Episode
Work that feels like cheating
- Podcast
- Hapitalist
- Published
- Jan 13, 2026
- Duration seconds
- 2771
- Processing state
not_requested- Canonical source
- https://podcast.hapitalist.com/p/work-that-feels-like-cheating
Actions
POST https://stenobird.com/v1/public/podcasts/hapitalist-7385743/episodes/work-that-feels-like-cheating/transcription-requests
Idempotently request low-priority transcript generation for this episode.GET https://stenobird.com/podcast/hapitalist-7385743/work-that-feels-like-cheating.md
Read the agent-friendly Markdown representation of this episode resource.
Summary
* Listen on the app of your choice This episode is part of the January Joy(ful) Growth Club with Russell and Claire program I’m running with Claire Venus ✨ . Join and get access to special challenge and interviews all month. Join by clicking here. In this episode, we’re joined by education entrepreneur and writer Michael Simmons to explore a radically different way of thinking about work, learning, and growth. We start with a deceptively simple question: What if making a living didn’t have to feel miserable? From there, the conversation opens into practical and philosophical territory. We talk about how many people you actually need to support a sustainable life, why fractional work and contracting are often safer than they look, and how entrepreneurship can offer more freedom than traditional employment if you approach it creatively. Michael shares his own journey through ambition, burnout, and reinvention, including building a seven-figure education company in his twenties, and burning out because he didn’t enjoy the day-to-day work required to sustain it. That experience led to a major shift: choosing curiosity and energy as filters for what he works on, rather than goals alone. When he began writing only what he was genuinely excited about, everything changed—traction, resonance, and sustainability followed. From there, we dig into deeper ideas about learning and expertise. We talk about why it’s no longer possible, or desirable, to know everything, and why the future belongs to people who understand distributed responsibility : recognizing both the keys you hold and the locks you don’t. Rather than idolizing lone experts or pretending everyone has all the answers, real progress happens when people bring their specific knowledge together. The conversation moves flu…