There are basically two options for transporting your belongings while cycling: (1) on your person in a backpack or messenger bag, or (2) in a contraption attached to the bicycle itself, such as a basket, pannier, saddlebag, or other fixture. When it comes to most of my belongings, the choice on this is clear: I would rather not carry anything on my back while cycling, especially since my bicycles are fitted with racks and have great transport capacity. But when it comes to my laptop (a large MacBookPro), I just can't seem to "let go" and trust it to the care of a bicycle. I carry it either in the large leather satchel in the photo above, or in the Chrome messenger bag pictured below. The leather satchel is more suitable to my personal style, but the Chrome bag is more ergonomic and feels better on longer rides. Between the two of them, I have pretty much gotten accustomed to carrying my laptop on my back while cycling, even for long stretches.
Still, I am plagued with the question of why I do this, when my bicycles are rated to handle the weight and could make my life so much easier in this respect. There are panniers specifically designed for laptop transport and sturdy wire baskets for the rear rack that will safely do the job as well. Some even strap laptop bags directly to their racks with bungee cords, and some make their own panniers out of handsome vintage satchels using Arkel or Ortlieb attachments. So I suppose for me, it is really an issue of trust and control: Somehow it feels that the laptop is safer with me than attached to the bicycle. I have browsed countless times through all the panniers in the local bike shops, but ultimately I just can't imagine myself cycling with my laptop dangling over my rear wheel and out of my field of vision. Instead of watching the road and enjoying the ride, I'd be thinking about my laptop.
Is this a logical concern on my part? I am not sure. On the one hand, if I should fall on my bicycle, the laptop is just as likely to get damaged if it sits in a pannier than if it sits on my back. Also, the straps and closure of a messenger bag are probably no less likely to fail than the attachment points of a pannier system. However, if the bicycle itself should fall over without me on it, the laptop is more likely to get damaged. How statistically likely any of these scenarios are to actually happen, I have no idea. So I think it really comes down to one's subjective perception of security.
In the end, taking the first step towards trusting my bicycle with my laptop ended up being simpler than I thought. As it turns out, my leather satchel fits quite comfortably into the front basket on my Pashley, and the edges get lodged in the wicker, so that the bag remains sturdy when the bicycle is in motion. It never occurred to me that this could be a possibility, because I assumed that the satchel would be much too large for the basket and also that it would bounce. But there you have it. I am pleasantly surprised that there are no bouncing issues: Once stuck in the basket, the satchel does not budge; the wicker sort of closes in on it and holds it firmly in place. I feel comfortable with this set-up, because I see the bag in front of me at all times and know that it is doing okay. Not sure whether this will be my permanent method of transportation from now on, but it worked splendidly for some errands close to home.
I would love to hear how other people carry their laptops while cycling, and how those solutions are working out for them.