With the ten days of repentance upon us, I say we work on our pessimism this year. Not that it’s really going to help anything.

Some situations call for pessimism.

We all have pessimists in our lives. It could be someone we know, it could be ourselves, it could even be a little voice inside us that speaks in italics.

You’re talking about me again, aren’t you?

In the words of our sages, though, “Who is rich? One who is happy with his lot.”

See? Of course he’s rich. He has a LOT. Whereas I only have a little.

Very few things in life are 100% good or 100% bad. Most things fall somewhere in between. And it’s definitely better to focus on the good part.

I bet he’s going to talk about the glass thing again.

You bet I am. A pessimist says the glass is half empty. An optimist says the glass is half full. I’m not sure why they’re eating out together, or sharing a glass for that matter. Probably the optimist figured the pessimist wouldn’t raise such a big stink, at least this early in the meal. And now that he is, the optimist figures they’ll probably get a free meal out of the whole thing.

Sure, there are some situations that call for pessimism. Like let’s say the waiter brings you a cup of soda, and the guy next to you grabs it away and drinks half of it. In that case, you can turn to the guy and say, “What the heck? It’s half empty now!” and that’s okay. And if he counters with, “You’re such a pessimist! I left you half the glass!” you have the right to pour it on his head. Just because you have to be an optimist doesn’t mean you have to have table manners.

I’m a pessimist too, sometimes. Like whenever there’s any kind of raffle or lottery, I assume I’m going to lose. The one time I ever won, I won a year-long gym membership that I didn’t want, because my entire excuse for not going to the gym was that I didn’t want to pay for a membership. Especially for something where I’d have to do all the work. But with raffles, if a hundred people enter, the glass isn‘t half empty – it’s 99% empty. No one looks at the glass and goes, “That’s 1% full!” No, they go, “Why am I the only one in this house who can refill the water?”

And the world really does need both kinds of people. An optimist invented the airplane, and a pessimist invented the parachute. One can argue that parachutes save lives, but they don’t really save the lives of too many people who did not first go up in an airplane. A pessimist probably invented it even before the airplane came about, to be used in case someone was snatched up by a giant bird, but he didn’t make a big deal about it, because he figured no one would want to buy it. And he was right. Pessimists aren’t necessarily wrong, they’re just no fun to hang out with.

So it’s definitely better to be an optimist. For one thing, you feel like you get more to drink.

Are you a pessimist? Do you want to do something to fix the situation?

No, I just want to complain about it. Hey, how come I eat right and I exercise and I don’t lose weight? I feel like I’m living properly for nothing!

Either way, here are some tips to achieve a more positive outlook:

Tip #1: Ask yourself, “Could things be worse?”

Tip #1: Ask yourself, “Could things be worse?” A professional pessimist can probably come up with 500 ways things could be worse. And there you are!

Tip #2: Whatever happens, tell yourself that God is doing it for the best.

Yeah, but what if I’m one of those people he wants to punish?

Don’t worry. We’re all His children. He only ever punishes you to teach you a lesson.

Yeah, but I’m probably not going to LEARN my lesson.

Oh, for goodness’ sakes!

Tip #3: Remember that every cloud has a silver lining.

That’s not silver, that’s grey. It means it’s going to rain.

Rain does more good than bad, you know. It helps farmers grow food so you that won’t starve or be forced to pay five bucks a pound for tomatoes, but yes, it also means that that you won’t be able to go to the zoo today. A lot of things that might seem bad are really blessings in disguise.

Yeah, but that’s what I’m saying. Why don’t I ever get blessings that are not in disguise?

It’s not always easy to be happy with your lot. And even if you learn to be happy with it, that doesn’t mean the people who rely on you to support them will be. You might be happy that you can pay your bills every month, but your kids have way more time to watch commercials than you do, and to them, it seems pretty random that you tell them that a $100 toy is too expensive, and then you’ll turn around and spend $300 on a plumber. But even if you buy them the toy, there are always going to be more toys. Parents want to provide every advantage to their kids, but sometimes the advantage you need to provide is to teach them how to get by with less.

A pessimist says, “Uch, Yom Kippur. I have to spend most of the day in shul listening to the cantor go, “Ay ay ay ay ay.” Do I get more points from God the longer he chants, “Ay ay ay,” while I sit there with my Artscroll Machzor and count how many pages we have left? At this rate, we’ll be here until Chanukah!

An optimist realizes: “G-d is giving us a day to ask for forgiveness and make things up to Him by delivering a speech that for the most part has already been written for us? Let’s spend all day doing that!”

An optimist also realizes that half the pages are in English.

Yeah, we all count pages. If not for the little bit of pessimism in us, we wouldn’t have bothered showing up to get our slates cleaned in the first place. But a little bit of pessimism goes a long way.