Now imagine all cool stories your friends told you about what they did during vacation, including the expensive ones. This is how your average day could look like. Even if the money couldn't bring better experience (which it definitely could), it could still bring you the good experience more often. Most of the interesting things you can imagine, you could simply do them one by one, without taking long breaks; experience in one year as much novelty as other people do during their lifetime.
Altering your life would actually be easier, because if you'd decide you want to spend the next few months e.g. meditating in Tibet, you would simply go. No concerns about travel costs, or the impact such break could take on your career. Wanna try something? Simply do it. Change your mind and wanna try something else? Do that, too. Repeat as many times as you want. If you have a goal that requires cooperation of other people (e.g. you'd like to design a computer game, but you don't have the skills to do it alone), just pay someone to play along. You want to learn something? Hire the best tutors. Etc.
Even with today's poorest ever interest rate environment, $10mm in US treasuries is still earning you $133,000 a year in coupon payments and is not taxable by states or local municipalities. Leaving it with 24% taxed by Feds, before you come up with any deductions.
You already own a house outright, so 30% of that isn't going to housing.
$100,000 free and clear to play around with and occasionally buy food, every year, for the next 30 years (while your bonds also keep increasing in value), with both a home to always borrow against, and your $10mm in treasuries to borrow against if you really wanted to.
If you aren't flying private, airlines have already subsidized all your flights with an infinite amount of points.
If you are flying private, your netjets membership is already paid for, so you aren't really paying for that either, its an asset not an expense.
And once you get to Tibet you aren't paying for anything or using any money, because its so cheap.
This isn't billionaire status, this isn't Bezos status. This isn't even top 100 wealthiest, top 200, top 500, this is top 30,000,000.
You can get VIP treatment at Cannes Film Festival, and buy tables in Ibiza and St Tropez all summer, or pay $10,000 to an enterpriser for basic infrastructure at Burning Man once a year.
The reason I point this out is that its not rare enough to really make up these scenarios for. People do it for some time, and then they find something more fulfilling to do that keeps them in one place.
The abundance of money, like an abundance of oxygen, has diminishing ability to do anything for you.
The next life-improving expense would be to hire a personal assistant. Someone who would e.g. book the hotels and the airplane, so that I don't even have to think about the boring technicalities. With kids, I would probably also want a babysitter. And both of them need a room in that hotel, too. Seems like I have already exceeded the $100,000 a year. But maybe $200,000 or $300,000 would do.
Okay, I admit that at this point I am mostly out of ideas. I imagine I could use more than one personal assistant, e.g. one to take care about my everyday life (things I don't want to think about), and another to help me with my projects (things I want to think about, but prefer if someone else does the difficult research). More generally, in some situations being able to pay people to do stuff for me could save me time.
Above cca $500,000 a year I don't really have good ideas.
Both airline and hotels were mostly free using points and status.
I would only be booking for myself and only maybe a companion as the reality is that I have likely another companion in the destination. No kids, by design. The luxury wore off pretty quick and hostels were inherently more social, so the fixed dollar cost again dropped by an order of magnitude, with decompressing - and the improved possibility of privacy with a companion I may have met earlier in the week - happening at hotels on the weekend.
This is the first year that $10mm in a 30 year bond would only yield $133,000. Last year the record low rates would yield $300,000. I would probably speculate with some of it, hoping for a 10-bagger or 20-bagger. If not, oh well, wait for the next coupon!