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My first thought when I read the question was "my biggest obstacle to what exactly?". It's a good question but to answer it i'd first need to know what I wanted to do. I don't have a life plan. I got to where I am now without a plan, I admire people who have a life plan. I know quite a few of them and they say things like "I'm going backpacking around Asia for a few years, then I'm going to work in finance and live in Zurich". I even knew one guy who had his life planned out when he was 18, step 1 involved joining the army, I didn't ask what step 2 was. That's not me, I don't have life plans, I don't have a goal, I don't have obstacles.