Project Retirement, ep 1

The one where we lay out the plan.

I'm turning 53 in 2021. That's pretty young some will argue. My mind feels like 20, but my body feels like 70 at this point, and it's not like I spent my life picking stones and pulling teats... Like Blackwalt, and many others, I have a bad back, and it's amazing how much back pain just sucks the life and the joy out of you. In August of 2019, I threw my back out so bad that I was stuck in a position on the floor for hours until my wife came back home and found me. That kind of situation scares the poop out of you, and you come to realize that all it takes is a bit of bad luck and it's curtains for you.

So, do I want to keep working another 12 years, or do I want to have some fun for myself ? Duh. So, what's the plan ?

First, I need an objective. Something to aim for. My whole personality is obsessive and objective-driven... to a fault. It's both a power, and a curse. It's made me somewhat successful in business, but I fell like it's been a negative trait with my family and my friends. To wit, I might as well use it as a power here. By "objective" here, I don't mean something generic like "retire early", I mean something deterministic and measurable.

So, here we go: I want to spend a whole season sailing the Caribbean islands, as a skipper, during the winter 2022-2023.

"Do you own a boat ?" No.
"Do you know how to sail ?" No.
"Does your wife know how to sail ?" No.
"Are you in shape to actually sail ?" Well, kinda.
"Is your wife OK with this ?" I'm pretty sure we talked about it.
"Are you insane ?" Ask Stormblade... so, yes.

So, that gives me 2 years to learn and execute. 24 months. Roughly 730 days.

I want to document this so that I can force myself to progress, as well as giving a few lulz to the regular crew here and let them place their bets. Next episode, I will lay out more details and list out all of the category of things I have inadvertely committed to learn.