These things all come out of talking. Always be networking.

Agreeing with amro. Keep a busy schedule, and get out of the house as much as possible. Have an 'elevator speech' ready and use it as naturally as possible wherever it happens to make sense. Volunteer - especially if you can volunteer by using the talents and skills you have developed in your working life. Ask people about what's going on in their working lives - people know things from inside that they may never think to connect you with - unless you ask!

Definitely chitchatting. I also try to follow my instincts, which is how I wound up at Rita's last year.
I randomly swung through to get a green apple gelati and started chatting with the owner about how my roommate and I used to think there were plastic pieces in the cherry ice (they are actually real cherry pieces!) and I asked him about how long the store was going to be open and he said he was looking for daytime help. Just so happens--I needed a job. I wound up working my first shift on free ice day.

To get my current gig, I let my mouth run ahead of me when I asked about taking a ride on the forklift. No one else they had interviewed had asked that (and most people were scared to even get near the forklifts).

Happy hours!

1. Everything upthread. Like Alec Baldwin says, "Always Be Closing."

2. Surround yourself with the people you respect first. The only way you'll find that Amazing Job is to make sure the people doing Those Amazing Jobs know about you. Go meet them - bonus points if they're your friends.

3. Volunteer like mad - get a rep around town for being "the guy/girl everyone sees everywhere." Sooner or later, you'll start being thought of for stuff when you're not even around to participate.

4. If none of the above work, at least you're living your values, your network = all people who know and care about you, and it will be a far more pleasant way to deal with our current psychostressful economy.

4a. Make sure you volunteer doing something meaningful that benefits others directly. Don't turn yourself into a worm.

These things all come out of talking. Always be networking.

What does this mean? There's some sort of connect I'm not getting or not making. It's like hearing "oh you just paddle" but come to find out, year later, you use an oar, not your hands.

The point is that you can't make serendipity happen, but you can increase the chances of serendipity happening to you by being in more places, by knowing more people (or, to be more precise, having more people know you), and by talking more. The others in this thread have given some good practical ways to make these things happen.

More generally, the thing that both of your stories of serendipity have in common is that someone spoke casually about what was going on with them. Personally, I'm particularly bad at this -- my brain's default stance is to not 'talk to strangers', and to be worried about seeming self-centred if I ever dared to talk about me and my life. The key, I think, is to try break that default position (assuming it applies to you) and just be a bit chatty in everyday situations. I think most people appreciate a bit of conversation. And, as long as you don't turn every chance encounter into a rambling life-story thing, most people also appreciate being let into someone's life a bit, and that bit of information sharing can evidently open doors.

After being unemployed in Seattle for 2 months, I finally got a job offer in NYC which I immediately accepted. My friend picked me at at the Seattle airport, and asked if I didn't mind coming with her while she went for a job interview before driving me home. While she was being interviewed, I stayed in the lobby and started chatting to a gentleman I met in the hallway. It was a great talk. That night, my phone rang. It was the man I had been talking to in the hallway. I was shocked. He was the president and founder of the company. He had looked up my name in the phone book and called me at home and offered me a job - higher ranking than what my friend was going for and definitely higher paying. She didn't get the job. After discussing it with her, she wished me good luck and told me not to worry about her feelings. It was one of the strangest moments of my life. I stayed at the company for three years and it changed my life. The president of the company became a great mentor and we are still very good friends to this day.