How I navigated my biggest career transition

🌈 Abstract

The article discusses the author's experience of leaving their position as Google's Chief Decision Scientist to venture out on their own. It provides a candid and honest account of the challenges and lessons learned during this transition, covering topics such as:

• Importance of having a plan, but not being overly attached to a fixed destination
• Navigating ambiguity and being open to new opportunities
• The need to be selective and not lower one's standards when presented with many options
• The dangers of sleep deprivation and burnout when trying to explore multiple paths simultaneously
• The messiness of real-life transitions compared to the "squeaky clean" narratives often shared

🙋 Q&A

[01] Leaving Google and Navigating the Transition

1. What were the key lessons the author learned about having a plan when leaving their role at Google?

• Having a plan is important, but it's not the same as knowing your exact destination. The author had plans within plans, but acknowledged that the plan was more about increasing exposure and trying different things to find the best fit, rather than a fixed destination.
• The author emphasizes the importance of allowing your mind to hold multiple possibilities - both staying at your current job and needing to make an abrupt exit. This allows you to prepare for different scenarios.

2. How did the author's experience differ from the "squeaky clean" narratives often shared about career transitions?

• The author notes that most people only share the polished, hindsight-biased version of their career transitions, rather than the messy reality. The author aimed to provide a more truthful and candid account of the challenges and uncertainties involved.

3. What advice does the author give about being selective during a career transition?

• The author cautions against the temptation to lower one's standards and pursue "bad" opportunities, even if they are plentiful. Waiting for the right, neutral-to-good opportunities is better than settling for a poor fit.
• The author's friend advised being "uncomfortably selective" when evaluating options, as the right level of selectiveness can feel uncomfortable in the moment.

[02] Navigating Multiple Opportunities

1. How did the author approach exploring different opportunities simultaneously?

• The author reshuffled resources to allow for exploring multiple options at once, rather than making a "violent pivot" from one opportunity to another. This allowed the author to gather enough information to make the best choice.

2. What are the dangers of "burning your boats" and prematurely destroying your options?

• The author is skeptical of the "burn the boats" approach, arguing that unless you truly know there is only one version of your life worth living, prematurely destroying your options is a recipe for an unhappy life.
• The author cautions against survivorship bias, noting that many of the "losers" who burned their boats are less vocal about their stories.

3. How did the author manage the demands of exploring multiple opportunities?

• The author acknowledges that they were "juggling knives and sleeping too little" in order to make the most of the short-term strategy. However, the author cautions against the dangers of chronic sleep deprivation, noting that it can be a symptom of underlying anxiety.