The Playbook

How to actually leave

No hustle-bro fluff. Clear guides to the money, the logistics and the head-stuff of quitting — each one wired to the calculator that makes it real.

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How much should you really save before quitting?

Why "6 months of expenses" is the wrong answer, and how to find your actual number with a worked example.

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Quitting your job around the world

US vs UK vs EU vs Canada vs Australia — how severance, healthcare and safety nets change your number.

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Health insurance after you quit

COBRA vs ACA in the US — and why it's a footnote in the UK, EU, Canada and Australia. Plus the 60-day clock.

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The benefits you lose when you quit

Health, life and disability insurance, your 401(k) match and more — what each really costs to replace in 2026.

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How much does COBRA really cost in 2026?

Average premiums for individuals and families, why it's so steep, COBRA vs ACA, and how to pay less.

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Where to keep your escape fund

High-yield savings vs money market vs CDs — safety, yield and liquidity, plus a simple tiered setup.

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Disability insurance for the self-employed

The protection freelancers skip and need most — own-occupation cover, what it costs, how much to buy.

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How to negotiate severance — even when you're leaving

What's on the table by country, the high-value/low-cost asks, and when to get a lawyer.

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The exit timing checklist

Vesting, bonuses, benefits end dates and the COBRA clock — when you quit can be worth thousands.

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Quitting to freelance: the runway nobody warns you about

The income ramp is slower than you think. Here's the buffer that keeps you from crawling back.

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Geoarbitrage: the cities that triple your runway

The same savings buys a year in Lisbon or three months in London. Run the trade-off.

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Your first 90 days after quitting

The make-or-break stretch: protect cash, decompress without drifting, and set a no-shame re-entry trigger.

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Beating "One More Year Syndrome"

When you're financially ready but emotionally stuck — and how to actually pull the trigger.

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Burnout vs boreout: running from, or toward?

Diagnosing why you want out changes the plan — and whether quitting even fixes it.

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Coast, Barista, Lean & Fat FIRE — which exit is yours?

A plain-English map of the FIRE variants and which one fits your life.

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Every guide here is now live. Guides are financial education, not advice — each links to the calculator that makes it real.