Here is an interesting comment from Hacker News, on a story about someone turning down an early Google offer:
Similar thing happened to me in 1999. I realized Google was way cooler than alta vista and better at finding unknown things rather than Yahoo's directory. Truly the future, I thought. I sent in a resume to do some kind of work not development related; data center & sys admin stuff. They called me twice but I convinced myself that they would not have hired me anyways so I never called back.
Whether or not ignoring Google's calls was the right decision for him, his reason for not taking the call (fear of rejection) isn't great.
I don't have many positive memories from high school, but the one that has stayed with me more than any other comes from the first day of my 11th grade English class. My teacher (I believe his name was "Mr. May") shared a brief anecdote from the prior evening. He was driving home in the rain, and noticed two people on bicycles along the side of the road. He stopped to ask if they needed any help, and ended up driving them back to his house, where they dried off and had dinner with him and his wife. During dinner, the couple shared the stories from their ongoing bike ride across the country.
It's not a very dramatic story, but I loved the serendipitous nature of it, both on the part of the couple having adventures biking across the country, and my teacher who saw people along the road and invited them into his home. None of it was planned -- they simply allowed it to happen. It was inspirational to me because it felt like the right way to live, the fun way to live. I don't think that's how most people operate though.
My own story of how I ended up at Google in 1999 is rather boring. I was interested both in startups, and Linux (which was still somewhat fringe at the time), so I sent my resume to a few companies that I had seen mentioned on Slashdot (a rather lazy job search, in hindsight). Fortunately, most of them never even responded, and only one actually offered me a job, Google. I was skeptical of their business and didn't expect it to last long, but it seemed like it could be fun and educational, so I accepted.
Obviously that's an example of rather extreme luck, but I've noticed that most of the good things that happen to me follow that general pattern, and aren't part of any "plan". The story of how I met my wife is remarkably similar. Shortly after moving to California, I signed up for match.com, read a bunch of profiles, emailed three of them, and only one responded. I was very much not looking for someone to marry, but that's what happened anyway. As they say, "Life is what happens to you while you're busy making other plans."
My plans rarely work (unless they are boringly simple), but serendipity has been good to me, so over time I've tried to make the most of that. My theory of serendipity is still evolving, but from what I've seen, it's better to think in terms of "allowing" serendipity rather than "seeking" it or "creating" it. Opportunity is all around us, but we have beliefs and habits that block it.
The two biggest blocks to serendipity seem to be ego-fear and "other plans".
I'm using the term "ego-fear" to describe fears that go beyond rational concern. For example, you wouldn't run out into the middle of a freeway thanks to a healthy fear of getting run over by a car -- that's not ego-fear. However, the fear that often keeps people from public speaking, talking to strangers, interviewing for jobs, etc is typically driven by fear of embarrassment, humiliation, rejection, criticism, etc -- that's ego-fear. Sometimes it can be difficult to separate the two types of fear because ego-fear will rationalize itself as healthy fear, e.g. "I don't want to talk to that stranger because they could attack me, or waste my time."
The HN commenter quoted above who never accepted Google's calls because, in his words, "they would not have hired me anyways", seems to be experiencing quite a bit of ego-fear, fear of rejection and humiliation. That fear is probably blocking a lot of great opportunities.
It's tempting to try and think your way out of ego-fear, but I suspect that only makes the problem worse by generating a more complex tangle of rationalizations for the fear. Fear is defeated by confrontation -- avoidance only makes it stronger.
"You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face. You must do the thing which you think you cannot do." - Eleanor Roosevelt
The program for eliminating ego-fear and unblocking serendipity is very simple: seek ego-fear. Hunt it down and soak in it. Steal its energy. This is, by definition, scary. That's good.
The other big serendipity block seems to be "the plan". Serendipity and luck are by their very nature unpredictable, and therefore not part of any good plan. When something unexpected happens, things are no longer "going according to plan", and there is a tendency to view the unexpected event either as a distraction, or as a frustrating obstacle to success.
The difference between a life full of frustrating obstacles, and a life full of serendipity, is largely a matter of interpretation. It can be difficult, but the most beneficial response to unexpected events is a sense of gratitude. Even seemingly adverse events can lead to something great. Accept what is given. (see Yes Man for a cute caricature of this mindset)
"Plans are worthless. Planning is essential." - Dwight D. Eisenhower
Planning in itself is not a bad thing, but picking a single plan and obsessively sticking to it doesn't allow for much serendipity. The world is very complicated, and we humans are very stupid, so it's good to be flexible and open minded about things. Instead of having one plan, have one thousand plans, and revise them as necessary.
The desire to have "a plan" can also cause "paralysis of analysis" -- we put all of our energy into formulating the perfect plan, and consequently never actually do anything. The more effective approach is to simply pick a plan with the knowledge that it's flawed, set the plan in action, and then adapt, revise, or switch plans as the world unfolds.
I suspect the desire to have a definite plan is also partially rooted in fear. Uncertainty can be scary, and having a plan helps create the illusion of predictability in a very unpredictable world. However, if we actually manage to reduce risk and unpredictability, then we are also reducing serendipity. This is one reason why large organizations often have trouble producing innovation -- they want it to be planned and scheduled, but that just kills it.
The whole notion that plans are something that we should "stick to" makes them distracting enough that I prefer to call them "ideas" or "rough sketches" instead. Personally, I try to avoid having plans for my life, but I have many ideas. Which ones actually happen will be a surprise to me. It's more fun that way.