Posts tagged philosophy
EP. 39 - Enough: How Do You Know When You Have Enough?

More is everywhere. But where is enough?

Money. Work. Fitness. Achievement. Adventure. Information. Growth. Ambition.

Modern life is remarkably good at telling us what to pursue, but much less interested in telling us when to stop.

In this episode, Evan Sutter explores the idea of enough and why it might be one of the more difficult questions we can ask when thinking about a good life.

Is enough a number? A feeling? A decision? Something we discover only after we've gone too far?

And perhaps the more uncomfortable question:

If we don't decide what enough means, who—or what—will decide it for us?

The conversation continues the philosophical thread of recent episodes:

  • Death: What matters?

  • Attention: Where is my life actually going?

  • Enough: When is it enough?

Evan explores the tension between ambition and contentment, asking whether “more” is really the problem—or whether the more important question is more in service of what?

Because building a business for freedom can eventually leave you with no freedom. Pursuing money for security can become an endless pursuit of more. And ambition that once served a meaningful life can quietly become the thing around which the entire life is organised.

Perhaps knowing enough doesn't diminish ambition.

Perhaps it frees ambition from desperation.

And perhaps the real challenge is learning to recognise the difference between ambition and restlessness wearing ambition's clothes.

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EP. 36 - The Season You’re In: On boredom, restlessness, and knowing what deserves your attention

Evan explores:

  • Why we often confuse activity with engagement.

  • Whether boredom is sometimes a form of restlessness.

  • What a nine-month experiment in removing external distractions taught him about stillness.

  • Why travelling, achieving and constantly doing more don't necessarily make us feel more alive.

  • The difference between wanting something and needing it right now.

  • How to recognise the emotions underneath our decisions — curiosity, joy, fear, comparison, ego or restlessness.

  • Why every stage of life has its own season and demands a different kind of attention.

  • What fatherhood and building SwiftReporter are teaching Evan about staying present.

  • Why good leadership involves knowing not only what to do, but what not to do.

  • Why growth requires patience and why some of the most important work is invisible for a while.

  • The danger of treating the symptoms of restlessness rather than understanding its source.

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