[hennell]

As a largely solo dev I found I can't estimate well unless it's a common task, and it's easy to find tasks grow exponentially if it touches too many layers.

Asking "how long do you want me to spend on this?" got better results, because I got more idea how important tasks were to the business and can usually tell if something is going to take longer than they want. (Or know when we need to discuss scoping it back, or just abandoning the feature)

[zipy124]

It also helps because software is one of the rare engineering fields where code is non-destrictive and can be changed after the fact.

The carpenters trick of measure many times, cut once, can instead just be cut and re-size if wrong size, which can often be quicker.

Asking how long they want me to spend on it also let's me know how solid it needs to be engineered. Is it something that needs doing right then first time, or do we just want something rough that we can refine later with feedback.

[awesome_dude]

I think that that's how you solve the estimate problem - by having an understanding of how many layers it's going to touch, and how big of a change it's going to be for each layer.