Win the lotto for me and a buddy then toss some into investments and properties to sell/rent at a discounted rate following 2019 in comparison to those who inflated theirs. Instead of 2k/m I'll go $1,500 as long as it's still above the profit line I don't need hoards of wealth from it I kinda enjoy working.
Also I'd probably just dump a bunch of money into my kids name to let it start building interest for them.
I would buy stock in various companies such as NVIDIA, GME, AMC, etc. Bet on political events such as Obama getting to appoint a Supreme Court justice who doesn't confirmed, how Trump announces his presidency, Trump winning the presidency, January 6, and Harris being Biden's running mate, Harris telling Biden "We did it, Joe", and Biden winning the Presidency. Can't forget Pence's fly friend during the debate.
I would give it another go with my ex since I would be aware of the issues that developed. If it doesn't work again, that would be a major mind fuck.
Getting in business with my current business partner, wouldn't have such a rough start since I still have the skills and knowledge from running a business.
Realistically, I would grieve the loss of my children, who would never be born if I didn't line things up just right to cause them to happen again. I'd spend more time with my parents, who are getting along in the years, and I'd make the most of my time with them while they're healthy and happy.
There are a few specifics where I'd try to get some loved ones out of trouble before some critical tipping point that would later cause a bunch of heartache and stress.
There are general things about money and politics I'd probably do differently, knowing about how stocks have performed and what not, but that's not super interesting to me, because I'm mostly content in my personal life (including my career) and wouldn't want to upset that balance by doing anything too different from what brought me here.
I would start drinking coffee a lot sooner. I've found that it has a remarkable effect on my cognitive ability (supposedly a common thing amongst ADHDers), and in 2014, I'd have benefitted massively from that.