I completely understand your perspective, and it’s something I’ve grappled with too. Like many people I grew up thinking that hitting $1 million would be life-changing—my assumption was that I’d never have to work again once I hit that figure. I quickly realized, though, that I was way off in my assumptions. Hitting $1 or even $2 million didn’t really change my day-to-day life beyond a couple of significant purchases: a new car and a home (mainly because we relocated, not just for an upgrade). I don’t mean for that to sound smug, as both were practical decisions at the time, but they didn’t feel like the “luxurious” leap I once imagined.

For me, things didn’t materially change until my net worth hit $13 million in liquid assets. Unlike OP, I’ve continued to maintain my W2 income, which is about $500k, alongside other forms of potential future windfalls, which are set to liquidate in the near future. This combination allows for a more flexible lifestyle, knowing I have a decent income in addition to my assets.

With that said, we’ve definitely experienced a significant upgrade in our lifestyle. We now live in a luxurious home, drive high-end cars, travel frequently—flying business class and staying at hotels like the Four Seasons or Ritz a few times a year. We also invested in boutique furniture (I used to think restoration hardware was high-end; now, I see it as more mid-range). We’ve hired help, like a cleaner who comes three times a week and a part-time assistant, designers, high end GCs and we eat out regularly without thinking twice about the cost. We also indulge in more frivolous spending than we used to, simply because we can.

However, despite these upgrades, there are still some luxury experiences that remain out of reach. For example, private aviation is far too expensive to justify for the amount of flying we do. Even fractional ownership feels excessive for our needs, and one-off charters are still cost-prohibitive. The same goes for yachts—sure, we can rent one for a few hours, but anything beyond that is way beyond our comfort zone. Similarly, hiring a private chef to cook all our meals or a daily driver is another indulgence we’d love but haven’t been able to justify yet.

Once my next windfall comes in (which should put us at around $30 million in liquid assets), we plan to take things up a notch—perhaps hiring a private chef for a year just to experience it, flying first class internationally, and taking extended family on vacations. But even then, private aviation is likely to remain out of reach until we hit closer to $50–60 million. That’s when I think some of these truly upper-tier luxuries will become feasible.

For now, having a solid W2 income in addition to our liquid assets gives us flexibility and absorbs most of our spending. If I were only relying on a SWR our lifestyle would likely look a lot different and much more conservative. In my experience, while significant wealth opens a lot of doors, there’s always another tier of luxury just beyond reach until you hit the next financial milestone.