Biggest challenges besides finances and getting everyone where they need to go is this. Big kids mean big problems and mistakes with your toddler aren't going to have the same level of consequences as say making a mistake of letting your older kid get in the car with the wrong kid driving. Helping them grow up means that you have to loosen the apron strings and let them be independent. You think introducing daycare was hard, but for me it was nothing like putting your kid on the Metro for the first time and letting them come home alone without a sitter after school. There are no easy tricks like Magic 1 2 3 or time outs for when their behavior doesn't meet your standards. If any of your kids have school issues, it can be both time consuming and frustrating if the school is not responsive. As you parent, while you aren't trying to be a friend, but you can't alienate either because then you won't have any influence over your kids. Once they hit age 3 or 4, you are no longer the favorite playmate, which is definitely bittersweet.
If you're on the fence, I'd say don't do it. But if you think you'd like a bigger family, all I can say is that we're really happy that we went for number 3.
Oh, and, if I didn't say it already, kids are way more expensive as they get older. I always thought we'd have so much money when we no longer had daycare or diapers or aftercare. Sigh. I'm broker than ever and we haven't yet hit college.
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