
Tomorrow morning, I will fly to Nashville. I won’t be on the ground long before heading to meet recording artist client Kaitlyn Croker for an interview I’ve booked her into on one of the local network TV affiliates. And that’s just the start.
She has a new single coming out this Friday, so this week her schedule will be absolutely packed.
There is no doubt in my mind that she is all in on her country music career. But for the artists out there who aren’t sure if they want to continue or not, this is how you find out.
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Wednesday morning I have her booked for another TV appearance, performing on one of the other network affiliates in Music City. She also has a podcast interview that afternoon.
On Thursday she is performing at a special event and then later that day will be interviewed on a live radio show that gets done at a local music venue. The next night she (pictured above) will be performing at one of the long-running and very popular writers rounds in town. And then Saturday night will be her release party. I think I have even left out one or two other entries on her agenda for the week.
During all of this, we have booked her for at least two other interviews that are not taking place this week.
You come through all that and you either ride the high, loving every minute of it and being filled with excitement, or you get the slap in the face from reality and resign yourself to, “That was all just too much. I don’t like all that pressure. I don’t like having to be go, go, go. I wasn’t enjoying myself. It’s overwhelming having so many people calling me, texting me, pulling me in every which direction.” And you become a statistic and leave Nashville to go back to your hometown, perhaps even giving up music.

When I go out to speak, a lot of times I will bring up – especially when it’s a podcasting event – that if you go into something with the attitude that you’re “just going to try it out for x months,” then you’re doomed to fail. After all, you’ve already given yourself an out. Heck, you not only have the timer running, but you even wrote the excuse, the note from your teacher, before you even needed to hand it over.
“You’re stopping your podcast?” “Yeah, but don’t you remember? I said I was going to try it out for x months.”
For that matter, when I have gone to speak to college classes I extol the virtues of doing an internship. But then I throw the students a curveball. I’ll tell them, “Sometimes take an internship just to find out that it’s not what you want to do for a living once you’re done with college after all.”
Somewhere in all this I feel like I should be saying something about developing thick skin. But in reality, that’s really just one entry on a lengthy list of factors that you can weigh in making an informed decision as to whether this is where you want to be or not. And by ‘this’ I mean location-wise and vocation-wise.
You might love playing live music, but you just don’t enjoy doing it at one particular venue or perhaps in a city or an entire region. That’s fine. But Smokey the Bear would always say, “Only you can prevent forest fires.” So, in this case, stop pursuing bookings where you don’t want to be and go to where you find happiness doing what you love to do.

One of the many great things about podcasting is that – again, unless you’re hired by someone else to do a show for them – you get to choose the topic, the format, the running time, the release schedule, and more. So, pick a topic that you’re passionate about and can still see yourself talking about “on the air” more than eleven years later, as is the case with me and my weekly “Now Hear This Entertainment” podcast that I started in February 2014.
This life is too short to do something that someone else told you that you should do. It’s been long enough since I threw down this pet phrase of mine that it’s alright for me to drop it in this week’s blog. Take a step back and be honest with yourself. Do a self-audit. If you were in Kaitlyn Croker’s boots, would you keep going after the week that she will have had once her head hits the pillow this coming Saturday night? Or, would it be, in the words of the late Kenny Rogers, time to fold ‘em?
For more than twenty years I have been helping indie music artists, authors, actors, entrepreneurs, podcasters, filmmakers, small business owners, and more. What challenges are you having in your creator career that I can lend some insight to? Connect with me so you can take advantage of all my experience, and I can help and keep you moving forward.