Work that feels like cheating

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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 fluidly between AI, intuition, education, and systems thinking, touching on why the things that feel like “cheating” are often your greatest strengths, how we add by subtraction as we mature, and why so many people are over-armored for battles they’re no longer fighting.

If you’ve ever felt overwhelmed by how much there is to know, pressured to optimize yourself into exhaustion, or stuck believing work has to be hard to be valuable, this episode offers a generous reframe: you don’t need all the answers—you just need to know which ones are yours.

Here are 5 grounded, actionable takeaways from the conversation with Michael Simmons, written to land clearly at the end of the episode:

* Design your income around fewer people, not more. You don’t need thousands of customers to build a sustainable life. Explore models like fractional work, contracting, or high-trust relationships where a small number of people pay for deep value.

* Let curiosity be a filter, not a reward. If you consistently dread the daily actions required by your goals, something is misaligned. Prioritize work you’re genuinely curious about and energized by—momentum follows engagement.

* Trust the things that feel like “cheating.” The actions that feel easiest to you are often your highest leverage skills. If they work, double down instead of abandoning them for something harder.

* Stop trying to know everything and build relational intelligence instead. Expertise now lives in networks, not individuals. Focus on knowing what you know, knowing what you don’t, and knowing who to turn to when you need the missing pieces.

* Add by subtraction as you mature. Regularly audit the armor you’re still carrying from earlier seasons of your life or business. Keep what protects you now and consciously shed what no longer serves you.