If one has failed in material life, will they succeed in spiritual enlightenment?

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Can they? Sure. Will they? The odds say no. In short, nothing about failing materially makes one any better at spirtuality.

In fact, and this is the only reason I decided to answer this, the enlightened are more likely to find material success. There’s a very large cross-section of people out there who enjoy spiritual lifestyles and struggle to translate that to material success. What this kind of person struggles with isn’t really material existence though, they’re still struggling to get on top of their spiritual game. Once you’re on top of that, material success comes quite swiftly after. I know how that works because it happened to me.

Look, I’m not talking about the fabulously rich, impossibly vain people of the world. These people are rich because they were born into riches, anybody you see who is a rags-to-riches story often has religion at their side or is otherwise really spiritually gifted. An example of the religious story is John D. Rockefeller, and an example of a spiritually gifted person is Steve Jobs, who had a fire lit under his butt after he returned from a sabbatical in India where by all accounts he did lots of spiritual exploration, not to mention copious amounts of drugs. I won’t speak very much on the connection of drugs to spirituality here except to say that if you manage to succeed after you’ve done tons of drugs, very few things other than extremely proficient spirituality can succeed in turning that around.

No, that’s all kind of a tangent to the point I really want to make. If you consider yourself a spiritual person, and struggle with your material existence, I want you to think very hard about the prospect that this world is a test for your spiritual abilities and to consider making more leaps of faith, expecting Spirit to sort you out. Willingness to take leaps of faith is really what separates the weakly and strongly spiritual.

Another thing to consider in your life is, addiction, mental illness and personality disorder. If you need a hand up in the world, it’s more spiritual to let the world help you rather than try to go it alone. The people with weird and un-dealt-with mental issues I’ve met, invariably they have ego issues or keeping them from fully taking any real leaps of faith. Everything they do is focused on preserving a very severe delusion of their own aggrandizement. They can’t really let anyone else help them and have to hit what alcoholics call ‘rock bottom’ before they can start digging themselves out, with the help of others. At this point a spiritual journey begins, but which only very rarely ends in enlightenment.