Last year, I named a project 'Cydr' (read 'cite-r'). I loved the name. It was clever, short, and had a sexy startup vibe to boot.
It turned out to be a disaster of a name. You always had to spell it when chatting with people. And then, because the spelling was unintuitive, people had trouble remembering it--we got several emails asking "hey, what's the name of your thing again?" This doesn't include the 99% who didn't bother to ask.
Six months later, we moved to FastCitations.com. You could shout it across a room, and everyone who heard would know exactly what it was, how to find it, and have no trouble remembering it. When we switched, we got several notes complaining that Cydr was way cooler. It was. But it was a bad name.
People sometimes ask me what name I would give myself. Alexander, I say. Someone will say that I don't look like an Alexander, and perhaps I don't. I don't feel any innate connection with the name. Given the opportunity to rename myself, though, it's hard to resist Alexander's superb phonetics. Four syllables, a hard 'x' sound, and relative popularity make it impossible to mistake, even in loud environments, or when you mumble.
Unlike with websites, I think it's poor practice to rename yourself or your friends. A friend of the girl I'm dating decided that she would call me Lucas, because "Robert doesn't fit me". She could have picked a worse name--Lucas is actually quite good, with a hard consonant right in the middle, and an 's' at the end. (I still don't respond to it.)
Most of us do, however, frequently get a chance to pick a new name without consequence: when we select usernames. At MIT, you get to choose your email [email protected]. The automatic suggestions are things like [email protected], [email protected], [email protected], etc. Unfortunately, these are pretty bad in all the ways that cydr.io is bad, namely that you'll be stuck spelling them for the next four years. Although I ultimately chose [email protected], I think I'll register and use something like [email protected] for my day-to-day business. Completely unrelated to me, but easy to communicate and unambiguous, like Stripe.com or Square.com (two payment companies).
We're overly concerned with names that have some deep connection or meaning toward our lives. Put through the grinder of frequent use, names become just another tag for an entity. Go ask someone whether they feel a spiritual connection to their name when they're halfway through spelling it at a party for the umpteenth time.