I don't hang out at money.stackexchange as much as I used to. No hard feelings, though: I'm glad to see that the site finally made it out of the 3+ year beta purgatory it was stuck in. They even sent me a cute little green piggy bank for being one of the more active users (for a time, anyway).
The people there — myself included, I hope — genuinely do want to be helpful. And I give a lot of credit to people who come with basic questions and who are humble enough to ask.
Questions that make you flinch a bit
There were a couple of questions recently for which giving the answer is a bit hard. The questions were basic, and you just knew that the person wasn't going to like what you had to say, even if it was exactly correct, and what they needed to hear.
One of them dealt with disability insurance. The question was: “How to start disability insurance when already disabled?”
Ouch. We had to break it to this person that he was too late. Here's how I answered:
You may find some company who will insure you, but they won't pay anything based on what you already have. That's a pre-existing condition, and it's uninsurable.
It's a bit like asking the casino if you can bet on red after the roulette wheel has already stopped on red.
Though the insurance company won't cast it in those terms, when they issue you a policy, they're placing a bet on you. They're betting that your premiums, plus whatever they earn on your money, will be a lot greater than what they have to pay out in claims to you.
But, they can (will) only make the bet if the outcome is unknown. If the outcome is known — meaning they'd definitely need to pay out — then they won't make the bet.
He asked this question on June 6th. I answered on June 7th. The last time he visited the site (as of now) was June 9th. He may have just needed the answer to that one question, but I wouldn't blame him for not coming back, even if he had more questions! Not many people would want to risk that level of blunt honesty again.
But this kind of “too-late” problem is true of any kind of insurance. It's a no-go if a payout is certain. You have to get the policy before you suffer whatever you're insuring against.
It's a good reminder to take a bit of time to assess the risks you face (whatever they are) and insure against them appropriately.