Jay-Z’s 4:44 and our cultural obsession with entrepreneurship

If you are a hip hop aficionado or someone who is remotely familiar with popular culture then you’ve probably heard the buzz surrounding Jay-Z’s newest album, 4:44.

My musical tastes are quite eclectic, so I don’t profess to be an expert, but I will say that there were elements of Jay-Z’s entire album that really resonated with me as an entrepreneur, especially his discussions surrounding credit, ownership, and generational wealth. Listening to his album really made me think about the importance of messaging about entrepreneurship.

If you peruse most major financial publications like Forbes and WSJ, there is quite a bit of hype surrounding entrepreneurship. These outlets tend to be geared towards individuals who are formally educated, highly trained, and experienced in their industries.

Juxtapose that with 4:44 and it’s self-evident that its audience is slightly more nuanced and diverse—this is not to say that WSJ subscribers don’t also love hip hop. My point is that different mediums and messengers use different tools to reach their targeted audiences. Regardless of one’s age and education level, many of us see entrepreneurship as a chance to claim our slice of the American pie and live the quintessential American Dream.

As much as I love this push to increase entrepreneurship and make people more aware, I also think that it’s important not make it seem as if it’s so easy, because it’s not. In fact, being an entrepreneur is the most difficult thing that I have ever done. Six years in the game—as they say—and I am still figuring out how to navigate this space.

My point is that the pathway to entrepreneurship does not come with a universal GPS that leads everyone down the same road. In fact, sometimes the GPS may warn: Unknown roads ahead, proceed with caution (I actually encountered this for the first time over the weekend while driving in squares—not circles, but squares—in a small southern town).

Similar to my driving experience, there are many of us who enter this space not sure of where we are going; we just know that we are heading somewhere and that we will eventually get there, even if it’s not the way we planned. Along the journey, some of us decide that entrepreneurship is not for us. Some do it because a traditional work space is not an option, and others, like myself, are so deeply passionate about what we do that we figure the business “stuff” out along the way.

Between 4:44 and my second quarter (which was horrible with contracts falling through, unpaid invoices, and promises unkept) I have been thinking a lot about what it really takes to stick to this.

More than anything, entrepreneurship requires commitment. No matter how skilled you are or how innovative your services or products are, you must have the fortitude to stick with your game plan or revise it if it no longer works for you.

Like many of you, I sometimes work seven days a week and my daily schedule fluctuates. Because I offer both products and services, there are certain things that I can’t delegate to my team. And as much as I love automation and technology, I am old school and thoroughly enjoy responding to clients personally or doing virtual coaching sessions because a phone call isn’t enough. With clients on both coasts, I try to accommodate as many business hours as possible. However, I avoid promising anything EOD (end of day) or COB (close of business) because depending on the time zone, that is a recipe for disaster. My commitment to providing my clients with exceptional services and memorable experiences pushes me to be a better businesswoman. It also opens the door for failure.

Paradoxically, we must also accept that failure is often a part of our journey towards success. I can’t think of a single entrepreneur who I have worked with or taken on as a client who has not experienced some form of failure. Failure can be defined in numerous ways, but ultimately, I see it as something that did not go as planned—this can be as straightforward as not being awarded a contract to something as complicated as not having the cash flow to pay your business expenses. Regardless of the context, the key is not to stay in that space; instead, learn from your failures, grow from them and push forward.

I am, obviously, not trying to discourage anyone. I just want to add a sprinkle of realism to a larger cultural (and generational) conversation that we seem to be in the midst of.

So, whether you read about the entrepreneurial life, live it, or listen to it, just go into it knowing that your experiences will be as unique and highly configured as you are.