Dissecting dilemmas

The root words of “dilemma” are di- (meaning “two” or “double”) and lemma (meaning “premise” or “proposition”) and translates to “double proposition”–a situation with two contrasting premises or a difficult choice between two options. The dilemmas @jasonleow listed recently inspired me to look at my problem space framework again. I use it to situate writing advice in a diagram so I can explore the five types of solutions to these dilemmas that have two conflicting features.

1. Equal Neglect (lowest effort): Avoid or ignore both features; results in minimal progress or engagement, but that might be preferred given the cost of engaging with this dimension.
2. Lean into Feature A: Fully prioritize A while disregarding B.
3. Lean into Feature B: Fully prioritize B while disregarding A.
4. Alternate between A and B: Switch between A and B based on context, rhythm, or cycles.
5. Balanced Parity (highest effort): Integrate A and B into a coherent system that honors both without compromising either.

Each resolution type has:

• Valid contexts in which it is effective
• Tradeoffs or risks that must be managed
• Effort or cost level, ranging from 0 (neglect) to 1 (balanced parity)

What seems like the ideal solution isn’t always the optimal choice because there’s a cost: effort, energy, or expense. The cost might come down over time with gains in efficiency or deep insights, but usually the juice isn’t worth the squeeze.

In theory, every solution to the dilemma should fit into one of these five regions of the problem space. Here’s an analysis Gemini produced for the first dilemma of the overworked indie hacker.

Dilemma 1: “It’s the journey that matters” vs “What truly moves the needle”

• Feature A: “Journey that matters” – Emphasizing process, meaning, growth, presence, and the experience itself.
• Feature B: “What moves the needle” – Prioritizing results, impact, outcomes, efficiency, and tangible achievements.

Resolution Strategies:

1. Equal Neglect: Drifting aimlessly without engaging deeply in any process or achieving significant results.
   • Valid contexts: Perhaps a period of burnout recovery or intentional unstructured exploration, though typically not sustainable.
   • Tradeoffs/Risks: Lack of progress, feeling unfulfilled, missed opportunities for growth and impact.
   • Effort Level: Low
2. Lean into A (Journey): Fully immersing oneself in experiences, personal development, and the present moment, even if external achievements are minimal.
   • Valid contexts: Sabbaticals, artistic exploration without commercial pressure, focusing on personal well-being or skill mastery for its own sake.
   • Tradeoffs/Risks: May not achieve external goals, potential for self-indulgence, difficulty in environments that demand measurable results.
   • Effort Level: Medium
3. Lean into B (Results): Focusing intensely on achieving measurable outcomes and efficiency, potentially sacrificing personal well-being or the richness of the experience.
   • Valid contexts: High-growth startup phases, mission-critical projects, situations requiring rapid intervention or clear deliverables.
   • Tradeoffs/Risks: Burnout, feeling hollow despite success, damaged relationships, ethical compromises to achieve results.
   • Effort Level: Medium
4. Alternate between A and B: Structuring time and energy to focus on process and reflection during certain periods and then shifting to intense periods of focused work to achieve goals.
   • Valid contexts: Project-based work with clear cycles, academic semesters followed by breaks, quarterly business cycles, creative sprints followed by periods of rest and inspiration gathering.**
   • Tradeoffs/Risks: Requires discipline to transition effectively, potential for context switching costs, may feel disjointed if not well-managed.
   • Effort Level: High
5. Balanced Parity: Designing systems or approaches where the focus on process and well-being inherently drives positive outcomes and impact.
   • Valid contexts: Craftsmanship, purpose-driven organizations with strong cultures, educational models emphasizing experiential learning, personal practices where mindfulness enhances productivity.
   • Tradeoffs/Risks: Requires significant upfront effort to design and maintain the system, may be challenging to implement in rigid or purely results-oriented environments.
   • Effort Level: Very High

Then you repeat that for all 16 dilemmas on the list, ask the LLM to resolve all conflicts with a reasonable budget, and you have your life solved. 😉