I don’t often post questions on Facebook, but when I do, I meet amazing people like Elizabeth Guerrero!

A couple of months ago, I was really struggling with the concept of “hustling”—working your ass off, or according to the Merriam- Webster dictionary, “to make strenuous efforts to obtain especially money or business.”

Hustling also means swindling and to the entrepreneur crowd, working really hard and really smart to get ahead. It’s a flexible verb.

I’m torn about hustling. There is a lot of evidence to show that it works. If you look at it in terms of efficiency, it’s smart, but how most people seem to interpret hustling as a concept is working day and night solely focused on a big goal. Hard work pays off, right? Where I think most of us go wrong is that we hustle for the wrong things, things that aren’t really all that important when you stop to think about them.


After a few days of research and pondering, I did what any inquiring millennial does…I asked a Facebook group what the point of hustling is. And that’s where I “met” Elizabeth. She was struggling with this same conundrum, and wrote a very insightful response that implored me to see if she wanted to hash it out and publish the conversation. The result is this podcast episode.

It’s scary to say, ‘I’m not going to hustle’ because you’re afraid if you stop hustling, you’re not going to be able to do it again, you’re going to miss out or something, but give yourself the permission to take even just a month—not even completely off of your business if you can’t do that—but just to take a step back and give yourself time to feel…what it is you really want.”—Elizabeth Guererro, a woman I would happily hitchhike to a Starbucks for a couple of hours of deep-life exploration.

While Elizabeth and I talk about hustling as it pertains to starting a business, this conversation is relevant for anyone who’s trying to achieve something big, whether it’s trying out for the Olympics, starting a family, or working on whittling down your waistline.

Here’s the problem with hustling

Let me preface what’s about to become a rant with this: I believe in reasonable sacrifice for long-term gain when you know what you’re working for.

What’s the point of hustling? Some argue it’s to achieve a dream, to make a lot of money, to leave a legacy, to earn significance, to make it seem like your life matters to someone other than your mom. Gary Vaynerchuk wants to buy a sports team. Why are these things important, and why do you have to work so hard and sacrifice so much to achieve them?

Hustling can be a disguise for workaholism. Think about it—if you’re dissatisfied with your life, work probably offers you some things that make you feel pretty damn good: money, gratitude, growth, learning, connection. If you’re an overachiever, working can become an addiction because of the gratification you feel from checking things off of your to-achieve list.

Many really successful entrepreneurs regret the time they missed with their families, especially their children. They were too busy hustling to spend quality time with their kids or partners or extended family and friends.

There’s so much more to life than work, people! And one day, work will end. Then what?


No amount of hustling will ever make you feel good enough if you haven’t defined what enough is. People will be proud of you, maybe envious, but most people probably won’t pay attention. For Elizabeth, enough was being able to be a stay-at-home-mom who could pay the bills, enjoy her work and her family. Her hustle was worth it because she knew her priorities.

This isn’t to say you shouldn’t achieve great things. If people didn’t hustle, we wouldn’t have iPhones or Teslas or electricity. It might even be impossible to innovate without hustling.

This is to say beware of the rat race cloaked in a shiny word called hustle, which can become a speeding train to nowhere that’s almost impossible to get off of.

What’s important to you?

Before you go chasing after some giant dream, put the dream under a microscope. Dissect it. What does that dream mean to you? Why is it important? What will the costs be and will the outcome be worth the sacrifice? How do your family and other relationships fit into the picture?

After rewriting this post five times, I think the answer is to hustle some, but always tie your drive into something truly important to you, whether that’s saving a species from extinction or achieving financial freedom for your family. It requires creative thinking and planning, and every once in a while, a step back to breathe and go for a meaningless adventure.

Elizabeth‘s greatest motivation is to spend more time with her family. What’s yours? Let’s continue this conversation in the comments. What do you think about hustling and the possible myth of the work-life balance?

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