This piece was prompted by a recent comment from Ryan Roslansky, CEO of LinkedIn, who suggested that five-year career plans no longer make sense in an AI-accelerated world. I agree with the premise but find it incomplete. Paired with Cornel West’s thinking on work, dignity, and moral responsibility, it raises a deeper question: if systems now operate on short horizons by design, why do we still ask individuals to organize their lives around long-term loyalty?
Over the last decade, the way organizations operate has quietly changed — most people felt it long before having language for it. Planning cycles shortened. Decision loops tightened. Expectations began resetting faster than most humans can realistically recalibrate. This isn’t a critique of intent or values, but rather a description of how modern systems behave under pressure.
AI didn’t cause this shift — it exposed the underlying incentive structure by dramatically lowering the cost of change, iteration, and reversal across nearly every layer of work. What once unfolded over years now happens in weeks. Direction shifts without ceremony. Roles evolve midstream. Systems are rewarded for flexibility. Humans are still asked for loyalty. Most people feel the tension. The question is why we keep pretending it isn’t there.
Modern organizations operate on short time horizons by design. Venture-backed companies operate within finite fund lifecycles, typically ten years, with meaningful pressure for exits within three to five. Public companies live quarter to quarter, shaped by earnings cycles, analyst expectations, and executive compensation tied closely to near-term stock performance.
Employees are asked to align against rushed KPIs, deliver results this quarter, and demonstrate long-term belief in missions they don’t control. Deferred rewards like equity, progression, and stability are positioned as justification for patience and endurance. In practice, both sides often shake hands knowing neither expects permanence, yet perform the ritual as if it were a forever marriage.
Organizations may be constrained by markets and capital, but they retain the option to revise direction, reset goals, and reallocate risk. Individuals are asked to commit without access to those same levers. These timelines don’t align. That doesn’t make companies dishonest or employees disloyal. It makes the system incoherent. Organizations are rewarded for optionality and rapid adjustment. Individuals are asked for continuity and long-term investment of time. When conditions change, the system absorbs flexibility. Individuals absorb disruption.
Organizations are rewarded for optionality and rapid adjustment. Individuals are asked for continuity and long-term investment of time.
Leadership often celebrates the ability to “lead in ambiguity” as a sign of maturity. Ambiguity is real. Markets shift. Information is incomplete. Leaders rarely have full clarity. The problem isn’t ambiguity itself. It’s how unevenly it’s distributed.
In short-horizon systems, clarity is expensive. It requires trade-offs, prioritization, and visible commitment. Ambiguity preserves optionality. Over time, it becomes structurally useful. But it’s worth naming what that means in practice: ambiguity reduces exposure for decision-makers while increasing exposure for those executing decisions.
Product organizations often describe work as a series of bets. That language is meant to be honest. A bet acknowledges uncertainty and the possibility of failure. But in a real bet, three things are clear: who places it, what’s at stake, and who absorbs the loss. Inside organizations, those lines blur. Leadership defines the bet. Teams execute it. Individuals often carry the consequences.
We can see the impact in tenure. Median employee tenure in the U.S. sits under four years. Senior roles turn over even faster. VP of Design averages about 2.1 years; VP of Product, 2.3 years; CRO, 1.8 years; CMO, 1.8 years. In that environment, long-term attachment no longer reduces risk. Employees respond by bounding commitment, prioritizing learning, and seeking clarity early. That isn’t disengagement. It’s alignment with reality.
If loyalty is now conditional and time-bound, work needs to be designed accordingly. This isn’t a call for less commitment. It’s a call for more honest contracts between systems and the people inside them. Organizations should make time horizons explicit, distribute ambiguity intentionally, and stop using loyalty language to mask optionality. Individuals, in turn, should treat roles as bounded engagements, optimize for learning over promises, and seek minimum viable clarity early.
For me, product and design leadership matters most not by eliminating ambiguity, but by designing for it — making time horizons explicit, clarifying ownership of bets, and establishing minimum viable clarity so teams understand the risk they’re carrying. When systems are honest about how they operate, people can engage fully without mistaking loyalty for blind faith.
Ian Alexander
VP of Design — writing on leadership, AI product strategy, and building teams that ship.