Insurance & Risk

66% of bankruptcies involve medical bills [@ajph2019]. One uninsured hospital stay can erase a decade of savings.

Insurance isn’t an expense. It’s a hedge against catastrophe.

The Insurance Principle

Insure catastrophes. Self-insure inconveniences.

  • Catastrophe: Medical emergency, house fire, death of breadwinner → Insure
  • Inconvenience: Phone screen crack, appliance failure → Self-insure (save money for it)

The rule: if an event would financially ruin you, insure it. If it would merely annoy you, skip the coverage and pocket the premium.

The Essential Coverage

TypeWho Needs ItHow Much
HealthEveryoneAt minimum, high-deductible plan to cap max exposure
LifeAnyone with dependents10-12× annual income, term (not whole)
DisabilityAnyone relying on income60-70% income replacement, long-term
Renters/HomeEveryoneReplacement cost of belongings + liability
AutoCar ownersLiability + comprehensive if car is valuable
UmbrellaHigh net worth ($500k+)$1-2M above auto/home liability

Optimize Premiums

Higher deductibles = lower premiums. If you have an emergency fund, take the highest deductible you can stomach. You’re self-insuring the small stuff.

Bundle policies. Same company for auto + home = 10-25% discount typically.

Shop annually. Loyalty isn’t rewarded. Get quotes every 1-2 years.

Skip extended warranties. They’re insurance with terrible odds. The seller profits because you usually don’t.

What NOT To Insure

  • Extended warranties on electronics
  • Flight insurance
  • Credit card protection
  • Rental car damage waiver (if your auto policy covers it)
  • Life insurance if no one depends on your income

If the premium exists, someone calculated that they’ll profit from it on average. For small losses, the math favors self-insurance.


Insure what would ruin you. Self-insure everything else.