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Why We Need To Change Our Relationship With “Hustle” In 2020

Long hours and hard work are necessary sometimes — as long as you're doing it for the right reasons.

I’ll admit it. I was a hustler. Back in the early-Internet ’90s, I ran my first business — a mail-in matchmaking company called iFluRtz — out of my dorm room. I’d get up at 4:45 a.m., log a few hours of work, then race off to class. Then, I’d rush back in the afternoon to check my faxes and get on the phone with customers. At night, my business partner and I took turns grabbing a couple hours of sleep on the floor, while an old-fashioned Scantron machine hummed away next to us, spitting out the results of our dating questionnaires. 

I know what you’re thinking: that’s just a classic example of “bad hustle” — an entrepreneur pushing himself too hard for the sake of his business. But I’d disagree. I was doing exactly what I wanted to be doing and loved every minute. 

Right now, the entrepreneurial world is re-examining its relation with work-life balance — and rightly so. When Elon Musk broke into tears describing to the New York Times how his 120-hour workweeks damaged his life and business, he laid bare the dark side of a success-at-any-price mentality. Our generation has learned that working longer and harder doesn’t necessarily equal happiness. 

That being said, hustle will always be part of the entrepreneurial equation. Long days and sacrifices are the cost of admission. But, to me, the key to sustainability is recognizing the critical differences between good hustle and bad hustle. Here are some tools I use to identify good hustle — for myself and the entrepreneurs I work with — and ways to keep on track. 

Do you. 

First, stop thinking there’s a standard definition of hustle or success when your definition should be highly personal. I love Gary Vee, the serial entrepreneur and author. But his idea of full-on immersion in work, all-on, all the time, doesn’t work for me at this point in my life. Too many entrepreneurs treat success advice as gospel, when it’s highly contextual and situation-dependent. Even Gary Vee admits he’s an anomaly.  

Instead, do you. Stop listening to me — and all the other experts out there sharing advice — and take a deep look inward. We’re all wired differently, with different notions of success and different ideas of happiness. If you’re forever trying to live up to someone else’s idea of hustle, you’ll never really be satisfied.  

Hustle with purpose.

Hustling right — figuring out where to double down and where to ease up — has to start with the “why.” Why are you in this in the first place? What truly motivates you? For some people, this may be financial security. For others, it might be the thrill of changing people’s lives or the desire to give back. For me, initially, it was the simple excitement of being my own employer and seeing technology disrupt the status quo. 

The only wrong answer (albeit an all-too-common one) is to hustle for hustle’s sake — to log marathon hours just to say you have or because you think you should. That’s the opposite of purpose. Find your calling and work backwards to determine what kind of hustle will get you there.

Equally critical: your purpose changes … and that’s OK. For me, the financial motivations for hustle, like fancy clothes and cars, started to seem shallow when I was still in my early 20s. I had evolved, and my hustle had to evolve with me. Giving back — to fellow entrepreneurs, to family, to the community — became a big part of my “why.” I used to love lacing up flashy new kicks, but now I find far greater rewards teaming up with friends and fellow entrepreneurs to stuff Christmas stockings for a children’s charity like KidSafe

Make peace with sacrifice. 

So many formulations of good hustle today seem to imply that you can have it all, if you just achieve the right work-life balance. I’m not sure this perspective is healthy or if this type of perfect balance is even possible. Rather, good hustle is about acknowledging and being deliberate about what you’re willing to give up. It might be a hobby. Or sleep, for a time. Or even success itself. When I was young, I had a goal of becoming a billionaire and owning a sports team. But I was more than willing to sacrifice that for the benefit of having a family and a partner I love and spending time with my kids. 

The simple truth, to really tell it like it is, is that you can’t have it all. The sooner you stop chasing that unattainable ideal of perfect balance, the sooner you’ll be able to find peace with your sacrifices — making them in a way that’s deliberate, strategic and on your terms.   

Remember to take your “work heartbeat.”

Good hustle requires constant quality control. You can’t just set it and forget it. Instead, you’ve got to make sure you stop and check your “work heartbeat” — at least once a day. Ask yourself: “What am I actually putting my energy into right now? Does this really align with my “why”?” If you don’t take this pulse, it’s far too easy to let your hustle go astray.

This is especially true in the startup environment, where there are always 50 things you could be doing — enough to consume all your waking (and sleeping) hours. To keep on track, I put a simple reminder in my phone each day that describes my overall purpose and my three most-important tasks to get me there. That way, I’ll know to focus on getting my Q4 financials submitted, rather than killing the day on lesser priorities and then having to work late. I also use a low-tech metric to keep tabs on hustle — the tone of my wife’s voice tells me in a heartbeat if I’ve over-indexed on time at the office.

More is not better. 

We’ve probably all logged 60-, 70-, even 80-hour weeks. Yes, it sounds heroic. But be honest: after a certain point, there’s an inverse relationship between productivity and hours worked. At several stages in my career, I found myself working long nights and weekends. Invariably, these extra hours were poorly spent. When I stepped away from the office — when I made time for the gym, for friends and family, for sleep — I’d come back with renewed focus and get a whole lot more done.

Nor is working crazy hours sustainable in the long run. This hit home for me recently after a health scare — I’ve usually kept good exercise habits, but at times I’ve allowed work to push diet, sleep and time with friends and family aside. It took a doctor’s visit to see the true impact: skyrocketing cholesterol and concerns about clogged arteries.

Science tells us what we should already know: that we’re more productive when we get enough rest, eat a healthy diet and spend time with people we love. Yet, it’s so easy to forget those proven productivity boosters and try to power through with caffeine instead.

At the end of the day, all of these points coalesce into a pretty simple “good hustle” test for me.  Ask yourself: If you could change things, would you? I’m not talking about the small parts of our jobs we all have that we don’t love. But if you had the chance right now to do something completely different, somewhere else — would you jump at it? If so, you’ve just told yourself you’re hustling in the wrong direction, and it might be time to make a change.

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