Early Retirement Litmus Test – Willing to report to your colleagues?

From time to time, I come across or correspond with people who are wondering if maybe they are ready for early retirement.

Here's one test in case you are wondering too.
Think back to some of your work peers, colleagues that you were forced to compete with during performance appraisals. Now ask yourself this: If you had to, would you be willing to report to (work under) them? And, would you be willing to work for and report to someone who used to report to you?


If you don't feel comfortable with the idea, then, before you quit your corporate job, you should be really sure that your accumulated savings are more than adequate, or that you know clearly why you are leaving.

However, if you answered yes to the test question, then you may be one step closer to early retirement. Your response implies that you don't have any organizational ambition left. And your ego won't come in the way, should your finances go south in a bad way while you are in early retirement, and you need to find another job.

That said, over time, I have come to believe that the traditional way of thinking about retirement as two distinct 0-1 binary states – that one is either retired or not retired – isn’t really valid anymore. There are many states in between.

Now more than ever, there are many opportunities to progressively scale down from full time employment. One can find ways to earn sporadically, depending on individual needs, while also buying oneself autonomy and time, which is what early retirement means to most people.

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I picked up the term organizational ambition from Taleb in his book Fooled By Randomness. He uses it in a different context, but I think it has definite significance to those thinking of early retirement.

Let's assume that every now and then, you compute your net worth and idly contemplate taking early retirement and living a life of leisure. Here's one question you have to ask yourself: Do you have any organizational ambitions? In other words, are you excited by the idea of your next promotion, a new title, more responsibilities and the accompanying pay raise?

Answer this Yes/No question honestly. There are many valid reasons to want that success. You will be making your parents, your spouse, and your children proud by getting promoted. You may also want to prove yourself to your colleagues, or even to yourself with future professional successes in your field.

If the answer is Yes (i.e. you do have org. ambitions) then there is no point in getting frustrated about the lack of a life of leisure, because the time for you to quit is not imminent. Give yourself time, say 2 years or 5 years to re-evaluate things.

If the answer is No, and you indeed have no organizational ambition left, then that is one more thing out of the way. A lack of organization ambition is a necessary but by no means sufficient condition for early retirement.