I’m now a Conditional Breakpoint. It’s been a dream of mine for long time, and it finally happened at CocoaConf Chicago. There are folks who have played extensively with James Dempsey, and those are the Breakpoints. If you’ve only played occasionally (even once), you’re a Conditional Breakpoint.

Originally, I wasn’t comfortable being a full “Conditional.” I’m not much of a guitarist. I can play along reasonably if there’s someone to cover my mistakes, and a group probably sounds slightly better with me than without. But listening to me play alone is an act of love and friendship, not something you’d do on purpose. So I kind of wanted to be called a “Provisional Breakpoint” instead. But that was wrong. Someone who’s played at a Breakpoint Jam is a Conditional Breakpoint. That’s what it means. If you’ve done it, you’ve earned it.

Everyone who played guitar that night was a Conditional, but Ellen Shapiro was clearly our leader. She plays with an energy and style that I want to emulate. She’s much better than I am, but what I’ve played in years, she’s played in decades, so maybe that’s natural. Choosing the right people to copy is a worthwhile skill in itself. There’s nothing wrong with being a beginner. There’s nothing wrong with learning and flailing and trying again. There’s nothing wrong with letting someone mentor you. And there are a lot of ways to mentor. You might not even know when you’re doing it.

When I first asked to play with the Breakpoints a few weeks ago, James said yes, and I immediately panicked a little on the inside, and I asked for the whole setlist so I could practice. And he said sure and sent them. But then he said, you know, it’s fine to just play some of the songs, or even drop out of parts if you’re not up for it. It’s better to have a few songs you’re good at than a bunch you stumble through. And I said yeah, yeah, yeah, I know that. I’m cool. And I did kind of know. But not really. I’d been planning to practice them all and just beat myself up a lot everywhere I stumbled. I needed someone who knows more than me to give me permission to be a beginner, but still let me play. Sometimes you’ll never know the impact of a small kindness.

After the show, Eric Knapp asked me a very useful question. “So, that was your dream, and now you’ve done it. What’s your next dream?” It’s easy to lose your direction when you get to a destination. If you want to keep growing, your goals have to grow with you. My next goal is to be good enough that I can play alone and you’d rather stay than leave, even if you’re not my friend. It’s what I call “a mediocre guitarist.” Eric thought it was a good goal, but suggested a more concrete one: Play one song at an open mic night. And he passed on some wisdom he’d received and I needed. “Don’t wait until you’re ready. Go play before you’re ready. There are lessons you can only learn by doing.” Eric has forgotten more about playing than I know (and I don’t believe I’m exaggerating). It’s good advice.

I talk a bit about learning guitar and make a bit of noise about being a beginner. Some of that is because I love to tell stories, and I hope my stories can help other people. But of course saying “I’m a beginner” lowers expectations and overdone is a cheap way of getting praise. It’s a dangerous thing to make too big a deal about. For all my “I’m a beginner and I’m scared,” Laura Savino has been playing guitar for less time than I have, and this wasn’t her first Breakpoint Jam. So sometimes the brave ones don’t make as much noise. You have to look or you’ll never notice.

I may just have been lucky so far, but I’ve found the guitar community to be incredibly welcoming. James isn’t alone in inviting beginners to play, but the Breakpoints has a special history of it. Except for Ellen, the rest of us (Laura, myself, and Josh Smith) all made our first public performances at Breakpoint Jams. Creating that kind of opportunity is a gift and how you create and sustain a community. If we all “only hire the best,” where do you think the next generation will grow? Thankfully, James is willing to play with folks who are just trying their best. Are we as willing to develop software the same way?

There are senior developers and there are junior developers, and there are developers in between. Different people have different experience and skill. You might be a senior developer in one language or platform or style, and just learning another. But there’s no point talking about “real” developers. If you write software and it runs, you’re a real developer. That’s what it means. You develop software. If you’ve done it, you’ve earned it.

And if you develop software in Cocoa, then you really want to listen to Backtrace. Hope to see you at the next show to benefit App Camp For Girls!