Start by being awful. No, don't purposefully be terrible at what you do. Instead don't try and mask where or who you are. Example: bands using auto-tune. Is there any bigger turn off to musicians and listeners that long for authenticity?
The reason why is so that a foundation can be built. The only way that the foundation can be built is by being honest with yourself. Any beginning has to start with an assessment and acknowledgement of the starting point. If not, no progress can occur.
Does it really matter that much?
Yes. Yes, it matters that much because over time, what's real will show - illusions can only stay illusions for so long. That is what's called a correction in the marketplace, a tragedy in engineering when a building or bridge collapse after years of neglect, a break-down in Hollywood, or a scandal in politics. The truth may be arrive late, but it always shows up.
Put in the time and the effort, but don't wear a mask because there are two, maybe three paths:
Path 1) Each step leads to gradual improvements until a positive critical mass is reached. This is the case of the genius that was told he was a failure for years, until the sudden (10 to 20 year) breakthrough.
Path 2) Each step leads to gradual unraveling until a negative critical mass is reached. This is often the case of the fraud that is finally exposed.
It's okay to be bad, as long as you don't stay there. Societies are societies to allow newcomers to introduce themselves and their beginnings to the world. Naturally, there are going to be false starts (hypothesis testing), set-backs (limit stretching), and what seems like directionless wonderings (exploring).
That's all part of the journey.
By the way:
Path 3) Apathy. And, well, that's no fun.