Aka a first-principles approach at building my future, while avoiding getting stuck at a local minimum.

May 2021

The Tl;dr:

• Doing something is generally better than coasting along, unless you’re running in the completely wrong direction.
• Certain doors close as you get older and your risk tolerance declines
• Therefore, I should make a really thoughtful attempt at setting a trajectory (whether a single bet, or some distribution of my efforts). Then run at it with full force, cushioned against temporary setbacks by the fact that I made a thoughtful and deliberate choice.

The details

What I’m currently doing.

I all too often find myself guilty making career choices based on solely what's in front of me. Like a newbie chess player looking 1 step ahead and looking for the incrementally best solution.

https://lh5.googleusercontent.com/SUhSk0Q6ffTZ3eeyiV0RZWoZL1zvFIUWELKXE6B4xIc1cinB0rjhKmVcBz1I5cqNJF5Ox214XHRFVQDF19meQp7w7_31dmbmNq1bFq9wgNMOIACxueqPxNdAXFXS6zVQ1W3Kboaw5MD_yWOu7McLByM

From that standpoint, my approach to career progression has followed a pretty simple algorithm.

A. Arrive at my role and get cozy. Spend some time learning and getting reasonably competent.

B. List our available options for next step along trajectory. Mostly by looking at different things people in your current position went on to do as their immediate next step.

C. Evaluate each option based on how much it aligns with your goals and your probability of success

D. Learn the requisite skills time in capabilities that align with 1-2 preferred next steps.Then when an opportunity presents itself (or when sufficiently frustrated by current role) make the jump.

E. Repeat steps A-D ad infinitum.

Crucially, this means often taking an incrementally better opportunity that arrives on your doorstep  even if a lower probability bird-in-the-bush is better aligned with your ideal long term outcome.

The end result is a path that looks kinda weird each time you look back at it and requires regularly rewriting the narrative of ‘how did I get here’ so it doesn’t sound like ‘I just went for what looked shiny at any given moment’.

https://lh5.googleusercontent.com/D161MXzxGxMS4g-AEsfKQhWvi4fbGqSzbWN_c9miYoOI4K93FK1dWfF_0A5cuqV8I6hYn6TRP7cva1ssroSRdFKGzE1MZio8btdX81Rg5yxVNw5rHNINhyHJ_Q4m_t94_9icWQ2US6rtSV2g6ldh09c

This approach does deliver steady incremental improvement. But it also carries a few big risks: