Jackson, thanks for poking around over here. I think you’re exactly right, and perhaps I am over-romanticizing entrepreneurship in the traditional sense.

However, the beauty of FI, as you know, is that I don’t need to provide a living wage to be successful. To make things quantitative, I’d venture to say that a profit of $5-10k (USD) per year would be quite successful for me. With such a low bar, I have a lot of margin for creating something fulfilling without bending over backwards to make whiny customers happy.

In fact, it’s actually not advantageous for me to make much money at all. My goal is to stay in the lowest marginal tax bracket, living in that sweet spot of having supplemental income to hedge against sequence of returns, but not having so much that I incur higher insurance premiums and taxes.

Or I could just go rock climbing 😉

I was an ‘entrepreneur’ early on in my 20s. Brought up with a fair bit of ‘rich dad, poor dad’, and ‘millionaire next door’ I’d already decided that, in your analogy, that I did not want to be the ‘tail of the ox’. I made some good money through a couple of startups but in the end, none were successful. I lost a chink of money and went into the corporate world to a ‘real job’. I went to a lot of ‘entrepreneur’ events, and in retrospect I think that entrepreneurship is heavily romanticized, and the whole scene is rife with ‘survivorship bias’.

Family members and friends of mine have started their own businesses. Additionally my father-in-law runs an accounting firm, and my father was a tax auditor – both have given me good insights as they get to see into the books of many SMEs. It’s really an all-engrossing affair if done well. You go from being the tail of the ox, to the tail of 30 oxes. In other words, you go from having one boss, to multiple – your new bosses are of course, you customers. Only, your new bosses complain, and sometimes they don’t pay you, or they go broke, and they don’t care what hours you work etc. etc. Many ‘entrepreneurs’ would be better described as ‘self-employed’ I think.

I think at it’s heart the underlying idea of ‘being the head of the chicken’ just means have a level of self-determination. However, I don’t believe that being an ‘entrepreneur’ necessarily guarantees one any more power or agency than simply being a bit higher up the corporate ladder.

Thanks so much for the thoughtful comment! As a climber (clipping chains is also a climbing reference too), I like to think that my obsessive hobby will keep me busy. But a selfish hobby probably isn’t enough to keep me “satisfied”. Nor is early retirement. I need something that is fulfilling. Fortunately when time is on your side, that something will probably make a few pennies too. Thanks again.

I have also thought about other options that provide income. And I too would definitely want to be the head of the chicken. I have had the luxury of not really having a boss to answer to in my current job and I am not about to experience that again. Maybe I’d like to open a business and/or do some consulting.

Regardless, you raise some great points that people need to consider as they move toward early retirement. Great post thanks for writing it! Cheers, Pai

p.s. I love the clipping chains name to reference the FI goal! If I could retire in my 30s, I’d probably retire to climbing.