I’m certainly confident enough to offer a gentleman’s wager (that no one would take me up on). That within two years, the market’s going to far surpass where it is now.

If you’ve been in the market for years and didn’t panic on drops or dump loads of cash in on peaks, you’re probably doing just fine.

I didn’t unload any stocks or mutual funds at all after the 2008 crash. When I finally sold some equities to balance my portfolio, the market was higher than it had been before the crash. I lost nothing.

if we’re talking about trying to make big money by constant trading.

But to be fair, as a long-term investment it’s held up pretty well. I’d have no problem with younger people putting money into stocks, particularly using dollar cost averaging.

If you have lots of money, investing in real estate (cash-generating investments, not “flipping”) is good.

Being debt-free is a lot easier if you’re in a steadier business, and not putting two kids through college.

Refinancing is always a good idea, but any financial gains should be immediately plowed back into paying off the principal as soon as possible. A smaller debt is to be preferred to a lower interest rate, especially if you can do both at the same time. Interest payments are a function of principal, rate, and time. Total assets that exceed liabilities trump cash flow every time. Remember, everybody is telling you to put your money to work instead of paying off your debts; that you can invest at a higher interest rate than your mortgage. Don’t believe them, that’s exactly what they want you to do, and there’s no way you can beat those guys at their game. All you can do is refuse to play.

Runaway inflation is always a possibility, so excess saving is probably contra-indicated. My solution has been to direct my excess cash into buying durable goods I’m probably going to need to get anyway, eventually. Not luxury items, functional items. If you have a little extra cash, replace those aged appliances, get a new car, fix up the house (fundamental and structural repair, not cosmetic remodeling). Invest now in useful things you’ll only have to buy sooner or later anyway. You can always sell or barter hard goods in an emergency, even if it is at a loss, so they represent a form of savings. Infrastructure, for people as well as nations, is always a good idea. If you still think you’re saving too much,
you can’t go wrong with buying tools and firearms, especially if you know how to use them. You can always sell them if you have to.

One strategy is to borrow as much as you can, betting that what you have to pay back tomorrow will buy a lot less than what you can get for it today, even with that locked-in interest figured in. But a lot can go wrong with that, as a lot of underwater homeowners are finding out today. Besides, there is an enormous peace of mind (and a nice safety cushion)that comes with being debt-free with a bit of cash in reserve. Peace of mind has a real dollar value; when you don’t have any you’ll pay anything to get some. It’s better to be solvent now than potentially rich tomorrow. Tomorrow has a way of never showing up when you want it to, and you’re never ready for it when it does.

Of course, its all a moot point if you have nothing to invest, but optimizing our investment is what this thread is about, right? Pay your bills, live within your means, get out of debt, upgrade those things you will need anyway, avoid interest payments and keep enough cash in reserve to give you time to shorten sail if the wind freshens unexpectedly and suddenly.