What decisions are difficult for you? What to order at a restaurant, which shirt to buy, which mutual fund to invest in, which way to drive to work, etc?
When I don’t know what to do I wait for a bit and see if the situation changes.
Nope, then I just stay in my rut. My sweet, cozy rut. 
In advancing and in retreating
The perseverence of a warrior furthers
Repeated penetration. Humiliation
Two lines from the same Hexagram of the I Ching.
Like others have said, sometimes you just need to make a decision and go with it, even if you end up being wrong. For the most part, what does being wrong about the small things cost you? Very little. You spent $3 on some flavored coffee that it turns out you didn’t like. Ok, now you know you don’t like that. You wouldn’t have known if you hadn’t tried it. You bought a shirt that, a week later, you don’t like the looks of. How would you have known if you didn’t try? You took a left turn and hit a dead end. Big deal, it cost you a couple of minutes to find out what’s down that road.
I had a former friend who was utterly paralyzed with fear over the smallest of decisions and thus, lived in a very small, comfortable world (read: hell) of his own making. Seriously minor shit with no real consequences would drive him into a tizzy of indecision. He became the Poster Child for this sort of behavior in my own life, and thus became a former friend very rapidly.
I think Annie-Xmas quotes it best there; “Think about the worst that could happen. Then think about the worse that would plausibly happen. Then make your decision.”
If the worst that can happen is that it costs you a few dollars, or a few minutes, then why are you stressing about almost nothing? Make a move. If nothing else, you’ll learn something.
Maybe (but maybe not in this particular case which sounds like an important decision…) it might help to know that most decisions really don’t end up mattering in the long run.
Take your supermarket example. The WORST thing that can happen is that you end up with a brand of X that you don’t like. So you finish that package of X and next time you buy Y. Eventually you’ll have gone through all the choices and will have ended up knowing which you want to buy.
I think it works even with relatively big things. For example, we had a terrible time trying to decide if our second grade son should be pulled out of his regular school which he hated and be sent to a village school instead. There were numerous factors to the decision and it literally made me sick thinking about it.
In the end we went with the main point that he was desperately unhappy NOW and that making him endure it for nearly five more years in the hope that things would improve was not what we wanted to do right now. Now he’s approaching the end of 6th grade and Junior High is looming, we are pulled back to some of the reasons why this was not a good idea. However, he’s had four very happy years and is a stronger and more confident person because of it.
If we had left him in the school I think he would have acclimatized enough to have had a blah but not terrible four years and then been better prepared for the next stage of his life.
Which was the better decision? We’ll never know. We have to go with the one we chose and adjust accordingly but ultimately he’s still the same kid and just as loved by us whichever decision we’d made.
He’ll adjust his life to fit the next JHS decision, too. We can only do our best at the time with the information we have. Not to mention options!
This philosophy has helped me with other big things too - for example I recently realised that some of the assumptions about buying the house we live in now had been very wrong and we could have got a bigger and better house on more land had we known. On the other hand, we DIDN’T know; that land that I found out about recently nearly empty plots with no shops anywhere near them five years ago when we were househunting, and on the strength of what we knew then was a very inconvenient location. So I had five minutes of agonising and kicking myself, then was able to look again and see that I love my house, I love my garden and the fact that I can walk to the shops, and that NOTHING has changed about the comfort of my life, so ultimately yes, we might have had a better situation but what we have now is good enough.
I think I’m rambling so I’ll stop.
Edited to add that I see that while I was rambling, I’ve been beaten to the punch in a much more succinct manner!
With the very small decisions, I can usually recognize that I’m dithering and snap out of it. This decision is more like **Hokkaido Brit’s ** situation with his son.
Not to be too mysterious, I’m trying to decide whether my son should ride his bike to school. I didn’t want to just ask the question straightforwardly, because no matter how much detail I gave, no one really knows my kid or the effect on our financial situation, etc. And in the end, I’ll probably make an emotional decision rather than a logical one.
What I plan to do, thanks to **Inner Stickler ** and taxi78cab and WhyNot and others, is to let him do this on a trial basis, hold off on spending the money, and try to break the problem down to each little niggling issue so I can attack them separately. It’s a good enough temporary solution to keep me from lying awake at night thinking about it, and by the end of next week, I’ll know more about how it’s going to work out.
I’m a her, actually!
And having read what your dilemma is, I wouldn’t presume to advise, as you say, there are too many personal factors to weigh up. Good luck!
Well, if you’re talking about your son, the logic goes right out the window. Mothers can come up with the most godawful scenarios, and sadly, it never goes away, no matter how old they are (ask my MIL.)
That said, you can prepare your son. Make sure he knows bicycle safety, what do do if a car suddenly slows down near him, where to go for help if he gets lost, etc.
Then, you let him go and keep your worries to yourself, or, if you’re like me, spill them to your husband so he can laugh at you.
Mommies are never really ready to cut the apron strings. But the good mommies will let the kids tear themselves loose with a only a sad smile.
Thanks, Ms. Brit!
Ugh, I’m trying…
My kids are 16 and almost 19…and I still don’t relax until I know my son is home safe from work. (He’s living with us for the time being.) Oh, I know he can go out with his friends, but he’s not been driving long, and what happens if if if if if if if…
I told my husband that as long as we have to clean up the kids’ messes, I’m always going to worry about them. When they’re old enough to clean up their own mess (and I’m talking about dealing with a car accident or a stupid boss, not a pile of clothes on the floor) maybe it will get better.
I read this out loud to my mom, and she hasn’t stopped laughing yet. 
I said “get better,” not “go away completely.” So that doesn’t happen either? Crap.
I struggle a lot with decision making. I once spent 30 minutes in a Halloween store trying to decide between two sets of rabbit ears. I get overcome by anxiety and begin to feel like if I make the wrong decision, it has implications about my moral character. If I felt like my choice of rabbit ears had moral ramifications, you can imagine how I handle important decisions.
Last year I did not apply to graduate school because I could not decide. I almost immediately regretted my decision, and have been regretting it for the last year.
What actually helped me was somebody’s Post Secret.
It said, ‘‘I have finally learned that making the wrong decision is not nearly as great a tragedy as never making a decision at all.’’
I’m applying to graduate school this week. That quote is my mantra.
She said in some ways it gets better - you don’t worry when they are out late when they don’t live with you so you don’t know, and in some ways it gets worse - you can’t really force them to go to the doctor’s by making an appointment for them and plunking them in the car anymore.