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Actionable insights — Kaplan's Pain Index

Score a drawdown on two dimensions instead of one, benchmark it against 1929, and choose the buying mechanism that survives the recovery rather than the fall.
2026-MAR-17 · Compounding Quality (Substack) · Pieter Slegers · read ↗ · full analysis · transcript
How to read this page: each insight is a method used in this issue, written so it can be rerun on any drawdown — including one you are currently living through. Written post, so no timestamps.

1. Score a drawdown as depth × duration, then index it to a known crash

The repeatable method
  1. Record two numbers for the episode: the peak-to-trough fall in per cent, and the years taken to regain the peak.
  2. Multiply them to get the pain surface: drawdown (%) × recovery time (years).
  3. Divide by a fixed reference — the 1929 crash, 79% over 4.5 years = 355.5 — so every episode is expressed as a percentage of a crash everyone already understands.
  4. Use the index to rank episodes, and to sanity-check how the current one compares while it is still running (estimate the recovery time, and re-estimate as it lengthens).
Here: 2008 = 57 × 5 = 285; 285 / 355.5 = 80.2%. COVID = 7.1% on the same scale, because the recovery took months rather than years.
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2. Weight recovery time above drawdown when judging what you can withstand

The repeatable method
  1. Rank historical crashes by the pain index rather than by headline drawdown, and note where the two rankings disagree.
  2. Recognise that the formula's equal weighting still understates duration: "investors don't experience them equally. Investors suffer most from a long recovery time."
  3. Stress-test your own plan against a long shallow episode, not just a violent one — the shallow-and-long case is what breaks discipline.
  4. Set your position sizing and cash needs against that scenario.
Here: the oil crisis — 48% over eight years — outranks 1929 (79%), the dot-com bust and 2008 (57%). "It's not the crash that hurts, it's the crawl back."
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3. Plan for the lost decade as a normal, recurring event

The repeatable method
  1. Define it precisely: ten years or more in which the market rises but not enough to beat inflation — a real-return drought, not necessarily a falling index.
  2. Note the base rate: three since 1900 — 1914–1945, 1973–1985, 2000–2012 — which is a meaningful share of any investing lifetime.
  3. Build the plan so that a decade of no real return is survivable: contributions that continue, spending that does not depend on gains, and an approach you can hold without confirmation.
  4. Measure real returns, not nominal ones, so you can tell whether you are in one.
Here: the 2000–2012 stretch is the worked case, with the two crises named and the recovery dated to 2012 — and the note that the index can rise through it while purchasing power does not.
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4. Choose the buying mechanism that matches the market you might get

The repeatable method
  1. Fix a date and an amount and buy on schedule, removing the decision from the moment.
  2. Understand precisely when the mechanism wins: in flat-to-falling markets, later purchases are made at lower prices, so the average cost falls below a single up-front entry.
  3. Test it on the worst historical stretch you can find, comparing the same total capital deployed both ways.
  4. Be explicit about the trade-off — in a rising market the lump sum wins — and choose on the basis of which error you can live with.
Here: across 2000–2012, $14,400 as a lump sum → $11,181 (a loss); $100 a month → $16,351, an outperformance of 35.9%. Continuing to 2024 turned $28,800 of contributions into $88,197.
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5. Treat your own reaction as the risk being managed

The repeatable method
  1. Name the failure sequence in advance — self-doubt, emotion, then discipline fading — so it is recognisable when it starts.
  2. Automate the decisions that the sequence would otherwise corrupt: the purchase date, the amount, the instrument.
  3. Judge a strategy by whether you can execute it through the worst case on your own index, not by its back-tested return.
  4. Accept the conclusion literally: "The real risk isn't the market, it is how you react to it."
Here: the COVID coma parable is the argument for automation — the investor who could not react earned the recovery in full, precisely because they were unable to act.
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Methods distilled from the archived Compounding Quality post for personal study. Not investment advice.