If I Were A Rich Man . . .

In the trust business we have a few inside jokes. One is that you anxiously await each typical age threshold "expecting" to receive notice that you are the beneficiary of a trust you did not know existed. These dates are generally 18, 21, 25, 35, and 45. I've got just one left. I'm not holding my breath.

I have a few crazy stories about trusts that actually do exist while the beneficiaries are completely unaware. These include some with contingencies that range from bizarre to spiteful. If those contingencies don't play out, some other party will be the recipient. In the very likely event that I am not going to win the trust lottery, what are realistic goals for my wealth going forward?

I am not so much thinking about specific numbers. It is more about evaluating where I've been and where I'd realistically like to be in real terms. I think of these as levels of wealth.

Let's get it out on the table right now that upon reflecting on my current status I have to feel incredibly lucky (just don't call it "a blessing"). It is very likely that like myself, everyone reading this blog is in the top 1% of current human wealth. Basically every household in the United States above the poverty line is in this top 1% group. I enjoy riches that would be undreamed of by previous generations of Americans or current populations around the globe today. So with an eye of thankfulness to what I have, how would I measure being "wealthier" than I am today?

Somewhat in hierarchical order, here are the levels of wealth I would like to achieve. I reserve the right to change my mind on this including adding to it; which is to say, I recognize that what I value now may not be what I value in the future.

• New cars and more often - I would like to feel financially strong enough that without hesitation I would always buy brand new cars. And I would like to be able to replace cars about every 2-3 years rather than 6-8. 
• Top-level electronic, entertainment packages - I would like to have satellite radio in all cars (I do in one and I work to always get a discount for it (see the next item on this list)), all the premium channels and other packages for TV, full memberships in all the Internet radio desired like iTunes Match, Pandora, etc., the top-tier of Internet broadband and mobile data packages, et al. 
• No discount shopping/rewards programs - I make A LOT of decisions with an eye to how I can get a discount or participate in a rewards program. At some point it is not worth one's time. I would like to be wealthy enough that it is never worth my time. It would be a hard habit to break, but I would adapt. 
• [UPDATED] Dining out without limit - Eating at the kind of places where I most like to eat and ordering as I like to order is currently something subject to a sharp budget constraint. It would be amazing if that were no longer the case.
• Top-of-the-line furniture and appliances throughout my home - Like many of these, this presumes I am wealthy enough to afford the risk my kid, my kid's friend, your kid, etc. will destroy my leather chair from a place you've never heard of, guest-bathroom TV, ice-maker in the backyard kitchen, etc. 
• First-class travel - I want every flight I take to be business class at the least with first class an option. I want to stay in the best hotels at every destination and in the best room available. This might include something as small as staying on property at Disney and in a suite with a view. It might include the Ritz-Carlton's destination club. 
• Netjets is the natural next step within this item.
• Having a private suite at my favorite sporting events - We've discussed this one before.
• [this space reserved for future awesomeness...]

Yubby dibby dibby dibby dibby dibby dibby dum.