Most of what goes wrong with a bag can be fixed without replacing it.
Most bag problems have a fix that costs less than $40. Before you replace the bag, work out which problem you have.
If the answer is clear, a new bag may be the right call: the straps still hurt after you've set them, or the laptop doesn't fit the sleeve. If the answer is closer to "I'm just not happy with it," start with the list below.
That is a compartment problem: one big space with nothing to hold small things in place. A tech pouch for cables and a second pouch for the things you reach for every day, at $20 to $40, give them a place. Both move with you into any future bag. A new bag with more pockets gives the same things more places to hide, which is the argument of the organization trap. Pouches vs. built-in panels covers which suits you.
Packing cubes ($30 to $50 a set) are a trip tool. They earn their place on trips and in a top-loader or a bag with one big compartment. In a daily bag that already has compartments, they mostly add weight, and a pouch does the same job. See what cubes do and don't do.
Start with the straps, which cost nothing. A harness ships loose, and no one shows you how to set it. Pull the load lifters snug so they angle back to the bag at about 45 degrees. If the bag has a hip belt, set it on top of your hip bones, not your waist; the two kinds of hip belt explains which ones carry weight. Ten minutes of fitting rules out the harness before you blame the bag.
If the laptop is a bit small and slides around, a padded sleeve for $15 to $30 fixes it and adds a layer of protection. If the laptop is too big for the sleeve, no add-on fixes that, and it is a fair reason to look elsewhere. How laptop sleeves work covers what to look for in either case.
If water soaks into the fabric instead of beading up, the water-repellent finish (DWR) has worn off. It wears with use and washing. A reproofing spray, about $12, brings it back; how coatings work explains what you're restoring. A rain cover at $10 to $20 handles a downpour. What a bag's "waterproof" label means is a separate question, covered in the waterproofing spectrum.
Try a carry audit first. For a week, note what comes out of the bag and gets used, and what rides along untouched. If the bag is still too small once the untouched things are out, you need a bigger bag.
That counts. Looks are part of a bag you use every day. Separate "I don't love how it looks" from "it bothers me every time I pick it up." Only you know which one it is.
A new bag fixes a bag problem, and it can't fix much else. These are bag problems:
Anything short of that list is a problem a pouch, a spray or ten minutes with the straps can fix.
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