Four Things Every Artist Must Do to Fail at Their Career

June 22, 2018

Throughout my early 20s, in college and then in my career as a software developer, I nursed a dream. I wanted to become a professional singer–songwriter and make a living off my music. During the summer after my senior year at college, I wrote and recorded a six–track EP. It was nothing much, but I learned a lot about recording and songwriting, and I was proud of it. I even got my graphic designer roommate to design the cover art. I put it up on Bandcamp, and droves of people showed up to praise my genius and beg me to take their money.

Wait. Maybe I dreamed that part.

Probably a total of no more than 20 people have ever heard that EP, and most of the ones who did probably thought it was shit. You may think that I would’ve just hung up my guitar at this point, but nope, I had more in me. If I was going to fail, why not do it right? I’m writing this article so you can replicate my success (at failing). I’m going to outline exactly what to do, and why, in order to send your artistic career straight into the ground. This applies equally well to painters, writers and entrepreneurs, so listen up. Here are the secrets:

Avoid Facing Reality

I had a naive, rosy picture of being a musician that involved adoring fans swooning and screaming my name as I played my heart out onstage with only a guitar and a great song. I went to open mic nights and expected people to put down their beers and listen to me. They didn’t. They laughed with their friends and completely ignored me as I debuted songs I had poured myself into. So I got upset. I took my keyboard and went home fuming at their lack of respect for art.

I failed to realize this is the kind of thing musicians do to perfect their performance skills, hone their craft, and eventually, develop a following. You play bars, travel on a shoestring budget, making just enough money to get to the next town, and you’re happy about it. You love it, because you’re sharing your music.

That life sounded terrible to me, and that’s why I never faced the reality of what it would be like not to dream about being a musician, but to actually be one. I wanted none of the bars, driving hours just for a chance to perform for pittance, late nights, sleeping in my car, and waking up hungover the next morning to do it all over again.

I do think it’s possible to become a successful musician without that stuff. Maybe on YouTube or SoundCloud, through social sharing. But you still have to hustle. The quickest way to fail in any industry is not to get the lay of the land, not to understand what you’re up against. Once all your dreams are shattered, then you can start laying a solid foundation on which you can build a successful career.

So keep your head buried in the sand, and dream on.

Abandon Your Work

After recording my first EP, I realized I needed assistance to make a better record. I wasn’t knowledgeable enough about recording, and I didn’t have the proper equipment and experience to put together a really solid track. So, I asked Jeremy, a musician friend whose work I loved, to produce a new EP with me. I flew to Nashville for two separate sessions, and over something like four days total, we recorded six tracks. All in all, I think I poured $6,000 into it, as well as many hours of hard work. We had French horn, pedal steel, strings, and a great percussionist. Jeremy wrote some amazing harmony parts for the session musicians.

I remember chatting at some bar or restaurant in Nashville. We were talking about what to do with this project, thinking I could do a short run of 200-500 CDs and sell them online, by playing gigs, giving them away, whatever. Anything to get my music in the hands of people. I knew it would be a lot of work, but I thought I was ready to take on the challenge.

I wasn’t. I researched doing short runs of CDs, but I never pulled the trigger. I remember some technical hurdle relating to the cover art, but mostly, I was probably too busy spending my money elsewhere, and trying to avoid doing any of the not–so–fun tasks in a musician’s life. I had no audience, no fans, no following. No one had heard of me. Yeah, I made something that I thought was pretty good and worth sharing, but I abandoned it before it even had a chance. Records are a dime a dozen. Artists who stand behind their work and fight for it are the only ones who will be paid attention to. No one else is going to do the work for you. So if you want to fail, abandon your project before it ever sees the light of day.

Ignore Marketing and Focus on Creating Great Work

This is the “if you build it, they will come” fallacy. They’re not coming. They don’t give a fuck. No one cares about your work more than you do. That’s why you have to lead. You have to show them why you matter, why you’re worth listening to. And this has to be a major platform in your business. It can’t be dabbled in. Connecting with an audience is the lifeblood of any creative. It’s not a step you get to skip.

Without a solid marketing plan, your work will languish in obscurity. It’s not enough to be a great craftsman. Sure, that counts for a lot, and your chops will draw people to you, but first, they have to know that you exist. Obscurity is your enemy. Not piracy, not Spotify, or the poor tastes of the American public. If your work is good, people will connect with it. If it isn’t good, learn from it, and get better. Find the people who will become fans and champions of your work for life.

Being a musician, or a painter, or a writer, means going into business for yourself. Rid yourself of the notion of the solitary artist working away in her studio, letting someone else handle the money. You need to take control and handle your shit. Learn about marketing, contracts, publishing, record deals. Don’t let yourself be taken advantage of. Get creative with your outreach and find ways to connect with people authentically. Marketing can’t be an afterthought. And it’s not just running Facebook ads or trying to get your music video to go viral. It’s your strategy for having a great product, figuring out exactly who that product is for, and how you’re going to get it into their hands. But I urge you to ignore this advice, if you want to tank your fledgling career.

Give Up Early

Last night, I watched an interview with a writer who spent 16 years writing before he ever got traction. 16 years of tenacious effort with not much to show for it, until he finally had a breakthrough. I would’ve given up long before then. In fact, I suggest you do, too. Go dig ditches or write software or something. This shit is hard.

Some people appear to come out of nowhere and absolutely crush it. Leo Babauta got a book deal within a year of starting his blog, Zen Habits. In his book announcement post, Leo says:

I’ve dreamed of being a published author since reading Lloyd Alexander, Watership Down and other such favorites in elementary school. I always wanted to be a writer in some form, and during my years of journalism, I always told myself that even if I wasn’t writing polished prose, at least I was working as a writer, crafting words, and that my book deal would come … someday.

Years of journalism. Always wanted to be a writer. From what I can tell, it takes most people 5–10 years to become an overnight success. This is why you should give up early. Put in six weeks, or six months, then quit and watch Netflix. It’s more exciting, and the pay is better.

Seriously, though, expect to put in at least one to five years of hard work whose only reward is the work itself, and the lessons you learn. As Seth Godin says, you have to earn attention. It doesn’t come cheap. Be worthy. Or go eat chocolate.

But whatever you do, don’t take my advice. I’m a failed artist.