We are clueless about how long things should take
Great article.  When I worked at $OldJob, the leadership wanted an unsolved, research-grade problem solved in a few months.  They demanded estimates, then refused to accept estimates beyond their timeline, then tried to hold people &quot;accountable&quot; for missing the estimates.  Of course it was a mess, and of course we failed to hit our goals, and of course many many people burned out.<p>But I noticed that some people handled the situation fine.  They stayed on management&#x27;s good side, even though they were failing to deliver along with the rest of us.  I will try to distill what I observed them do:<p>1) They did not fight on the estimates.  If a manager forced them into a certain timeline, they registered their disagreement and just accepted the new timeline.  I think they realized that fighting would just make the manager judge them less capable.  (Pick your battles, eh?).<p>2) When the schedule slipped, they would communicate it in a way that made them seem more competent instead of less.  The explanation usually had three parts: unforeseen events kept us from hitting the deadline, we accomplished some great things in the meantime, and here&#x27;s why we&#x27;re in great shape to hit the next deadline!  For example: &quot;When we made this schedule, we did not realize that AWS nodes were so unreliable!  Despite this, our team has made incredible progress on implementing a fast method of storage and solid compression!  We have reworked the schedule to reflect this new information, and we are already on track for the first milestone!&quot;<p>It&#x27;s possible that this trick just worked for the specific situation at $OldJob, but I really enjoyed learning it.  They seemed to understand that certain explicit rules were not important, but that other unspoken rules needed to be followed.  Are accurate estimates important?  It depends on the situation!  Sometimes wrong estimates can be more valuable than correct ones.  Construction companies give wrong estimates all the time in order to win projects.  Is staying on good terms with your boss important?  Yes!  Even if they are total shitbags, being adversarial won&#x27;t help, only leaving will.  These people demonstrated that there are often ways to fix a bad situation by breaking some explicit rules and carefully following implicit ones, and I wish I had the acuity to see these possibilities on my own.