What Grinds My Gears

Danielle Gillespie
5 min readMay 12, 2021


You have a great idea, now it’s time to grind. Or is it?

It seems that for the past few years we have all been bombarded with the message that in order to achieve any level of success, we must grind, grind, grind. People of all ages, but especially inexperienced entrepreneurs, appear to be susceptible to this flawed message. I believe that there are two fundamental problems with this model.

First: how is professional success defined?

Professional success means something different to everyone. For some, it’s the amount of happiness derived from the job, for others it could be the size of the paycheck, the number of layers between you and the top dog, the number of satisfied customers or countless other random qualifiers. What troubles me, though, is the emergence of a new, seemingly artificial, category: namely, the number of followers on a person’s collection of social channels.

There is an alarming trend to measure success by digital social clout rather than by the quantification of value creation. Admittedly, it’s easier to measure success in terms of likes, views, engagement, etc. rather than by intrinsic or long tail value being generated by intentional methodic progress toward an end game. But can digital social activity be accurately correlated with long term value?

I was recently doing some research for a company I advise (to provide context, it’s a gratitude app) looking for competitors in the space. While on Instagram we discovered a whole host of mommy ‘influencers’; women using photographs of their kids as a way to gain digital social currency. THIER KIDS! They dress them up, make them look PERFECT and take pictures that are then broadcast to millions of people on the social channels. This happens every day, sometimes multiple times a day. I can’t even imagine the therapy bills for those kids later in life.

Is this our new standard of success where the goal is to amass tens of thousands of followers and likes and maybe even an occasional paid sponsorship or two?

One particularly interesting subject is Mrs. Rachel Hollis, a woman who built an entire brand for herself by grinding day and night. Her most recent brand was based on a lie and when that bubble burst, she rebranded to something new. This seems pretty slippery to me but, she’s got millions of followers and a staff of people to push her rhetoric out on her social channels multiple times per day. Is that success?

Another one of my favorite examples is David Dobrek. Here’s a guy that published a vlog once a week on YouTube and amassed a following of 18m YouTube subscribers and 13 million Instagram followers. In the past year some of his controversially bad behavior was made public which ultimately lead to him being dropped like a hot potato, canceled from various platforms and sponsorships. The question is: in a year, except for his bad behavior, will anyone remember who he is. Is that success?

It’s hard not to look at epic digital social success and think, I could do that if commit to grinding every single day. But, before pursuing that path, I would suggest pausing to reflect on what happens to these people once they stop the non-stop posting on their socials? My guess: the world forgets about them. They haven’t left anything meaningful behind because there is no long-lasting legacy of genuine value creation. The entertainment they provided in the moment will be immediately filled by the infinite supply of other amusing content on the internet.

Success to me means that there is some lasting, genuine value being created that will endure even if the grind stops. I could be wrong though.

Second: what is the definition of grind?

As a founder looking for advice on how to hit the gas, too many roads point to The Grind. There are countless articles, books and certain unavoidable, well-known influencers (ahem, Gary V) selling grind like it’s at $2 floozy on 2nd and Broad. Here’s a news flash though, if these influencers stop grinding about The Grind, they become irrelevant.

Sure, in a handful of cases it’s been possible to translate millions of followers into some kind of paying customer but the problem is that once the grinding stops, there is nothing of substance left behind. The grind is necessary because the content has no “stickiness” meaning, the content being pushed out doesn’t have the staying power of substantial bodies of work.

So, what is grind? I found this interesting article that defines Grind versus Hustle and states, “Someone who is a grinder can work tirelessly and see no return. Their sense of fulfillment is found in the chaos of moving at a fast pace, juggling multiple tasks, or simply being busy.”

Grind is inextricably connected to social media and the constant demonic treadmill of producing content, liking, sharing and engaging.

If your main objective is to be Instagram famous for a hot second, then by all means, take the path of The Grinder. But, if you have a deeper, more complex objective and you feel stuck or stalled because you’re working hard but making no progress, you should stop what you’re doing right now. Take some time to evaluate your situation and start making intentional moves. I’m not saying you should stop working hard, I’m saying you should be intentional about how you spend your time. There is a reason that the phrase “work smarter not harder” is a thing.

With intentional hustle, the main question you should always be asking yourself is this: how does what I’m doing right now serve my customer in some meaningful way?

Understand what’s important to your customer and do more of those things and you will certainly find successful outcomes.

PS I’m currently collecting real-life stories about grind versus hustle to create a Hustle How-To. If you would be willing to spend a few minutes on the phone with me, I would love to hear what you’re up to and offer any help where I can.



Danielle Gillespie

Defining the intersection between technology and human connection (I also help entrepreneurs build rock solid tech products: daniellegillespie.net)