Never Retire - What To Expect

Free Post #1

Thanks for subscribing to my newsletter. You probably let me into your inbox because this idea of Never Retire resonates with you.

In this free installment of the Never Retire newsletter, I’ll let you know what to expect from your free or paid subscription.

Nutshell version—expect content that goes deeper in the weeds than what you get from me on Medium. What works and connects with you on Medium probably doesn’t make sense—or provide as much value—via a free or paid newsletter. This doesn’t make one platform better than the other. They’re just different.

I’ll explain why.

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I have written about money—in some fashion—since around 2008.

Initially, I focused on individual stocks and general investing in freelance and full-time capacities at financial media platforms, Seeking Alpha and TheStreet.com.

Over the last 18 months, I shifted almost wholly into writing about personal finance—the decisions we make with our money in the day-to-day.

Up until the years before the pandemic, I believed I had to find a way to traditionally retire. Just past forty years old at the time, I clung to the idea of accumulating the magic number you see in most retirement-themed articles—$1,000,000.

Every time a personal finance writer published one of those articles telling you how far behind you are on your retirement savings and what you need to do—based on your age—to catch up, I’d freak out.

So I’d amp up my investing only to freak out a little more, as I sold stock to beef up the cash balance in my savings account.

I’ll save details of this experience for future installments. For now, all that’s relevant is that I knew I had to do something different with my money.

As I thought and started writing about this, I discovered I actually didn’t need to do anything radically different with my money other than stop investing (or trying to invest!) so much of it and think about how money can facilitate my present and future differently. I needed to let go of traditional retirement as a goal and wholly embrace a new way of approaching my personal finance.

Both versions of this newsletter will expand on that process and the money and money-related strategies I have developed (or adapted from others) alongside it.

Here’s how what I’ll publish here will be different from what I publish on Medium.

Medium pays writers based on engagement, particularly how long readers spend with an article. This model requires a particular type of writing. Typically 3-to-7 minute reads with equal parts information and some form of entertainment.

I love this model. If you understand it, you can provide value to readers without giving into the allure of clickbait headlines followed by a story full of empty words and hollow promises. In other words, there’s nothing wrong with a provocative headline as long as the content delivers on the stated intent of that headline.

I understand this. I like to think I execute on it pretty well.

At the same time, I’m a personal finance nerd. I don’t nerd out about much—money, cities, Bruce Springsteen—but when I do I appreciate the opportunities to approach the subject the way I can on Medium and the way I intend to with this newsletter.

With this in mind, in the free version of this newsletter, you’ll receive the quick, sometimes fleeting thoughts that simply don’t work as articles on Medium. However, individually and taken together they add to the discussion and help weave the narrative you’re having with yourself and your readers. These little thoughts often help generate the bigger ideas and subsequent strategies.

The paid version of this newsletter goes deep in the weeds on the development and realization of these bigger ideas. Deeper in the weeds than it’s feasible—if you want to build a following—than I can (or think I should) go on Medium.

That’s the beauty of building a following on a platform such as Medium. As you gain traction, a subset of readers emerge. The people as nerdy and passionate about what you focus on as you are. Maybe they’re inclined to follow you beyond Medium and hit the subscribe button for something like this.

That’s the beauty of a platform such as Substack, at least the way I will use it.

You can deliver a slightly more dense and academic approach to this subset of readers. Dense and academic in the sense that you spend more time defining terms, discussing the underlying motivations for your ideas, and digging into the step-by-step minutia of how to execute on the strategies that spring from these ideas.

So this is what I’ll do in the paid version of this newsletter.

Longer reads with an abundance of geeky brainstorming, more thorough explanation, rigorous analysis, and nuts and bolts dissection of how to actually do the things we talk about together.

Expect to hear from me two to four times per week (generally speaking) with personal experiences and actionable personal financial strategies to help us figure out how to live the way we wanna live now and for the duration under the nuanced umbrella of Never Retire.

Rocco