Diary of an upcoming rapper

Taiwo Ash
7 min readOct 18, 2022

Years ago, I read one of Barack Obama’s memoirs. In it, he described his successful career as a lawyer, and the good reputation he enjoyed. When he disclosed to colleagues and community members that he wanted to go into Politics, they commonly asked him, “You’re a nice guy. Why would you want to get into Politics?”. Barack would then proceed to give one of his great speeches on why politics needed a nice guy like him.

In today’s world, there are many popular careers and public positions that the average Joe could go for, thanks to the Internet. You could be a politician, like Barack Obama became, an Instagram Influencer, an actor, or most infamously, a rapper.

There used to be a time when rock stars — artists in the rock genre — were the most successful in terms of sales and public celebrity. So much so that the phrase rock star has come to mean a person who is wildly successful. In the 2010’s, rappers are the new rock stars. The music space is more fluid than ever, with genres continually merging and evolving. But rap has enjoyed a level of mainstream success that is unrivalled by any other genre. Rappers are famous, controversial and cultural icons.

I am a lot of things. An ardent Christian, from a good home, with an envied professional background. Gifted in many ways, friendly, and with a positive outlook on the world. When I tell people that I am into music, it is fair. A lot of people are into music these days. Heck, the internet of things has made it possible for hobbies to be explored and developed like never before. When I go further and say that I rap, I feel the concern that Barack’s friends felt for him. You’re a nice guy. Nice, normal guy. Why would you want to be a rapper?

If this was all, it would be fine. But it goes further.

Can you rap, actually? What do you rap about?

Do you think you stand a chance? In a world where everybody raps, and an illiterate gang-member can crossover from a life of poverty to all the success the world has to offer using this art form, it’s a good question. When Lecrae was told by his sister-in-law that a friend of hers rapped, a friend who turned out to be Derek Minor, who became a colleague and longtime collaborator of Lecrae’s, he responded “Everybody raps.”

If this is someone who knows I’m a Christian, the question is Oh, gospel rap?

If this is someone who is not a Nigerian, the question is Oh, do you rap in Nigerian?

I used to sing and still can. If this is someone who has heard me sing, the question is Why not sing instead?

People would also tell you to instead become a songwriter or an audio engineer. Anything but be a rapper who raps. That’s too big a goal, too unrealistic.

I don’t think there’s any successful person — rapper or not — who did not have to overcome rejection and naysayers to get where they are. Every rapper has their story. One of the most inspiring, as it relates to me not being a good candidate, is Drake. A mixed-race, well-spoken Canadian actor from a broken home, who grew up in poverty. One who loved music and had a dream. It was not enough for him to get a good job and live happily ever after. He went for his dream and manifested it, as he likes to say. I think if he could make it, anybody can.

Often, at job interviews, one is asked about an entrepreneurial venture they have tried their hands at. The aim is to see that the person has drive and the necessary skills to pursue a goal and execute it. Being an entrepreneur is challenging in a unique way. I’ve heard it said that being a CEO is the most fulfilling job for a multi-talented person because though it’s challenging, it enables expressing one’s different abilities. I was told once by a Life Coach who had been through a lot in life, that being an entrepreneur was the hardest thing he had ever done, harder than beating drug addiction. I think being an upcoming artist — having the dream of being a viable rapper and working towards it — is just like being an entrepreneur.

I think it’s no different, maybe even more challenging. You have to be ready to fail a thousand times and get back up again. I see this pattern in the stories of rappers like Nikki Minaj, J.Cole, Kendrick and Kanye West. Rappers like Falz and M.I. Kanye with all his production credits and being close to many industry experts, still had to fight hard to be heard and become successful.

In a way, I think it’s an honour to be a rapper. There’s this head-swell when you hold the mic, and anticipate the beat-drop. Knowing that people are waiting to be scintillated. Few things compare to the crowd going wild when you climax. I think it’s an honour and a designated position in society, like a priest or a doctor. It’s being trusted to fulfill a role, the role of being cool and relevant and inspiring. It’s like being a prophet, almost. I have enjoyed some success, some validation. I have also had times of necessary failure, times of putting out substandard output and not realizing it till after the fact.

What do I really want out of this? Someone asked me this once. He said I could not possibly perform at parties and get paid for it. This was such a comical, fairly insulting thing to say. Sometimes I wonder just how silly they must think me to be. Clearly, they did not know about things like streaming and merchandising, and shows? Regardless, my ambition is pure and not inclusive of greed or hope of gain. Pure in the sense that, I just like to do it. I just like to tell stories. What I want out of it is not necessarily to make a living out of it. That’s a great desire, if someone wants that, but that’s not me. To quote a South African rapper: There is the music industry, and there’s the music business. Or Pimp C who said You’re over there rapping for fun, we’re out here rapping for money.

I don’t dream of getting money from this, but if it comes, that’s fine. We know that it possible to gain notoriety without income ; ask David Chapelle. I can’t get cheated like he did because I would never sign anything — thanks to the internet for enabling the average Joe like me to pursue his rap dream. If it was possible to get leverage without fame, I would choose that too. I know I have different tickets to celebrity, and this is only one of them.

I think I would be in good company to be a rapper. Lots of rappers are really smart people. But, before getting validated, I have to live that reality of looking like a bum. Ah yes, that’s one of the perils of this path. When nobody feels what means so much to you, you are forced to question your own taste and sanity. Am I deluded? You’re forced to deal with shame and scrutiny. I wonder sometimes, why I am putting myself through this? I know many friends who have outgrown their love for rap and settled down. Am I stuck in a childhood fantasy? Is it too late for me? Am I just not good enough, and will I ever be? These are questions I have to live with everyday. It’s tough out here.

I’m grateful to be alone. I have had some girlfriends who really believed in me. They were amazing people. One of them even offered to help me with getting my music out there — this was one of the first things she said to me as a stranger, and she was not even a marketing professional or anything. The other one was always happy to listen to anything I did, and offer feedback. We even wrote lines together sometimes. But they aren’t here anymore. Not even as friends or anything. I think it’s good to keep building in obscurity. Proving my work to myself. As the Bible says about God, even if we are unfaithful, He is faithful as He cannot deny Himself. I think it’s good if I succeed, so they can see. Not to spite them or anything ; they were great. Things just happened. Succeeding would be something they would like to see, even though they may be spiteful of me presently based on things that happened. This isn’t about that, but I am fine admitting my wrongs because I tried my best to make them right, and never intended to hurt them.

It’s not easy being a wanna-be. Burning through contacts and acquaintances you can share your music with. Often, they don’t give feedback, or let you know that they don’t feel it. You don’t enjoy going from a monkey on a tree, to a fish on a tree. That is, being clearly agile on adept in other things, but appearing to be lame and inept one this one thing. You don’t enjoy people feeling used after a while, because here you come again asking them to listen to your stuff. You don’t enjoy how this music puts a strain on relationships. You’re upset because they did not support, and they’re trying to avoid you because of how you get about all this. But we have to keep going, and keep learning how to do manage relationships and do things better. I do want to prove to everyone who came across my music that this dream was valid after all. It’s honourable to be in this position where it’s you against the world. It’s honourable to dream and believe. To put your dream above your ego and feelings in the short term. It’s honourable to keep going.

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Taiwo Ash

writing is the primordial soup from which all [my] other expressions evolved.