When we make something new, people often ask "why don't you just add that to Basecamp?" There are a number of reasons, depending on what it is. But, broadly, making something brand new gives you latitude (and attitude) to explore new tech and design approaches. It's the opposite of grafting something on to a heavier, larger system that already exists. The gravity of existing decisions in current systems requires so much energy to reach escape velocity that you tend to conform rather than explore. Essentially you're bent back to where you started, rather than arcing out towards a new horizon. New can be wrong, but it's always interesting. And that in itself is worth it. Because in the end, even if the whole new thing doesn't work out, individual elements, explorations, and executions discovered along the way can make their way back into other things you're already doing. Or something else new down the road. These bits would have been undiscovered had you never set out for new territory in the first place. Ultimately, a big part of making something new is simply thinking something new. -Jason

Whenever I talk about working in real-time, making decisions as you go, figuring things out now rather than before, I get a question like this... "If you don't have a backlog, or deep sets of prioritized, ranked items, how do you decide what to do next?" My answer:  The same way you do when your made your list. You make decisions. We just make decisions about what to work on next as we go, looking forward, rather than making decisions as we went, looking backwards. Why work from what /seemed/ like a good idea before? Instead, work from appears to be a good idea now. You have more information now — why not use it? It's always baffled me how people who pluck work from long lists of past decisions think you can't make those same kinds of decisions now instead. It's all yay/nay decisions. Same process. Before wasn't magical. Before was just now, then. Why not look at now, now? Now is a far more accurate version of next. The backlog way is based on what you thought then. The non-backlog way is based on what you think now. I'll take now. One's stale, one's fresh. We'll take fresh. Then is further, now is closer. There's nothing special about having made decisions already. They aren't better, they aren't more accurate, they aren't more substantial just because they've been made. What they are, however, is older and often outdated. If you've got to believe in something, I'd suggest putting more faith in now. -Jason

One of the great lessons of nature: Randomness is the most beautiful thing. Every forest, every field, every place untouched by humans is full of randomness. Nothing lines up, a million different shapes, sprouting seeds burst where the winds — or birds — randomly drop them. Stones strewn by water, ice, gravity, and wind, all acting on their own in their own ways. Things that just stop and stay. Until they move somehow, another day. The way the light falls, the dapples that hit the dirt. The shades of shades of shades of green and gold that work no matter what's behind it. The way the wind carries whatever's light enough for liftoff. The negative space between the leaves. Colliding clouds. The random wave that catches light from the predictable sun. The water's surface like a shuffled blanket. Collect the undergrowth in your hand. Lift it up. Drop it on the ground. It's always beautiful. However it comes together, or however it stays apart, you never look at it and say that doesn't line up or those colors don't work or there's simply too much stuff or I don't know where to look. Nature's out of line. Just right. You too. -Jason

In the end, judgment comes first. And that means hiring is a gut decision. As much science as people want to try to pour into the hiring process, art always floats to the top. This is especially true when hiring at the executive level. The people who make the final calls — the ones who are judged on outcome, not effort — are ultimately hired based on experience and judgement. Two traits that are qualities, not quantities. They are tasked with setting direction, evaluating situations, and making decisions with limited information. All day long they are making judgment calls. That's what you hire them to do, and that's how you decide who to hire. Presented with a few finalists, you decide who you *think* will do a better job when they have to *think* about what to do in uncertain situations. This is where their experience and judgment come in. It's the only thing they have that separates them from someone else. Embrace the situation. You don't know, they don't know, everyone's guessing, some guess better than others. You can't measure how well someone's going to guess next time, you can only make assumptions based on other assumptions. Certainty is a mirage. In the art of people, everything is subjective. In the end, it's not about qualifications — it's about who you trust to make the right call when it matters most. Ultimately, the only thing that was objective was your decision. The reasons were not. -Jason