One Million Words
Many times we see a thread on Twitter (or your favorite social network) from someone who has made a significant amount of money writing online or through a newsletter offering the perfect recipe for monetizing your blog. After all, the Newsletter industry seems to be blooming.
The problem with those step-by-step recipes is that even if you replicate most of their strategy, it's almost impossible to know what posts you write will resonate and do well and which will do poorly. From Taylor Pearson, who besides other things has been writing for more than a decade:
My honest, but not-really-helpful advice for people that ask me about starting a blog or newsletter is to first write one million words online and by the time you get there then you’ll know the answers to all those questions.
This applies to many other areas where randomness plays an important factor. Even The Lean Startup approach suffers from this blind spot: it's difficult to be certain what makes someone use your service or not.
Have a strategy to reduce randomness as much as possible, but don't spend time overanalyzing what's outside of your control. Decide early on what you should learn from others, and what can only be learned first-hand by trial and error.