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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.

My recipe for personal finance success isn’t complicated

The other day I had a couple beers with a friend.

He asked how I managed my money. I surprised him — I think — when I said I no longer invest any of it.

To the beginning of the end of our conversation about money first.

I asked my friend to consider $100,000 in association with $10,000 in monthly fixed expenses. Not very hard to do in Los Angeles, where, presumably, more than a handful of people have that much overhead and, in some cases, considerably more.

Then I asked him to consider $100,000 on $5,000 or $2,500 in…


Making money in the stock market doesn’t make you a bad ass

Study after study tells us one thing about a crucial element in the relationship between individuals and their money decisions.

Here’s one of the latest mentions via Acorns:

Overconfidence: The tendency to overestimate one’s own abilities when making financial decisions. Someone who considers themselves well-versed in cryptocurrency may be more likely to buy a new digital coin without fully considering or understanding the risks.

Overconfidence — it’s one of the worst things you can experience when dealing with money, particularly if you’re investing it.

I’m afraid we’re seeing several factors coalesce to create a crisis of overconfidence, especially among young…


#3 and #4 are the main reasons why I’ll rent for the rest of my life

As my article history shows, I consider home ownership a bad idea. At least for me.

While I don’t like to prescribe my preferences on others, I’ve witnessed more than a few people go through the personal and professional motions. They buy a home, which is sometimes followed closely by regret, if not downright misery.

Personally — you meet someone. You fall in love. You commit to them.

You didn’t ask the questions I asked my girlfriend on one of our first dates (if not the first):

  • Do you like Los Angeles?
  • Do you want to stay here?
  • Do you…


There’s nothing wrong with work ethic, as long as it works for you

I’m to the point in my life where I value my lifestyle, as it relates to work, differently than I once did.

I love the work I do. I get a lot out of it. And I’m lucky to have it.

In my world, it doesn’t get any better than writing articles for the internet (on Medium) and finding writers who can do likewise (on Seeking Alpha).

At the same time, I’ve been talking some shit about work in my recent articles.

For example —

In this article, we clarify a few points about work in general, hard work in…


Even if it takes forever, it’s the clearest path to financial freedom

You don’t need a million dollars to retire. In fact, saving $1,000,000 is probably a waste of time.

It’s unlikely, impractical, and wholly unnecessary.

Instead, maybe you only need one year’s worth of expenses to take semi-retirement to the next level.

I say you need, but I speak only from my experience and vision for my future.

Take what you can carry and leave the rest.

In this article, we consider how a strategy of recycling cash can work on the ground — in the day-to-day — after you hit the impressive benchmark of saving enough money to live on…


We all have different ways of looking at 30 years worth of life

I love renting.

For many of us who happily rent, it’s one key component that enables (in a good way) our preferred lifestyle. We actually use apartment living as a way to achieve a relatively low cost of living in seemingly expensive cities such as Los Angeles and San Francisco.

We tend to receive thoughtful responses to articles on the rent versus own debate. So, in this article, I share a few with a focus on the perspectives of people perfectly happy to throw money away on rent.

I’d be remiss if I didn’t thank Medium for including me a…


I know what I’m talking about. I’ve made mistakes with credit.

We all want to have and do cool shit.

Some of us run into a problem when we think we’re entitled to be able to have and do cool shit.

When I left home for my first full-time job — I was 19 turning 20 — I experienced this sense of entitlement.

I got this job.

I was living in this big city — Miami.

So I had to live the lifestyle I associated with my first full-time job, moving from home, and living in Miami.

Even though I made a paltry $26,500 a year at that job.

Like so…


To get what you want, give other people what they need.

Prior to the pandemic, I took a break from online content to work in the craft cocktail industry.

It was one of the best moves I have made in my life. I met some of my favorite people, including my amazing girlfriend because of the last bar I worked at.

You have lots of fleeting and long-lasting social interaction when you work in a bar, obviously with guests, but also— like with many other jobs — co-workers.

However, unlike office work, these interpersonal encounters happen almost nonstop. The pace is almost always fast.

Probably because of my place in life…


We use work as an excuse to not do life on our terms

I can’t get past the hysteria sweeping the nation over unemployment benefits during the pandemic.

I wrote a bit about it in a recent Medium article:

I have also written about my own experience with overwork.

In this article, we tie the two conversations together and consider how we can place work in a healthier context.

Roughly five years ago, I was pushing 200 pounds. While I’ve always had a somewhat stocky build, that’s still too much weight on a five-foot, six-inch frame.

This happened because I was working too much.

I was working too much for two reasons:

  • I…

Rocco Pendola

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