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?