It's not so clear to me that you don't deserve your life as that others less fortunate don't deserve theirs. Scarcity will always result in unfairness, even if scarce things are raffled off. The winners of the lottery don't deserve to win the lottery. The system is fair, but the outcome is not just.
The goal, then, should be to reduce scarcity and to create as much bidding power as possible for as many people as possible. That does not necessarily require confiscatory taxation. It starts with money-printing commensurate with technologically driven growth in potential outputs.
Some of the printed money can be used to create human capital that will enable more people to compete for goods and services. But those born talented will always have an advantage unless we adopt a Harrison Bergeron handicapping regime. Progressives are paying too much attention to reducing the grand prize and not enough to improving the participation trophy.