How It Works (and Why It Doesn’t)

How It Works (and Why It Doesn’t)

From 2023: The Most Depressing Place In America?

Your environment - and your attitude - matters more than anything in life

Rocco Pendola's avatar
Rocco Pendola
Dec 30, 2025
∙ Paid

As the year winds down, I’m resurfacing a few pieces that mattered—some popular, some overlooked, some that quietly predicted what life abroad would actually feel like.

Today’s speaks for itself as it relates to everything we discuss on these pages. It’s about looking back on where you’re from, where you’ve ended up, and the distance between the two places.

Get 50% off here!

From November 2023

I’m sure you have an entrant you know well. And, of course, it’s all relative, dependent largely on the context within which you define depressing. But, in my experience, my hometown might be the most depressing place in America.

In today’s post, I explain why as we contrast where I’m from to that hotbed of urban vibrancy we’ve been talking about—the West Side of Buffalo.

But it’s about more than what is truly an objective comparison. It’s about discovering several times throughout adulthood that you have not only become the polar opposite of the place you’re from and most of the people who remain, but that everything you have accomplished and want to accomplish in life happens despite their influence.

They like to think they sent you off into the world prepared when it was merely some stroke of luck that YOU stopped THEM from holding you back.

None of this means you don’t have love for the place you’re from and the people who populate it. It just means they have more than their fair share of unresolved issues that impact them and their children more than they’re able to see. Of course, we all have unresolved, resolving and—thankfully—resolved issues. Having them isn’t a problem. In fact, they’re a key element in growing as a person. The problem is a refusal to acknowledge, then address them so you can create healthier environments for doing life.

Get 50% off here!

Make no mistake, I thought long and hard about writing this. In fact, I have hesitated for years. Out of fear that my parents, relatives or friends might read it (none that I know of actually read my work). Out of fear of hurting feelings and making people I know and love feel as if they didn’t do a good job. Or that I think I’m somehow better than them. It’s not at all about better or worse. Or even parenting. It’s about the environments we create and normalize as they stagnate and proliferate over the years.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 Rocco Pendola · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture