When Everything Depends: Navigating Decisions as an Aspiring Liveaboard

For aspiring liveaboards, “What’s the best boat?” or “Where should I start?” are questions you’ll hear (and ask) a hundred times. The frustrating answer? “It depends.”

From choosing a boat to deciding on gear, routes, or timing, there’s no one-size-fits-all solution.

But instead of seeing this ambiguity as an obstacle, we can approach this with creative frameworks to embrace this unique opportunity to shape a lifestyle that’s entirely your own.

‍

1. Start with Your "Why"

One of the most pivotal questions for aspiring liveaboards isn’t logistical. It’s existential. Why are you doing this? This was a question my husband and I wrestled with when we seriously began exploring life on a yacht. We needed to articulate what this lifestyle could bring into our lives that we didn’t already have.

That's what led me to write what I call a Voyage Manifesto. Think of it as your personal north star - something to look back at when you're drowning in decisions or doubts. There's actually some cool science behind this: writing down your intentions helps them stick. Plus, it's amazing how much clarity you get when you put thoughts to paper.

‍

You can read more about the voyage manifesto here.

‍

2. Simplicity vs. Complexity: The Physics of Decision-Making

Here's something that really messed with my head:

Living on a boat is both incredibly simple and surprisingly complex. It's like this constant balancing act. Take boat size, for example. That performance cat with all the bells and whistles is clearly amazing. But it also means more things that can break (usually at the worst possible moment). BUT it also also means there might be more redundancies so it's less of a danger...

Physics provides a compelling lens for this challenge: simple systems are easy to manage and fail gracefully, while complex systems offer adaptability but can fail catastrophically.

For example:

• A smaller boat with basic systems might limit your range but is easier to repair and maintain.
• A larger, more equipped vessel offers comfort and capability but increases complexity, cost, and upkeep.

This balance mirrors the concept of Occam’s Razor: when faced with competing solutions, the simplest explanation (or in this case, the simplest choice) is often best.

However, simplicity doesn’t mean sacrificing functionality; it means choosing solutions that work with minimal unnecessary complication.

• Practical Tips:
  • Assess the simplicity or complexity of your choices.
  • Ask: Does this solution add value proportionate to the effort it requires?
  • Prioritize decisions that align with your capacity to manage complexity.

‍

3. Build Antifragility Into Your Lifestyle

The liveaboard lifestyle is inherently unpredictable, requiring systems that not only survive uncertainty but thrive in it. This concept, antifragility, coined by Nassim Nicholas Taleb, is about building resilience and adaptability into your life.

Antifragility for Aspiring Liveaboards:

• Boat Choice: A well-built older boat with simple systems may weather storms and repairs better than a high-tech but fragile design.
• Skills: Learn basic navigation, weather interpretation, and engine maintenance. These skills transform challenges into opportunities for growth.
• Mindset: Loose itineraries allow you to adapt to weather, mechanical issues, or serendipitous discoveries without frustration.

Example: Special Forces teams embrace antifragility by preparing for uncertainty with decentralized systems. They train not just for specific scenarios but for the unknown, relying on core principles (like teamwork and adaptability) to guide them through ambiguity. Similarly, aspiring liveaboards can build a framework for decisions that accommodates uncertainty.

• Practical Tips:
  • Test antifragility by starting small:
  • Take short voyages to experiment with gear, routes, and routines.
  • View unexpected challenges as opportunities to refine your approach.

4. A Critical Thinking Process for Clarity

When faced with ambiguous choices, a critical thinking framework can help illuminate the best path. Here’s a simple yet effective method tailored for aspiring liveaboards:

REDS: Recognize, Evaluate, Decide, Scale

1. Recognize:
   • Identify the decision clearly. For example, are you choosing between boat models or deciding whether to sell your home?
   • Separate decisions into manageable chunks to avoid overwhelm.
2. Evaluate:
   • List the options, pros, cons, and trade-offs.
   • Use the Pareto Principle (80/20 rule): What option achieves 80% of your goals with 20% of the effort?
3. Decide:
   • Align the decision with your "why" and core values.
   • Don’t let perfectionism paralyze you; often, there is no single "right" answer.
4. Scale:
   • Start with a small, low-risk version of your decision. For example, rent a boat for a month instead of buying one immediately.
   • Gather feedback and adjust before committing fully.

Example: Critical thinkers approach decisions by breaking them into measurable steps, reducing emotional noise and increasing clarity.

‍

5. Embrace Scenario Thinking

Special Forces operators and successful sailors alike use scenario thinking to navigate uncertainty. Instead of focusing on a single outcome, they prepare for the best, worst, and most likely scenarios.

Scenario Thinking for Liveaboards:

• Best Case: You buy a boat within budget, adapt quickly to liveaboard life, and discover a vibrant community.
• Worst Case: Unexpected costs or challenges lead to frustration, requiring adjustments to your plan.
• Most Likely: A mix of highs and lows, where preparation and adaptability determine your success.
• Practical Tip:
  • Map out three scenarios for every major decision.
  • Develop a response plan for each, ensuring you’re ready for any outcome.

6. Accept Uncertainty as Part of the Journey

I'll just leave that here.

‍