Assessment

In which I take a hard, critical look at the newsletter

I’ve been writing Thinking Ahead for a little over a year, at roughly one post per week. We’ve journeyed through various aspects of AI, introvert diaries, critical looks at our modern ideas about work, and other things.

And it’s not working.

A bitter pill to swallow, but a necessary one. I have fallen woefully short of any goals/benchmarks I set for this newsletter. (The ‘I’ at the beginning of that last sentence is not a good sign, but that would lead us too far down a dark alley.)

Perhaps I’ve been blinded by stories of newsletters that grow exponentially and buy their owners a tropical island and carefree lifestyle. Perhaps I have nothing to say/write that is worth hearing/reading. Perhaps I’m stuck in an uncanny valley of slightly odd but not weird enough to be special. Perhaps my voice simply drowns in this age where everyone has a newsletter, e-book course, Youtube channel, and consulting business. (Perhaps I’m not negative enough?)

Perhaps, perhaps, perhaps. Comparison may be the thief of joy, but comparison against an illusory ideal is the destroyer of worlds.

So, options?

• Rethink Thinking Ahead.

• Blow it up and delete all the things.

• Do a Dory and persist in banging my head against a self-made wall.

(Feel free to let me know your preference, if any. No pressure, of course.)

Instinctively, my brain latches onto option two. I have, however, learned through experience that it rarely works and that my initial reflexes can do more damage than good. There are even a few posts I don’t want to delete just yet because they contain tiny glimmers of a good idea.

Rethink or persist, then?

To simply keep going would be similar to walking into a wall over and over and thinking that, eventually, a door will appear. Sadly, here too I have learned not to expect such things. There are no magic doors and I will break before the wall does, no matter how stubborn I can be.

Transformation it is.

But into what?

I admit I’m drawing a blank here. No, that’s not true. I’m drawing a bunch of cards, but none of them screams ‘ooh shiny’ to me.

It’s exhausting to keep throwing snowballs in hell and being the fool who thinks one of them will do anything more than melt into insignificance. Maybe that’s the problem. The expectation of (and need for?) relevance. Or maybe not relevance, exactly. Validation? Acknowledgment? I suppose we all want to be seen in some way.

Conclusion?

I’ve deleted and rewritten these final sentences at least a dozen times. It went from deflective whimsy to gloom and back again, but I couldn’t settle on the right words. It’s weird to be this open to (mostly) total strangers. Are we allowed to do that, be vulnerable? Is my male membership card revoked? Ah, the sweet sarcasm is still there. Not all is lost then.

One of my favorite, often misunderstood, fictional characters sees it clearly, as he tends to do:

“If you don't know where you want to go, then it doesn't matter which path you take.”

- Cheshire cat

See you soon.