Reader Beware: Context Matters

Published on October 11, 2023


1 min read

Are trees green? Is the sky blue? Yes, of course. Everyone knows that.

However, looking out my window, what do I see? Trees that are red and orange along with a sky that is gray.

To make sense of the information around us we must assess context. My writing is no different. I’ll do my best to be honest and present information that I hope will be of use to others. However, the reader must critically evaluate the information. Part of that is considering the perspective that I’m viewing things from.

Here are a few details that color my perception.

Company characteristics

Number of staff

Range of possibility: Sole proprietors to millions of employees.

My experience: Organizations of just under 50 to just over 1,000 people. I’ve led single teams of three up to departments of over three hundred. Prior to this I spent seven years as a sole proprietor.


Range of possibility: Some businesses were started yesterday and others, amazingly, are over a thousand years old.

My experience: I’ve specifically worked at companies that identified as “startups”. Some were founded less than two years prior to my joining, while others had been in business nearly a decade.

On-site vs remote

Range of possibility: On-site, hybrid, remote.

My experience: I’ve worked at companies that did all three and have personally worked both on-site and remotely. However, the bulk of my professional experience has been remote, exclusively so since 2008. Prior to that, as a sole proprietor, I worked for over a year from a small mountain village in Panama.


Range of possibility: Too expansive to attempt to list.

My experience: I’ve worked at technology companies. The majority of these were B2B. One was B2C. Most of these focused on providing software or services to software engineers, such as: distributed database, in-memory data grid, Ruby on Rails PaaS, log storage and analysis, etc. I have also worked at two FinTech companies, one directly servicing end consumers and one that provided BaaS.