I am in need of a change and I have an idea.

Sure, why not?

Exactly, I am struggling to come up with valid reasons not to.
Aside from the obvious risks associated with sailing across the oceans and other such non-sense.

which direction would you go first? - where would you want to dock first, and do you know the language there?

what if you run into pirates? (I'd wear an eye patch on my trip just for the heck of it)...

should you buy pet parrot and teach it how to sing a sea shanty? a pet parrot or dog would be a cool traveling companion

of the following statements which one stirs your thoughts?

• "I remember when I was 34 - best year of my life - I sunk 40 grand in the stock market and made a mint!"

• "I remember when I was 34 - best year of my life - a native island girl kissed me and smiled!"

I wish you all the best, OP, whatever you decide

Keep a job but do this on the side.

Don't fuck your life over for some stupid hippie shit for no reason man, you'll always regret it.

You should go with the parrot.

"which direction would you go first? - where would you want to dock first, and do you know the language there?"

I am presently located in Ontario, so I have no choice but to go east, my present thought is to go up through the St. Lawrence, head east to the Magdelen islands, then northeast to St. John's, East by Northeast to Iceland, continue along the way to Jan Mayen, aim south into the Shetland Islands and Scotland, continue onward through Europe, southeast into the Med, through the Suez into the Persian Gulf, Cross the Indian to Thailand, on to Singapore, east, east, east, east, etc.

Regarding languages, not really no, but I do have time to learn fundamentals and virtually everyone speaks English or French to some degree thankfully.

"what if you run into pirates? (I'd wear an eye patch on my trip just for the heck of it)...

should you buy pet parrot and teach it how to sing a sea shanty? a pet parrot or dog would be a cool traveling companion"

Not overly concerned about pirates, though maybe I should be, definitely things I need to research.
Totally down to have a pet parrot for the passages!, dogs, unfortunately, get tricky when traveling abroad, every country has different laws, too many require full quarantine so your furry friend can't even get off the boat when you make port, unfortunately.

"• "I remember when I was 34 - best year of my life - a native island girl kissed me and smiled!"

Absolutely this, While I could use more money I am in no way hurting either, would far rather live and have experiences I can share than have a heavy bank account.

My Father and Grandmother both saved as much as they could so they could die with fat bank accounts, seems ridiculous to me, I mean at least my grandmother traveled, my father on the other hand just drank and worked, no desires, no ambitions and was a dick.
When my time comes I would far rather have all the experiences I could have ever had and die knowing I lived with purpose than consume myself working in a shop (Not that there is anything wrong with working in a shop or anything for that matter, just not my bag.)

Thank you, AC, Cheers.

Definitely!

I am actually pretty lucky in this regard, I can do both assuming I have access to the internet.
I don't really see traveling as "hippy shit" tbh, seems more anarchistic but meh.
You may very well be right in regards to regret but I think if you live life without regret than you really arent living.

Circumnavigation is for sailors not "boat guys".

Yeah, I'm aware...

You will probably crash into some reefs and the boat will sink. You will either drown in the sea or hopefully be rescued.

You are left with no job or boat. All of your belongings are lost at sea.

Just sayin... be aware of the risks. Not trying to destroy your dreams. It sounds like fun but it does have risks

Well, I generally expect to have to deal with worst-case scenarios, Regarding reefs though my boat has a 5' draft so I should be okay for the most part it is definitely a possibility, however.
My job would be fine, I mentioned further up the thread that as long as I have access to the internet I have my job.

Boondock in a trailer around the country.

Good change.