We are on walking in the margins, between our current chapter, and the next.
As artificial intelligence reshapes what is possible, many talk about workflows and what the future of work will look like.
For decades, we’ve built our institutions, and our identities, on the pushing of the boulder as to where significance lies.
What if the boulder disappears?
What if the myth of Sisyphus, the eternal labourer doomed to repetition, was not just a story of punishment, but a mirror held to our inherited structures of worth?
Who do we become when the hill flattens and the struggle is no longer the only measure of meaning?
Yes, it will be a technological shift, and also a trust shift. A shift in how we define work, a shift in how we stay meaningful when the world around us keeps accelerating.
When the systems get smarter, we are not asked to compete, we are asked to level up. For decades, our assumption was work is where value is created, identity is affirmed, and contribution is measured.
That foundation may shift going forward.
With innovation, the labour market is evolving. Institutional and world leaders now face an existential question: how do we build systems that honour distinctly human contributions in a post-efficiency economy?
From Workforce to Worthforce
The question we’re pondering is, “How do we design systems that recognize and value human contributions in an AI-augmented world?”
Trust, once an institutional default, now requires deliberate cultivation.
In this new landscape, maybe competence will be expected, integrity will be scrutinized, and empathy will be essential.
Leaders will need to increasingly become interpreters of uncertainty, and no longer just enforcers of process. The days of maintaining control are numbered, it will be around fostering alignment within systems that no longer guarantee consensus.
Power now lies in the ability to hold paradox, not just provide answers.
The old playbook relied on control. The new era calls for alignment without certainty, coherence without unanimity, and leadership that is relational, not positional.
What Leadership Requires Now
The leaders positioned to navigate this shift will embody a different architecture:
- Humility
The strength to ask the questions no one can answer yet—and to hold space without rushing to fill the silence.
- Narrative Clarity
The capacity to translate complexity into coherence across teams, markets, and missions.
- Design Fluency
The ability to shape human-centered systems—not just policies—that protect dignity, elevate trust, and reward discernment.
Legacy leadership prioritized efficiency.
Future leadership prioritizes existential relevance—the ability to guide others through uncertainty with presence and meaning.
A Redefinition of Human Contribution
Do you think the 9–5 may change? Titles may lose predictive power?
What do you think about the freedom to untangle identity from utility,
to create not just because we have to prove our worth, but because the soul insists?
What do you think it’ll feel to step out of Sisyphus’ cycle – by asking deep questions:
What is the future of work, if work is no longer the price of belonging?
What happens when the hill and the boulder disappears, and we are left with the freedom to become something new?
And maybe… just maybe… what comes next will feel like Kierkegaard’s dizziness of freedom, scaled to systems, beyond selves.
The institutions.
The leaders.
The humans holding little hands.
All staring into the wide-open unknown.
Not with paralysis though, not this time.
With a willingness to build what it truly means to be human.
Home » Notes to Self » Lessons From Existential Philosophy in the Age of AI
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Lessons From Existential Philosophy in the Age of AI
We are on walking in the margins, between our current chapter, and the next.
As artificial intelligence reshapes what is possible, many talk about workflows and what the future of work will look like.
For decades, we’ve built our institutions, and our identities, on the pushing of the boulder as to where significance lies.
What if the boulder disappears?
What if the myth of Sisyphus, the eternal labourer doomed to repetition, was not just a story of punishment, but a mirror held to our inherited structures of worth?
Who do we become when the hill flattens and the struggle is no longer the only measure of meaning?
Yes, it will be a technological shift, and also a trust shift. A shift in how we define work, a shift in how we stay meaningful when the world around us keeps accelerating.
When the systems get smarter, we are not asked to compete, we are asked to level up. For decades, our assumption was work is where value is created, identity is affirmed, and contribution is measured.
That foundation may shift going forward.
With innovation, the labour market is evolving. Institutional and world leaders now face an existential question: how do we build systems that honour distinctly human contributions in a post-efficiency economy?
From Workforce to Worthforce
The question we’re pondering is, “How do we design systems that recognize and value human contributions in an AI-augmented world?”
Trust, once an institutional default, now requires deliberate cultivation.
In this new landscape, maybe competence will be expected, integrity will be scrutinized, and empathy will be essential.
Leaders will need to increasingly become interpreters of uncertainty, and no longer just enforcers of process. The days of maintaining control are numbered, it will be around fostering alignment within systems that no longer guarantee consensus.
Power now lies in the ability to hold paradox, not just provide answers.
The old playbook relied on control. The new era calls for alignment without certainty, coherence without unanimity, and leadership that is relational, not positional.
What Leadership Requires Now
The leaders positioned to navigate this shift will embody a different architecture:
The strength to ask the questions no one can answer yet—and to hold space without rushing to fill the silence.
The capacity to translate complexity into coherence across teams, markets, and missions.
The ability to shape human-centered systems—not just policies—that protect dignity, elevate trust, and reward discernment.
Legacy leadership prioritized efficiency.
Future leadership prioritizes existential relevance—the ability to guide others through uncertainty with presence and meaning.
A Redefinition of Human Contribution
Do you think the 9–5 may change? Titles may lose predictive power?
What do you think about the freedom to untangle identity from utility,
to create not just because we have to prove our worth, but because the soul insists?
What do you think it’ll feel to step out of Sisyphus’ cycle – by asking deep questions:
What is the future of work, if work is no longer the price of belonging?
What happens when the hill and the boulder disappears, and we are left with the freedom to become something new?
And maybe… just maybe… what comes next will feel like Kierkegaard’s dizziness of freedom, scaled to systems, beyond selves.
The institutions.
The leaders.
The humans holding little hands.
All staring into the wide-open unknown.
Not with paralysis though, not this time.
With a willingness to build what it truly means to be human.
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