What It Means to Me to be a 9-to-5 Side Hustler

2020 was a year of many things.  A shit ton of crappy things, but some pretty cool things too. 

Like writing and publishing my third book.  Which I never intended to do in 2020.  But it seemed like the right thing to do at the time.  And it opened the door for me to have a very serious conversation with myself about where I take my business next.

You’ve heard “The riches are in the niches.”  Well, I finally got hit over the head so hard by that concept (thank you, Lindsay Maloney) that I nailed it.  I mean, REALLY nailed it.  And now that I’m putting my time and effort into all you full time, career professionals who are looking to find time for your side hustle, I think it’s about time I told you what I mean by that.

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FIRST OF ALL:  

Let me tell you about the incredibly taxing conversation I had in my head about my title:  “The 9 to 5 Side HUSTLER.”  

“Kris, that’s just a little bit polarizing.”

“People are going to think about Larry Flynt and strippers.”

“No one says ‘Side Hustlers,’ they say “Side Hustle.”

And so on, and so on, and so on.

And then I happened upon Ramit Sethi’s website…which was not on accident.  While he’s a stark raving millennial, I’m a crotchety Gen X’er, but I love his work, his writing, his sense of humor.  Ramit is a genius.  

I read his book, “I Will Teach You to Be Rich,” when my sister (same sister in the dedication) shared her Audible account with me.  I had heard Gen X friends of mine tell me that I would not enjoy this book; that Ramit was kind of a snot.  But as you’ll learn shortly, I have had money mindset issues for years.  I listened to Ramit’s book and learned something cool about him which applied directly to some of what I do in my day job.

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In that day job, I run a scholarship program at a community college (among other things), and Ramit’s story about preparing for college and applying for scholarships is quite impressive.  

Ramit’s parents told him that if he was going to go to college, he’d need to apply for a lot of scholarships.  So he did.  He went to his high school counseling office every day and looked up scholarship applications.  He spent 1-2 hours every day working on scholarship applications.  He found his niche in how to write scholarship essays (write about what his peers would NOT write about).  By the time Ramit was ready for his freshman year, he had earned about $100,000 in scholarships.  He attended Stanford University with no debt.  And then you might say the rest is history.

Anyway - I was looking up this story because I wanted to include it in my Fall 2020 Scholarship Workshop slideshow, and I happened upon one of Ramit’s quizzes.  His “opt-in.”  The lead magnet that’s used to get people onto his mailing list so they will eventually buy things (Which I have been known to do with Ramit and several other online entrepreneurs.    

The quiz I took is called, “What’s Your Earning Potential?”  And I discovered that I fall into a category called “The Hustler.”  

Ramit is quick to explain that I’m not going to be working the blackjack table anytime soon (or playing pool with Fast Eddie Felson, although that would be cool - RIP Paul Newman).  And then he said THIS:

Characteristics of The Hustler.

As a lifelong learner and doer, you don’t need a quiz to tell you that you are constantly trying to improve.  Whether in your personal or professional life, you are always trying to be the best and experience the best life has to offer.  You are never complacent - you are firmly on the path of self-development.

You feel that life is a journey of learning.

You constantly feel like there’s more in life for you and you are always looking for opportunities to grow and learn something new.  Even if you can settle for some periods, there will always be something else to chase - the next big thing for you.

As a Hustler, you…

1.  Know there’s more to life and are always striving for the next challenge.

2.  Are fiercely independent, but you know you can’t do it all yourself.  You work best on a team of A-players.

3.  Are a strong, caring person…but if someone breaks your trust, you are quick to move on.

4.  Are creative, although not necessarily an artist - your creativity often shows up in more subtle and practical ways.

You find yourself often overflowed with ideas.  There’s no shortage of options and ideas for you and often the hard part is to pick the right one at the right moment.  Frustration is not unknown to you as you often struggle to find the right resources to execute on all those great ideas. 

You always end up getting there.

You always find a way to go around whatever is in the way of your goals.  You’re confident that even if you don’t have a direct answer to a problem, you know you’ll find a way to solve it.  

As a Hustler, you’re constantly looking for the smartest way to solve a problem with the minimum amount of time and energy invested.  It’s common for you to have tons of tabs open in your browser.  Watch out, though, as often you find yourself stuck trying to find the “right” option.

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Well, shit.  If that didn’t hit me over the top of the head with a cast-iron frying pan and leave me for dead.  I have since read that section of text about a thousand times.  Here’s what always grabs me:

  • Lifelong learner and doer - Yup

  • Creative although not artistic - You know it.

  • Looking for the smartest way to solve a problem with the minimum amount of time and energy invested - oh, hell yeah.

  • Strong, caring person - multiple tabs open on the browser - how the fuck did he know??

So, yeah, the title of this book and the person I’m writing about is a total Side HUSTLER.  

Not a Larry Flynt, J-Lo, or New Jack Hustler. 

That’s what Hustler means to me.

P.S. How should you choose your side hustle? With THIS assessment!