The Independent Artist’s Grind – How To Make It Work (I Think)

As a performance/recording artist, I wear a lot of hats. I have yet to come to the point in my artistic career where I just sit around and focus on creating while everything else takes care of itself. I still have to write, record, find music, producers, musicians, conceptualize my live performances, book shows, work out the logistics of the shows I book, organize rehearsals, promote, build/update my website, style myself, purchase onstage attire, arrange transportation to/from shows, get payment from venues, and all that other stuff really successful artists have other people do for them. I have had a measure of success at doing those things, and from time to time I get asked for advice on how to do those things successfully. I always feel weird about giving “advice” per se, because I don’t feel like I’ve done so well that I’m in a position to advise anyone. But what I will say is that I’ve seen a lot over the years, and I have seen what worked and what didn’t work for me and for others. And I definitely don’t mind sharing what I’ve observed, so…here are the things I recommend an independent artist do if they wish to place themselves in a position of being a professional independent artist – meaning making money at what you do. This is the shit you gotta do to stand half a chance and you still probably won’t make it as big as you want to.


This is part one of two parts.



I’ve seen lots of artists make the mistake of actually trying to become friends with the people they want support from. They mistakenly believe that this friendship will automatically translate into support for their artistic efforts. Nope. I mean on occasion it does, BUT more often than not it doesn’t work like that. You know that saying “familiarity breeds contempt”? No place is it more true than in the artistic arena. Most of my friends, the people I’m closest to, have NEVER actually brought any product of mine, or paid money to see me perform at my shows. Many have never heard my work. And this is especially true of my friends who are artists themselves. You have to make a distinction from your “fan/friends” and your “friend/friends”. And you have to have more of the former than the latter if you’re trying to make money with your art. As soon as someone feels a great deal of the familiarity with you that comes from genuine friendship, or the camaraderie that comes from having a similar level of talent, they don’t feel as compelled to spend money on your art – in part because they support you in so many other ways if they’re actually friends with you. I have lots of artist friends who I don’t speak to very often, but they’ve hit me up late at night or early in the morning (because artists just don’t sleep at night for long periods of time) for conversation about different things that have meant a lot to me, helped me, uplifted me, even inspired me. They will NEVER buy a CD from me. And I’m okay with that. It would never occur to me to ask them to. The more you befriend your fan base, the less money you’ll make on what you’re trying to sell to that fan base. Fans can be cordially acquainted with you, but at the same time need to feel a certain distance from you, even if you’re in their circle. They need to feel you do something they could never do. There has to be a certain kind of awe they have for you. When someone thinks they can do what you do, chances are they won’t buy what you do from you. Most of the people who spend money on my CDs and shows are strangers who are just amazed at what I do. That is what you need as an artist to make money – more fans, less friends. Learn the difference.



If you are a musical artist, there is less and less money in recorded music these days, so an artist has to be prepared to perform live to make money and sell product. And your live show needs to be good enough to make people buy product and become interested in you. And because only the superstar performers can fill the huge venues anymore, the small/mid sized venue ends up being the place that sees the most action as far as live entertainment goes, and where most artists end up. So that is what you should shoot for as an independent artist ONCE YOU HAVE A GOOD LIVE SHOW. But many artists overestimate their talent because they go to a few venues where they are “known”, perform in front of an audience full of mediocre/non-existent talents who gas their heads up, and the next thing you know the artist starts to think that they “run this city” or whatever. Nothing is worse than seeing a bunch of local artists at a venue all performing for each other and “bigging each other up” while the actual fans (of which there aren’t many in the audience in the first place) walk away. Performing at your local hangouts endlessly will give you a totally twisted sense of your skill and abilities as an artist and your ability to market what you have to offer. It’s the worst thing you can do if you really are trying to get “out there” and trying to be more than a big fish in the small pond that is your local scene. Of course you should support your local venues because they are a great place to get your feet wet and get exposure early on. They are a good place to start building a fan base too. BUT you have to know when it is time to leave those places and try your hand at other spots. The truest test of one’s skill as a marketer is the ability to book a show in a venue or at an event where NO ONE knows you. If a promoter or booking agent has to go on your website and look at your promo kit, will they take you on the strength of that alone? The truest test of one’s skill as an artist is to kill a show where NO ONE knows you. I can’t stress how important it is to perform in unfamiliar places and to see other people that you don’t know performing too. It gives you a much better sense of how good you actually are, it exposes you to new people (and artists always need new fans), and it gets you outside your comfort zone. The worst thing an artist can ever be is comfortable.



Independent artists don’t have a lot of money to spend, so they have to careful where they do spend it. One place that one shouldn’t be cheap is when it comes to your online presence. That means a fully functional website with lots of statistical data for you to review, a blog, a Facebook page, a Twitter account, Instagram, Reverbnation, Soundcloud, and on and on and on. And all of these social media should display professionally done pictures of you, especially those of you performing. Your head shot is great and definitely an asset, but pictures of you onstage are gold, and professional shots are platinum. This also goes for performance video of you – you need to have some that is professionally shot and edited. If all of your You Tube footage is from various camera phones, that is a problem. And professionally done shots of you should be updated fairly often; every year and a half at the most. Why? Because when it comes time for you to book a real gig, this will probably be the only things a booking agent will have to make a decision about you. So you need to make the best presentation possible IN ADDITION to your stellar talent.



The idea of presenting a “tester” to get people hooked and ready to pay next time around is a concept as old as time. But illegal free music downloads really began perpetuating the idea that free music is the norm, and should be expected. Now I’m a rather old school person and the idea of totally giving away what I worked on so hard really just makes me sick, especially since I grew up in a time when people didn’t expect free music. To me, you can’t get people to pay for something once they’ve gotten used to getting it for free, and I personally think that’s a lot of the reason why artists just don’t sell as much as they used to. But these days if you’re a hip hop artist especially, it seems to be expected that you do a mixtape. And I do hear music fans say “if I like an artist’s mixtape, I’ll be checking for them when they release something”, so again I get that concept. But then you have those situations where the mixtape music is better than the actual release. And then as an artist you have to consider if you give away a lot of your music on mixtape after mixtape, are you devaluing yourself as an artist? After all, the point of all this was to sell some music at some point, so if you get to be known as the “mixtape artist”, will an audience pay for your music, or will they just say “I’ll just wait to hear his next joint on that next mixtape release”? With all that said, I get the idea behind mixtapes, but I do think it is crucial to be strategic about putting them out. If you’re going to do mixtapes, I think you should be clear about what you’re trying to accomplish with them, what you’re trying to build with them, and where do you plan to go with them. Mixtapes should be a vehicle, like a bus or a train, something you use to get somewhere. If you’re just putting out mixtapes because “me and my man made some beats today”, that’s just crazy, and every time you put out something that is less that your best, someone is going to hear it and pass you by. Plus the market is so flooded with mixtapes why should someone pay yours any mind? So every mixtape you release should have a plan, should accomplish certain goals. You should know how long you plan to be on the mixtape circuit before you finally make the leap into paid music/performances. So release your mixtapes with good solid work, understand what you’re trying to build and create with them, and make sure you have a plan to transition from mixtapes into a product that makes you money.

Lastly…and most importantly…recognize when you’re gaining momentum and capitalize on it.

I’ve learned about this one the hard way. If you’re good at what you do, work hard in a strategic way and get really lucky, opportunities will come your way. I’m not saying you should jump on every opportunity just because it shows up, but WHEN they show up, take full and complete advantage. Have no pride and have no shame. Go as hard as you can to look at every possible thing that opportunity could offer you, and go after them all. I have been in the position many times where I was offered an opportunity that could have pushed me forward, and I didn’t take it. In my experience, missed opportunities occur when you are too shy to fully access everything the opportunity could offer you OR when you’ve got some kind of shit going on in your personal life that messes up your judgment. For me, most of my bad decisions regarding my artistic career happened when I was going through some drama with some dude. I let the energy I should have been putting towards the opportunity go towards him or whatever we were dealing with and I fucked up. Or my feelings towards the relationship compromised my business sense. I am happy to say that after having this happen more than a few times I finally got it, and now I am becoming savvy enough to understand the rare gift that opportunities are, and the dire importance of capitalizing on them. Please learn from my mistakes. Don’t think another chance will come around because quite likely it won’t. So when fate smiles on you, drop everything and make it work.


That’s all I got. Good luck to you!