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Enough With the “Side Hustle”

Hustle away. But let’s reframe the conversation.

Of the many popular terms to which I am viscerally allergic, “side hustle” might be the one that makes me twitch the most.

“Side hustle,” how do I loathe thee? Let me count the ways.

#1. The “Hustle” 

The connotation is not of a coach calling after you, praising your speed and agility. This is not the, “Hey, nice hustle out there! Keep it goin’!” Nor is it the dance that nearly everyone can do.

No, hustle in this sense gives off a vibe of doing something clandestine or under the radar – but in a bad way. While I’m all for shirking convention and flipping a metaphorical bird to the status quo, in this context “hustle” seems to imply a con or something that’s somehow unethical – that we are being urged to become hustlers. It also suggests that we have been pushed to a place where the unethical or furtive is all we have to rely on: we have to “hustle” or we won’t make it. We have to “hustle” because the standard system of work is broken and inefficient.

#2. The System

That System* is why a side hustle has to happen—on top of everything else we’re doing, of course. That side hustle becomes the accompaniment to the main idea—the cole slaw to the triple decker sandwich of our lives.

As a person from Detroit who grew up middle class (when there actually was such a thing) in the 1970s and 80s, I recognize and have benefitted from what was once the ideal of the System. At that moment in that city, everyone was, directly or indirectly, working for one of the big three – GM, Ford or Chrysler. You did that for 30 years and then retired. Unions, pensions, vacations, and predictable financial circumstances – that was a win. And it was a win in many ways.

That’s not the experience most people have today, but it’s imprinted on our collective unconscious. Our culture has been trained to believe that the singular, steady, 8-5 job is the right thing to do and have, and so it is. Anything out of that norm of a steady and single-source income is on the “side.” This is true if you work for yourself. This is true if you own a small business and also have another source of income. This is true even if your “side hustle” is three miminum wage jobs, all necessary to barely afford your rent. 

The System told you that if you work hard, you’d be OK and that you wouldn’t need anything else. But that is not the current experience for many, if not most. But the System is only one vantage point from which to look at how “work” can or should work.

#3. Hard Work 

I’m a fan of hard work. I’m such a fan that, after years of working in physically demanding fields, doing something largely knowledge-based is psychologically difficult for me. I completely value the work of writers and artists and mathematicians and researchers, but when I do those things, I feel like I’m not really working (yep, go ahead and unpack that psychic landscape). 

Through overt and subtle reminders, our culture tells us again and again that, if we aren’t achieving our dreams or meeting our goals—especially our financial goals—then we must not be working hard enough. And underneath that implication is that if you don’t have a side hustle to make ends meet, then you aren’t hustling hard enough and are, therefore, lazy. And being seen as lazy is the proverbial Scarlet L in a culture that prizes hard work. It’s a badge of shame.

In a system built on ideals anchored in an era of production and productivity we’re never going back to, we are now trying to transition to what “hard work” looks like, and it’s psychologically tricky. We’re accustomed to working hard: to putting in overtime, staying late, getting the job done. This is not just for the sense of pride and responsibility connected to completing a specific task or project, but because long hours and chronic busy-ness have become the status quo. The “hustle” is the norm. We must be in constant action and hustling all the time because doing more and working harder is supposed to make us better, is supposed to be better. More hours means more achievement means more recognition ad infinitum… but… why? 

While I truly believe people like to work hard, feel good about their accomplishments, and strive toward their hopes and dreams, the concept of the side hustle speaks to the fact that in our current framework is one where perpetual motion = success. And in the American culture, less than that means we’re failing. That standard is not only impossible, it’s ridiculously self-destructive.

And what does this do to our character? It makes it really difficult to live with character and embody the values you care about. Cultural pressure to work and economic pressure to survive makes character-based choices difficult to perceive and to make. If you are told that staying busy and having a side hustle and constantly working like mad is the only way to succeed, then it’s easier for your decisions to run counter to the character traits to value.

So, what do we do? The System is real at the moment, so what to do with the “side hustle?” Multiple sources of income are generally handier than fewer, so let’s start with its name.

1. Without getting all 1984 and mislabeling things for the sake of redirection and obfuscation, let’s agree to call it what it is: work. Let’s make it less of a “hustle.” Let’s bring it into the light. Let’s call it “income,” or “the thing I do for insurance,” or “the thing I love to do more than anything else.” And let’s understand why we need—and want—to work to create lives we want to live.

2. Check the System. What are we hustling for? Food and roof are good reasons, but are status and overt consumption good reasons? We need to evaluate that bigger system and how it influences our daily choices and actions. Are we hustling the System, or is it hustling us?

3. Act with character. Do you know your primary character traits? The ones you hold most dear, the ones that steer your heart? Knowing these requires that we all do the anti-hustle for a moment and slow down long enough to figure out which way is up. We all need to pause and get to know our values and our character. Because once we know those, there is no need to “hustle.” Then we just act and work in the wonderful ways that are true to our character. And that is awesome because not only does it change how we work, but it starts to change the System that told us to hustle in the first place. 

So, go forth and reconsider your “side-hustle.” Work. Strive. Create a life that you enjoy. Just don’t buy-in to the idea that you have to “hustle” to deserve it. 

*The System can be labeled many things. Yes, capitalism is one of them; the shift from the Industrial to Information Age is another. Those conversations are worth diving into, but those are for other times and other topics of character. 

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