When to Climb, When to Stay, When to Step Off
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When to Climb, When to Stay, When to Step Off
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What if the ladder you’ve been climbing your whole career… is leaning against the wrong building?
In this episode of Coffee Unlimited with J & D, we unpack the powerful metaphor of “the ladder” — success, ambition, promotions, and the unspoken rules many of us inherit about what it means to live a good life.
Inspired by Janelle’s Monday Mindset newsletter, we explore:
- Why so many people chase upward mobility without ever asking where they’re headed
- How societal conditioning shapes our definition of success
- What it really means to pause, reassess, and choose intentionally — even if that means staying put, stepping off, or switching ladders entirely
- Why turning down promotions, redefining ambition, or choosing freedom over status isn’t failure — it’s wisdom
We also talk about transferable skills, sabbaticals, entrepreneurship, and how to recognize the moments when you feel most alive as clues toward what’s next.
If you’ve ever felt restless, burnt out, or quietly wondered “Is this it?” — this conversation is your invitation to pause, reflect, and choose on purpose.
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