The Rise of the Side-Hustler

Why this move is here for the long run


Jill Ebstein

3 years ago | 3 min read

In the litany of one-liners spoken at college commencements, here is one told to me years ago that I haven’t been able to verify but am also unable to forget:

“This generation will go to their grave with their options open.”

It was purportedly said at a Yale graduation — a group that would likely have had many options.

The notion of “leaving one’s options open” has morphed into a noteworthy side hustle. The side hustle is loosely translated as activities undertaken outside of a person’s main job to earn additional income or satisfy a passion. Side hustles can lead to a new career path or simply test a fantasy like, “I want to be the leader of a band.”

The accountant by day becomes a photographer by night. A teacher hires himself out as an elite caterer on weekends. They can be as simple as driving for Uber or buying and reselling stuff and as complex as tutoring or being a social media influencer.

It is not an overstatement to say that side hustles pervade our universe.

The theologian in us might wonder whether side hustles are more beneficial or costly to our social fabric. The historian in us might wonder whether this is truly a new phenomenon or have we been doing it all along — probably to a lesser extent — without naming it.

There are clearly many positive aspects to having a side-hustle. The decision to undertake a mini-venture encourages innovation and fosters continuous learning and an expanded social network. The side hustler gains a broader perspective about people, business, and life itself.

Parents are squarely in the backseat with low to no guiding privileges. Side hustles also serve as a hedge in case the day job goes south. Even if the hustle doesn’t pay the same, it opens new paths and can reduce anxiety.

Still, there is a downside if you believe in Malcolm Gladwell’s 10,000 hours. He asserts that committing time and practice are essential for mastery. Since a day still has only 24 hours, including sleep, there are only so many ways we can divvy up our time.

There is also the risk of burnout. If we are constantly working, when do we refuel our tank? A recent survey by Spring Health cites 76% of U.S. workers are experiencing burnout. Other surveys show similar findings. Running hard in multiple lanes bears associated health and emotional costs. There really is no free lunch.

This trend raises other questions too. How will the workforce look when we go from a rickety ladder to a gig economy to a side hustle? How do educational institutions prepare students for this complicated dance? How do parents help their children for what feels like a shapeless journey?

Dinner conversations are often a good time to broach these topics. When I asked my son why he felt the need to simultaneously be a teacher, gardener-for-hire, and a crypto-maven, he cited an IRS study about the value of having seven streams of income. More to the point, though, he enjoyed all three and didn’t want to choose if he didn’t have to.

In that same conversation, my husband and I realized we had our own small side-hustles. My husband, a scientist, is also a singer and part-time cantor. I write for fun and sometimes pennies, but I pay my way with a business consulting practice. The new, new thing is a variation of the old — with a twist and born of necessity.

What’s different is that social media shines a light, and technology enables a broader range to our side hustles.

What’s also different is the voice we each hear. If we grew up to Benjamin Franklin’s words,

“A penny saved is a penny earned,”

our children have grown up to words like Stephen C Hogan’s,

“You can’t have a million-dollar dream with a minimum-wage work ethic.”

Different times call for different voices and different marches. The side hustle is here for the duration.


Created by

Jill Ebstein

MBA, consultant, author, speaker. Fan of tennis, dogs and being a leader of my pack.Interested in the intersection of life, family, and modern-day peculiarities. Authored "At My Pace" series







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