There’s a term drifting around that a lot of people (especially the younger generations) are using these days: side hustle. While many people consider it slang, it nevertheless has entered into our cultural lexicon and has become a common fixture of our daily speech. How did this happen? Is the term here to stay, or will people use it for awhile and then discard it as a relic of the past?

Before we discuss its origins, we have to first discuss its meaning.

So… What Exactly Does “Side Hustle” Mean? (And Is It A Good Or Bad Thing?)

Mirriam-Webster has an excellent summary that you can read here. Generally, a basic definition of side hustle is “work performed for income that is supplementary to one’s primary job.”

A side hustle can be defined as work performed for income that is supplementary to one’s primary job.

They also expound a bit on its origins. The word “hustle” comes from a Dutch word “husselen“, which means “to shake”. Extended meanings soon followed: “to crowd or push roughly”, “to obtain by energetic activity”, and “to obtain money by fraud and deception.” Nearly in parallel, it was also used as a noun. A “hustle” could be an act of jostling, a job, or a swindle.

A note must be given here to the duality of both neutral and nefarious meanings, because this duality carries through to this day… though its more lawful meaning seems to be the norm. The neutral, “non-swindling” version is of course preferable for us side-hustlers wishing to stay on the more reputable (and sustainably safe) side of the law!

Then, of course, there was the disco song and dance of the same name which should have been outlawed… but then, we won’t talk about that.

On a personal note, my own experience with the word “hustle” came from my dad, who was my pee-wee league baseball coach when I was a kid. I wasn’t the most energetic lad, and prone to distraction to boot… so when the crack of the bat was heard, I could count on my dad’s encouraging voice saying, “Come on, Mike! Hustle to the ball!”

At some point in the 1950’s, the word “side” joined “hustle” to become the Voltronic superphrase that it is today. Here it is in use in a 1950 newspaper article:

Alex Barnes of the Capitol Times was doing a public relations job at the conference as a side hustle.
The Chicago Defender, 12 Aug. 1950

Ever since, the term “side hustle” has been a fixture of our language. Up until recently, it has been used relatively sparingly, and seems to have carried with it that dual definition of something either neutral or shady.

When The Side Hustle Phrase Really Took Off: The Post-Recession Blues

In 2008, something changed. The Great Recession caused lots of people to lose their jobs. In the resulting fallout, even those who regained regular employment were forever changed. Many of them would never again rely on a single source of income.

They would, instead, take matters into their own hands: by seeking money-making opportunities on the side.

This was the birth of the “gig economy”, fueled by this newly minted sense of independence and a proliferation of technology that made it easier for people to get money from “a side gig” or “side hustle”.

A search of the phrase “side hustle” on Google Trends reveals a major uptick in use of the term in the last couple of years:

Google Trends search for the term "Side Hustle"

It’s safe to say that Side Hustling has reached a tipping point in society… and that a culturally significant quorum of people are engaging in one (or at least curious enough about it to inquire of the Google hive-mind).

The “Single-Source Income Myth” Of The 20th Century

I remember when I used to have faith that a large company could provide a certainty of job security for a person, as long as they worked hard and provided value.

I also remember very clearly the day that naive sense of faith died.

It was the spring of 1996, the year after I graduated college. I sat on the edge of my bed talking to my dad when he dropped a bombshell: he had just been fired.

You might think this is no big deal. Being “let go” by a large corporation is pretty commonplace in the post-recession era we live in today. To understand why this was so surprising to me at the time, you have to know a little bit about my dad.

Lewis Hine Power house mechanic working on steam pump

He’s a hard worker raised by hard workers who toughed out the depression in the south and fought in World War II. He worked three jobs when he married my mom at seventeen. One of his jobs was to clean the toilets in the warehouse of a large leather company. Due to his work ethic, leadership skills, ethical behavior, and natural charisma, he was promoted within the company.

He eventually became president of the leather company, and finally CEO of the holding corporation. During his tenure at the helm the company’s stock split two times, generating tremendous value for the shareholders (which included employees, because he had instituted an employee stock ownership plan.) His coworkers loved him, and one example of their admiration was when they chipped in and bought him a golf cart for one of his anniversaries with the company.

Now you might understand a bit more clearly why I was so shocked at his being fired. So was he.

Fortunately, he rebounded from that and eventually went on to start his own oil change business. That business is soundly profitable today, and helping him with it is one of my own side hustles.

The Death of the “Company Man”

We in Generation X (generally agreed to have been born from around 1965 to 1980) are truly a “bridge” generation. We came of age as the economy shifted dramatically from an industrial economy to an information economy. With this old mode of thinking went our parents’ and grandparents’ mantra of “go to school, get a job, work hard, then retire with a pension.”

StateLibQld 1 186707 Businessmen of Mackay including Adam Roy McGregor

Seymour Willis (back row, left) looked on in hope… would his pension (and his mustache) ever be as grand as that which the other Company Men enjoyed?

During the 70’s and 80’s, things fundamentally shifted with how companies regard employees. Rather than espousing a long view of training and developing employees through periods of change, companies listened to suited geniuses who chanted a newly minted term: “shareholder value”.

The race to create short-term profits was on. Massive swaths of employees were laid off as large companies tried to make their books look pretty to investors and Wall Street. The technology revolution only accelerated the pace of this profit frenzy, as computerized systems made entire industries (and the humans who ran them) obsolete practically overnight. This techno-lust feeding frenzy reached its peak in the late 90’s, creating the dot com bubble and the resulting crash.

During this transition something else fell by the wayside… the idea of the “Company Man“, the faithful employee who put the needs of his corporate benefactor over his other priorities and who molded his ideals to that of the company. That the very term itself leaves out half the workforce in its gender bias is proof of its antiquity. Managers and executives like to complain that “employee loyalty” is hard to come by, but who shot first?

Then again, maybe the “Company Man” idea was always flawed, a co-dependent relationship that never really was sustainable. Perhaps it was a transitory step on the way to a truly independent “gig economy” workforce which would be the standard of the future.

Where Is The Real “Job Security?”

In this crazy, always-changing environment, is there really such a thing as “job security?”

Up until I got that crazy phone call from my dad, I really did think it was possible to work comfortably and securely for a single company your whole life as long as you had value. Now that mode of thinking seems as old and rusted out as the Titanic.

And after seeing scores of friends and family members lose jobs they thought were more permanent than they really were, where can we find some kind of certainty and predictability?

If there is any concept of job security still in existence, where can it be found?

Answer: closer than it ever was.

I’d like to propose that true “job security” exists in a person’s ability to find not one job, but a portfolio of income that matches their talents, assets, and abilities with reliable sources that need and value them.

In other words: one or more viable side hustles in addition to, or even instead of, a single “job”.

A “Side Hustle” Is More Than Just A Second Job

There’s another term similar to “side hustle” that used to be more commonplace than it is now: “moonlighting“.

What’s interesting is that when you search Google Trends for this term, it seems to have decreased in use over time while “side hustle” has increased.

Why is this? Well, I have a theory.

When you look at commonly used definitions of moonlighting, you see it used when talking about a second job.

Notice the subtle difference… “side hustle” talks about secondary “income“, while moonlighting refers to a secondary “job.” The difference is minor, but significant… and could be an indication that the very idea of a “job” is becoming antiquated.

Fundamentally, a job is something that you do for someone else… a hustle is something you do for yourself.

I propose that it’s that thread of independence, of personal empowerment, that has caused us to adopt “side hustle” instead of just retreading “moonlighting”.

(Sorry, Bruce and Cybill! Still, you had a great run there for awhile.)


So… Is Side Hustling Here To Stay?

So, will “side hustle” as a term be here for good, or will it just be a passing fad, like leg warmers and Garbage Pail Kids?

I think it’s here to stay. Because it means much more than simply making more money… it’s a way of life, an expression of our ability to do something we like or even love, to be independent, and to seize our destiny by the horns.

Sure, some enterprising generation may try to retire the phrase itself and put another in its place to be “cool” and standoffish… but it will still remain as a concept.

Human resources departments and wistful ex-employees may be waiting it out, hoping for some stable period where the “company man” (or, even better, company “person”) term will resurrect itself, but I think they’ll be waiting in vain.

We of the side hustle have had our taste of independence. The connection age is here, and with it comes an environment where people will always be able to connect with each other to seek out value and provide it in the most efficient way possible.

And that’s always good for business… whether it’s on the side or otherwise.