Danny woke up slowly. He didn’t remember falling asleep.

The bed was soft but short–his feet hung off the end. He did remember knocking on a drawbridge to a tiny castle.

I’ve found a lot of people who know are experts in their fields and have a certain level of charisma, but then when they move into a leadership position, it’s apparent that it’s not their strong suit.

These cycles gain momentum like freight trains over time, and eventually they seem unstoppable. But things were good once before they went bad. And many thing which were once bad are now good. From the leadership side; what advice would you give for turning a vicious cycle virtuous, and for preventing a good thing from turning bad?

– A Serious Dan

Brother, to be honest, I didn’t expect you to follow through and write me a public letter to discuss leadership principles across bartending and software. But I’m glad you did.

Brother, one of the patterns I’ve noticed in industry is the tendency to job hop when troubles arise. This isn’t just in software. Feelings are hurt once so people move on to a new friend group. Marriages are hard, so they divorce and try to find the next The One. Staying power seems to be lacking.

The other side of it is the “stay and fix it no matter what” attidude, but that can lead to stagnation in a horrible situation. At some point it can turn into a “stay because it’s familiar” instead of injecting positive change.

What’s the tipping point between making where you are a better place vs leaving a bad situation? Are there obvious signs that it’s time to move on, or should there be a timebox on affecting change in a situation? When is it premature to move on?

It’s been too long since I wrote last. I finally got a habbit formed that I really enjoyed (writing on the bus) but destroyed it by getting a Prius. I really enjoy my ‘08 Prius, don’t get me wrong, it’s very comfy and fuel efficient. There are a few things that bother me, but the benefits definitely outweigh them. With regard to writing, it’s removed the need to take the bus, and I don’t think I could do this in audio form–