Everything is 100% optional when you have a certain level of wealth so under this definition rich people could never have jobs.

I do a lot of free legal work. If I started charging for it would you call that a running a business?

I think the way Canada approaches the question of taxation with respect to gambling is a good test to determine if something is a hobby or a buisness / work.

Do you engage in an activity in an organized manner, with considerable time commitments, and an expected positive return? If yes it is a business. That you also enjoy it doesn't change that.

So yes I think your Magic playing would be business income.

Lets not talk resort. Lets say going to NYC for the three days. Say I want to go next weekend. So plan my trip starting Friday March 19tth returning Monday March 22nd early in the morning. So 3 days and 3 nights.

1) What hotel do I stay at?
2) What do I do Friday night?
3) What do I do Saturday during the day?
4) What do I do Saturday night?
5) What do I do Sunday during the day?
6) What do i do Sunday night?

Lets say I need $100 for gas and am willing to drive (normally I would fly as the two times I've made this drive it is just too long) but a $400 flight would blow half my budget.

Just to be clear, I'm not saying people should strive for more material wealth. That's more of a personal preference thing. I'm just saying people shouldn't act like people who want to earn six figures are slaves to the man, bad human beings, or anything else. That point of view irritates me, and more importantly, it's not even relevant to this topic. Some people are more than satiated off $50K a year, others strive for a lifestyle that $50K just won't cover. I think both of those preferences are completely reasonable.

Anything one does with a commitment to excellence for pay is "a job": directing another movie, making another album, doing a 100 city book tour, posing for a nude centerfold.

And I doubt I'd want your "free legal work"... I'm better off paying a good lawyer who is committed to his career and excellence $300-400/hour.

Basically, your statement is true for reclusive millionaire hermits... but if you are rich and socially and business connected, NOTHING is 100% optional without screwing people around you.

Currently the tax rate would be 15% on dividends if you are making more than 34k per year. Depending on what happens with the Bush tax cuts that could change.

As for companies, there are several I like. This list at dividendgrowthinvestor is pretty good (from 2008). I have not researched each company there but saw several I like. As always do your own research.

Just because your job is optional with respect to money does mean that it is entirely optional, and I think the fact that you're interpreting optional to only mean with respect to money is disingenuous.

If I am running a business and have many employees and others who rely on me, and have 10 billion dollars, I still have to continue working or put hardship onto others around me. This isn't the case with any of the things I mentioned, so I do not think they are equally optional.

When you are doing free legal work, you technically can quit in the middle of helping someone, but you know as well as I do that this is morally repugnant if you've agreed to donate a certain amount of your time to helping them, since you've put them in an even worse position than they started in if you stop helping them in the middle.

It's not the same as someone who plays magic but could decide not to play on any night or even for the rest of their life without harming anyone.

lol. When math fails... try philosophy.

This is off topic, but I'm curious. Henry, in your past trips to NYC how did you check into a hotel without a credit card. I'm sure there's a mechanism, but what is it?

You give them cash for a deposit. They return it when you check out.

Of course it is optional. You promote or hire someone to do your functions and the business goes on.

I was thinking a little less immediate than that. Obviously quiting after saying I would do something is not acceptable but this generally means I'm suck with something for a few days or weeks. I was thinking of optional in the sense that I can choose to say no in the future and could have said no here. Also I could always just pay someone else to do it for me allowing me to quit mid-project with no issues.

How much cash? Would it cover a significant amount of damage to the room?

It varies considerably and there doesn't seem to be any sort of desirable patten. I've had a Sheridan require $1600 and then considerably more upmarket places require $300-800. Some places it is a flat amount and other places it is $x per night of stay. Some places will give you the option to have a smaller deposit if you don't have a mini-bar and they simply lock it. If you take that option then room service is pay as you go as well. I think you might also lose phone use if you take that option or at least long distance. Some places after you stay there enough just let you stay without a deposit.

Interesting. Thanks for the response.