Living The Semi-Retired Life: The Time I Went To A Meeting With The CEO Of HBO Soaking Wet

Sometimes 'follow your passion' has less to do with the work you do and more about the life you want to live

In case you’re new or haven’t opened this email in a while, my name is Rocco. I write a Substack about Living The Semi-Retired Life.

We’re forming a community here built around our experiences with and expectations of retirement, which, for quite a few of us means Never Retiring and working in retirement. Don’t worry—these can be good things!

I lead the discussion with details from my journey—past, present and anticipated future—which includes plans to move to Spain. I also detail and discuss ways to manage money as it intersects with work and life and research on the broad spectrum of issues dealing with retirement.

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Thanks to Kevin W. for this great response to Gary Foster’s recent guest post, where he detailed how and why he lives his semi-retired life.

There’s lots in Gary’s post and Kevin’s response that I relate to.

Specifically, Kevin’s comment reminds me of an opportunity I had—and didn’t pursue—several years ago during a different iteration of my writing career.

The story I tell today took place when I was writing about stocks for TheStreet.com.

I’m not a big name dropper, which is one reason why I shy away from telling these stories. For some reason, I get anxious (like I am now!) and embarrassed when I discuss this stuff. However, I recently received some advice—that I should write about these experiences more often.

So, here it goes, the time the former CEO of HBO loved me so much, he tried to get me a job at CNN, and almost succeeded.

Don’t worry. Turns out this has everything to do with Living The Semi-Retired Life.

And it’s actually, in parts, a funny story.