At some point, the question changes.
It stops being "can I afford this?" and becomes something harder to answer: "is this actually worth it?" You can afford business class. The help. The membership, the better hotel, the second home. What you're really asking is whether any of it returns what it costs. Not in dollars. In how you live.
No one teaches you how to think about this. Financial advice is designed for accumulation, not deployment. It will tell you to max out your 401(k) before you upgrade your flight. It won't help you decide whether the flight upgrade makes your life materially better, or whether you're spending because you can.
I think about lifestyle upgrades the way I think about wealth: as infrastructure, not reward.
The three questions
Before any significant upgrade, I ask:
Does it buy back time?
Time is the only resource you cannot earn more of. If an upgrade returns hours to your week, real hours, not theoretical ones, it's worth considering. A housekeeper is six hours you don't spend cleaning. A driver in a city where you'd otherwise circle for parking is calls you can take, emails you can clear, or simply stillness.
The calculation: what is an hour of your time actually worth? Not your billing rate. Your lived experience of an hour. If the upgrade costs less than the time it returns, it's not an expense. It's arbitrage.
Does it remove friction you've stopped noticing?
Some friction is obvious. Most isn't. The gym you never go to because it's twenty minutes away. The vacation rental that requires you to project-manage every detail. The financial advisor you avoid calling because the conversations are tedious. These aren't minor annoyances. They're taxes on your life, compounding quietly.
Friction removal often pays for itself in ways that don't appear on a spreadsheet. The boutique gym three blocks away that you
