Debunking The “Dress For The Job You Want, Not The Job You Have” Adage

Photo by Ben White on Unsplash

Much like Gatsby’s Nick Carraway, in my younger and more vulnerable years, I, too, was given advice that I’ve been turning over in my mind ever since. Dress for the job you want, not the job you have, boring middle-aged white guys used to say to me. While at the time I wasn’t entirely aware of the advantages bestowed upon these men i.e. going to college for the price of a gallon of milk and the promise of cushy retirement pensions once they turned 60, I took their advice seriously as I matured and did my best to put it into practice. Dress for the job you want, not the job you have, my dad’s on-again-off-again friend Gary had said. Okay, Gary. I’ll try.

As a pubescent middle schooler, I got my first job working as a bag boy at the local grocery. Aged 13, I was still a bit of a dreamer, so when I arrived my first day, I did so dressed in full baseball attire. Glove, cap, high socks, jock strap, and all. You see, I wanted to be a pro ballplayer, and so I had dressed the part. As one might expect, my attire was not well received by the management team. Wearing a ball glove as I worked made bagging the groceries difficult, and during the brief shift I smashed several packages of hot dog buns and at least one carton of eggs. Still, it was not until I put a significant dip of chewing tobacco in my mouth that I was asked to clock out permanently.

Undeterred, I went about my professional life as if nothing had happened, eventually returning to the workforce as a 17-year-old mowing lawns throughout my subdivision. By that time I was quite certain that I was to be an astronaut. So with my sights set on NASA and exploring the skies, I went about mowing and weed whacking the lawns of my neighbors in a full space suit. This was impractical for a multitude of reasons, chief among them the cost of the suit, itself, (thousands of dollars) and the untenable temperature inside during the scorching summer months. In short, I passed out midway through my first lawn. Dressing for the job I wanted, not the job I had, had gotten me in trouble once again.

As time passed, my goals and interests began to change. As a college junior, I began my semester-long tenure as a student teacher of English. And yet, despite having spent nearly four years preparing for this very moment, I found that when I arrived in the classroom that morning that I wasn’t dressed as a teacher, but as that of a zoologist. As the bell rang on that first day and 30 high school freshmen looked to me for direction and support, my safari hat with mosquito netting and cargo vest did little to command their respect.

In debt up to my eyeballs and without a better option, upon graduating I accepted work as a telemarketer, cold calling geriatrics about reverse mortgages. When I arrived my first day at the downtrodden business complex and took my seat beneath the harsh fluorescents, I realized that I had once again fallen into the trap that had cursed me many times before. Sitting there, awaiting my headset and a conversation with my new manager, I felt as if my three piece suit, oversized top hat, and detachable black cape, was perhaps my biggest blunder to date. I knew in my heart of hearts that dressing as a magician had been a mistake, and yet when the manager approached, he greeted me with a smile and an enthusiastic handshake, complimenting my duds and noting that he appreciated someone with a sense of humor. I was pleased that dressing for the job I wanted had provided some sort of an inroad with an employer. During my tenure at (name redacted for legal reasons), I become the go-to telemarketer on staff, renown for my dazzling outfits, my ability to take advantage of the decrepit and senile, and, occasionally, being able to pull a rabbit out of my hat.

As the years passed, I eventually transitioned into the sexy role of a marketing manager, settling into a shirt, tie, and khakis lifestyle. After a failed stint as a bagger, mower of lawns, teacher and a not-quite failed, but unfulfilling time as a telephone satanist, I had finally arrived at that middle portion of the venn diagram where the job I wanted and the job I had overlapped.

Now approaching 50, I find myself in the same position as all of those boring men who felt so compelled to give me the same piece of useless advice over and over again. Did they mean well? Maybe, but there is great likelihood that they felt some strange obligation to give a young boy a piece of advice because they thought that was what was expected of them. And there is an even greater likelihood that they just wanted to hear themselves talk. Should you dress for the job the job you want and not the job you have? Sure, if you feel compelled, but better advice might be to dress for the job you have and just work hard. I’ve taught Shakespare in safari garb and mowed lawns as if I was going heading to Orion’s Belt. I don’t regret these things as they led me to where I am, but I often looked very stupid and out of place and from a professional perspective that’s always going to be a bit of hindrance. So if a boring old white guy tries to give you a piece of advice, nod your head, thank them, and go on your way. For every Nick Carraway’s father, there’s a Gary who took over his father’s successful paint company and whose mom gave him a down payment for his first house just dying to tell you how to make it in the world.

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