There is more information available to artists today than ever before. The problem is that most of it is overwhelming, a lot of it is inaccurate, and much of it is designed to build an audience on social media rather than actually help anyone. There is far more incentive online to go viral than to be correct. That environment makes all five of these mistakes worse.
Mistake 1: Making short-term decisions for a long-term career.
If your plan is to have a music career a decade from now, every decision you make today needs to support that. You cannot make career decisions based on desperation or short-term financial pressure and expect them to hold up over time. I see this most often when artists are at their most vulnerable, when they need money to market and promote in the early stages and someone offers them a lifeline. They give up far too much in exchange for what they think they need, often without even knowing what they actually need to succeed. It’s heartbreaking, because having one knowledgeable person in their corner at that moment could change everything.
Mistake 2: Spending money the wrong way for the wrong stage of their career.
Artists who don’t yet fully understand how the music business works, or how to build a fan base, often spend money in the wrong places. Specifically, they look at what established superstars are doing and try to replicate it. That doesn’t work. If you are at the discovery level of your career, you should not be spending like someone who is already touring arenas with a built-in audience. The strategy, the spending, and the priorities have to match where you actually are, not where you want to be.
Mistake 3: Signing agreements without an entertainment attorney.
This one still shocks me. The newest version of this mistake is artists running contracts through ChatGPT and convincing themselves that’s sufficient, in order to save $1,500 that could negatively affect their entire career and the rest of their lives. There is still no replacement for an experienced entertainment attorney. I have been in this business for 34 years and I still have one of my lawyers beside me every step of the way when I am negotiating a deal. That is not a luxury. That is just smart.
Mistake 4: Trusting the wrong people.
And it is not always strangers! Sometimes it is family members or people from their own inner circle who are leading them in the wrong direction, not out of malice, but because they simply don’t know any better. The music industry is highly specialized. The people who are genuinely great at what they do are usually great at one specific thing, whether that’s social media, content, radio promotion, publicity, or marketing. It is rare that one person has real expertise across all of it, yet I constantly see artists hire someone to manage every aspect of their career with no track record and no experience. I have seen more careers derailed by bad hiring decisions than by any other single factor. You would not let a dentist operate on your heart. Apply that same logic to who you let run your career or advise you.
Mistake 5: Not building a sustainable funding structure before they need one.
Too many artists wait until they are in financial crisis to figure out how to fund their career. By then, the options are limited and the desperation is high, which feeds directly back into Mistake 1. Artists need to understand early that a music career requires consistent capital, and that capital needs to come from somewhere that doesn’t cost them ownership or creative control or land them in prison. Building revenue streams, understanding your numbers, and having a financial plan before the pressure hits is not optional. It is survival.
And I want to end on something I genuinely believe. Most people in this industry are well-meaning. They came here because they love music and they want to help artists succeed. I do not think the majority of people in this business are here to intentionally destroy someone’s dream for a quick dollar. Maybe I have rose-colored glasses about that. But I have seen enough people come into this with real passion and real intentions to believe it. The mistakes I described above are mostly the result of inexperience and bad information, not bad people. That is actually the hopeful part, because inexperience and bad information are both fixable.
Learn more about Wendy and the resources she offers:
Through her coaching company, PowerPlays, she works directly with artists and entrepreneurs who are serious about building careers on their own terms. If you're ready to stop making costly mistakes and start making smarter moves, that's the place to start: www.ThisIsPowerPlays.com
She also writes regularly on the music business — no fluff, no gatekeeping — over on her Substack. It's free, and it's exactly the kind of clarity she brought to this conversation: wendyday.substack.com
