To be successful today, it is important to make your mistakes early. The mantra is “Fail Fast, Fail Often”. However, that doesn’t guarantee success. It just guarantees you will fail a lot.
The key thing is that you learn from your mistakes. That’s implicit but not obvious. When you are down in the muck and bullets and trying to keep going, the natural inclination is to get your head down and push harder. You don’t naturally reach for the pipe and violin and reflect “Hmm, very interesting” whilst reeling off a bit of Mozart (think Sherlock Holmes).
To avoid repeating your mistakes you must build in a mechanism to reflect and learn. This could be a time set aside at the end of each week for this purpose, or a meeting with your team, or by writing in your journal. It’s often helpful to have someone else involved, a coach or mentor or other trusted advisor, to give a different perspective and make sure you are being honest with yourself. The learning is what’s valuable here (this is a core principle in Eric Reis’s book “The Lean Startup”), and it has to be part of your routine.
It’s good to fail but not if you keep failing at the same thing. You must aim to fail at something once, learn, change and never repeat. Fail often, but fail only once at each thing.