February 9, 2026essay

In the Grander Scheme of Things, Do These Even Matter?

Originally published on The Wicked (Substack), 2026 — preserved here permanently.Original

Vibe living with AI across work, personal, play

In less than 48 hours, my personal AI assistants have:

ported my expiring Skype number to a new service

freed up massive storage on my legacy Google Workspace

applied and inquired across HMO options

researched trip details for Valentine’s weekend

analyzed lab tests in prep for a doctor’s consult

They’ve also:

created a competitor-intel workflow to stalk other companies doing content operations

prepared and downloaded finance data across fintech platforms for reporting

turned long-form CEO content and data into role-specific briefs with clear next actions

sorted through my inbox, labeled my emails

automated incoming meeting notes into tasks for my Things app

created cron jobs so these workflows can run on repeat without me

Meanwhile, humans…

That’s where I froze.

Because on paper, this is the kind of post that’s supposed to end with a triumphant punchline. Look at how much I got done with AI. Look at the leverage. Look at the operational glow-up.

But what actually surfaced in me was something closer to: If the machines can do all of this, in the grander scheme of things… do these even matter? Do I matter?

Founders are professional plate-spinners. We’re conditioned to measure our worth in:

revenue

headcount

number of tasks cleared

number of hours “crushed”

So when I hand off a huge chunk of my cognitive load to AI and watch it complete in minutes what would have taken me days, there’s a quiet panic under the productivity high.

If I’m not the one doing the work, then… what am I?

There’s a growing conversation about this in the AI era: that we’ve fused self-worth with productivity so tightly that once the productivity can be automated, the self feels suddenly negotiable. Replaceable. Optional.

And when your business is your identity, that hits hard. It’s not just that tasks move faster now. It’s that the very thing you used as proof you deserve to exist in the arena — your output — is no longer uniquely yours.

Here’s what those bullet points don’t show.

The AI did not:

decide that Valentine’s weekend was worth planning for in the first place

care about which HMO actually protects my family, not just looks good on a spreadsheet

feel the anxiety behind the lab tests or the relief of having them analyzed before a consult

carry a mental map of competitors because it holds a long-term vision for DashoContent

discern which CEO thoughts matter enough to turn into briefs, and which to quietly delete

know my personal thresholds: what I refuse to drop, what I can tolerate, what I’m optimizing for as a human being

I did that.

I’m the one who woke up with a knot in my stomach about health, about time, about missed opportunities. I’m the one who decided that buying back my hours was worth the friction of setting these systems up. I’m the one who cares about not dropping the ball for my team, my clients, my people.

The AI runs workflows. I hold the why.

So what did I mean with that trailing “Meanwhile, humans…”?

It was a mix of frustration and grief.

Frustration, because I can now see how much pain, burnout, and busywork is actually optional - and yet most people are still drowning in it. They don’t have the language, the experiments, or sometimes even the permission to offload what machines can absolutely handle.

Grief, because this shift is not just about technology. It’s about identity.

If my worth is tied to how many emails I clear, how many reports I prepare, how many workflows I manually grind through, then no — in that narrow frame, I will become less and less “special” over time.

But that frame is broken.

Where I still matter — where you still matter — is in the things no model wakes up wanting to do:

to love particular people in a particular way

to hold a specific vision for a specific business in a specific community

to feel responsible for how your work touches real lives

to suffer when things go wrong and to grow anyway

to decide, consciously, what a good life looks like for you, not just a productive one

My AI assistants have become part of my team. They are powerful, obedient, and relentlessly scalable.

But the most important thing they’ve given me is not leverage.

It’s a clearer view of where I end and the machines begin — and a deep, quiet conviction that in that boundary, there is still more than enough space to matter.