Harvard Business Review LogoAugust 10, 2026Deagreez/Getty ImagesCareers are becoming harder to plan because two long-term trends are unfolding at once: working lives are growing much longer, and AI is making the future of work increasingly unpredictable. As“For decades I’ve been told that managing a successful career begins with a plan,” Bill, a senior leader in a financial institution, told me during an executive education program I was running. “Decide where you want to be in five years. Build a roadmap. Acquire the skills you’ll need. Then work steadily towards your destination.” He paused. “That advice made sense when the future was reasonably predictable. What if it isn’t?”
The Predictable Executive Career Arc Is Over
Careers are becoming harder to plan because two long-term trends are unfolding at once: working lives are growing much longer, and AI is making the future of work increasingly unpredictable. As the traditional career timetable breaks down, professionals can no longer rely on fixed milestones or detailed long-range plans. Instead, they need practical decision rules that help them navigate uncertainty. Three are especially valuable: prepare through small, low-risk experiments before change forces action; invest in capabilities, relationships, health, and curiosity that compound over time; and protect time for reflection so better judgment can guide important career choices.
TL;DRAI
Traditional five-year executive career planning is becoming obsolete as working lives extend and AI disrupts job predictability. Longer careers combined with rapid technological change demand agile skill acquisition and portfolio strategies rather than linear roadmaps.
107 words~1 min read
