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    How long would you say one has to stay in a "real job" to gain the necessary experience?

Once you have gotten to the point where you are feeling stagnant, bored, or burnt out, it's about time to start looking to move on. You can't learn if you are feeling those things and without learning, reflecting, and growing, then there is nothing more to gain. However, the transition period can be a long one. Whether you are finding a new job or finding the confidence to do your own thing, it may take a lot longer and be a lot tougher than you would imagine. Luckily, this process is also something that can teach you a lot and change your perspective on things.