Embrace the Chaos
Crashes are the price of admission, not a system failure.
Toby's framing of crashes is not 'manage them' but 'they are the thing'. Half of the biggest crashes of the last 100 years happened since 2000. Black Swan-type events — 2008, covid, deepseek flash-crash — are not anomalies; they're the texture of market participation.
The practical move is to pre-commit to a strategy that assumes chaos is constant. You're not betting on a calm market; you're betting that businesses keep making money in aggregate over decades, and that you'll keep contributing through the noise. The boomer generation lived through the Cold War, '70s strikes, Black Monday, dot-com, and 2008 — and ended up wealthy by holding through it all.
The mindset reframe: every newsfeed will tell you 'this time is different'. It always feels different. The plan only works if you've decided in advance that 'different' doesn't change behaviour.
- Every generation thinks the current crisis is uniquely terminal — it never is.
- The cost of long-term equity returns is paid in volatility along the way.
- If the market goes to zero, your portfolio is the least of your problems.
- News fear is engineered for clicks, not for action.
- Holding through chaos is rare because it's psychologically hard, not because it's intellectually hard.
- Pre-decide your crash responseWrite down what you'll do if the market drops 20%, 30%, 50%. The default for index investors should be 'keep buying on schedule'. Pre-commitment removes the emotional decision in the moment.Pro tipAdd a clause: 'If I'm tempted to sell, re-read this document for 24 hours before acting.'
- Internalise the long-term chartPrint or save the S&P 500 long-term chart with every crisis annotated. Look at it during drawdowns. The visual shows that wars, pandemics, and recessions are speed bumps on a multi-decade up-trend.
- Reduce news consumption during chaosFear sells. Doom headlines have appeared in every generation about every crisis. Reducing news exposure during a drawdown is one of the highest-leverage behavioural moves.
- Reframe drawdowns as discountsWhen you're a net buyer (still contributing), a crash is a sale on future returns. Toby's covid story — buying airlines and stocks at the dip — illustrates the upside of being psychologically prepared.Pro tipDon't try to time the bottom; just keep your scheduled contributions running.WarningThis only applies if your time horizon and asset allocation match — don't catch falling knives in stocks you'll need to sell next year.
- Trust the floor of catastropheIf the market truly goes to zero, money has no value, businesses have stopped operating, and you have far bigger problems than your portfolio. This thought experiment caps the catastrophic downside emotionally.
Boomers lived through the Cold War, '70s strikes, Black Monday 1987, the 1990s rate spike and repossessions, dot-com 2000, and 2008. Every decade had a story that 'the world was ending'.
During covid, Toby and his co-host bought airline stocks on the assumption people would fly again. They were buying scared sellers' liquidity at irrational prices.
Toby developed this from reading The Black Swan by Nassim Taleb and overlaying it with the chart he calls one of his favourites — the S&P 500 with every recession, war, and crisis annotated. The visual point is that the long-term line goes up despite the chaos, not because the chaos was avoided.
Living through covid, the 2022 drawdown, and the deepseek flash-crash as a YouTuber forced him to articulate the message in real time to scared subscribers. The phrase 'embrace the chaos' is what he landed on as the durable frame.