By no stretch of imagination do I fit the description of living big. I have friends who do, and I somewhat envy them not for their ability to live big but their psychological make up that grant them the inner security to do so.
I am not timid with big ticket investments. Even if they were proven to be bad bets eventually, I had no emotional hang ups about it. But ironically I am with small ticket expenses.
Timidity breeds contempt.
The issue isn't about the amount of money spent per se (though it's always a trigger). It's about having spent without the conviction for a worthy outcome. The pain of parting with the money was never overtook by the joy of experiencing the product. Spendings are taken as bitter pills to swallow, the only way forward is to minimize it.
This posture has ironically ensured that the immediate people around me are never financially desprate. It's an excellent survival policy for war time; it's socially awkward in boom time.
Frugality is a feminine quality.
This is sometimes entirely a matter of will, choosing to focus on the pain or extracting more joy than what was paid for.
The countermeasure is about believing with full conviction that out of thousands of other ways to that the money could be spent, the choice we made is the one that gives us the best return of them all. It may come natural to many (mostly when they don't think about it) but for a rationalist, faith is not a matter free will, you believe it or you don't.
Side note: The larger the spending, the more conviction needs to follow. This is probably how most people deal with such reverse logic. The more expensive something is, the more they have a need to convince themselves they made the right decision, they more they want to reinforce that with social validation. "No the breakdown doesn't matter, this is a Beemer, it's great. Look at my Beemer."
Expanding the material scope
There's another cheat to living big I can choose if I want to: by expanding the scope of 'big' beyond materials.
For that we revisit what it truly means to live-big. It may sound like having yatch-parties, but the heavier and less enjoyable version of the same question is whether you have wasted your life.
'Big' can measured by materials, achievements or experiences. There are no wrong choices, only fulfilling and unfulfilling ones.
People often expressed the regret of not having travelled more, experienced more as an expression of living big. But that only comes from the failure of imagination for being a consumer.
Side note: I find people who are spiritually fulfilled by stuffs lucky, where having eaten good food gives them genuine meaning above simple pleasure. When it's a void that money can fill, the problem becomes a closed loop, life is solved.
Here's an alternative definition: living big is being the more intense version of your true self.
In my case the true self is described by Enneagram Type 5w4. Being that does not necessitate travelling more or owning more stuffs. It does mean acquiring insights, observe, create, maybe occasionally teach. Feel free to inject your own model of personality map that describes you.
Taken this way failure mode becomes clear. If you live a timid version of yourself, that's failure.
In that sense I'm still not sure if I'm living big, but with this each of us get a benchmark that's unique to us without being subjected the consumerist idea of living big.