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Disruptive questions break your incremental thinking towards problem-solving, will shake up your reality, and help you find success in music.

The quality of your life, you personal satisfaction, and success in music are determined by the quality of your questions. So… what are you asking exactly? Are you stuck on asking, “Why not me?” Guess what? That will get you nowhere. Studying and improving your questions improves your understanding and the quality of information you receive in return. As you improve the way you think and understand by asking better questions, the more you’ll be rewarded with quality answers.

Let’s think about this within the dynamic of dealing with a significant other. If you are interested in getting to the core of a problem, assuming you want to stay invested in the relationship and you have any experience in maintaining a sincere connection, you know exactly what to ask to get to the truth. The truth can sometimes be painful to deal with, but the truth will set you free, right? If you’d rather dance around a potentially damaging issue, you ask vague, nondescript questions because you don’t really want to know what’s at the heart of the matter – or you don’t really care.

Some people are doomed to fail at relationships simply because they haven’t learned or are scared to ask the right questions. The same is true for your music career.

How many musicians are condemned to a life with a day gig they don’t really want because they don’t, won’t, or are plain afraid to ask quality questions? When you begin to seriously ask yourself disruptive questions, you’ll see a change. It’s the beginning of the quest to seek the knowledge you need to solve whatever problem is in your way.

Q: What are disruptive questions? A: Questions that are unsettling to your current status quo.

Disruptive questions are ones that poke holes in the stories you’ve been telling yourself. They are disturbing, and quite valuable. Successful people, corporate executives, even military organizations use an exercise called “Red Teaming.” The red team is a subsection of a committee or group whose job is to blow holes in current methods, assumptions, and theories. This exercise is designed to cut through the crap pretty quickly.

Disruptive questions

What’s the worst that could happen? So many times, the answer to this is, “They’ll say ‘no,’” or “I’ll be out fifty bucks.” So we sit around and do nothing instead.

What assumptions am I making and how can I test them? We all tell ourselves stories. This question attacks the stories – AKA assumptions – we all tell ourselves. Successful people do this all the time to ensure these stories have substance and aren’t just another excuse to not do something new.

I want to mention, the inspiration for this article is an incredible podcast where Tony Robbins interviews Tim Ferris. In the podcast, they discuss billionaire Peter Thiel, who loves to ask potential business owners, “Why can’t you reach your 10-year goals in six months?”

Questions like these break your incremental thinking towards problem-solving; they are practical skills you can put into practice to shake up your reality. Too many people see problems and not opportunities; they tell themselves stories like:

  • “I’m terrible at marketing”
  • “I can’t stand marketing, I’m an artist.”
  • “I’m stuck recording at home, so I can’t create competitive recordings.”
  • “I am dreadful at social media.”
  • “I’m a tech goon.”
  • “I have ZERO money to spend on ________________.”

Don’t believe everything you think

Successful people have the ability to recognize patterns, and so do you. When you first learned an instrument, you practiced other people’s patterns over and again until a mental synthesis happened and you naturally began creating your own patterns, standing on the shoulders of the songwriters you learned from. You’re unique, so your singular perspective is infused into your patterns, creating something that never existed before.

Whether you chose to take lessons or you cultivated an ability to pick up on patterns simply by listening to the artists who inspired you, you were getting an education. You were asking the right questions, so you were getting real answers and then executing a plan of attack. This same synthesis will happen with marketing and social media if you seek to be as exceptional at them as you are with your musical endeavors.

Seek an advantage: the more the better

Whether it’s you personally or someone on your team, you’re going to need some marketing chops to succeed, regardless of your talent level. But the best marketing won’t elevate a lame-ass product, so if your product isn’t competitive, you’d better start by fixing that.

This happens at every level of competition in any field. Take Terrell Davis, two-time Super Bowl winner as a running back for the Denver Broncos. Davis was not the fastest or biggest running back – not to mention his famous proclivity for migraines. What was his advantage? He outworked everyone else. He was the first on the field at practice and the last to exit: he earned success by working harder than his peers.

This is the kind of advantage that anyone can employ but almost no one does. If you outwork everyone else, 80-90% of all the artists out there disappear from your competition. And I don’t just mean play more gigs, record more songs, and practice longer than everyone. You also must work on educating yourself. Learn something new – like how to be a master at social media – and watch how it contributes to your success.

Everybody has different natural advantages. As the 4-hour self-help guru Tim Ferriss says, “We’re all flawed creatures, we’re all imperfect. The most successful people maximize one or two strengths.”

Which sets up these questions:

  • What are your strengths and what are your weaknesses?
  • How can you maximize your strengths?
  • How can you improve on your weaknesses?
  • Can you see an opportunity for growth and change?
  • What are you going to do about it?


Music Release 101

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