Shoes Never Make the Man


His experiences do.

An introduction I wrote for a collection of stories about how a few men chose to grow up not out of responsibility but from their own poignant discovery.

[2184 words]

WITHIN A MONTH of starting my new job, the company began to punk me regularly. This particular internet startup, also my first out of college, fancied pranks in the form of special company themed days. Some were believable like Suit Day and others as absurd as Camping Day, where I was told we were going to camp in the office, the CEO’s house at the time, and grind the weekend away, all the while telling ghost stories in between breaks. Yet, for a company that operated an online bunk bed store, made $320 organic denim, and authored a once popular online quiz “How Long Could You Survive on a Gay Pirate Ship?” walking in suit and tie or bringing a sleeping bag to work didn’t seem too far fetched. So naturally, despite the collegiate level of proficiency I had just so proudly secured, each and every trick was far too effective in steering my innocent credulity down a rabbit hole of forthcoming disappointment.

To my defense, I had cohorts who were anything but slacking in the ongoing effort to relieve my suspicions. During the eve of Suit Day, they took a group break to pick up their suits from the dry cleaners and later, on Camping Day, propped the employee I trusted the most—his older age and newfound fatherhood concealing any and all trace of ostensibility—to actually bring his camping gear into the office with him. I counted numerous cans of food, flashlights, a lantern, and then concluded oh man this shit just got real. As everyone else left to get their gear, they asked me to set up camp until they arrived back. I, of course, obeyed, leaving me at the mercy of their alleged integrity. And then just like every doomed romantic waiting atop of the Empire State Building eventually has to admit, so did I later that night: they’re not coming.

None of the trolling attempts bothered me the least bit. Being the impressionable college graduate in a startup of seven reminded me of my days of pledging a fraternity. Admittedly, this time getting voted in the group confirmed my ability to pay next month’s rent, not just a future chance at scoring with a sorority girl. And like any other rite of passage, you deal with the hazing until there’s a new guy to take your place. If you didn’t play along, the others would feel almost offended by your indifference to tradition (they always tell you it’s because of tradition). But being no stranger to adolescent rituals nor adversary of middlebrow humor, I readily looked forward to their attempts at half-baked gags.

Soon after growing tired from hatching childish illusions, the others doubled down on their attempts at levity by making me get the CEO’s lunch every day. The first time the CEO asked me to do this, he penned his exact order on a yellow post-it note and handed it to me. I then read over his request: a veggie sandwich tricked out with things like extra olives, cucumbers, oil and other garnishes; never considering the irony of it all. You know—asking someone to go all the way to Subway to get a sub chock full of everything but meat. Rather, I felt honored to save time out of his day so he could be more productive. Sucking up to the boss didn’t hurt either.


I kept that same post-it note in the back of my wallet for the entire four years I stayed with the company. It represented a sort of trinket, awarded to the lucky few who took the time to inquire how I got started. Every time I pulled it out of my wallet, I received a look of amazement the second they learned this top manager really had his start playing lunch duty running back to their very own QB1. People seemed to enjoy hearing my beginnings as a gullible neophyte as much as they liked learning we all started $200k in debt and possessing no background in the one of the most competitive lead-gen internet verticals. Years later, we’d be out of the CEO’s bedroom into a lush 100 person office, accompanied by hundreds of cheers from our friends and family after an embarrassing first act of multiple product failures but never forgetting this only happened because we avoided throwing in the towel. All these narratives created a past I was really proud to recall for any eager audience, and it was also a past requiring an official goodbye.

At the very end of my last day, I walked over to the CEO’s desk. He was absent but that was fine, my official debrief already having been earlier that week. This only required a moment to leave him a letter written minutes prior. It went like this:

Today is my last day. I’m almost done on finishing the new initiative for our portfolio. I think you’d like it. I just wanted to give you this back. It’s something I’ve kept in my wallet since I first started to show to people who ask how I started here. 

I kept it because I think no matter where you are at in life, you should never forget where you came from and how it all started.

Everyone needs a place to call home. 

Thanks for the memories. 

Relinquishing the old post-it note left a warm feeling of sentiment, identical to the one encountered the day I received it. There wouldn’t be any more lunch errands; no more story time for beady eyed analysts. I didn’t let it resonate too much. There was something else far more pressing was on my mind.


The real reason for that closure was to embark on my plan for taking time off from a career. Indefinitely. I had this romantic notion of discovering freedom for myself after many years of stale 60 hour work weeks and relentless startup anxiety. Similar to a real breakup, my actions were predictable, right down to the immediate act of seeking someone opposite from your previous lover—an instinctual direction we’ve all felt compelled to do at least one time in our life. Out of spite, I dreamed a less complex, more spontaneous woman would fit me better. They always seem perfect at first, right? That is until you move on, granting the past forgiveness and allowing it to be less of a rubbernecking wreck in your rear view mirror. In reality, we’re all chasing a harmful fantasy not all independent from the constraints of what we experienced before. One simple truth I’d learn later on.

Deep down inside, I also really thought I earned the escape. An itch of entitlement spread to my head because I helped build a successful startup. Remembering college graduates often take a year off gave me sufficient reason to join the ranks of the unemployed not actively seeking a new career. Jokingly, I told my friends this was my “born again college graduate phase.” I felt it helped legitimize my so called plan for not having an idea of what I’m going to be doing in the future. Such a vision was lofty, even under the calculated assumption that it’s all okay as long as I find it before I need to start paying rent again. And that date could be very far in the future because my exit cashed out my equity, leaving this author here a very elated bachelor. I had my logic (if there is enlightenment, I could get it without work), assumptions (happiness can come from nothing / I’m ready for this) and enough financial security to play through all the proofs until I deduced a viable theorem for my life.

One year ago it seemed all roads led to that biased decision: not working because of choice.


Think Back to the Future or the obvious example The Little Mermaid. These stories place the protagonist in an environment foreign to them and what proceeds creates a fulfilling tale of character development. I didn’t go back in time, kiss a younger version of my mom, grow legs or make friends with a talking lobster. Marry a prince? Well I think I got laid just once—the engagement so quick and dismissive, I question at times whether it’s fair to even count it. What started happily flapping fresh off the shore of naive optimism quickly entrenched itself within short lived peaks and laborious, muddy valleys. I know I hated the sea, but dry life was certainly no paradise, especially when I realized just how damn good a swimmer I had become.

I thought my life would be the dream rebound: evenings solely consisting of hasty trips to the bedroom and painless exits afterward made possible by the perks of non-committal detachment; all the fun without the seriousness or emotional turmoil. But it turned out to be the same old bed partner I previously despised. She was now hidden under the foxy guise of a new, misleading face—a face whose most affectionate pillow talk was nothing more than a disappointing parity I’d heard a million times before. Each night I’d go to bed feeling a similar angst as the nights when I was employed, eventually realizing my bets were horribly misplaced: I wasn’t even getting paid to loathe myself this time around.

No, things weren’t really what I expected. You’ve probably already heard or experienced this if you’ve taken time off. Yes, life goes on, maybe not how you’d planned it. But in situations like these you’re given an opportunity to slow things down enough to feel every tread make its mark in the pavement as you roll into the next day. Noticing that very traction is what I spent many nights thinking about—not the next project due, meeting to prepare for, feedback to be given or payout to be received—just the next day I’d be living.

When you start thinking about things on a day to day basis, you’ll realize who we are is made up of more of the daily decisions and thoughts than our grand plans for success. Changing these thoughts, none of them poetic notions like I intended, ended up mattering most to me in the following year. It would be the only way to navigate out of those muddy valleys and see glimpses of the elusive peaks I’d been hoping to discover all year long.

I didn’t find a grand solution to redeem my worries into millions or anything else I planned to do—who really does? I ended up doing different stuff. In fact, much of it was confronting regular stuff normal people had under control well before me. I just never took the time to notice. Or care.

And that wasn’t so bad. Turns out I needed to start thinking about the regular stuff again.


I’VE ALREADY DIGRESSED far too long about my experiences. You may be wondering what exactly is all the regular stuff I ended up caring about and how did it affect me. Well, I’ll be the first to admit the details are better described by someone else. Because any noble moral requires an equally polished form of lesson, I’ve found some young men with better stories to tell than a guy who openly chose to freeroll a year, complained a bit, and believed his musings can provoke more than his own smug approval.

So here are a few stories to take to heart. They’re written by guys around my age, who on the outside looked fine, but were hindered by weaknesses that slowly infected their wellbeing, one remorseful night after the next. The authors never struggled over extremities—maybe making their cases less sympathetic yet still interesting nonetheless—but with the common vices of men: career addiction, judging yourself, avoiding the past, worrying about the future, unwillingness to change, recreational overdose, and undermining one’s own integrity. You know, the regular stuff.

In the end, each recalls how they were the ones holding back their happiness. For every complex case of anxiety, there was a simple solution that was oh so obvious to everyone but the sucker inside: The same regular, common revelation that’s probably familiar to you because you’ve realized it before or know someone who does. None of the writings are very different than any other reality people our age struggle with, have faced, or soon will. These are special to them yet still universal to us. Sometimes conflict doesn’t have to take the form of David versus Goliath to inspire change—we may find difficulties in the mere idea of growing up and giving away the past, and once you get over it all, having already welcomed the smile that is rewarded from any youthful err, you simply accept that’s really not a bad thing at all.

Because what’s different isn’t always good, just like what’s obvious isn’t always easy. That would be a virtue I’d eventually come to know and love over the past year.

And I hope after these stories, with of course a little more luck than us, you may too.

Photo credit: Geometric