How much should you actually plan when you want to have a baby?

Hubby and I have been doing birth control since we got married and are wanting to start trying but I feel like we're hesitating over a bunch of different factors (brother's wedding next year, I just started losing weight, his promotion, etc.).

Should we go into that much thought about it? Or just go for it and see what happens?

Help. I just feel like we're WAY overthinking it.