I think long and hard (most of the time) before making a purchase of any kind. I'm not one to regret my decisions and am very happy 99.9% of the time. I agree with Hello, that every time you pull one baby out of the sleeper, it is a new exciting experience and you fully enjoy the bag. At this price point, boredom in my opinion, should not be an option. Perhaps there are too many spur of the moment purchases out there and some need to rethink their buying habits or better yet, examine why they have fallen into this pattern. Buy, regret, and try to sell is not very healthy IMO. If one starts out with the mindset of buying to use the bag a few times and then sell and move on to the next exciting bag, that is a preconceived plan and entirely another situation. Have no intent to offend anyone by these comments and I apologize in advance if I have done so, but I find it sad that this is happening with greater frequency and I am beginning to think that it a symptom of some greater unhappiness.
I think engaging in retail therapy too much is a form of acting out a greater unhappiness. I can certainly testify. If other aspects of your life are going wrong, retail therapy does the trick - it gives you seduction, mystery, unattainability, and then the final conquest after great odds (charge your card).
I'm not one to say "Oh, get a shrink," or other solutions. Everyone is capable of finding a balance.
What I've regretted are filler, "IT" bags and they all ended up being sold.
It's only been a few months that I imposed a strict criteria - roominess, timeless style, good leather, good craftsmanship, hand-made, and Haute Couture
I don't know how many cute, small bags I have. At one point that's all I bought because I wasn't working, but now I need roomy bags, so that's where the roomy Valentinos, H, Valextras, etc. come in. I really regretted Chanels, Diors, Guccis, and LVs - completely uncomfortable, transcient, impractical, and ordinary.
Sometimes... your lifestyle changes! Sometimes you become a mom or working full time or stay away from home for 10-12 hours! You certainly need different bags or a wardrobe upgrade.
Don't guilt-trip yourself though. As soon as you're aware of the pattern, recognize it and be kind to yourself. Greater self-awareness is all that's necessary sometimes.