By now, I have spent more than half of my 15+ year professional career as a remote employee.  My first job, back in 2000 was as a developer working for a Boston-based company from my apartment in upstate NY.  We exchanged source code via CD in the mail, used a telephone and screen shared with Microsoft Netmeeting.  That... was hard.<p>Several companies later, I find it actually difficult to work in an office environment.  I&#x27;m not a hermit or even a strong introvert.  I enjoy the company of other people from all walks of life, but there are so many distractions in an office environment that prevents me from doing my best work.  As a Technical Operations engineer (SysEng, DevOps, SRE, or buzzword-dujour), most of my work is contemplative and best performed away from a keyboard.  At home, I am free to work while running, walking, or sitting in the bathtub (TMI) with no fear of judgement from my peers. When I do need access to someone, I have a variety of tools at my disposal to suit the required latency and interactivity of the conversation.<p>Plus, pants are optional and slippers are the prescribed footware.<p>There are always challenges, though.  For me, strict enforcement of work hours is a must.  Sometimes I still get in the zone, lose track of time and work late, but usually I sit down around 9AM and take off around 5-6PM.  Otherwise, work takes over my life and I end up neglecting my responsibilities as a husband, father, and homeowner.  I am lucky to have a wife who understands my work boundaries and children who have never known a father who leaves the house for work each day.  &quot;Daddy is working&quot; is enough for them to get them out of my office. Oddly, I grew up in a similar environment, as my father worked from a home office when I was a kid.<p>The biggest challenge for me has been while working for a medium-sized (1000+ employee) company in a Director role for a mostly colocated company.  As an individual contributor, communication with my team and boss is relatively easy, but as a leader it is incredibly difficult to inject myself into important conversations via chat and email when those people are literally sitting next to each other.  Having trusted &quot;spies&quot; within the organization that will keep their ears open and report back is a must or else you end up completely out of the loop.<p>Having worked primarily at colocated companies where I&#x27;m in the minority as a remote employee, I&#x27;m very excited to be joining an established remote first company next year and seeing how they do it in the &quot;big leagues.&quot;