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Those Never Ending “Side-Hustles” and My Search for Meaning


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My first real job was at a Best Buy store in Indiana years ago. It was a great first experience working and actually getting paid. I’d held volunteer positions before that at various non-profits, but this was my first time trading my time for actual cash. It wasn’t much but I enjoyed the opportunity to be around tech, help people, and learn new things on a regular basis. I got a crash course every day on marketing, customer service, management, pay, and merchandising.

I spent the next several years trying to figure out what I wanted to do in the future. Retail had its benefits. I held other retail jobs along my journey at Waldenbooks (remember them?), Menards, Walmart, etc. All the while I picked up side-jobs to make some extra cash. Retail, after all, isn’t a profit center for those not in charge. The grunts get the work of the company done but don’t benefit like say a general manager or stockholder does. I did freelance work on computers, with local publications, and general labor stuff. I even spent several weeks in Europe convincing the love of my life to marry me. It was led me into an ever-evolving search for meaning that included questions like…

What am I to do with my life?

What matters to me?

Why am I so worried about what others think of me?

Can I find a job that I enjoy and that pays the bills without needing to work a million hours a week or every holiday?

I then fell into a job at a church in the western burbs of Chicago that continued my non-profit experience. I found a listing for the position I’d later take and spend the next 12 years working in via Craigslist in 2006. Three months after my wife and I got married. It didn’t pay well and had zero room for professional growth. I, however, spent that next decade-plus working there for various reasons: wife getting put on furlough twice, becoming a father twice, a somewhat flexible schedule, etc. I went from being a Christian to being fairly anti-religious while I worked there. The staff kept shrinking, my responsibilities kept growing, and I experienced many of the ugly sides of “Church.”

There was a time I went back to work for Best Buy, while I worked at that church, to make rent. I ran a few Kickstarter campaigns for people like Five Iron Frenzy and Babe Scott. Helped with album releases from MxPx and mewithoutYou. I took part in a nationwide awareness campaign called Speak Your Migraine. I did some blogging projects with Netflix, Starbucks, Pampers, and others right here on Daddy’s Grounded.

Fast-forward to 2018 and I’ve moved on from that day job. While those side-projects remain, I know there’s more I want to do. I’m just not sure exactly what. It doesn’t seem like I’m suited for a normal day job at the moment with two young children to care for and watch over while wife travels for work.

I do know what I’m currently working on launching next though. My podcast is finally coming back with new episodes. I even attended an open TV casting call recently with positive results.

I don’t know where my future is headed and I’m comfortable with that right now. My meaning is found in family and the small community I’ve built for myself. I’m interested to see where this all leads though. Wish me luck!


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  1. Nice post. I’ve been in between real jobs and side hustles for a long time. As a single dad the financial obligations and support of the ex are more intense. Keep going for your dreams. Keep your eyes on the family as a priority, I think you’ve got that right. Take care.


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