If you work in the creative industry and your job includes estimating how long your work will take, you’re likely to make mistakes. Things can take a lot longer than expected and sometimes even shorter.
What do you do when your estimation fails significantly?
You can wait for the last possible moment, exactly before the deadline, to reveal the problem you’ve found. (Because an obstacle can disappear as unexpectedly as it appeared.)
Or you can proactively share every bump you stumble upon: “This is the unexpected problem I’m facing today. It might mean nothing for my estimation, but it might double the time needed. I don’t know right now, but I’ll tell you more as soon as I know more.”
If you know that the first option is a lie, why do you keep repeating it?
And if you know that the second option would raise the bar, clearly show that you’re a professional, and improve your position among your coworkers and within your company, why not act this way always?