My commute is giving me old lady posture. This is a problem.
Every day, I trek about 4 blocks to the el stop, get on the el (where I invariably have to stand for the entire 40 minute ride), and then walk another two blocks to my office.
Accompanying me on this daily journey is my trusty messenger bag. Some lawyers might carry fancy leather briefcases, but those are lawyers who have enough discretionary income to spend some of it on something as unfun as a leather briefcase. I have to save my limited discretionary income for gin, so I carry the same bag that I have carried since 1997:

The problem.
(Those Timbuk2 people do not lie when they say their products last forever. This thing has lasted for 10+ years of heavy daily use, first carrying huge college textbooks, then heavy teacher’s manuals and student work, then a laptop and huge law casebooks. And no, I cannot for the life of me figure out why my 18-year-old self decided to purchase a bag in Packers colors. The Bears fan in me keeps hoping the thing will wear out so I have an excuse to buy a better color scheme. It’s not cooperating.)
Now it does not hold textbooks, or teacher’s manuals, or casebooks. Most days it does not even hold a laptop. But it is still bothering the heck out of my neck.

A peek inside
So I thought it was time to take a cold, hard look at the ridiculous amount of crap I’m schlepping on a daily basis, to see where I can lighten the load.

The wallet stays.
Wallet. Can’t get rid of this for obvious reasons. Plus, contains very little actual money, so is surprisingly light.

Lunchbox
Shut up. Seriously, stop laughing. Bento lunchbox is awesome. It is flat, and fits easily into the bag, and holds lots of food, and saves lots of money that would otherwise be spent on subpar sandwiches at Corner Bakery. I love lunchbox. It stays.

File Folder, Notebook, Book
These things are, admittedly, kind of heavy, but I can’t give them up. The file folder contains work to do at home, which enables me to leave the office at a reasonable hour. The notebook I try to always have with me to jot down notes, phone numbers, etc. After years and years of losing the envelopes and scraps of paper I used to write that stuff down on, I’m committed to my notebook system. The book is a fabulous tome containing the history of and recipes for old-timey cocktails, and while I suppose technically I could attempt my commute without a book, I find that it’s important to have something to look at other than your fellow passengers, so as to avoid accidental eye contact which seems always to lead to (ugh) early morning conversation with a stranger.

Rain accouterments
We had a storm. You may have heard about it. My hair is very sensitive to rain.
That’s it for the main compartment. Time to turn to the pockets:

Pocket dwellers
Well…gosh. I appear to be deeply concerned about lip care. Let’s take a closer look:

So! John! All those times I asked you in accusatory tones why you had stolen my carmex/burt’s bees and hidden it from me? Um, my bad. Also, glad to see that I’m keeping the two nicest cosmetic items I own (those two Chanel lip glosses) in the ratty dingy depths of my work bag, considering I don’t wear lipstick to work, like, ever. This also might explain why I ended up swiping Vaseline on my lips in a fit of desperation before the wedding we went to this weekend when I couldn’t find any lipstick anywhere in the house.
So, what have we learned here today? Clearly I can remove, oh, a half dozen lip balms/glosses/sticks from my bag. But I have a hunch that the combined weight of a burt’s bees, a carmex, two lip glosses and a kiehl’s tube is hardly going to make a difference for my poor neck.
I guess the only other option is to invest in one of these:

That, plus a pained expression and a hunch to my shoulders, ought to be enough to buy me a seat on the train so I can set the damned bag down, dontcha think?
Here are the comments I can give you:
Get paperback books at Costco. Then swap them for other books. Then keep swapping for more other books. There are sites that do this. I’ll send you a couple to gt you started if you’d like.
Switch the shoulder the strap goes over. If you’re standing on the train for 40 minutes, your feet are at least one foot apart to brace for balance. Put your bag on the floor between your feet during the train ride.
Excuse me while I laugh at your lunchbox. Please post a pic of your lunches so we can see how much it holds. Thank you.
I say you should just spend a couple dollars on an old lady folding cart, place your 10-year old bag in it and push it in front of you to work. That way, at least your posture will match your accessories.
hee. i am not laughing at your misfortune. honestly! ish!
i’m with green – i’m always FAAAR too lazy / annoyed with my bag to actually keep it on during standing train rides. it lives on the floor after about 30 seconds.
I tote more stuff on the bus than I am proud to admit and large men often marvel at how heavy my bag is. I envy those people with just a money clip and a lipstick to their names. My only suggestion is the same as above- keep it on the floor as long as possible.
I like Nilsa’s suggestion. It made me laugh out loud. My coworker now thinks I’m crazy.
Also, maybe a shoulder bag isn’t the best idea? Or at least switch it from one shoulder to another to balance the load.
Ooh! I feel your pain! I have, I believe, that exact same bag from 1999. And while I often use it for specific instances such as bike rides or something, I find that I can’t use it much anymore for the same reasons you listed. It hurts, and the strap is like a blade when it’s heavy! And, while it seems built for a large load, if you put more than two things in it just gets so poofy you can’t close it. I like Timbuk2, and they’ve improved their bags, but you or I will probably never wear out the current ones in order to justify a new one. My verdict: your items are all pretty much essential (commute with no book? Never!), so keep this one for biking or the gym and get a bag that is not a schmancy leather briefcase but something nice and reasonable and cute. There’s a new Brooklyn Industries on Milwaukee, perhaps.
And your lunchbox is awesome. So many others think it’s awesome, in fact, that they take hundreds of pictures of theirs. Type lunchbox into Flickr and there are all kinds of lovingly shot meal examples…
What is it about the cosmetic-y products? They seem to multiply in the dark corners of my bag, too. Particularly the lip balm/gloss contingent.
I still blame you for my Chanel lip gloss addiction.
I recommend getting a massage
I think I’ve found your solution, and it’s not even very dorky:
http://www.skymall.com/shopping/detail.htm?pid=102686011&c=