Taking on a Second Job…for Fun?

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When I was in high school a few years back (okay, more than a few), I traveled to Italy with a small group of American teenagers. We stayed with families for three weeks, and then spent another three weeks visiting such cities as Venice, Florence and Milan. Our group was led a woman whom I’ll call “P,” a teacher during the school year who led programs like mine during the summer.

I recently reconnected with some of my travel mates, and we discussed how insane P must have been to have taken a group of American teenagers all the way to Italy, where they could drink, get lost at a time before cell phones were pervasive and exist without parental supervision. Or was P on to something?

After all, she got a free trip to Italy, as well as a stipend that allowed for the indulging in some pretty fabulous meals. And while we stayed with our families, P was pretty much free to do as she pleased, although she did have to remain close by in case we needed something. Not a bad way for a single, relatively young empty-nester to spend six weeks.

P’s situation reminds me that some people find ways to incorporate interesting side gigs into their work life. Teachers, who are typically off during the summer, are arguably best positioned to make this happen. But those in other professions can also find ways to take on a seasonal, contract, or other type of short-term role during a break as well, as long as it doesn’t conflict with the primary employer. It’s a way to boost your income, sharpen your skills, expand your network, or simply dabble in something you love, as was the case with P.

Have you been able to take on a side job in addition to a full-time role? If so, how?

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