A Rich Man Works His Whole Life to Retire Like a Poor Man by the Sea

It’s not generational wealth. It’s not to keep up with the Joneses. It’s not an arbitrary 7-figure net worth.

It’s subjective. It’s hard to define. It’s always evolving with age.

It's freedom.

Freedom means something different to everyone. The man dying on the hospital bed might view freedom as simply awaking to see another day. Another might view it numerically as a $2,500,000 net worth. To the average client during my previous life as a financial advisor, it was them outsourcing their thinking to me, the licensed professional, to handle the inputs to my corporation’s trusty freedom calculator. If only it was so easy. To think a retirement calculator that is just the corporatized version of Mr. Money Mustache’s 4% rule can give you a holistic answer to the boundlessly complex question of, “When can I achieve freedom?” is a tragic product brought to you by some soulless corporate entity. We shouldn’t outsource the most important question of our lives.

Imagine someone you just met asks you - What does freedom look like to you? What do you say? “No socks, No alarm clocks.” I had this answer ready to go throughout most of my 20s. I had it preplanned since I was usually the one asking the onerous question of, “What freedom looks like to you?” in the place of small talk. Nowadays my definition is largely unchanged although I might throw in the ability to own my struggle as another piece to the ever-evolving freedom puzzle.

Up until 2019, the vast majority of the jobs I held were in knowledge work or underway on a boat. From a Sales Manager running a small team at a Vitamin Store in my late teens to Poker Player to Financial Advisor, all of these roles were mostly mental and largely sedentary. My time trading my brain for money greatly outweighs the time I spent trading physical outputs for money.

Since 2019, I have spent 6 days a week doing some form of construction renovating one of our 3 old houses. The first couple of years renovating our 1862 rowhome required every ounce of concentration as I was very untrained working with my hands. Being 4+ years into my new role as an accidental General Contractor, nowadays its much different. Whether I’m repointing some stone, running water lines or redoing a load carrying beam, it doesn’t require me to do much mental work. At the cost of my physical body, I’m allowed the daily space to explore my mental curiosities. This is a freedom I had never experienced but now I never want to be without again.

This is why I consider freedom to be a perpetual puzzle. A puzzle that can’t be solved by a calculator or any static piece of technology.

If you asked me in 2019 what financial freedom looked like to me I would’ve told you an investment property that brings in $2,000 per month in passive income and allows us to stay there anytime we’re off the boat. We achieved that a couple years later. Unfortunately during that time period our $2,000/mo income lost a whole lotta purchasing power due to inflation. The goal posts were then moved to building an all-weather portfolio that is domiciled in geographically and politically diverse areas that produces $5,000/mo in income. Our bet is still very concentrated in short-term rentals for the time being so we don’t want to have all our eggs in one geographical basket and then fall victim to changing rules and regulations. By this Fall we will have achieved our $5,000/mo goal mostly due to the fact that the income is largely residual - not passive - and we are simply being repaid for our 5 years of grueling renovation work.

Having had a good go at playing the part of the rich man working his whole life the past ~5 years, I’m more than ready to be that poor man by the sea again. A “poor man”, who has no need for alarm clocks since he rises with the sun, has no need for socks since they’ll only get soggy and slow him down while he toils away maintaining his much too-small, brightwork laden traditional bluewater boat that can take him and his family anywhere.

A dying man’s wishes are to be healthy and live. The longest years of my life were the ones I spent living aboard. I long for simplicity by the sea again. Call me a poor man by the sea or consider me a dying man. Either way my days of playing the rich man working away his whole life are numbered.