Alexa, Schedule My Midlife Crisis
How tech made our work lives efficient—but forgot about the meaning part.
A few weeks ago, I asked Alexa to reorder my matcha (yes, I am obsessed), play a podcast, and remind me about a 1:1. She did all three flawlessly. I was impressed… and then immediately unsettled.
Because while she can optimize my to-do list, she can’t answer the question that’s been lurking under my perfectly prioritized productivity system:
“Wait... why am I doing all this again?”
Welcome to the modern workplace, where everything is smarter—except our sense of purpose.
We’ve become exceptionally good at the how.
Automation, AI, apps, bots—every week there’s a new tool that promises to make work frictionless. Email that writes itself. Slides that design themselves. A calendar that finds the perfect meeting slot across four time zones.
But while everything around us has been engineered for speed and scale, no one’s really addressing the part that keeps people motivated in the first place:
What’s the point of all this “work” work?
Most of us have confused efficiency with clarity.
We're running faster, smoother, and cheaper.
And we still don’t know where we’re going.
Let’s talk about that quiet voice in your head.
You know the one. The one that pops up during your fifth Zoom of the day. Or when you’re scrolling job posts “just to see what’s out there.” Or when you stare at your color-coded calendar and feel a sudden urge to throw your laptop into a river.
That voice usually asks something like:
“Is this what I actually want?”
“Do I even care about this?”
“Why does everything I accomplish feel a little... empty?”
If you're nodding: congrats, you might be having a quiet existential crisis—right on schedule. Not because you’re failing. But because you're finally succeeding at the wrong things long enough to notice.
The data backs it up. (Sorry.)
According to a McKinsey study, 70% of employees say their personal sense of purpose is largely defined by their work. But only 18% believe they get to live that purpose at work. That’s a staggering gap.
Meanwhile, Gallup reports that employee engagement continues to slide, especially among younger generations. They’re not slacking—they’re seeking meaning.
And they’re increasingly unwilling to pretend that ping-pong tables and AI-generated performance reviews are enough.
In short: we’re productive. We’re smart. We’re deeply misaligned.
So... what happened?
Somewhere along the way, we got distracted. We chased titles, milestones, “dream jobs,” and optimized career ladders without ever stopping to ask where the ladder actually leads.
Leaders got especially good at playing this game. We chased scale, growth, capital-E “Excellence.” But as teams got bigger, stakes got higher, and tools got more automated, something quietly left the room: meaning.
It’s the thing we’re all secretly craving—but don’t have time to talk about because we’ve back-to-backed ourselves into oblivion.
AI isn’t the enemy. But it’s also not the answer.
Let’s be clear: AI didn’t create this crisis. If anything, it’s just sped up the moment of realization. When the robot starts doing the job you thought made you special, you have to ask:
What actually makes me valuable?
Hint: it’s not your ability to respond to emails quickly.
It’s your judgment.
Your perspective.
Your courage.
Your humanity.
Ironically, the rise of AI might be the best thing to happen to human-centered leadership—if we choose to pay attention.
And if you’re a leader, you don’t get to skip this part.
The higher up you go, the easier it is to avoid these questions. You’re busy. You’re responsible. You’re supposed to have it figured out. But I talk to C-suites and founders all the time who whisper versions of the same thing:
“I don’t know if this is it anymore.”
“I’ve hit all the goals I set—and I’m still not satisfied.”
“I keep telling my team to ‘find their why,’ but I’ve lost mine.”
This isn’t failure. It’s honesty. And it’s an invitation.
So what do we do now?
First: pause. Not forever. Just long enough to notice the autopilot.
Then ask questions that your calendar won’t:
When do I feel most like myself at work?
What do I want to be known for—not just what am I good at?
What would I be doing if I wasn’t so good at this version of success?
Because you can’t automate your way to meaning.
You can’t ChatGPT your way into purpose.
And Alexa cannot—and should not—schedule your midlife crisis.
That part?
That’s yours.