of the company, answer questions, and generally appease the masses who owned some minimum arbitrary number of shares of Microsoft (read: literally any idiot with spare cash and a newspaper subscription, a public library nearby or internet access). There were also internal issues at Microsoft that needed his attention; there was undoubtedly always a product feature brainstorm, a manufacturing issue to be ironed out, an HR benefits meeting to weigh-in on, and so on. Gates circa 1998 did not control his time.

Bill Gates was one of the most powerful men in the world at the time; his decisions impacted markets across the world in a way that all but a select few world leaders of the time could only dream of. Yet, he wasn’t free as is his time always belonged to someone or something else. He couldn’t spend half of the day laying out on a beach, see his kid’s Little League game, or just not show up to work despite his 11-figure net worth. The job is absolutely relentless and only a fool would deny that.

Contrast that with how he spends his time now. Gates no longer runs Microsoft, and instead is wholly focused on his true passion; philanthropy. While there is no doubt that he loves making the world a better place through his namesake foundation, Bill Gates is definitely freer now than he was in decades past. In 2019, Netflix released an amazing documentary about his life. Gates, despite having more money than he could possibly ever spend in a single lifetime, spent an exorbitant amount of time secluded by himself in a small cabin in the woods. This cabin had just enough electricity to power a few basic appliances (notably a minifridge full of Diet Coke), no internet access, and, most importantly, a stack of books and notepads. His desire to was to read about as much as he could handle on any given topic, furiously take notes, and then try to solve a pressing problem. He’s known for spending weeks at a time in this cabin, cut off from the outside world and only emerging when he felt like doing so. There were no shareholders to answer to, meetings he didn’t feel like going to, or senators to meet with. For my money, that is the mark of true success.

Truthfully, I idolize the man who has a net worth in the low seven figures that answers to nobody but the market (and hence is free) more than I do the multibillionaire whose entire day is pre-filled in and has no wiggle room, not even for a 20-minute nature walk during his lunch break. The former can choose to go on vacation at a whim, stay longer than he originally planned, and not think twice about doing so. Good luck getting Elon Musk to do that!  

Buy freedom, not useless shit…


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