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.<p>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 &quot;I could never do that&quot;.<p>I don&#x27;t think the author wants people to make poor time estimates  and suffer budget overruns.<p>To me, the message of the article reads: &quot;If you think something looks worthwhile but difficult, take a stab anyway. Often the hairiest, prickliest parts of the undertaking from an outsider&#x27;s perspective aren&#x27;t that tough at all once you&#x27;re in the thick of it&quot;<p>I 100% agree with you about how valuable conservatism is when you&#x27;re planning, but I think the author&#x27;s encouragement is intended for people who haven&#x27;t even considered planning yet.