By the time I was 16, I was sick of babysitting. And so, when my brief holiday gift wrapping gig came to an end, I scoured the want ads in my school newspaper for something new. Something different. Something interesting.

“Tobacco Prevention Educator for the City of Berkeley. Seeking Motivated High School Student for non traditional position educating youth on tobacco prevention. $7/hour. Inquire via 555 555 5555.”

Since my pager clearly didn’t make phone calls, I waited until I got home for a landline. After a couple of basic interviews, I got the job. I had good grades, I was motivated, and I didn’t smoke. I fit the bill.

Over the next two years, I spent around 10 hours a week attending community fairs, making and passing out thousands of fliers, and helping in tobacco prevention trainings in schools. But the best part of my job and the most lucrative was when I got to participate in police “stings.”

Not being entirely sure what a police “sting” is (to this day), I can’t be entirely sure that’s what these were. But they sure felt like them.

Here’s how a typical “sting” went

I’d wake up early on a Saturday morning with two plainclothes policemen rapping at my door. We’d get in their non police car and drive to the bad parts of town. They’d stop at a corner and point to a shady looking liquor store across the street. My job was to go in and buy cigarettes. If the store carded me for being under 18 and then didn’t sell to me as a result of my being underage, they were smart. If they didn’t, the police gave them a fine, and put them on a list. A bad list.

At lunchtime, we’d hit McDonald’s, where I’d pepper the policemen with questions about what their normal workdays looked like.

Throughout the day, they’d ask “You want to call it a day?”

My response “No way!”

After all, the city was paying me on commission $5 a store for what was considered an assignment outside my normal work duties. This, I knew, could net me a big daily paycheck. On my best day, I came home with $360. Seventy two stores! I was highly motivated, apparently.

Although being a Tobacco Prevention Educator for the city didn’t shape my career very dramatically, it did teach me some key things about work that I have carried through to this day.

Here are a few of the most important lessons I learned

  • Eschew Tradition I haven’t had a traditional career path, and undoubtedly the seeds of some of my past career choices (like traveling the world for a year and writing about it, starting a nonprofit in Africa, or full time blogging) were laid during my time touting the horrific side effects of tobacco. The reason I went after the Tobacco Prevention job in the first place and didn’t seek a job at the FroYo stand was because of my pattern of knocking tradition to the curb.
  • Find Flexibility at Work Expanding upon the lesson on eschewing tradition, I’ve never been one for a traditional work day, or a traditional corporate work environment. In every job I’ve had, I’ve found enjoyment when it allowed for an exciting mix of activities, from office time to field work to corporate travel. This is something I value in what I do and always will.
  • Have a Personal Passion for Your Work Buying illegal cigarettes for policemen wasn’t necessarily my be all end all passion, but as a teenager I was passionate about the negative effects of tobacco, and why more teens needed to know this. This helped me to do my job well, and taught me the lesson that jobs must relate to one’s passions.

At the end of the day, I have to thank the City of Berkeley for an unusual, rewarding, and bizarre first job. It was perfect for me.

For more from Claire, read her free ebook on developing a morning routine, check out her blog, follow her on LinkedIn, or find her on the Twitters via claire.

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Photo grandjean seb/Flickr

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