The Beauty of Being a Moonlighter

Wear your flats to work but make sure you pull out your hooker heels after hours.


Organizations are taking greater steps to improve employee engagement, however surveys reveal people are increasingly unhappy at work. Perhaps part of the dissatisfaction has less to do with peoples’ jobs and more to do with the multitude of alternative possibilities that are available.

Opportunity overload is real, and it makes decisions feel more permanent and the margin for error slim.

When we feel pressure to decide what to dedicate our lives to, passion gets tossed into the conversation faster than you can say, Caesar Salad.

Amongst millennials, there is a growing anxiety around discovering one’s passion, but this is only the first step. The second is learning to walk the tight rope between enjoying the reasonable pleasures of life while still dedicating ourselves to our passions.

Walking this tight rope between indulging in reasonable pleasures while simultaneously making sure that our day jobs don’t soul-fuck us into oblivion is a difficult feat. No one wants to turn forty-five, haggard and drawn out, with dark circles under their eyes, looking like an anorexic panda.

At the same time, going “all in” on our passion is a tall order. For many of us, “all in” is not a reasonable option. We may have a responsibility to take care of a sick family member or support a household. On the other hand, we could be insecure and unsure about the quality of our work and feel we need more time.

Contrary to the word on the street right now, it not necessary to eat shitty junk food and sleep on a futon in order to pursue your passion. There are people who have done it that way, but their way doesn’t have to be yours.

It is reasonable to want to get a paycheck every two weeks, pay your bills on time, take two vacations a year, and splurge on the ones we love.

For those who don’t care to pursue their passion and are satisfied with spending time with their family, getting new toys, having cookouts, and doing home renovations, I say, “Do your thing baby. Keep on keeping on.”

However, for those who want to indulge in their passion, moonlighting is not just a viable option; it is the best-case scenario.

If we are serious about pursuing our passions, then we are massively undermining the power of moonlighting. There is a beauty in being a moonlighter and there are tons of gifts that this vocation brings.

Moonlighting allows us to become chameleons who can enjoy the benefits of both worlds. We can have conversations about how high taxes are, what the best mortgage rate is, and the benefits of contributing to our RRSPs early, while simultaneously banging away at our crafts.

Having a day job protects us from the disappointed parent, the judgmental family member, our partner’s friends, or new acquaintances at dinner parties.

There is a pleasure when someone asks, “What do you do?”, to answer succinctly and to the point, “I work in sales; I am an accountant; I am an HR representative.” There is no pressure to be any more interesting than we already are. There are no follow up questions, explanations, or justifications required. Just complete peace of mind that we have sufficiently answered the question.

Moonlighting protects us from all the logical, yet unwarranted questions people ask. If you are a creator, answering these logical questions can feel like you are being photographed in a room butt naked, while having to lean against a cold tiled wall.

By moonlighting, we become privy to the gift of not having to over identify with our passion while having the space to find the answers to questions that we are already asking ourselves.

When I started writing my first book, I quit my full-time job as a Sous Chef, took on a part-time gig as a bus boy at a café and started writing full-time. When I started, I had the best of intentions and was on a roll, but I slowly found myself brooding in coffee shops longer than required, smoking too many cigarettes, and showering too little. I became an expert at talking about the plot of my story and getting a kick out of seeing people’s reactions. Very soon I was talking more about the book and avoiding the harsh reality that I hadn’t thought the plot through and that I lacked the maturity to finish it. As a creator it is easy to get caught up playing the part rather than being it.

As a moonlighter there is no pressure and we get to navigate the world confidently, on our own terms and on our own time. By conforming, we give ourselves the freedom to deviate.

“All in” is a great way to go, but for every Dave Chapelle, Dr. Dre, and Kendrick Lamar there are hundreds of thousands who did not come up the same way. For those of us who are not willing to forfeit the reasonable pleasures of life, moonlighting is the way.

When we moonlight, we have a secret that no one else knows about and we can walk into a room and not have anyone else’s judgement follow us in. This allows us to create and master our work uninhibited.

If you are unable to go “all in,” wear your flats to work but make sure you pull out your hooker heels after hours so you can hit the streets, do what you love and eventually get your money’s worth.