Early Retirement and The Likelihood of Regret

When I discovered the FIRE movement, I had a pretty good idea I would be ready and able to retire early from medicine at some point.

Crunching numbers and considering some family dynamics, I came up with a roughly five-year plan to retire quite comfortably with a healthy margin of safety.

I didn’t want to retire as soon as I realized that I could; I would have regretted that. Conversely, if I had worked a decade longer than necessary, like this guy did, I’d regrettably still be working in a job that never felt like a true calling to me.

Early Retirement and The Likelihood of Regret

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First, you must satisfy some pre-requisites: 1. Financial Independence achieved via saving at least 25x anticipated annual expenses  2. Passive plus active income will cover your expenses

When is the best time to retire?

There are two distinct likelihoods of regret that must be considered. 1. The likelihood you’ll regret retiring too soon. 2. The likelihood you’ll regret working too long.

What is the Likelihood of Regret?

More money would allow you to have a lower withdrawal rate, allowing you to sleep better at night. Sure, a 4% withdrawal rate works looking backward, but our lives are looking ahead to an uncertain future.

Why might you regret retiring too soon?  You could have earned more money.

Golden handcuffs can come in many forms.  Pensions or pension increases. Provided healthcare when retiring after a certain age. Bonus payments tied to length-of-service or project completion.

You may be wearing some golden handcuffs.

Early retirement for me is all about freedom. Many of the things I’ve got in mind for this early retirement are incompatible with the public school schedule, and we’re now better able to do them while worldschooling.

Life might not change that much anyway۔

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