The Side Hustle Juggle: How A Fair Game Taught Me The Secret To A Happy Life (Part II)

Dawn’s glow broke at 5:30 am, heralding my latest side hustle juggle. As the sun peeked above the horizon, the whine of the laser printers wound down. The parlor-converted-into-a-newsroom fell silent, but the hot, inky tang of the freshly printed pages lingered. The pages themselves sat neatly arranged on the brightly lit layout table. Hours earlier, my co-publisher scoffed, ‘Chris, it’s impossible,’ and left for bed. Her husband stayed to help finish a job that couldn’t be finished.

The paper was done. The deadline achieved. The fumes of adrenaline pumped through my veins. Juggling a newspaper, a job, and grad school, sleepless for twenty-four hours, most people would have flopped into bed at this point. I didn’t.

I couldn’t.

Everything was working just as the system promised. An outside observer would not have believed what had just happened. Even if they saw it with their own eyes.

The Master Juggler

The previous day, my co-publisher hit a snag. In charge of daily operations, our new technology proved too much that day. She was used to the old way of the newspaper business. Just like the two other publishers competing to land the coveted wealthy zip codes in our coverage area. Their strong and successful experience burdened them.

I wasn’t.

That’s why we won the race for subscribers.

We “got there first” with the Sentinel because we premised our business model on the (then) latest technology—laser printers and a piece of software called “Pagemaker” (a predecessor to Adobe’s InDesign). Our competitors, traditional publishers, weighed down by their expensive older equipment, were too afraid to replace those sunk costs.

This is the advantage of starting from scratch. You don’t have to justify “but we always did it this way.” By embracing the new way of thinking offered by technology, we were able to create a newspaper publishing business out of nothing in three weeks. Compare this to our competitors. They needed three months before publishing their first issue. By the time their papers came out, we had already been on the newsstands for two months. We got there first. We won the market.

If you’re not familiar with The 22 Immutable Laws of Marketing, by Al Ries & Jack Trout, you should be. It helped me master the art of the side hustle juggle. Their first rule—The Law of Leadership—states, “It’s better to be first than it is to be better.” With the Sentinel, we were clearly first. On the plus side, I think we were better, too.

Using the technology skills developed at my daytime job, I designed a newspaper business model based on the (then) latest technology.

Oh, wait. It gets better.

Why was I up so late into the next day’s morning? Why hadn’t I slept for 24 hours? Why couldn’t I sleep when I was done with the paper?

At the same time I was starting my newspaper side hustle, I was working full time designing a new profit center at my full-time job. I was also attending graduate school. With a full-time class schedule, I couldn’t begin working on the paper until late at night, often finishing on deadline day just as the sun rose.

That rising sun signaled I had to get ready for “work.” I couldn’t go to sleep because it was time to wake up. Fortunately, success produces a hefty dose of dopamine. That rush kept me going. Not just with the paper, but with my professional work and my schoolwork.

That profit center at work soon produced new revenues literally out of nothing because it required no additional costs. The doubters couldn’t believe how quickly it succeeded. Having shown them how to do it, it was only natural that they let me turn that into a full-fledged bank trust company. In two years, that business grew from literally nothing to a billion dollars.

My capstone project for business school wasn’t the usual “create a make-believe business plan that maximizes profits.” I told my professors it offered no challenge for me because I had already done that in real life. Twice. My new project—design a political campaign that maximizes votes—eventually became the blueprint I used to win two successful elections.

Doing any one of these things would enhance your resume. Doing all of them simultaneously was downright unbelievable.

Newspaper, job, grad school—three balls, one juggler, no sleep—racing dawn’s arrival.

This is master juggling. This is the ultimate side hustle juggle.

This is the power of the system forged from a grandfather’s wisdom, a carny’s hustle, and a book I never ordered.

AI Supercharges Side Hustle Juggling

As life would later confirm, it was all about this system I developed in college. Every success, from jobs to ventures, leaned on that system. As a young adult, I used it to master a job I had no right doing. It allowed me to jump from one position to a higher one, not once, not twice, but three times. All the while, I also lived a satisfying life outside of the office.

How? By treating each area of my life as a distinct series of steps, then integrating those steps into a whole. That blend of Grandpa’s wisdom and the carny’s hustle proved the system’s staying power.

It gave me the confidence to move forward into new ventures and enforced a discipline that allowed me to keep the old. Indeed, I kept my baseball card business and market research company operating as viable side hustles. I even ordered letterhead and envelopes—because a side hustle should always look the part!

Over time, I enhanced the system from strictly business activities to other areas important to my life. Again, I stacked all these activities on top of each other. They ran effortlessly in parallel. I used the system to go to graduate school. I used it to start the Sentinel. I used it to run my political campaigns. Heck, I even used it to plan Betsy’s & my wedding. (Turns out, the system had a few things in common with Pre-Cana.) It was the ultimate side hustle juggle.

I didn’t stop there, either. With this growing body of experience, I became perhaps what fate always intended. Both of my grandfathers started successful businesses. This was natural for their generation. Like many of their peers, they worked at the Bethlehem Steel plant. As a steelworker, you had to live with the ebbs and flows of the broader national economy. When you get laid off, you better have another source of income, or your family won’t eat.

My paternal grandfather started a masonry business with my father. He had to teach himself (and his son) how to lay brick. They built many familiar buildings in the towns south of Buffalo. My maternal grandfather, inspired by my mother’s teenage dictate, started a pizzeria that morphed into the pizza stand at the Erie County Fair.

Is it nature or nurture? My grandfather taught me how to run a pizza stand. My father taught me how to lay brick. Those weren’t just jobs. They were systems. That’s what I bake. That’s what I build.

By the time I reached middle age, I had created two profit centers from scratch for the firm I worked for. Clearly, I had honed the system to a point where I could confidently go out on my own. And that’s what I did. In fact, to fund this full-time entrepreneurial effort, I had to sell one of my side gigs (the newspaper). It was the first and only time I ever sold a business. (Spoiler: We bought it back. Some things are just meant to stay in the family.)

That dopamine hit? Still works as well now as it did back in my twenties. Even when most people think of retirement, I am birthing new side hustles. I qualified for Social Security several years ago, but I haven’t taken it. I’m having too much fun creating new ways to make money.

And now, it’s gotten to be more fun. These hustles, juggled without AI, proved my system’s power, ready for technology’s boost. As easy as it’s been to start, maintain, and sustain side hustles, generative AI platforms have supercharged this process. AI has opened up even more windows of opportunity. Tasks that once took hours now take only minutes. Of course, if I told you what platform I am using at the time of writing, it might be a totally different platform by the time you read this. That’s how fast things are changing.

But that’s not all. There’s a whole new world of business models out there. It’s a race to see who can get there first. I’m not worried. There’s enough to go around. Just getting there first for a few of them will keep me busy well past the age when the government requires me to take minimum distributions from my IRA.

Isn’t this what life’s supposed to feel like? Isn’t this what happiness looks like? It’s all thanks to a carny’s game, my grandfather’s truths, and a book that hatched a system I still use to juggle family life, community volunteerism, and professional ventures.

Today, the system allows me to continue to juggle an array of seemingly unrelated ventures and still live the family life I want to. Who wouldn’t want to benefit from this?

I call the system “The Lifetime Dream Process.” I happily share it when I can, though one-on-one coaching takes time. That’s why I carved out a shortcut focused just on launching a side hustle. Think of it as a timesaving method that gets you extra cash quicker.

How will discovering this help you?

Your Turn to Juggle

Being a parallel entrepreneur, I’ve honed that part of the process down to a tee. If you’re reading this column, it’s because you’ve already decided to, at the very least, consider starting a side hustle. And why not? No matter what your age, you can do it. I know this because I’ve lived it.

Don’t feel like you need to work in parallel. You don’t need to perform the side hustle juggle. Pick one skill—writing, selling, coding (I’ve done them all)—and test it with my system’s first step: set a goal, hustle it out. My system’s first step: list your priorities, chase one opportunity, repeat. With AI, you don’t have to do this in a vacuum. You can brainstorm your ideas all in one night.

Besides, in this economy, who wouldn’t want a side hustle that’s easy to start, easy to run, and delivers actual cash on the side? Whether you’re a retiree wishing for something fun to do, a young adult looking for supplemental income, or a teenager seeking to take that first step as a budding entrepreneur, a small-time side gig presents a low-cost, low-effort opportunity to test the waters.

Are you ready to arrive, survive, and thrive?

Spoiler alert: This isn’t about reading. It’s about doing!

The midway’s open. Opportunity abounds. Juggle your own happy life!

Click here for the first part of this series: The Side Hustle Juggle: How A Fair Game Taught Me The Secret To A Happy Life (Part I)

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