I keep blowing past my own estimates, and I'm trying to figure out if there's a way to get more accurate. Every time I think I've scoped something out, the actual work takes way longer than I planned. What's helped you close the gap between what you think something will take and how long it really ends up being?

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First, it is nearly impossible to accurately predict the schedule for making any software beyond a certain complexity. Anyone who says differently is trying to sell you something they have made before or they are selling you project management software. A few ideas will help as you navigate: 1) Most time is spent on getting people to agree and communicate 2) Many tasks that get done by others get forgotten or underestimated. Identify the chain of work and the natural loops that emerge. 3) Your stakeholders may have a different definition of done than you. This can cause people to get frustrated when they get a different timing or quality than they expected.

The best approximation the industry has for the impossible estimation problem is to iterate and collect feedback model embodied in the agile approach to software. Look at the agile manifesto in its pure form, stripping away any work/people management layers like scrum and kanban to get an idea of what teams working together to ship working software looks like.

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Have to audit why you keep going over on estimates. Sounds like you're not estimating properly or taking some variables into account? Are the story ACs clearly defined? Do your stories have constant scope creep? Should be pretty clear why you're always underestimating.

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