Professional Pathfinding

1,000 Hours to Plan the Next Step of My Career

Between my 9-month notice period and a 6-month career planning gap I plan to take, I have about 1,000 hours to figure out the next step of my career. In typical Joey form, I want to optimize not just the outcome (the most impactful career I can find) but also the process itself. As I've shared my career change plans and planned methodological approach with others, many have expressed interest in following along and adapting elements for their own career considerations. So the plan is to document the journey on this Substack, with this introduction serving as a rough draft roadmap of the process ahead and key steps I'm eager to take.

Self-Assessment (~100 hours)

• Personal Inventory: Conducting deep introspection on my core strengths, weaknesses, and unique competitive advantages (I haven't done this comprehensively in nearly 10 years).

• 360 Review: Comparing trends and recurring themes from external feedback and 360 reviews I've received over the last ~5 years.

• External Assessments: Gathering structured feedback from colleagues and mentors about my capabilities. Probably implementing a form with forced rank order of weaknesses and strengths.

• Working with Me: Updating my "Working With Me" guide (current version) based on all of the above and distilling everything down to a concrete but concise 2-3 page self-assessment.

What the World Needs (~100 hours)

• Ecosystem Gap Analysis: look at the top three areas I think are most impactful right now (global health, effective giving generally and farmed animals) and determine what the top gaps that could be filled by someone like me.

• Time vs Money: Create a formal model for the value of talent vs money for each of the three areas.

• Expert Impact Consultation: Interviewing 20 individuals whose judgment I respect, using a standardized question framework to gather career insights (questions like “What is a career or idea you think would be really impactful if it worked but you would put a sub 1%-10% chance on it working”).

Exploratory Crosscutting Research (~100 hours)

• Leadership Archetypes: Analyzing founder vs. CEO personality traits and identifying career paths that align with founder mentalities. Investigating whether there's recurring data on founder types and how they can select careers that fit long-term.

• Comparative Personality Analysis: Examining potential career correlations with personality assessments I've already completed (e.g., Principled You, Big 5, etc.).

• Strengths Deep Dive: Conducting thorough research into possible career paths for each of my top 3 strengths, looking for useful correlations or overlapping recommendations. For example, which jobs uniquely benefit from high creativity and how valuable is creativity as a skill set?

• Most Important Skill Deep Dive: Analyzing skills that would be extremely valuable but that I don't currently possess, including concrete time estimates for developing or mastering each skill (e.g., how long it would take to become an 8/10 or better writer).

Career Option Iterative Depth (~100 hours)

• History of High-Impact Individuals: Compiling a long-list of high-impact individuals who have generated substantial value (equivalent to $10M+ to GiveWell organizations per year of impact).

• Comprehensive Ideation: Developing at least 100 viable career paths, including specific variations (targeted organizations, potential ventures). Each with an soft subjective overall rating.

• Cross-Compare: Creating a weighted factor model analysis including an explicit cost-effectiveness analysis for the top ~20 options.

• Deep Dives: Conducting detailed analyses of the five most promising broad career paths and specific versions of them (e.g., which exact NGO to found), including interviews where possible.

Pilot (~500 hours)

• Pilot Planning: Creating detailed two-month pilot frameworks for the top three options.

• Run a Pilot: Executing 1-3 pilots with pre-specified criteria for success. These could take 1-2 months each.

I'll share each component as I complete it. If you're considering your own career transition, interested in how mine progresses, or simply keen on analytical structured approaches to work and life, this is the Substack for you.

P.S. My likely future posts on this Substack will also include expanding my 3H principles (currently listed here) into summarized two-pagers on how to optimize each one, so stay tuned for those in the future as well.