&gt; when you&#x27;re &lt;10 employees, you can literally just raise your voice in the room and say &quot;Any reason we shouldn&#x27;t send Joe to FooCon to speak about the FizzBuzz? It&#x27;s a bit pricey, probably $1100, but it&#x27;s it worth it right?&quot; -- that&#x27;s a much more transparent decision than anything written in a handbook.<p>This handbook doesn&#x27;t preclude that; it just says that this is the minimum that every employee can expect without having to wonder what is reasonable or not. Every company, large or small, has exceptions to policy, and the handbook is just a way of making those guidelines common knowledge, so everyone can feel comfortable knowing what expectations are completely reasonable and what will require special consideration.<p>&gt; so why do they feel the need to specify how many weeks of vacation you should have taken in the year leading up to the sabbatical you earn in your fifth year of employment?<p>One disadvantage of &#x27;unlimited&#x27; vacation policies are that expectations are oftentimes unclear, and many people end up taking far less vacation time than they otherwise would or could. This disproportionately impacts women and minorities in the industry for a variety of reasons[0]. People who are used to being marginalized in the workplace (not necessarily at their current job, but in the past) tend to be less aggressive with their demands, even when their demands are completely within reason.<p>Furthermore, for people looking at long-term planning (people with families, or people with other obligations outside work), having clear expectations for not just the short term but the long term as well is a <i>huge</i> bonus.<p>[0] This isn&#x27;t an argument not to have unlimited vacation policies at all - just that, if you do, you should be conscious of mitigating this effect.