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I write about doing life and personal finance, focusing on the psychology of our relationships with other people and money. I’m anti-guru, pro-empowerment.

What you might need to do to stop living beyond your means

Source: Author

Even though I think I know better, I still fall for the small expenses add up personal finance fallacy.

This idea that if you buy a coffee every morning or drink beer in a bar, you’re missing out on the power of compounding. Save the $5 you spend on your latte and, at an annual interest rate of six percent, you’ll have $296,514.03 saved after 10 years.

I go through these psychological motions sometimes in bars.

Four dollars for something standard like a Molson Canadian (a staple beer I drank most often on a recent trip to Buffalo) or six…


Hint: It’s not New York or San Francisco

Source: Author

That’s the view from the coffee shop my girlfriend and I liked best on our recent two-week trip to the northeast United States.

We spent most of our time in Buffalo, New York, a stone’s throw from my hometown of Niagara Falls.

There’s a quiet renaissance happening on Buffalo’s West Side. It’s an urban transformation I first noticed about 15–20 years ago.

Professors and other urban professionals initiated the process of buying, fixing up, and inhabiting the Victorian homes that dominate a neighborhood called Elmwood Village.

At the time, I toyed with the idea of buying an income property there…


They’re living in a fantasy world

Photo by La coccinelle on Unsplash

I often write sitting in front of a coffee shop on a busy stretch of Sunset Boulevard in Los Angeles.

I see all kinds of shit. I watch all types of people. And I eavesdrop on dozens of conversations.

You know you do this too. All of the above. Especially the eavesdropping part.

Anyhow, this morning I heard two things in the span of a few minutes that, coupled with my years of experience paying attention to this stuff, led me to write this article.

We’ve been cash poor for the last two years. Really cash poor. Like broke.

We…


Trading and investing in stocks only complicated my life

Photo by Joshua Mayo on Unsplash

I know several people who have done from decently to amazingly well in the stock market.

I know many more than several people who say they have done amazingly well or better in the stock market.

In today’s environment, you’d think it’s the easy, carefree norm to get rich in stocks.

But that’s bull shit.

Today’s collective chronicling of stock market success is akin to the way people use social media.

You only see the good stuff. The happy times. When things go well.

You post. Your “friends” see your victories. Not your anxiety, trials, and tribulations (save the people…


Try working two jobs that pay $15 an hour — if you’re lucky

Photo by Joshua Newton on Unsplash

I’ll try my hardest to not be a dick in this article.

Because it sort of irritates me to see people lament the hardship of trying to put together a budget on a $100,000 salary. Actually, it doesn’t sort of irritate me.

It does irritate me.

However, as this article took shape, I realized I went about writing evenhandedly.

You can tell me if I’m being a dick.

I have come to realize — after more than a decade of writing about money and, over time, applying what I write about to my own life — that people often believe…


You can do things for yourself, and maybe a lot of good

Source: Author / Hayes Valley, San Francisco

I was walking in San Francisco recently when I came across a flyer on the window of a building housing a company that sells real estate.

In one of the nation’s most expensive real estate markets, this company — who I presume doesn’t own the building they work out of (or maybe they do?) — plants the message to passersby that if you rent, you’re paying somebody else’s mortgage.

What a load of black-and-white, either/or bullshit.


And even then, I’d probably continue to rent

Source: Author / Hayes Valley, San Francisco

I love urban environments, particularly in places such as Los Angeles (where I live) and San Francisco (where I used to live and where my daughter now lives).

Even if I wanted to, I could not afford to purchase a home in these places, particularly in the neighborhoods I like best.

Tons of people move to new places, parts of cities, or the outskirts of town they don’t prefer just to own a home. This isn’t for me. I’d be miserable if I made such a move.

Ask most people I know who fled San Francisco for the suburban fringes…


With a little work, you can live off of cash for the rest of your life

You can live off of cash now and for the duration.

The process to get there takes time. It goes in phases. It requires patience. It’s not easy.

You gotta respect the process.

Over the last year-plus on Medium, we have covered each phase in-depth, not in any particular order. But it’s all there in dozens of articles — picking apart everything from a low cost of living to credit card debt to emergency funds — throughout my article history.

In this article, we cover the home stretch phase of cash-based personal finance. The point at which you’re pretty much…


5 keys to ensuring you’re ready practically and financially

Source: Author

After nearly ten years writing and editing articles for the internet, I had enough.

I was a full-time editor for a financial media platform, working stupid hours.

Sitting at a desk (my kitchen table) all day turned me into a fat mess.

I knew I needed to make a change and do something other than work with online content day in and day out for a while. The question was simple — what else could I do?

Each step of the trajectory I went on satisfies the promise of this article’s title.

My real-life experience informs how to quit your…


Rent versus own comes down to more than your house

Photo by Seth Yeanoplos on Unsplash

If all went according to plan, you’re reading this article on day seven of a 15-day vacation my girlfriend and I are on.

A month before this trip commenced, I set out on a writing experiment:

Given my line of work, there’s no reason why I have to interrupt my cash flow while traveling.

So here’s what I’m doing. You can likely adapt this approach to your own situation, particularly if you do work where you set your own schedule.

Over the next 30 days or so, I’m going on a writing sprint. I actually already started. I’m doing it.

Rocco Pendola

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