Path to Confidence: Build an Investing Playbook

Everybody has a plan until the market punches them in the mouth. In this episode, Stephen and Andrew break down how to remove emotion from investing by building a mechanical “if-then” playbook—rules you decide ahead of time so you don’t improvise when fear hits. They connect the idea to real-world high-stress training (military, first responders, pilots): when things go sideways, you fall back on rehearsed systems, not gut reactions.

They walk through how to write rules per stock (not just for the whole portfolio), why selling rules are rarely discussed, and how to set “eject button” triggers that protect you from sunk cost fallacy and self-justification. The episode closes with a listener's question about receiving a large sum of money—how to slow down, define your time horizon, avoid paying “tuition” with a big lump sum, and choose an investing path you can stick with.

What You Will Learn

How to create if-then rules that reduce panic decisions

Why you should build rules before buying a stock (not during a crisis)

How to think about sell triggers (and why most investors avoid the topic)

How to use “do nothing” as a legitimate strategy when markets get chaotic

What to consider when investing a large lump sum (time horizon, pacing, confidence)

Timestamps

00:00 Why this episode: removing emotion when you “should” be panicking

01:05 Training under stress: why systems beat gut instincts in real life (and investing)

02:10 Hydroplaning analogy: don’t overcorrect when things get scary