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Ada Chen Rekhi

Feeling stuck? Here's how to know when it's time to leave your job

career longevitystrategic thinkingexperience advantage

Tip

Ada Chen Rekhi uses the boiling frog metaphor for career inertia. Drop a frog in boiling water, it jumps out. Put it in cold water and slowly turn up the heat? The frog doesn’t notice the change degree by degree. By the time it realizes the danger, it’s cooked.

Turns out staying too long in the wrong role works exactly like this.

Two years ago, your role was perfect. Now the AI strategy feels misaligned. Your manager changed. The work that used to energize you feels routine. But you tell yourself: “One more reorg will clarify things. Just get through this quarter. The next promotion will unlock better projects.”

The question isn’t whether you’re comfortable today. It’s which direction the temperature is trending.

Use learning as your thermometer. Are you genuinely challenged? Building skills that compound your expertise? Deriving real satisfaction from the work? If yes, stay—even if it’s been two decades. But if you’re hitting fundamental walls—you disagree with the AI direction, the role constrains your impact, you’re delivering value but not growing—that’s the temperature rising.

You’ve watched colleagues stay too long. The VP who kept grinding because “the IPO is 18 months away” (it was 4 years). The director who thought “one more product cycle and I’ll prove myself” (they never did). The exec who rationalized “I just need the right team” (the problem was the company).

You know how those stories end. Younger managers can’t see the pattern—they haven’t watched enough people boil slowly. You have. You recognize the early warning signs because you’ve seen the full arc play out. That pattern recognition is what lets you act before it’s too late.

Context

Ada Chen Rekhi uses the boiling frog metaphor to illustrate the danger of tolerating incremental degradation. For experienced professionals navigating AI-driven transitions, pattern recognition from watching peers’ careers is the advantage—you’ve seen people stay in roles that slowly dimmed their relevance.

You recognize the trajectory before the outcome is locked in.