So more has developed.
The realization, as others have mentioned is that the issue has nothing to do with others. It has everything to do with myself. I get that.
My Adult Life[year 1 - 10] - Went to college. Worked hard. Went back for post-grad. Started career, started family. Responsible, Worked hard, raised family. Good Salary.
[year 11] - Responsible, Worked hard, raised family. Good Salary.
[year 12] - Responsible, Worked hard, raised family. Good Salary.
[year 13] - Responsible, Worked hard, raised family. Good Salary.
[year 14] - Responsible, Worked hard, raised family. Good Salary.
[year 15] - Responsible, Worked hard, raised family. Good Salary. Hit Millionaire Net Worth. Woohoo!
[year 16] - Responsible, Worked hard, raised family. Good Salary.
[year 17] - ????? Guessing it'll be "Responsible, Worked hard, raised family. Good Salary."
[year 18] - ????? Guessing it'll be "Responsible, Worked hard, raised family. Good Salary."
[year 19] - ????? Guessing it'll be "Responsible, Worked hard, raised family. Good Salary."
[year 20] - Early/Semi-retirement living off $50-$60k a year of passive income from investments and a paid off house. Worked tens of thousands of hours to get there.
I've spent my entire life being responsible. I've taken moderate risks which have been good but I haven't bet the farm. I haven't been reckless and I don't know if my excuse is that I have a family, or if it's simply being responsible?
So my life has seemingly been a continual upwards trending boring line graph. Stable home, stable family.
His life has largely represented a scatter graph.
Brothers Adult Life[year 1- 10] - Went to college, dropped out. Pot head, mooching, partying, etc, broke.
[year 11] - I lend him money. He's broke and living in parents house. Irresponsible.
[year 12] - I lend him money. The next year he gets fired and starts his own company. When he doesn't have work, he lays his employees off and they live on Employment Insurance.
[year 13] - I lend him money. He earns $200k doing construction with a crew. Blows it all. Nothing left. He's just managing the projects and essentially working part-time. Partying, etc. Takes winter off.
[year 14] - Builds a $15 million condo unit for a client and another $10 million condo unit for another. Turns down full-time job offer because he doesn't like the commitment.
[year 15] - Gets one of his billionaire clients to invest millions in a waterfront property to "flip it". Sells his own home and he lives in the boat house on multi-million dollar property while renovating. Agreement is to split the profits with billionaire.
[year 16] - ?????
This upcoming year could be the worst year of his life or it could project him into multi-millionaire status. He's now working with Billionaire's.
He's lazy. He's lucky. He's smart.
Do I fault him? No. Does it make me look at myself under the looking glass? Yes.
The issue isn't with him, it's with me. But I don't know how to be reckless? I've always thought
"Be careful who's advise you buy. For everyone who's successful enough to write a book, there's 1000 others who have done something very similar and lost it all." The feeling is like Grimey and Homer Simpson.
https://www.youtube.com/watch?v=BA1RgpYS2IQ