What Happens If You Over-engineer Your Life?
Tim Ferriss agrees 100% that if you over-engineer your life, you are almost definitionally less receptive to life that emerges. There is no magic answer for leaving room for serendipity that you apply every day in an ongoing way, at least not for him.
You can have periods of heavily engineered focus, and you can have periods of reasonably engineered serendipity. In a serendipity period, he places things in his calendar that are likely to produce chance encounters. His approach embraces the belief that engineered focus and engineered serendipity are not mutually exclusive. One example is that he may very deliberately try to interview people who completely disagree with him and have totally different sets of opinions. Interview, in that use, just means talking to people.