The Long, Hard, Stupid Way
Katelyn Lesse on why you can't avoid the hard part if you're building a brand new product or feature:
So you have to ask: can we avoid the hard part and still succeed? If the answer is yes, then by all means avoid it. But if the answer is no, then the incremental path isn't actually safe. You're just delaying the inevitable failure.There's another option where you attack the particularly hard part head on, likely requiring you to take some big, risky swing. One of my favorite problem solving approaches is to hold 1 thing constant and assess the rest. In this case - assume you take the big, risky swing and it actually works. Is the rest of the plan solid such that the overall project is likely successful? If the answer is yes, and if you really want to tackle this project and succeed, you should take the big swing.
It reminds me of this great David Chang line from his cameo in Treme:
Just because we’re a casual restaurant, doesn’t mean we don’t hold ourselves to fine dining standards. We try to do things the right way. That usually means doing things the long, hard, stupid way.
And Frank Chimero, reflecting on Chang's comment:
I think that, from the perspective of someone who makes things — and I bet that a lot of people out there are also folks who make things in some capacity — when you work the long, hard, stupid way, it looks a lot like toiling and worrying and starting over and scratching good ideas to look for better ones. It’s staying up late; it’s waking up early; it’s all of those sort of romanticized things. All of those actions are inspired by just caring a lot. That’s not to say that you can’t be efficient and care about your work: I think that’s totally possible. But I don’t know how to do that, because I have to do things the long, hard, stupid way.
Returning to Katelyn Lesse:
If you want to be a team that takes the big, risky swing, 2 things have to be true.First, you need people who can get really fired up about the challenge. You don't need consensus, and you definitely don't need everyone to believe it will work. Most people will look at the hard part and assume it's impossible, and that's fine. You need the ones who see the most interesting challenge they've maybe ever gotten to tackle. Give those people the problem and let them take a lot of ownership over how to solve it.
Second, as a leader, you need to be willing to take accountability and cover the team to go after it. If it doesn't work out, it's on you, and there's a host of consequences that could come with that. Taking on this risk requires you to personally feel 2 things: first, you actually really want this project to be successful, and second, you actually believe this big, risky swing is necessary.
The line is shifting - some hard things are becoming easier than they used to be. If my team at Stripe was writing code with Claude Fable, we may not have found encapsulation to be so daunting. What's really happening is that AI is leaving all of us with the truly hardest parts. So really, the crux-y question hasn't changed: can you avoid the hard part and still succeed? If the answer is no, the safe path is just pushing your failure out. If you really want to succeed, you have to take the big swing.
The safe path is getting shorter.
What's left is the long, hard, stupid way.