Would play Mega Millions for $360 Million. Then buy part of the Chicago Cubs with my winnings and then go on to win a World Series. Being a part of this team would mean I would never have to buy a drink or pay for dinner in/around the city ever again. Then I would go home to my wife Oliva Wilde, our two kids, and of course the dog.
Find the answers to the universal truth of my life, in a hut in the woods, where I never have to pay bills and worry about society. People will visit me, dote on me with life sustaining supplies in order to ask me questions of the universe and I will set them on a path to find their own personal answers.
After I find my truth, I would die.
So in summary, what I am currently doing, without the hut in the words and visitors who bring me supplies.
A failure is only an experience that someone fails to glean wisdom from. Yours, and others. Since, I have taken many negative choices and experiences from them, I don't see it as a failure.
First I'd solve all the financial and economical problems with this country starting by firing 95% or more of the politicians in office and finding suitable replacements. Other things would apply such as being able to sit in on congressional meetings with a tennis ball launcher, lots of pepper spray, and foam hard foam bats with Globo gym purple cobras and make sure they don't do anything stupid. Once the country is back on track I would...
Find a cure for spinal cord injuries and then move to an area of the world that is extremely gun friendly and build a cabin next to a large lake only accessible by plane. No roads within say 30 miles. Move there with a pair of German shepherds and live the rest of my days there. No tv. No internet. I would bring hundreds of books and spend my nights sitting by my fireplace reading books. Get resupplied by plane every once in a while, but mostly fend for myself growing crops and hunting. I'd keep a radio to contact outside world if I felt like it.
I'm 24 and felt like I was born a century too late.
As an inventor, Edison made 1,000 unsuccessful attempts at inventing the light bulb. When a reporter asked, "How did it feel to fail 1,000 times?" Edison replied, "I didn’t fail 1,000 times. The light bulb was an invention with 1,000 steps."
So I guess it's all perspective.
Having said that, I would play the lottery (preferably with a large jackpot) because I'm a bit impatient.