I feel like this is good advice but presents only one side of the coin. Underestimating how difficult something is, is exactly what leads to ''planning fallacy''. I would rather err on the side of caution and overestimate how difficult something is
The most important time to apply the advice from the article is after you have decided a project is worth your time and before you start planning in earnest.
The examples of difficult subject matter the author gives (particularly math) are so intimidating to some people that they miss out on a lot of great stuff because they conclude "I could never do that".
I don't think the author wants people to make poor time estimates and suffer budget overruns.
To me, the message of the article reads: "If you think something looks worthwhile but difficult, take a stab anyway. Often the hairiest, prickliest parts of the undertaking from an outsider's perspective aren't that tough at all once you're in the thick of it"
I 100% agree with you about how valuable conservatism is when you're planning, but I think the author's encouragement is intended for people who haven't even considered planning yet.
Thanks for stating it more clearly than I did! You've nailed it. It's always bothered me when people dismiss their ability to learn a thing, because they think some part will be difficult. They really have no idea. Yes, the task as a whole will have difficult parts, but we as individual human beings are far more capable than we give ourselves credit for.
My take-away was - never estimate confidently without knowing anything about the task. Because the initial assumptions might be very incorrect. Invest maybe 2-5% of the time to start doing something (ie begin learning Korean to realize that it's a phonetic language, and reading is easy within just 1 day). This will allow you to come up with the right estimate. Thoughts?
I have a framework of thinking about learning new things, which I sometimes call the 10-100-10k approach. I wrote about it year ago[0], and the responses helped me refine it.
I think the investing 10 hours in learning a new thing is more than enough to get the initial estimate you describe. Probably even 5 would be enough. That's 10 pomodoros. It's something I'm willing to consider to throw at totally random things to see if they are actually as hard as I think, and if I actually want to learn them.
Most people don't really spend even 15 minutes, to the clock, on things they think are hard to learn - and so underestimate just how much you can progress with as little as few hours, if you actually sit down and do it.
In my experience it's usually not as tricky as predicted, but requires more boilerplate, cleaning and communication with other people, so it takes more time than predicted.
