Thought about this extensively. But I feel the imposter syndrome creep up every time I go this route. My mistake is that I spent too much of my career working

Thought about this extensively. But I feel the imposter syndrome creep up every time I go this route. My mistake is that I spent too much of my career working for tiny startups with 1 or 2 engineers, doing grunt work. I never got the chance to lead big projects and prepare myself to be competitive in that bracket. I have friends who are in that space, or higher (CTO, etc...). Although I hold my own with them in terms of technical knowledge, they all have backgrounds leading teams and working for big companies. I made a mistake in trying to chase the startup dream.