What an interesting day.

It started off with a long conversation with my boss about work related issues. The only thing to say about that is that for some reason the more I want to impress someone the stupider I seem to sound. When I talk to my brother, for example, I am clear and deliberate and speak with a kind of verbal alacrity that I seem to totally lose when I’m talking to someone I’m trying hard to impress. I much rather have it been the other way around, but, what are you going to do…

I left work a bit early to head out to Philly for this month’s Ruby meetup. The group, formerly known as Philly on Rails and now known as Philly.rb (due to interests in frameworks other than Rails), meets twice a month: a pub night, where people sit around, drink beer, and talk about geeky things, and an instructional meeting, where people get together in a classroom environment and talk about more geeky things. Today was the first instructional meeting I’ve attended.

Getting there was a bit of an adventure. Due to today’s nasty weather in the Northeast, traffic was slow as hell. The drive to Philly took about three times as long as it should have normally taken. Stop and go, stop and go, stop and go all the way. Then, when I get there, I have to deal with city driving, which I’m not terribly fond of. Somehow whenever my Garmin says “Turn left in 200 feet” I always either turn too early or too late. After several wrong turns and angry honking horns later, I found my way to my destination… almost. I found a parking spot, walked another 15 minutes to the address I had written down and wouldnt you know it: it wasn’t the right address. Great. I walked back to my car, paid my parking ticket and attempted to leave the garrage, but putting the ticket stub in my wallet reset it so that when I finally got to the gate and attempted to exit, the ticket reader machine rejected me. I had to politely ask the six people behind me to back up so I could go back and talk to someone. I got that taken care of and made my way to the right address, and finally, after a long adventure, I found it.

I arrived at about 7:40. I had planned on getting there at 6 when it started. There were about 15 guys gathered in a dimly lit basement classroom at the college building where the meeting was being held. I quietly walked in as a guy was finishing a presentation about iPhone development. I didn’t understand most of what he was saying, but got the impression that iPhone development is a complicated beast.

When he finished the organizer — Colin — asked if anyone else was interested in talking. I had previously mentioned to him demoing Domain Pigeon. I thought it was very tactful of him to ask if anyone was interested even though he knew I was there and I had mentioned demoing. He could have called me out, but did the polite thing for me and the other guy who mentioned talking and just asked if anyone else was interested.

I said sure, he said something like “Oh yeah, you wanted to demo your domain site.” I got up, hooked up my Macbook, and started talking. I had a rough idea beforehand of what I wanted to say but mostly winged it.

On a scale of 1 to 5 I’d say I was about a 3. Not bad, but not great either. I noticed myself saying “uh” a bit too much and I hunched over the podium more than I should have. I added unnecessary details to my explanations and omitted important things. There was a general flow of the demo, but I should have practiced a bit more beforehand. After a few minutes of heightened self-awareness I loosened up and things were good, but I feel like I’ve got a ways to go in this area. My philosophy on things like this is that you have to do something and suck at it for a while before you can become proficient and eventually good. Some people may be able to jump directly to good by sheer talent, but for me at least with this, I have to do it for a while, however poorly, before I pick it up. It’s kind of frustrating to know you’re doing something poorly but lack the knowledge or skills to do better, but I’m happy that I at least realize it and know that it’s part of my process. It’s similar with web page design. ALL IN Expert was probably a 2 on the 1 – 5 scale. Domain Pigeon will probably be about a 3.5 or 4. Without taking these steps I won’t be able to get to the 5 one day, whatever that may be.

The feedback was generally positive. They asked some very good insightful questions about how it would work and gave me some helpful feedback on a few usability, coding, and design issues.

The two meetings I’ve been to have been very humbling. While I consider myself a pretty good programmer, these guys having an amazing amount of technical knowledge. Most of them talk way over my head when it comes to the intricacies of a programming language and how one languages compares to another and what not. I recall some of the terminology from my computer science education, but have forgotten a lot of it. It made me realize I care more about what I can do with the language than how it works. There are pros and cons to that but overall I’m happy with my bent towards practical vs theoretical considerations.

Afterwards, I got into a conversation with a guy named Eric. Eric’s a 50 year old serial entrepreneur who now specializes in buying and selling small businesses. He’s got a strong technical background, but doesn’t limit his work solely to that area. I started picking his brain and when it was clear that we enjoyed the conversation we decided to walk over to a nearby Starbucks and continue it over some coffee.

It was quite the discussion. We wound up talking about the significance of leverage and its current role in the economy, using neural networks for speech recognition, the philosophy of science, the long term value of an MBA, mobile phone startups ideas, the ideal size for a tech startup, differences in business structures, personal guarantees, the importance of passion for your job, equity considerations when raising capital, and the risks of getting married in your early 20s, among other things. We talked for over an hour and I walked away feeling that the night was well spent despite all the earlier difficulties.

And now I must sleep, as I have to get up in 4 hours… =)