The Duality of YOLO

How to align two opposing philosophies on only living once

Why do some people race to beat the sun, while others squeeze in as much sleep as possible?
Why do some people find fulfillment in their careers, while others would rather party and go to concerts?

While people aren’t necessarily as binary as the above depiction, most of us do have a default as to what we enjoy doing, and we know intuitively whether that thing yields a sense of fulfillment in our lives.

The truth is, both the worker bee and the socialite share much the same philosophy: ‘You only live once.’

Both schools of thought agree that ‘life is short…’ but their means of ‘so make the most of it’ is where their inherent differences lie.

While one branch asserts that a life filled with little stress and lots of simple pleasures leads to a happier state of being, the other side finds its stride in hitting goals and making an impact in areas bigger than the self. The truth is, neither side is wrong, but during circumstances when a workaholic is forced to relax and a slacker is forced to work, each side has to learn to be comfortable with this unfamiliar yet essential part of life.

Stop working, start playing

Most people consider working a nine to five for five days a week reasonable, spending the remainder of their time on what they would call ‘themselves.’ This is normal. We learn to work in anticipation of play, it’s used as a reward for a job well done.

The problem with this mentality is that we yearn to play more, and as a result, antagonize work. While playtime isn’t made more fun after a hard day on the job because we feel like we’ve earned it, worktime feels more boring. The fragmentation of ‘work’ and and ‘life’ in the work/life balance leads to an ironic imbalance in our self-perception.

As Zachary Slayback writes in a post titled Against the Work/Life Balance,

“…[W]hat we need is a conception where you don’t even conceive of work and play as being separate things. Your job is your play just as much as your time at home is your play. The job-life and the home-life don’t strive towards different ends as they do in the typical conception. Rather, they both ought to strive towards the same thing: fulfillment. However you define fulfillment, bring your home and work lives into sync with each other as both attempting to form a life that you are happy with.”

There’s no shortage of people in the world who spend time doing what they love, but whether they’re successful boils down to more variables than passion alone. For every one person to make a living following their dreams, a million more dream they could make a living.

How to Make Money Having Fun

Every hobby has an industry, and every passion can make you money. There’s people right now earning serious bank hosting music festivals and nightclubs, producing makeup tutorials on YouTube and setting up shop walking dogs or renting out gear for extreme sports. Many people even pickup hobbies like tai-chi or chess by practicing in a facility someone else made to monetize on that hobby.

Whatever your YOLO is, you can find a way to profit from your leisure. The common denominator between these different passion-turned-moneymaking lifestyle is a blend of practicality mixed with giving people what they want. Just because you can’t make it into the NBA because you’re 5'7" with a mediocre shot doesn’t mean there’s not money to be made on basketball — it just won’t be playing for the Lakers.

Here’s an image of the ‘Still Trill’ team winning a quarter of a million dollars playing NBA 2k17.

Even more practical than competing among thousands of players for a chance to win big, HoopMaps is an app that lets you arrange basketball games in courts near you.

There’s two inherent ways to make money doing what you love: practice, practice, practice to be the best, or find a way to build around your passion.

Of course, these two points aren’t mutually exclusive. While the 2k video game franchise is a byproduct of the real NBA, it’s likely that the Still Trill team couldn’t make it onto a league team in terms of athleticism. With that being said, they’re probably even better at the video game version of basketball than most NBA players.

Similarly, the HoopMaps team offers an immediate confirmation of an inability to go pro: if the founders were NBA material, they likely wouldn’t step foot on an empty park court, choosing to practice in their well-maintained facility instead. Instead, the business partners spotted a weakness in the way most of the country approaches the game, and worked their way on from there. While they didn’t refine their actual basketball skills, they still had to flex their entrepreneurial skills to build an empire around their YOLO.

There’s dozens more examples like Still Trill’s and HoopMaps’s, both within the basketball realm and across every other field you could point to beyond charity work.

The secret recipe to making a living both financially and emotionally is fortunately quite simple, it looks like this:

Diagram originates from ‘The $100 Startup’ by Chris Guillebeau

Bringing It All Back

Like any line of work, doing something fun doesn’t imply it will always be easy. Whether your money revolves around hitting the gym or baking a cake, you have to give an equal amount of love to spreading the word as you do getting better at what it is you’re doing.

The top performers are the people who are always doing, which is an inherent difficulty for one hemisphere of the YOLO globe. It’s for this reason that you need to ‘do what you love,’ because ‘doing,’ as arbitrary as the term is, doesn’t feel as arduous when it’s enjoyed.

While there’s certainly a compromise that comes with the difference of doing something exactly as you would want it, versus doing something for others within the realm of what you enjoy, you’ll really be able to hit your stride in this line of ‘work’ because doing it will perpetuate your fulfillment in career, which will also happen to be one in the same with your personal life.