If I think about it, there really aren't any digital games I regret spending money on. That's an interesting little thing I never fully noticed before.
The context is... I see this work I do trying to develop the craft of making interactive, artful, meaningful digital experiences as something that isn't likely to pay financially. Maybe I finish one of my experiments to my heart's content, maybe I'm proud of it, but it wouldn't be something anyone would pay for, or almost no one.
Then I look at this little factoid. I don't regret any of the dollars I spent on digital games. Most of the ones I've bought, I've never even installed or played. Yet I like having them. If they suck, I'm interested in analyzing why, and seeing what still worked regardless.
So if I were selling a game to me, just to me, I wouldn't feel bad about selling something I'd worked hard on and was proud of, for the humble but operational and possibly novel and moving thing it turned out to be. I wouldn't feel bad at all. But then, I'm really not a tough customer. Oh, I'll be dissatisfied with everything on some level. Nothing meets my overall standard anymore. But I'm not interested in games just as an escape - in fact, I'm a little bit allergic to that. Most games I play, I feel like they're trying too hard to draw me into a seemingly infinite world full of trivia and "lore" to memorize, stuff that sounds really half-baked to me and corny and I don't know why I'd want to remember any of it. But that feeling doesn't make me regret buying the game. It makes me regret my allergy, and I put aside the game and think, "Maybe some other time."
I'm not trying to be mean. But in some ways my standard is very high, almost impossibly, and I recognize that and don't hold it against a piece of software that was very difficult to create. (Also, there is still magic in these works. I still feel it.)
So maybe I should try a little bit harder not to hold imperfection against my own projects. Maybe I'd feel less blocked, get more deeply absorbed in the work again, and more consistently, and make quicker progress.