What you find when you stop looking

🌈 Abstract

The article discusses the author's experience of leaving their job as a software engineer and going on a 3-month backpacking trip across Latin America. It explores the author's reflections on the limitations of rigid planning and the benefits of embracing uncertainty and spontaneity.

🙋 Q&A

[01] Leaving the Software Engineering Job

1. What were the key challenges the author faced as a software engineer?

• The author worked in high-pressure environments where they were expected to provide detailed estimates and plans with very little information, like "making a police sketch of the Boogeyman based on a crying child's description of its nightmares."
• The author describes the extensive use of project management frameworks, tools, and ideologies (like Agile and Scrum) in the software engineering world, where "we work on the way we work more than we actually just...work."
• The author found this planning-heavy approach to be often inefficient and disconnected from reality, especially when faced with unexpected events like a global recession.

2. What prompted the author to quit their job and go on a backpacking trip?

• The author felt unfulfilled in their software engineering career and had doubts about it being the right path for them, despite their love for the work.
• The author decided to quit their job with no future prospects lined up and go on a 3-month backpacking trip across Latin America, driven by the belief that "the pain of change is nothing compared to the pain of standing still."

[02] The Backpacking Experience

1. How did the author initially approach the backpacking trip?

• The author initially planned the first two weeks of the trip down to the hour, booking hostels, transportation, and activities in advance, and mentally assigning "OKRs" (Objectives and Key Results) to each activity.
• This highly structured approach quickly fell apart when the author's luggage was lost and they encountered unexpected challenges, like not being able to communicate effectively or find the best deals on the ground.

2. How did the author's approach evolve during the trip?

• As the trip progressed, the author's planning horizon gradually shrank, from 2 weeks of detailed plans to just knowing where they would be in the next 3 days.
• The author learned to trust their instincts and be more spontaneous, which led to serendipitous experiences and connections that they would have missed with a rigid itinerary.
• The author's fear of failure and FOMO (fear of missing out) began to subside, and they felt a sense of freedom and authenticity in listening to their own gut.

3. What were the author's key takeaways from the backpacking experience?

• The author realized that rigid planning and control can be an illusion, and that embracing uncertainty and being open to the unexpected can lead to more meaningful experiences.
• The author learned to trust themselves and their intuition, rather than constantly micromanaging their life and trying to plan for every contingency.
• The author acknowledges that a perpetual state of backpacking-style freedom may not be sustainable, but they have gained a new perspective on the value of balance between structure and spontaneity.