What to pack?

I'm a pretty experienced traveler. Between personal and business travel, I fly over 50K miles a year. I'm not in United's top tier of travelers, but not far from it. I travel mostly domestic, but sometimes international. So with all this experience, why am I finding myself staring at piles of clothing, cycling gear, toiletries, travel books, maps, etc? Between my piles and my wife's, our bedroom looks like a combination of a travel store and bike shop. At least the piles are organized. Cycling stuff in one  corner, regular clothing in front of the closet, running gear under the window. My strategy, if there is one, seems to be get everything out and then staringt to decide what's really important. So, do I need four jerseys or just three? If the weather is slightly cool and I don't sweat a lot, the smell many not be too bad after a ride or two. Besides, since I'll be at the back of the pack on most rides, I'll  be down wind anyway. Decision made. Now it's on to jacket, vest, and arm warmers. Does the same logic apply? I can't wait to make the decision on bibs or shorts. 

We attended a dinner party over the weekend with the people traveling with me to France during the first week of the adventure. During the course of the evening, the topic of luggage emerged. Proudly, a couple people, non-cyclists, mentioned they are only bringing a single carry-on bag. That's all. One bag the size of large bread box. I can't fit all my toiletries and my laptop in my carry-on bag. Maybe I need a bigger carry-on. Not! I need a U-Haul. When I started talking about all the biking gear I need to bring, especially since I'm outfitting a new bike, there was a lot of head shaking. The conversation then turned to perhaps we need bigger cars and could I wear my helmet on the plane to save space.