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How to shape my strategy towards life, be it career or otherwise

How to approach and make big decisions in life

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Calculation: An assessment of the risks, possibilities, or effects of a situation or course of action

Serendipity: The occurrence and development of events by chance in a happy or beneficial way

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- Initially aimed to sell larger bikes to compete with the likes of Harley Davidson, but was seen as a "poor man's" bike

- Gave employees smaller bikes "Super Cubs" to run errands

- Super Cubs gained traction as an off-road bike, with customers asking to purchase them.

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Developed "from unanticipated problems or opportunities", and are "sometimes explicit decisions, or coalesced from a myriad of day-to-day decisions."

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"A continuous, diverse and unruly process"

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- His deliberate plan was to be a Wall Street Editor

- Took up various roles, including being a consultant, starting a business and eventually, becoming a professor.

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- Reacted to opportunities as they came

- When his career provided clear motivations, he set new deliberate goals to work towards

- Never shut the door on emergent opportunities and problems

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Just like how the story shifts to one that impacted the author on a personal level, we can see that the author's lessons can apply to us on an individual level, and guide our strategy in navigating life.

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Calculation: Taking deliberate steps to achieve goals that have clear motivations.

Serendipity: Always being open to react to emerging opportunities and problems.

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Striking a balance in Strategising: To be more careful with chosing which strategy to adopt, yet being more open to allowing this strategy to diverge and adapt.

Living with less regrets: Treating experiences as part of an iterative journey, rather than a means to an end.

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Which strategy should we actually pursue? 

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Which strategy should we actually pursue? 

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Deliberate vs Emergent

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Do you know what you want to be?

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What has to prove true for this to work?

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What has to prove true for this to work?

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1. Articulate assumptions

2. What needs to be true for these assumptions to work

3. Retailor our expectations

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Disappointed Student at Venture Capital Firm 

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Disappointed Student at Venture Capital Firm 

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Based expectations of initial assumptions

Felt deceived

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CAG Internship Experience

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Refine Initial Assumptions

Develop better predictions

Raising the barrier