Tomorrow Sidekick
Stories and gentle guidance for exploring AI in your Second Act.
Welcome To Tomorrow Sidekick
Stories for the Second Act — and the companions who help us step into it.
Most of us grew up with sidekicks.
Not in real life, but in the stories that shaped us.
- Robin to Batman.
- Sam to Frodo.
- Tonto to the Lone Ranger.
- Sancho Panza to Don Quixote.
Companions who made the journey possible—safer, lighter, and just a little more fun.
Somewhere along the way, many of us forgot that we still get to have a sidekick.
We forgot that our Second Act is still a story.
We forgot that we don’t have to walk it alone—especially now, in a world that moves faster than any of us asked it to.
That’s where Tomorrow Sidekick comes in.
Tomorrow Sidekick isn’t about mastering AI.
It’s about feeling less overwhelmed by it.
It’s about companionship—about the small, surprising ways life opens when you let a helper walk beside you.
Sidekick first. AI second.
This is not a technical newsletter.
You won’t find tutorials here.
No pressure to “keep up.”
No frantic lists of tools you “must” learn.
Instead, you’ll find:
fables
metaphors
narrative experiments
small stories with big meaning
glimpses of what’s possible in the years ahead
gentle human wisdom wrapped in fiction and truth
Some stories are real.
Some are fictional.
All are written with one purpose: to open a small door—one that leads to curiosity, courage, and possibility.
Because the future isn’t something you age out of.
It’s something you walk into.
And walking into tomorrow is easier when you have a companion beside you—someone (or something) that makes the next step lighter.
So if you’re exploring AI for the first time…
or exploring what it might mean for your life to have a sidekick…
or simply wondering what comes next…
Welcome. You’re in the right place.
Second acts can begin anywhere.
Some doors open at 17. Some at 57. Some at 87.
Tomorrow doesn’t care how old you are.
Let’s walk into tomorrow together.
Side by side.
Story by story.