Self-Employment Tradeoffs

Simone reflects on freelancing: control and choice versus loneliness and needing to self-impose boundaries.

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Episode notes

What happens to creativity when anyone can generate “good enough” writing in seconds?

And how do you keep your voice — your taste — when machines want to average everything out?

In this episode, Sara and Dan sit down with Simone Stolzoff — author of The Good Enough Job and the upcoming How to Not Know — to talk about the real skills we need in an age of nonstop change: uncertainty tolerance, identity beyond work, and the confidence to experiment even when everything feels foggy.

But we go deeper:

What does originality look like when AI can draft anything?
How do writers protect the parts of their work that only come from human judgment?
What’s worth delegating to AI — and what should never leave your hands?

Simone breaks down how he uses AI to push his ideas, not replace them, why first drafts should still come from humans, and why taste, discernment, and creative rejection might be the most important skills of the next decade.

💡 You’ll learn:

How writing is actually evolving in a world of large models
Why taste is the new competitive edge
How to use AI as a developmental editor without flattening your voice
The danger of tying your identity to work in a volatile economy
Why uncertainty isn’t a threat — it’s what gives life meaning
The mindset shift that reduces anxiety and increases agency
How to anchor yourself as everything around you changes

🔥 If you’re navigating AI, career uncertainty, creative work, or the pressure to “figure it all out,” this episode will give you clarity — and momentum.

⏱ Timestamps:

00:00 Introduction: The AI Awakening

00:21 Navigating Uncertainty in a Polycrisis World

00:52 A Confession and Reconnecting with an Old Friend

02:15 The Good Enough Job: Rethinking Work and Identity

04:10 Generative AI: Transforming the Creative Process

11:10 How to Not Know: Embracing Uncertainty

20:07 The Future of Work: Autonomy and Adaptation

24:39 Segmenters vs. Integrators: Work-Life Boundaries

25:32 The Role of Generative AI in Work Autonomy

26:29 Transitioning to Self-Employment

28:10 Balancing Self-Employment: Pros and Cons