Mission Accomplished

I launched my daily baseball, media, entertainment and culture newsletter, Cup of Coffee, on August 12, 2020. That was nine days after I was laid off from NBC, where I wrote for over 11 years. When I launched I had a modest short term goal and a bolder longer term goal.

The modest goal was that it’d provide enough money that, combined with my NBC severance, I’d be able to ride out what figured to be a long and tough job search. At least if I wanted to find something I was truly interested in doing as opposed to doing something drastic and horrible like reactivating my law license.

The bolder, longer term goal was to grow it enough to make it my full time job forever. To that end, I set a subscriber/income goal that I felt could make that work. I pegged that goal to August 3, 2021, the one-year anniversary of the day NBC shitcanned me. It was a pretty optimistic goal, I felt. Aggressive, even. Going out on one’s own is tough in any business but in sports media, where there are so many free options and where reader loyalty is historically poor, the idea seemed pretty daunting.

At 8:27 am this morning I hit the bolder, long term goal, meeting my desired subscriber count over four months early. It had been apparent that I was going to be able to do that, and to make this my full-time job, for a while now, but the fact that I hit that goal on baseball’s Opening Day of all days is extra special. It has me dancing on a damn cloud.

Making the leap from lawyer life to being a professional writer all those years ago seemed like a once-in-a-lifetime thing. I figured that that was all of the career and life luck I could ever reasonably hope for and to wish for anything more would be greedy. But dammit, I did it again. I went from a writer whose livelihood depended on a big media company to pay him to one who could make it work on his own.

Not that I’m going to credit dumb luck alone here.

My father likes to tell people that the difference between my brother Curt and me is that, if you ask Curt to go out in the backyard and dig a hole, he’ll grab a shovel and start digging while I will spend twice as long as it would take to dig the hole arguing with you about why, actually, the hole is unnecessary and that it shouldn’t be dug. There is more than a little truth to that, and it explains more about us than just why Curt joined the Navy and I didn’t.

I can’t speak for my dad’s view on this, but I think what that describes about me is not my inherent laziness but my inherent stubbornness. I do not like to do what I do not want to do and I will go to great lengths in order to do things in the exact way I want to do them. The worst way to get me to do anything is to order me to do it and the degree to which I will work in order to maintain my autonomy is staggering to the point of self-defeating. Ask my old bosses at the law firm how that worked.

All of which is to say that I was always gonna do better by not having a boss. Now I don’t have one and, if I play my cards right, never will have one.

Did I mention that I’m dancing on a cloud?

I want to thank each and every one of you for subscribing or for offering me encouragement both over these past few months or, well, ever. It’s been a life-changing decade and change.

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at Craigcalcaterra.com. He lives in New Albany, Ohio with his wife, two kids, and many cats.