Following up on my feature articles (part one, part two) in which I considered the term approachable luxury, I’ve been thinking about how to define the term luxury itself. It should be obvious, and yet it’s not. An idea that occurred to me was to think about luxury as a series of questions.

It started with a series of three to five questions, comparable to my three-question Tradeoff Audit for evaluating approachable luxury. Then the questions multiplied. And then they became less comfortable. Not so much “What are you gaining? or “What are you giving up?” but “How would it make you feel if…?” And I realized these were questions I needed to start asking myself.

Now I’m sharing them with you: 20 questions you can pick and choose from to ask yourself about any luxury purchase. Not to define whether something is luxury, but to answer whether it’s worth your money.

I don’t expect anyone—not even me, and I wrote these—to remember 20 questions. But you could pick one or two that resonate with you and remind yourself of them before the next time you walk into a luxury boutique.

I’ve ordered these, more or less, from less awkward to more so. If you get to the last few and find that applying them to your most recent purchases makes you even a bit uncomfortable, then consider that a useful data point.

These questions may sound judgmental. I don’t mean them to be. Honestly, I can point to at least half the questions on this list and think back to purchases I’ve made in the past that I might have skipped had I asked them of myself at the time. I’m the last person to be judging anyone else’s buying habits. This process—asking yourself one or more of these questions and answering honestly—is private to you. No judgment.

Question 1. How long do you expect this item to last? If it doesn’t last that long, will you regret your purchase?

Question 2. Do you know what this item costs in other countries? If not, do you not care? If so, and if it’s significantly cheaper elsewhere, are you comfortable with that?

Question 3. If the company were to disappear tomorrow, would that change how you value the item? How important is the brand to your enjoyment of the item?

Question 4. Can you describe exactly what the company’s exchange and return policies are? If not, do you care?

Question 5. If the item were to break or malfunction in some way, and the company refused to help, how would you feel? Angry? Foolish? Unlucky?

Question 6. If you’re paying in part for heritage, can you describe that heritage? Can you explain to yourself how that heritage makes the item better in some way?

Question 7. If the item were to fall out of fashion next year, how would that make you feel about your purchase? Do you think that’s a distinct possibility?

Question 8. If someone you know copied your look for a tenth of what you paid, would that change how you feel about your purchase? Why?

Question 9. If an expert disassembled or even dissected the item, what would you be afraid they would find? Do you care about what’s under the hood?

Question 10. Would you feel comfortable telling a friend what you paid for the item? If not, why?

Question 11. If you couldn’t post about, mention to friends, or even be seen with the item, would you still buy it? How much is social approval worth to you?

Question 12. Could you justify the item’s price premium to a skeptical friend in three sentences or less? If not, could you justify it to yourself?

Question 13. Can the company tell you how the item was made sustainably? If so, do you believe them? If not, do you care?

Question 14. Do you believe you’ll still be using the item in five years? If not, are you comfortable with that?

Question 15. What is the single best thing you can say about the item? Are you willing to say that out loud? To a friend? If not, why?

Question 16. Are you buying the item to enjoy it, or to quiet an insecurity? Be honest with yourself.

Question 17. If you were to learn that the item was made using labor that was legal but less than uplifting, would you regret purchasing it? What value do you place on social good?

Question 18. If you were to learn that the item was made using products from animals treated legally but less than ideally, would you regret purchasing it? What value do you place on animal welfare?

Question 19. Would you recommend the item to the friend you respect most in the world? If not, why? What’s holding you back?

Question 20. If the item didn’t have a logo, would you still want it? How much of a discount would you expect? What are you really paying for?

I can’t reiterate this enough: these questions aren’t a moral judgment. If I’ve done my job well, they’re a tool to help ensure you’re as happy with your purchases a month or a year down the road as you are the moment you walk out of a boutique—nothing more.

Also, not every purchase needs to meet some set of criteria. Sometimes a purchase is just emotionally satisfying, and that’s okay.

In college, I took a class during which we did an exercise around decision-making. Each student picked a decision they had to make and then listed out the advantages and disadvantages of each option before considering the decision. It may sound simple, and it was, but it was a useful thing to learn at an early age.

After we had finished the exercise, though, the instructor told us a story. He had a friend who had always wanted to own a Porsche and had finally reached a point in life at which he could afford one. He wanted to be rational, so to be sure he was making the right decision, he went through an exercise like ours, listing the pros and cons of buying a Porsche versus a different make of car. By the end of the exercise, the other make had won out, and so he went out and bought that car. I still remember what the instructor said:

So with that in mind, I hope you’ll remember two or three questions from this list and try them before your next purchase. But I also hope you’ll remember that you’re the best judge of what’s going to make you happy—not anyone else, and certainly not me. I hope you don’t use this list to talk yourself out of joy you can afford and genuinely want.

If you’re going to pick one question from above to keep in mind in the future, which one is it, and why?

If you ask yourself one or more of these questions about a past or future purchase, and are willing to share, how did it go?