Considerations on That Startup Life

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In 2008, I was working for a major telecom company, handling calls for large business and government accounts. One day, while looking at an organizational chart, I realized my only available career moves within the company were lateral. I could shift to data support or something similar, but there was no clear path upward. I needed to move on. I searched online but couldn’t find many customer service options in New Jersey, where I lived. Then one night, it dawned on me to check New York. Believe it or not, I found my first job at a startup through Craigslist. Here, I'll share some of my thoughts on startup life.

First, in a startup, you wear many hats. I was hired to provide "white glove" service to our clients, but with only a handful of customers, my primary role became content preparation. I processed investment newsletters from print, email, and PDFs into a format that our web application could display. Along the way, I also took on minor technical tasks, like fixing a computer that was mysteriously missing a part (weird) and writing the HTML for our 404 error message. As I said, one person can wear many hats in a startup, which means there’s a lot to learn. On the flip side, stepping outside your defined responsibilities comes with risks, especially in a fast-moving environment.

Second, startups are high-pressure environments where work often goes late. With only a small team, everyone is working toward a major goal—whether it’s a launch, relaunch, redesign, or some other big push to attract users or potential buyers. Mistakes are noticeable. If something goes wrong, there’s no hiding; everyone will know who was responsible.

Third, startups can be unstable. If the money runs out, people can be let go without warning or severance. On the other hand, well-funded startups have a cushion against market forces and economic downturns. That was the case for me during the Great Recession. The stock market crashed, people lost jobs, but my day-to-day remained the same because I was working for a startup with solid financial backing.

Fourth, and finally, startups can be cutthroat. At one company, I led the engineering team through an agile transformation, helped guide a major refactor of the web application, and oversaw a complete site redesign—only to be let go the week after relaunch. The reason? It looked to me like they didn’t want to pay the agency placement fee that was about to come due for me.

Honestly, I’m not sure if I’d work at another startup. If someone personally invited me to join a well-funded and stable one, I might consider it. 

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