How Much Fun can You have While Making Money?

How Much Fun can You have While Making Money?

21:07 08 May in Careers, Generations, Jobs, Workplace

How much fun can you have while making money? This was the big question for me when I got my first job right out of high school. I had only two motivations… to have the best time a girl could have while making as much money as possible. I was ready to rock the world, or preferably rule it. 

My high school friends got summer jobs at the local pineapple cannery or flipping burgers to work their way through college. I got lucky when my mom helped me get my first job at the town’s weekly newspaper where she worked. My mom’s manager hired me on the spot during my first interview.

There was an important lesson here not lost on me, even though at the time I didn’t have a name for it: I had networked my way into a good job.

I started working in the newspaper’s production department. It was super interesting to learn how the newspaper got put together and to be part of that. Everyone was friendly. We all worked hard to meet our deadlines. It was fast-paced, exciting and fun. I liked it.

I liked making money, too. The job paid better than the minimum wage most of my friends were getting.  I had earned my own money before babysitting and with odd jobs like walking my neighbor’s dog, so I could buy music and go to movies. My first “real” job paid a lot better. That first paycheck was exhilarating. It said: “You’re an adult now.” I blew the whole thing on a killer pair of shoes.

Never mind that my mom wanted me to save money and go to college. Boomers call this a reality check, and it’s funny how many of them now seem a little horrified that Millennials entering the workforce insist on liking their jobs. But regardless of the generational differences, everyone wants meaningful work. Boomers called it “dedication” then. Employers call it “engagement” now.

Reality did set it when I moved out of my parents’ house. I learned the hard way that life wasn’t always easy, and it’s almost always unfair. Things don’t quite work out the way you planned as you make your way in the real world.

I didn’t last long in jobs that were boring or where I didn’t get along with the people. I found mentors who helped me get ahead, I improved my skills, and got progressively better paying jobs. I went back to school to fill in the gaps of my real-world education. I tagged along with my coworkers to business association meetings, joined professional organizations, made new friends.

My bosses took me to lunch with clients, and I caddied for them on the golf course. I learned that people do business with people they like, and that you can find more business opportunities in restaurants and on the links than in the board room. Networking was profitable – and fun. “There’s a lot of opportunities, if there aren’t, you can make them…”

As the world changed, I lost the desire to rule it. I gained a desire to make a difference instead. I have yet to figure out what I’ve been put on this Earth to do, so in the meantime, I became a mentor to others in my profession, and found ways to give back to my community and help others wherever I can.

I learned there are many rewards that are better than money.

So until I find my life’s purpose or higher calling, I simply follow the bliss. I’m happy when I have a fun job that pays me well to do stuff I’m good at, and work with people that I like. While my long and winding career path has taken me in unexpected directions, my professional goals haven’t changed: Have fun. Make money.


This article was originally posted on February 2016


Photo courtesy of Buster Benson.


Sylvia Dahlby

Sylvia Dahlby is a Rainmaker at SmartSearch, an industry-leading applicant tracking system developed by Advanced Personnel Systems (APS). Sylvia has worked in the recruitment advertising & technology industry since 1978, and has teleworked from home since 1990. She currently resides in Hilo, on the Big Island of Hawaii. She's an active member of SHRM Hawaii, Social Media Club Hawaii, Hilo Woman's Club, and volunteer at Kipaipai School of Art.

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