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Girl asking question of guy wearing glasses staring at whiteboard
By: Bruce Wawrzyniak

So many times we’ve heard the hypothetical situations posed to us.  “What ONE person, dead or alive, would you have dinner with if you could?”  Or people, of course, ask, “What would you do if you won the lottery?  How would you spend all that money?”

There’s a long list of these types of scenarios, none of which are anything realistic.

So, when it comes to your career – as a songwriter, as a YouTuber, as a podcaster, or even as an entrepreneur (many times a solopreneur) – what if you could only ask ONE question to someone you see succeeding in your field?  I’m not being hypothetical here.  I’m actually going to tell you what that one question should be.

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In fact, if you’ve been listening to my weekly “Now Hear This Entertainment” podcast long enough, you should already know the answer.

It’s not even a specific question, meaning, there isn’t an exact script you need to follow.  But rather, it actually just boils down to one three-letter word that you should be asking those people.  You’re seeing them have success with what you’re trying to do so you obviously want a formula, some tips, some insider hints so that you too can be optimistic about getting similar results.

Nail Your Media Interview

That word that you want to start your question to them with is, “How.”

Using the podcast example, I’m often heard asking guests, “How did you get your latest recording project entirely funded through (insert platform here, such as Kickstarter, Indiegogo, etc.)?”  Or I might say, “How did you get to open for (insert A-lister here, such as Brad Paisley, Alan Jackson, etc.)?”  A lot of times I inquire with my guest, “How have you gotten film/TV placement for your song(s)?”  Plus, since I know that a lot of people listening to the show are aspiring performers themselves, I’ll ask, “How have you gotten booked at all of these great venues (such as The Bitter End in New York, Hotel Café in Hollywood, House of Blues, etc.)?”

Think about it.  You want to get similar, if not the same, opportunities that you envy seeing others like you get.  Right?  You watch what’s coming their way and you think, “I’m as good as them.  I should be doing the same types of things they are.  What the heck?”

And so, you ask them HOW they are getting these opportunities.  Specifically.  The worst that can happen is they don’t tell you.  But hopefully they will tell you something helpful.  It might be who the person was that made it happen.  Perhaps they even offer to connect you or at least give you a name and phone number and/or email address (in which case you say, “Can I drop your name?”).  Sometimes they might be vague and say, “Oh, a friend of a friend.”  In that scenario you have to tactfully see if they’ll open up a bit more.

Don’t be afraid to ask those follow-up questions.  If they tell you about something that they got paid for, once you get the contact information then say, “Do you mind if I ask what something like that pays?”

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In all of these cases you have to keep in mind that the less you ask, the less information you’ll get, and you really won’t be too much further ahead after all, as compared to sitting back and watching this all unfold in front of you as you wonder, “Why them and not me?”

In fact, I’ll bet you have questions like that for me, what with all the people that I’ve helped across the country for close to 20 years now.  I’ve been fortunate to work with indie music artists, authors, entrepreneurs, podcasters, and small business owners.  Let’s chat through the Owwll app so I can help you out with answers to whatever has been challenging you.  I’d welcome the opportunity to speak with you.