Escape the Dream Job Trap | Simone Stolzoff
The Art of Charm
Intro
This chapter focuses on the journey from traditional employment to self-employment, highlighting the challenges and realizations that arise when becoming one's own boss. It emphasizes the importance of finding balance and redefining success in a self-directed work environment.
In this eye-opening conversation, we sit down with Simone Stolzoff, author of The Good Enough Job, to explore why modern work culture traps so many of us in cycles of burnout, identity crises, and unrealistic ambition. Drawing on research and personal experience, Simone challenges the “dream job” myth and offers a liberating framework: redefine success on your terms.
We explore the dangers of workism, the importance of building an identity outside of your career, and the power of setting clear boundaries. For high-achievers who feel stuck on the hedonic treadmill, this episode offers a roadmap to a more balanced, meaningful life — without abandoning your ambition.
[00:00:00] Introduction
[00:02:26] The real meaning of a “good enough job” — and why it’s not about slacking off
[00:08:16] The rise of workism: why your job became your identity
[00:13:33] The difference between boundaries and guardrails — and why we need both
[00:21:14] The myth of the dream job (and why passion usually follows skill, not the other way around)
[00:27:41] How to rebuild an identity outside of work and escape workaholism
[00:39:28] The surprising reason people at both ends of the ambition spectrum struggle
[00:50:00] Why defining your “enough” number is the antidote to endless striving
[00:56:08] Simone’s personal lesson: why time autonomy is his ultimate luxury
Episode Takeaways:
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Your job should support your life, not become your life.
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Stop chasing perfection — a “good enough” job can free you to thrive in other areas that matter.
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Identity is like an investment portfolio: diversify it beyond just work.
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Intrinsic motivation (mastery, purpose, autonomy) beats external markers of success.
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Define your personal “enough” — financially, emotionally, and professionally — or risk falling into the endless “more” trap.
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Play, beginner’s mindset, and non-work communities are secret weapons for resilience.
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The Good Enough Job: Reclaiming Life from Work
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