I know a few folks who have left jobs and then said &quot;I wish I had stuck around that company longer&quot;.  In all cases, it was never financial.  Rather, it was &quot;If I&#x27;d known what I didn&#x27;t know, I would&#x27;ve stuck around longer so I could pick &lt;ex-coworker&gt;&#x27;s brain about it.&quot;<p>Even in my own case, where I joined a company thinking I&#x27;d leave after a year but stayed 5 years because I was still learning things (and had optimized my career for learning the whole way), there were still some times after I left where I thought, &quot;Man, if only I still had access to &lt;old design doc or code&gt;.&quot;<p>I see financial motivations coming up much more often when people say &quot;Man, I&#x27;m glad I stayed.&quot;  Vesting cliffs are really easy to predict, and even IPOs and acquisitions have some hints coming; if you&#x27;re about to get a major windfall, you&#x27;ll probably know it.