A friend with two-year-old twins called to say she started putting them on time out. She was frustrated because her children always seemed to act up at a time when putting them on time out would make the family late for church, a family dinner, a doctor's appointment, etc. She asked me how I handled it.
Here's my time out trick. When we first started putting them on time out, I used to do it when it wouldn't interfere with anything -- aka when it was convenient for me. Yes, I know that sounds very selfish, but there's a method to the madness.
If the girls did something wrong, I would put them on timeout to make the point that being bad means punishment. When we first implemented the time out as punishment, I tried to do it when we didn't have to be anywhere. I wanted them to have a nice long time out, not one cut short because we had to be at the doctor's or a class. I wanted them to understand that being on time out was a bad thing.
There were many times when a good, consistent parent would have put the girls on time out, but this Mom didn't do it. I want to make the point, but I also recognized that the girls became a bit wilder when we were going somewhere important like the pediatrician, Gramma's, church, etc. I let those moments slide. I wanted their full attention when I put them on time out.
Now that we've done it enough, we rarely actually put them on time out. Now we just threaten them with time out and they change their behavior or actions. It's not a perfect system, but it works for us.