My Dad found great success in business consultation, owned a historic three-story home in one of the best neighborhoods in Chicago, had an oceanfront home on Lake Michigan and was constantly traveling the world. He was also the most unhappy person that I knew.
He followed a path that was lined out by his over-controlling mother, always feeling like he couldn't live up to her expectations (even though she died before I was born). He divorced my mom when I was five after becoming a CEO (I think), hid hundreds of thousands of dollars from my mom (forcing us to live in literal poverty). He married a woman who was exactly like his mother. When he lost his job after 9/11, she turned around divorced him. She somehow managed to take all of his money and his Chicago home (and then promptly married a lawyer at the same firm she used during the divorce). He tried to rebuild his life, but could never find a job working as a consultant that would pay the bills he now owed. His last job paid him well over $200,000 a year - he still couldn't make ends meet. He felt he couldn't find a job in another line of work as he just didn't know how.
He ultimately killed himself in 2007.
I never really had the chance to know who he was as a person, though in the end, I felt like he was someone who I may have forged a friendship with had I gotten the chance to know him. I rarely saw him due to my then-stepmother, but he has taught me so much.
He taught me never to rely on one path. To continue to learn and grow, and to find the joy in whatever work that I do, regardless of what that work is. He taught me to be creative in learning how to support myself and that two sources of income is better than one. He taught me that money does make life easier but it can be found again if lost. He taught me to choose my own path and strive to be my own person and not what someone else wants me to be.
The biggest lesson? Not to be an utter dick to the people you claim to love. I'm currently going through a breakup essentially akin to divorce, and no argument over what little money or possessions is worth being miserable for the rest of my life. I still love my ex and he's going through mental illness issues, just as my dad had gone through. While I feel bad now, just letting it go without the name-calling, money-hiding and legal bullshit won't just be better for him, but it'll be better for me as well.