I got to attend an Apple shareholder meeting in 2000. I was a total fanboy and had bought a bit of stock in the late 90s with money I made doing Mac tech support. My mom suggested that it'd be fun and educational for the two of us to go to the annual shareholder meeting. It was the first time I went to the valley and in fact the first time I went anywhere in California. Visiting 1 Infinite Loop was literally a dream come true.

Jobs had returned to Apple a few years earlier. Apple's comeback was still in its early stages; they'd launched the iMac and the iBook, but there were no iPods or iPhones or iPads. They hadn't even shipped Mac OS X Public Beta. The tech bubble was bursting, and despite their recent successes, many pundits still considered Apple a niche player, if not "beleaguered."

The room for the shareholders meeting felt like a theater at a small liberal arts school: Cozy and a bit modern, with a low ceiling and a small stage not more than a foot or so off the ground. I don't think there were more than 100 people there.

Jobs was characteristically mesmerizing. Apple wasn't exactly killing it at the time, and many of the shareholders asked pointed and even adversarial questions. Apple's next-gen OS plans were unproven and they'd recently suffered some public embarrassments, like reducing the clockspeed on the latest round of PowerPCs. People were frustrated. What was remarkable was that even when Jobs dodged the question or told the shareholder something he didn't want to hear, he did it in a manner that left the shareholder feeling happy and satisfied. I've never seen anything else like it.

After the meeting was over, the Apple execs stuck around on stage, and people walked up to chat. I was a shy and awkward teenager, so I held back until I had the guts to approach Fred Anderson, who was CFO at the time. I don't know if I said anything beyond "Hi." Then I talked to Avie Tevanian, VP of Software Engineering. I remember asking him if OS X would ship with a terminal app. He said yes.^[1]

But I waited too long and there was a swarm of people around Jobs. I was nervous, and chose not to try to talk with him.

I have very few regrets in life, but that is one of them. I should have met Steve Jobs when I had the chance.^[2]

When opportunities present themselves, take them, even if it's uncomfortable.

1. It probably sounds odd that this is the question I chose to ask the guy in charge of Mac OS X, but it was actually a hotly contested topic at the time, at least in some circles. All the folks coming from NeXT were certain that OS X both should and would have a terminal app. The classic Mac OS guys were certain Apple would never do such a thing, since it would inevitably lead to software that relied on a command line (the thinking went something like: "can you imagine if tech support people told Mac users to type commands at a prompt to resolve their problems? It'd ruin the Mac's ease of use!") Like with so many things, the NeXT camp won. ↩
2. Luckily that's my only regret from the trip. I'm so glad I went, because my mother passed away just a few years later. ↩