Hustling: Unfiltered –– The Real World of Side Gigs

​These days, everyone wants to be a #hustler. 

Not in the long-con, steal your inheritance kind of way –– but in the Rihanna work-work-work-work-work kinda way.  

Thanks to a society that served up the gig economy in lieu of stable, high-paying positions, and a generation of purpose-driven job hoppers seeking world change through their professional lives, the landscape of work as our parents knew it is changing –– fast and epically.

A work revolution is taking place, right under our keyboards. 

Where once, landing a steady full-time job at a respectable company spelled success, young and seasoned adults of today are taking another path, ready or not. 

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Our Lord and Savior, Entrepreneurship 

Now, many are flocking to entrepreneurship, startups, and digital nomadism as the promiseland –– escape from the cubicle jungle. As location becomes as irrelevant as dress code, and purpose rivals profit in a company’s projection for success, we are winding through this new work world, writing the rule book as we go along. 

Perhaps more accurately put, we are burning the rule book altogether –– opting for flat companies, where the top-down hierarchies of a businesses past are laughable relics. Or virtual companies, with international teams and offices in the cloud. Or working for ourselves –– the ultimate freedom. 

With these changes, the partitions of work life and personal life have begun to crumble. 

If you don’t work from 9 to 5, and you make your own schedule, how do you know when you’re done working? 

The answer? You just kind of work all the time. 

Apart from your full-time gig (if you have one), you pick up work on the side –– aptly named, your “side hustle”. 

You freelance, you build your own business, you blog. 
You flip books, or you sell homemade jewelry, protein powder, or makeup. 
You drive for Uber, sell online courses, or teach private piano lessons. 
You take your skills and thrust them into creative projects during your mythical free time.
You chase down clients to build a business that is yours. 

All signs indicate the gig economy (with the sharing economy and purpose economy right alongside), is here to stay. 

Shining City on a Hill –– The Hustler Paradise

This shift means that more and more of us twenty, thirtysomethings, and above riding this new professional train have adopted this buzzword to describe our work lives: hustle. 
 
If you’re a hustler, you make shit happen. 
If you’re a hustler, you work harder than most. 
If you’re a hustler, you wanna be your own boss –– a lifestyle we now revere as the glorious alternative to working for The Man. 

Hustling work seems to help many people find creative fulfilment outside of regular work that just doesn’t cut it. 

You’ve gotta admit, it does sound pretty cool. 
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With hustling entrepreneurial greats a la Oprah, Gates, and Zuckerberg, to name a few bigwigs, hustlers tend to associate with pretty impressive company. 

Not to mention the other under-30 tech wunderkinds and other “overnight successes” that have helped ignite the coding fanaticism and tech startup incubators around the world. 

Then, we’ve got non-conformist porn in the shape of hundreds of bloggers writing about quitting their day job and traveling full time have added fuel to the fire. “You can do it too, “ they claim. “Stop wasting your life away at a desk.”

The call to action has sounded –– do something extra, or risk missing out on "real life", making money for someone else. 

It’s a great time to be a renegade. And if you’re not, what the hell are you doing?

I’m Not Like Other Girls –– Hustling as Non-Conformity

To be honest, there is a lot about the hustle revolution that I like. As someone who cried with joy the day I got my first pay check at age 16, with money that was my own to spend how I saw fit, independence has always landed high on my list of priorities. 

I like to hustle.  

But I wonder if we fully understand the implications of hustling as the new professional deity. 

In other words, hustling sounds trendy and anti-establishment, a way to set yourself apart from all the other squares who just work 40 hours a week for one company, those lazy bastards. Don't they know it could be different?

Wait just a second.

What about for those who like the status quo? The ones who like having a steady paycheck and a more secure future and a 401(k)? Are they actually just lost little sheep who haven’t figured out that the grass is greener on the hustlers’ side of the fence?

I doubt it, but their idyllic scenario is becoming harder to find.
So, the hustlers wave their flags of pride. 

They're gonna beat this system, dammit, and do it with Warby Parker glasses on, 

Right?

You might have already guessed where I'm headed with this.

The reality may not be as awesome as the hashtagged #hustle tweets might claim… but the doesn’t mean it can’t be awesome. 

Hustling –– The Reality

So… what does hustling look like in real life? 
Like your relationship status with your ex you still bang –– it’s complicated. 

What is hustling actually? A few examples: 

Hustling is turning down plans with friends on Saturday night so you can spend hours bent over your laptop creating and designing your business’ website. 

Hustling is spending hours trolling Upwork for new freelance clients. 

Hustling is getting home so late, you fall asleep with your shoes on and a half-eaten sandwich next to you.

Hustling is trying to be a good parent with enough money to pay the bills, while finding the hours and energy to work on your side projects.  

Hustling is choosing to save your pennies for a new camera or training course rather than getting that takeout or that new pair of underwear you need. 

Hustling is finding the strength to keep going even when everyone has you convinced you will fail. 

Hustling is staying in the apartment with the weird smell and the shoebox square footage because your lower rent helps cut down your overhead costs.

Hustling is working 80 hours a week not because you want to, but because you have to. 

Hustling is not infrequently annoying people with your persistence and self-promotion. 

Hustling is facing friends, family, and loved ones who whine that “all you do is work”. 

Hustling is making the daily hard choice of spending your “free time” with people you love, or working your ass off for a dream that even you might not fully understand.

Hustling is meeting daily failures head on, and persisting anyway.  

Hustling is waking up ridiculously early on a Sunday morning in your glasses and pajamas, pounding coffee and writing a blog post about hustling, in the hopes a few people might read it. #meta 

Ultimately, hustling is a commitment to a bigger dream that only you can envision. 
And it can feel like the loneliest thing in the world. 

Ouch. 

The flip side? When you do succeed, in achievements great or small, there is no higher high.
You built or did something that is yours, and it worked. You did it. 

It’s an exhilarating, awesome, captivating –– but fleeting –– feeling.

The rush is addicting. It's what brings hustlers back for more. 
For a true hustler, there is always more to be done.   

But I’d argue, that’s part of the magic.

The End and the Beginning — Hustling Toward the Future

So, does hustling still sound great to you? 

I’m genuinely curious. I don’t write all this to simply decry the new normal when it comes to work lives, nor rejoice it. We all know there’s more nuance than that here. 

My aim is that we see hustling for what it really is, behind the Facebook humblebrags and pithy memes.

Like I said before, we’re entering a whole new world, so we better damn well know what it looks like, the good, the bad, and the unfiltered.

Most of us are just fighting every day to stake our claim in one little piece of this new place, call it our own, and not only work hard, but work creatively, and work for meaning. 

In the end, we want the blood, sweat, and tears of our hustle to matter. 

Today, hustling is cool. 

Tomorrow, it may just be reality.

If you liked this, you should check out Why Millenials Are Leading the Entrepreneur Revolution.