I'm a year into this, and in that cycle of "I've got to have this watch!," then I buy it, then I wonder if I should have... So I've been trying to learn about my preferences, and in doing so connected to my lifelong love and learning about wine. Wine and Watches are fundamentally similar in two ways I think: 1). The essence of the good, 2). the market segmentation. In wine you have history, geography, varietals, new releases, multiple dimensions of character, and all that is present in watches. In short, there is a lot to learn and and a lot to love about watches. The markets are also similarly segmented. You have blue chip wines (first growth Bordeaux for example) and blue chip watches, you have cult wines from the new world (like Harlan) and cult watches (think Ming). You have massed produced plonk and mass produced serviceable wines, and the same for watches. You have low yield, low production wines and the microbrand and independent watches.
Together, these traits lets you learn, grow, explore, and also have an opportunity to find great value that matches up with what you really love.
But I'm still making regret purchases... Any thoughts/insights on how to minimize them?