How I Became a Private Eye

My career occurred by accident. I was an early 20-something, college drop-out—an aged-out former hockey player with zero prospects—and had no idea what my future would bring. On a lark, and desperate to find my place in the world, I reached out to an investigative firm owned by a relative in the suburban Metro Detroit area. He said the work was hard, with long sits on targets for hours, even days, and the job had a high wash-out rate. For reasons I’m unable to articulate, this discouraging advice only whet my appetite.

For three years, I worked under a licensed private investigator—essentially as an apprentice—starting from the ground up and knowing nothing of the industry, the skills required, or the grueling intensity of this new career. At that time in my life I was what is commonly referred to as a “normie.” A suburban white kid with no knowledge or experience working in low-income/high-crime urban areas, virtually no street-smarts as they relate to working in hostile environments, and unknowing of the difficulties of working in predominantly non-white cities.

My first day in Detroit, I dug into a lower-east side suburb with drug dealing, corner lookouts, and all manner of overt criminality. We successfully surveilled a municipal employee committing workers compensation fraud and working under the table for an event promotion company while remaining discreet and unseen. Within a 14 hour surveillance, I changed my clothes and appearance several times, switched vehicles twice, and had to bullshit my way into two different businesses to keep an eye on the target.