In 2016, after five years of working in technical Product Management, I made a decision about my career. I was going to pivot into Product Marketing. I had some strong beliefs in my youth, but chief among them was the belief that selling software is harder than building software. I…

I haven’t even written a handful of words yet, but I already feel like, without some significant divergence from the norm, this year’s customary reflection will ring contrived. It’s 12:21 PM EST, NYC time. I’m sitting in an empty Manhattan apartment in an emptier Manhattan. …

Perched upon the windowsill, plain in sight to see, I sat and looked out the window and past the balcony. Parched was I of mouth and tongue that I could scarcely be, and yet I sat and beckoned him, glowing oh so pleasantly. I curse the pane that you slid down which kept you, from I, away; oh, how I longed myself through the glass with bounty of dismay! Yet there he sat, fat on mat, captive mind somehow shackle-free of the obligation he still has to fucking water me.

“So, a cow, chicken, and a pig walk into a bar, right. They sit at the bar next to each other in a row. The bartender comes up and serves them, and as he does, he asks each about themselves.” “The cow, he asks, ‘so whadya do for a living?’” “‘I make milk.’” “The chicken, same question.” “‘I lay eggs.’” “As he turns to the pig, the pig loosens his collar and sighs loudly in anticipation of the question that goes unspoken.”

So stood Times Square: empty but for the few locals in transit as attention-starved ads sheened and shimmered like the brilliant stars above a desert night in desperate competition for the attention of an audience below. The odd native tourist-in-own-town stopped for a fleeting moment with smartphone in hand to…

“Change is the only constant.” This is how you start a decade recap on LinkedIn or Medium now, right? Ugh. I hate truisms—especially the implicitly condescending ones like that. That particular soundbyte is one some bandy about as mantra’d badge of honor — a would-be battle scar from what was…

Amidst a sea of uncertainty in life, we return to our comforts as old, worn jeans and childhood bedrooms, if we are so fortunate as to be still afforded the luxury to seek solace in them. So, then: to writing and to video games. It’s 8:10 pm. I’m sitting at…

I remember the precise moment in 2018 when it happened—the very second an ephemeral moment of clarity so farfetched as to seem entirely fabricated and yet so starkly vivid as to be indisputable. I was sitting in a boardroom meeting with two coworkers and two senior representatives from a potential…

In these periodical posts, I opine on prose, products, and profits. I do this for your entertainment and education (and, of course, to shamelessly promote myself and my team, as that’s what you do these days.) Here’s a surprisingly and seemingly difficult question to answer, particularly in Toronto: who ultimately…