What is happiness for you ?
Is it earning a lot of money ? Having a beautiful wife ? Building a family ? Succeeding in business ? Possessing expensive objects ? Travelling around the world ?
Solving difficult mathematical problems, and be known for that ? Having lot of sex with beautiful partners ? Drinking the most expensive alcohol ? Having good kids ? Helping others ?
In fact, you are seeking for pleasures and not for happiness.
Of course, you can find a lot of pleasures in life, in a lot of various ways. But what is happiness ?
Happiness is very easy to achieve, since it's not related to the outside.
It can be reached when you feel at peace, for example when you had an orgasm (but this sentiment vanishes quickly).
Your problem is that you are thinking too much, and that's the curse of the intellectually gifted.
If I did that, or that, or even that, could my life have been better ?
The answer is: NO !
Why are you doing all these things ? Do you seek recognition or fame ?
I'll give you a little technique, which doesn't require meditation (although it would tremendously help in your case, but meditation is difficult when you are so obsessed with your thoughts):
act without expectation
This is called Karma Yoga, and the goal is to purify your mental from expectations.
Since you seem to have plenty of money, it should be easy for you.
In your job, work without expecting promotion nor bonus (but you still have to be paid !).
If you want to help others, do it without expecting thanks from them.
If you don't want to help others, it's also fine.
Do things that you love during your free time.
If you can have a job from that passion, I'm jealous ;-)
In fact, when you receive a promotion/gift/thanks, be thankful and surprised.
Discover your passions, what you can do without focusing on money.
Focus on your inside, instead of your outside.
When you'll stop focusing on the outside, on expecting something from your actions, you'll discover that happiness is here and now, not elsewhere and in the future or in the past.
Good luck !