Flops 005: The Song of Regret

Flops 005: The Song of Regret

Karen Beattie:
Some things need to be just right before they're shipped, like the Boeing 737 Max, which had a faulty flight control system and tragically caused two fatal crashes, leading the plane to be grounded for nearly two years. Other kinds of products can be released well before they're finished or before it's even clear what they'll eventually become.

But creative work falls into a murky gray zone. When is a piece of art ready? When is it done and ready to ship?

Right before halftime of Super Bowl XLI in 2007, musical icon Prince was about to go live with the 12-minute set that would be widely considered the greatest halftime performance of all time.

But right before he and his band stepped out on stage, Prince made a last-minute decision to ax three horn players. They had been key elements of the show, right until the 11th hour and 59th minute. But as soon as he stood on the precipice of performance, Prince saw something. He knew what he wanted and it didn't include horns.

No one can say how the show would have turned out if the horn had been allowed to play. Nonetheless, the results of his decision are hard to deny: It was a show for the ages.

Prince was a notable perfectionist, but he also had an incredible discipline and work ethic. His engineer, Susan Rogers once said, "He would have been a great general in the army. He has this extraordinary self-confidence coupled with extraordinary self-discipline and tempered by a really clear self-critical eye." Yeah, Prince was special.

Even the most talented musicians, like this week's guest, Jason Myers, sometimes find that trust in one's abilities doesn't always carry the day. Sometimes you need something more to push you to call it done and actually ship your work. To have the confidence to finish the album or make a call to boot three of your instrumentalists moments before you're all about to go on stage.

Today, Ray talks to Jason Myers who spent two decades recovering from a big break that broke him and coalescing his own new vision of how to create a fulfilling artistic career.

Welcome to Flops.

Welcome to Flops, where we uncover what happens when business plans go up in smoke and what we can learn from sifting through the ashes. I'm Karen Beattie.

Ray Sylvester:
And I'm Ray Sylvester. Now Karen, there's a line in the interview for this episode that I think sums up so much of what it's about. And it's a paraphrased quote from the Bhagavad Gita, the Hindu holy book, and it is that you have the right to your labor, but not to the fruits of your labor. Or as Jason who I spoke with for this episode puts it, you can control your output, but not your outcome.

Karen:
Well, that sounds like the kind of thing that's maybe easier said than done.

Ray:
Yeah, definitely. I think it's something that many of us learn the hard way, and Jason is someone who definitely learned that lesson the hard way. And he's still working his way toward clarity in his life, his artistic career. His story is ostensibly one that has a lot to do with quote unquote, trusting the process and quote unquote, knowing when to ship, like you said a few minutes ago in the cold open, but it's really about a lot more than that as well.

Karen:
Yeah. There's always more to the story isn't there?

Ray:
Yeah, let's get to it.

All right, Jason, welcome to Flops. Thanks for being here.

Jason Myers:
Thanks for having me. I really appreciate it, Ray.

Ray:
Of course, of course. So Jason, you are a musician, you're a keyboardist, a composer. I don't know how else you'd like to describe yourself, but did you always want to be a musician? How did you get started?

Jason:
Yeah, when I was five years old, I was able to pick out “Silent Night.” We had this old, pump organ where I grew up and my mom used to play it and she'd sit me on her lap. Every time she was done playing, I would sit down and fool around. And when I was five, I figured out how to play “Silent Night” with the melody and the chords in the left-hand. And from that point on my grandma who was a local piano teacher, she said, “Okay, time for lessons.” And my grandma was great because she knew enough to steer me in the right direction, but not enough to really screw me up. So I studied classical with her, but she always encouraged me to — or never discouraged me as far as popular music.

Cause I was listening to what my older brothers and my friends were listening to and everybody was listening to back then, you know, in rural Pennsylvania, you know, was Led Zeppelin, AC/DC. And I had aspirations of being a big rock and roll star like Billy Joel or Elton John. And then when I was about 15 or 16, a friend of mine asked me if I knew two songs and they were “Deep Purple” and “Moonglow,” which were from the thirties and the forties. And so, I got a music book that had those songs in them, and of course it had other music from the thirties and forties. And as I was playing this, I thought, Oh my goodness, where has this music been my whole life. And so that kind of got me interested in jazz and the jazz standards. And when I was 18 I went to Boston to attend the Berkeley college of music, I stayed there for a couple of semesters. Then I found a mentor there and studied jazz with him, then moved to Cape Cod and I'd commute once a week for my lesson. And then, moved out to California in ‘89, two and a half weeks before the big earthquake.

Ray:
Perfect timing. And so you've made — so music has obviously been your passion for maybe as long as you can remember. And you've, you've built a career out of it. Is that fair to say? Many career?

Jason:
You, that is fair, many careers, yeah. Fits and starts. And yeah, that's, that's mainly what I do. I have a couple side hustles too, but, yeah, the majority of my income comes from music.

Ray:
Got it. And so what are you doing with the music right now? Like, what's your, what's your music business like?

Jason:
It's funny because my side hustle is, I have a house cleaning business and, I never thought, before the pandemic I never thought that I wouldn't have house cleaning to fall back on. Turned out that, you know, a lot of my clients, a couple I've had, you know, 25, 30 years that, they're high risk, so I'm not going into their house. And then as far as music, obviously, the performances — “we've had to pivot” and “you're muted” have been the two phrases we've heard the last year. “Your mic is muted.” Yeah, so I, the main thing, as far as performing I've done is, going to retirement communities. I've done that the last 16 years because I have such a large repertoire of music from the twenties through the forties, 16 years ago, that's when I decided that would be a good place to go with people that grew up with this music. And unfortunately with COVID, we've also, you know, haven't been able to do that. So fortunately, because of Zoom and the technology available to us, I've been able to put those together as far as the performing for the retirement communities. And then also I've been doing private parties and events via Zoom. So that's worked out pretty well.

Ray:
That's great. Glad to hear that you're, you're able to pivot, as you said, and make it work. So we talked a little bit about what you're doing today, and I'm sure we'll get back to it, but you do also have a failure story that you were willing to share with us. So I was wondering if we could go back in time a little bit, and you can maybe just tell us a little bit more about that failure and, you know, kind of what led up to it.

Jason:
Sure. So it was around 1996 and I'd seen a flyer on a telephone pole that said Steve Allen was performing at a local bookstore. For those of you who don't know who Steve Allen is, he was the co-creator of The Tonight Show. And basically he invented the talk show format. He also had written over 8,500 songs and published over 53 books. I think it was about 53 and one of them that he was going to be at this bookstore promoting was a children's book. I got a bee in my bonnet to go and take him — I also write novelty songs. So the compositions I do are anywhere from like really melodramatic instrumentals to like, country novelty songs. It was really hot that day and there was a huge line — I'd missed his performance, but there's this huge line to get books signed.

So I figured that was my opportunity. Again, he was tired, it was hot, and the lady right before me was really obnoxious about autographs and getting pictures, and he started getting annoyed and perturbed it with her. That's, I’m like, “Oh great.” So I'm shaking, I'm really nervous. And I said — it was my turn, I say, “Mr. Allen. I'm a huge fan.” And I had written out the song, you, the music, “I'm a huge fan. Here's a song I think you might like,” and he takes it. He goes, “Well, I don't really read music. Maybe I'll get someone to play it for me sometime. What do you want in the book?”

Yeah, move it along. Then I thought, okay. I thought nothing of it. I thought, okay, there's just a chance. You know, I gave it my best shot kind of thing. Three weeks later, I received a box of 25 cassettes from him. And it was compilations, these compilation cassettes of all the recordings of his songs that had been done by, you know, Ella Fitzgerald, Louis Armstrong, Steve and Eydie Gorme and all these kinds of things. And in that letter, he had said, “I would love to hear some of your music, you know, on a cassette, even if you just record it at home.” And I was just, I couldn't believe it. I was blown away.

And from that point on, I was just like, Oh my God, what am I going to put on the tape? When am I going to put on this tape? And, you know, I really delayed, I don't know, weeks, maybe a few months. And then I thought I'm just going to put some stuff on.

Ray:
And we're talking in the era of like literal tapes, right.? Literally actual cassette tapes.

Jason:
Exactly. Yeah. So I finally put, you know, I sent him a tape. I don't know how many songs were on it that I had written. And I also did some standards on there and I sent it off and didn't hear from him. And I thought, Okay, that was it. He didn't like anything.

So let's see. Would've been... it was probably a year later. Yeah. So it was in 97. It was in May in 97. And that month was just tremendous. Two weeks prior, I was playing in a restaurant and Liza Minnelli came in and she — I was actually doing basically after all the guests had left besides her entourage. So we're sitting there and I was basically their private piano player. And I caught on that they were listening to what I was doing and commenting on it. So I started playing my own stuff.

And one of her entourage came over and said, “We really liked that song, but we don't recognize it.” I said, “Well, it's one I wrote.” And after I was done playing, she said, “Did you really write that song?” I said, “Yeah.” And she said, “Well, is it published?” I said, “No, not yet.” She said, “Well, can I publish it?” I was like, “Sure. And there's a lot more where that came from.” And she goes, “Well let's hear it.”

And so she had come over and, you know, invited me to her concert the next day. And she was playing at Davies Hall and in San Francisco and all this kind of stuff, I went back to the dressing room, so on and so forth. And I got the number to the resident hotel she was staying in Central Park from her personal assistant.

And I thought, okay, this is cool. And, she was in the middle of the tour. She said, “When we're done with the tour, give me a call, then we'll go from there.” So, two weeks after that, my wife and my young son were — I was going to meet up with them. They were at a wedding. And I wake up in the morning, and still back in the day, this was actually an answering machine that had a cassette in it too, with a tape in it. Right. And it was blinking. So I thought it was her saying, “Hey, you know, don't forget to bring such and such, you know, to, for our trip.” And I turned it on . . .

So from that point on, I spent the rest of the morning calling everyone around the country, said listen to this, you know, playing the recording. And so I thought, “Man, this is, you know, when it rains, it pours.”

Ray:
Yeah. It sounds like you had a week or two or three where the stars really, really aligned for you there.

Jason:
They really did align. And then the following month in June in ‘97, I went down, I drove down to LA and hung out with Steve and, and, yeah. So when I showed up, he already had lyrics to one of my songs with him. He’d dubbed himself singing over the tape I'd sent him.

Ray:
That must have been kind of a rush for you.

Jason:
Oh my God it was unbelievable. And if you've ever seen any clips of him and like the TV show and all that, what you saw on there, that's how he was in real life, you know. Just a gracious guy and always, you know, he’s just funny, you know. We were playing tunes for each other and he said, what's the title of that song? I said, “Well, I don't know. It's based on a Chopin waltz. And I just call it etude.” He goes, “Let's call it, there's a spot on the carpet.”

Ray:
Little, little lower brow maybe than a Chopin would have...

Jason:
Right. Right. Well, he also did it as far as to remind himself of the melody. You know, he had some funny phrases. So from there we were collaborating back and forth and it was in the spring of 2000, he had asked me to record a CD of his tunes. And so he sent me 80 songs to choose from. So I narrowed it down to about 20 and I was really, really struggling with this. And at this point I had already, I'd done a CD of my own stuff. And I, you know, I was working on another one. And so, but I was really struggling with this because I was thinking, “Oh, it's gotta be a certain way. It's gotta be perfect. I don't want to let him down. He's put his faith in me in this project.”

And I was really… it wasn't so much procrastinating, like avoiding it. It was avoiding… I felt like it had to be all written out and so and so forth. And finally, I went to my mentor, at the time and I was talking with him about it and he said, “Look, man, he goes, just relax, just play it like you'd play any other tune. Like you're doing your own thing and it'll be fine.” And so that just, I felt really good about that. And, and I did, I narrowed it down in the songs I was going to do.

And then unfortunately, five days later Steve had passed away. Yeah. So I had missed that opportunity and it was, it was pretty devastating. Not only from the missed opportunity, but because he had been a real validation to me, you know, it's like, what I'm doing, you know, it is recognized by somebody who I admire.

Ray:
Yeah. So how long did you kind of stew over the project before he died? Like how long were you kind of working and trying to perfect it, and...

Jason:
That was probably like, four or five months.

Ray:
If there had been less pressure, how long do you think it would have taken you to select the songs and send them over?

Jason:
Oh, I would have done it right away. That's a good question because the pressure came because it was someone of his stature, you know, as opposed to like, if a friend said, “Hey, I'd like you to do this album.” And like, you know, no big deal I'll do it. But yeah, that's a really good question. So I think it's... then again, it wouldn't have been as meaningful, you know? Cause it wouldn't have been... you know what I'm saying.

Ray:
Right, right. Yeah. But perhaps something that would have taken, you know, a week or two, as opposed to a couple hours, you could have put some thought into it, but it didn't, it didn't need to take four or five months.

Jason:
Right, exactly. Yeah.

Ray:
And so I was curious about some of the details of like, what inspired you to send to send your songs to Steve in the first place? Was it just, okay, there's a book signing, I'm just gonna put this out there and see what happens, or had you done this a lot before with other people, or is this just kind of something you did regularly as a musician, just trying to get your compositions out there?

Jason:
You know, it's funny Ray, because I don't, I remember seeing that flyer on the telephone pole and I don't know what hit — what the hit was. It was just one of those things and yeah, sure, like I've gone up to people in the past and, you know, put myself out there. But this was, this was really unique. I mean the day of the book signing, I went to my wife who was pregnant with my son, I went to her office so she could photocopy it. And I mean, I was like sweating it getting there. So it was just one of those things. It was just some hit from the universe or whatever said “Hey man, you should, you should do this.”

Ray:
So when the moment in the day you found out that he died, where were you exactly? And what went through your mind when you heard the news and kind of in the immediate aftermath?

Jason:
Well, again, you know, this was, he died in October, 2000. So you know, the internet wasn't as ubiquitous, certainly as far as getting information, cell phones weren't that, you know, I mean there were still flip phones and even then they were… not everyone had one. I didn't have one at the time. I actually came home and turned on my answering machine and it was my friend saying that he had heard the news and he said, “Sorry, you know, sorry about Steve.” And yeah, I was standing in my kitchen and I couldn't believe it. I was devastated. Again, he was just such a warm and generous guy. I mean, that's what really hit me hard first and then realizing that the project probably wasn't going to come to fruition. Cause things, after the dust kind of settled, his son had kind of taken over the business part of it and they weren't interested in continuing the project.

Ray:
So did you follow up with them and say, “Hey, can we still do this,” or did you just not hear from them? Or how did that unfold?

Jason:
Correct. Yeah, I sent — there is a gentleman who had been kind of Steve's assistant, especially dealing with all the recordings and things that he had done. And he said, “Yeah, they're stopping any projects that were in process,” at that point.

Ray:
What else were you working on at the time? Like, did you have other projects or jobs that you were focused on?

Jason:
I had this gig that was, at that point, turned into five nights a week and that started in ‘98. And, so that was going strong. Like I said, I wasn't doing the retirement communities until 2005. And you know, I was pursuing other gigs, you know, weddings and funerals and private parties and all those kinds of things too. So the situation when I met him, initially, I was just doing restaurants and things like that. And I always thought that this was going to be a stepping stone. You know, I’d eventually get my music out there because I had been writing a lot. And, I was always trying to, at that time, you know, looking for a publishing deal or something like that, something where, you know, I could be writing more and less of doing those types of gigs. So, yeah, I thought between him and Liza Minnelli I was going to be okay. I tried contacting her several times and never heard a word back.

Ray:
Even to this day?

Jason:
Even to this day, yep. Yeah. In fact, she was performing a few years ago in San Francisco and I went down there and tried to... you know, I couldn't get past the gatekeepers.

Ray:
So in the weeks and months that followed, did this linger with you, did it continue to affect your life and your work or were you able to kind of brush it off and just kind of keep going?

Jason:
Well, I wish that could have been the case. Personally, also I was going through, you know, my marriage was… it was pretty imminent that it was going to end during this time. I was about ready to throw in the towel. Which I didn't want, I didn't want it to end, I didn't want it to happen. And so I looked at this project, at least I had this as a consolation. My personal life might be falling apart, but at least my professional life was kind of taking off. So it seemed. So, yeah, I was devastated. I was devastated that the marriage was ending. I was devastated that I lost this project and a really good friend and mentor in Steve Allen.

And, I mean, because it wasn't just that project. There was a company that did, for the, like the player pianos. And back then it was a floppy disk you put in. Now actually, I guess you get it, if you can get it through the internet, you know, player piano. But he actually took it upon himself to send a letter to this company saying, “Hey, you should check this guy out. He's a friend of mine.” You know, he really went up to bat for me as well as other people who he really enjoyed working with. So I lost that and it's not just this project. I went into a tailspin for several months and, you know, I don't know if I ever quite recovered from it to tell you the truth.

I ended up remarrying in, you know, a second marriage should never have happened. And I had some other personal things that went on as peripheral to that marriage. And so for about 10 years, I was just struggling. Really, really struggling. And although, you know, I did maintain that gig I had that ended up going for 13 years solid. We had a trio, we did a recording, live recording from that. I did do another recording, solo recording. And 2005, you know, I started playing at the retirement communities, which was a great project too. But even like the next two recordings I did, I wasn't as focused as the first one. And so a large part of my life has just, since that time has been trying to find something and it's always been kind of fits and starts.

Like, I'll get a project going. I don’t know if it’s — as Tony Robbins would say, a neuro association I had from like having some brief success in it and it not coming through, but it's not until honestly the last two or three years that I've really kind of picked myself up and started focusing again and trying to figure out, you know, what my step is. And I've, I've just been kind of — the last 20 years, it's difficult to admit, but the last 20 years I've just been kind of flailing. I lost a lot of confidence. Yeah, just, it's been difficult, to say the least.

Ray:
What has, what has helped you the most, especially in the last two or three years, as you said, just kind of re regaining that confidence, that direction?

Jason:
There's been a ton of self-reflection. A lot of journal writing, looking into self-forgiveness, forgiving myself for missed opportunities, forgiving myself for choices I've made that intuitively I knew probably weren't the choices I should have made, including that second marriage. There were red flags at the beginning. But you know, I was heartbroken from my first one. But really a lot of self-reflection, a lot of listening to self-development stuff, AKA, you know, Tony Robbins, that kind of thing. Friends, you know, having friends as far as support. And really the last six months or so, I've gotten into a… of course, you know, several years I've been listening to Tim Ferriss and listening to a variety of people, people that are inspiring, David Goggins. Finding people that have gone through way worse than I ever suffered and saying, you know, if they can do it, I can do it too. And of course, the last six months, well, I guess, in December, I joined SPI and SPI Pro and just having that community of support and people to draw on. You can be vulnerable there, you know, people will tell you straight, but also supportive.

Ray:
When you think back to that time, you know, when you were, when you were perseverating on those songs and just couldn't couldn't pick the ones that you wanted to send to Steve, and then when you think about like the tools and the resources and the community you have now, what would have been most helpful for you back then, whether it's a person, you know, another mentor, or just a community?

Jason:
Yeah. Definitely finding a community, and maybe another mentor. My mentor was great. Or actually, let's put it this way, taking an advantage of what I had, you know, because I had a great mentor. And I think sometimes we get stuck and thinking we need other resources than what we already have around us. And I think what the challenge comes with is having the courage to say I need help and asking those questions and asking for help.

Like, for instance,I thought I had to do this project all on my own without getting input from other folks. And as we're talking I realize that's a common theme in my life. You know, having the courage to say, “Hey, I don't really know.” That's also been a lot of help in the last couple, three years. Being humble and just saying, “I just really don't know.”

I had an English teacher in my junior year of high school. We always have those one or two teachers that stick out. And I was really struggling during that period too. But she said that you're mature when you can say, “I don't know.”

Ray:
Yeah. And as you said, it's tough, but I think it's also, it's so common, especially for people who are doing something entrepreneurial, to feel like they just have to put their head down and figure it out. When you're — you said that your mentor was the one who kind of flipped the switch for you when you were working on these songs and said, you know, “Just ship it, just pick five,” or whatever it is. Did you reach out to that person or did they, did they have to come and tell you, or what was that moment when you realized, or when that happened?

Jason:
Yeah, so I, I was still taking, you know, still taking lessons from him.

Ray:
Was he an instructor of some kind?

Jason:
Sorry, sorry. Yeah, he was a piano teacher. He was my last like, main mentor as far as music was concerned. And he was, we were really close. He was like a musical dad, I guess you'd call it. I was just telling him, “Man, I'm just struggling with this.” And that's when he said, “Hey, just, just pick ‘em and play ‘em like you normally would do any other song, whether it's yours or somebody else's.”

And so that was helpful. and you were asking what I’d do differently. Yeah. I mean, I would have taken more advantage of that mentorship that I had with him. I guess I kind of took it for granted, what I had with him, and I think that's an important lesson for me as well as other people, just again, have the courage to ask the questions of your mentors and be humble enough to accept what the answer is, whether good or bad.

Ray:
And it seems like with creative work, like music, it can maybe sometimes be challenging to know when something's ready or done, or to decide what, you know, what's the best of these 50 songs that I have. There's something inherently subjective about it. Does that kind of fit into the mix for you, in terms of the challenge of making that decision?

Jason:
You mean for the Steve Allen project?

Ray:
Yeah, or it just in general, but especially for that project.

Jason:
Yeah. I can address both. For that project, definitely. ‘Cause Steve Allen wrote over 8,500 songs, but I'll tell you what man, some of them were stinkers. Including within that 80. So, yeah, but it's also what you resonate with when you're doing a project like that. ‘Cause there was also the challenge of, you know, I'm playing his music, but I want to play stuff that I resonate with so I sound okay, you know, so I'm presenting it well.

There's also, well you mentioned just ship, you know, of course Seth Godin, that's always his line. I've done two projects since, just on my own. One was, it was actually loosely base on Steve, it's called Dare Me to Write a Song. I did it in 2013. For 12 weeks, each week I had to write and record a song. And I had to be a brand new song. Didn't necessarily have to have lyrics and people could challenge me, you know, as far as the title or they could challenge me as far as the style. And I got some people to participate, only a few actually participated.

And the whole point of that was just to get it out there. And I had succeeded in the 12 weeks. And what was interesting about that, the first three, four weeks were a real struggle and my commitment was it had to be submitted by Monday. And there were a couple of Mondays where it was like nine or ten at night. I was just getting in under the wire. But then the interesting thing that happened was towards the end of that project, like the last three, four weeks, like songs were just coming, ideas were just coming in and out, in and out, and just like tons.

And like the last week, last two weeks I had written like six or seven songs, you know, that I really liked and really enjoyed.

Ray:
And I was on your website earlier, I noticed you had, it was like 30 days of, you had like uploads to YouTube of different songs you did? Was this the same project or was that something else?

Jason:
That's completely different. That was, that was called The Daily Dose. And that was, kind of tried to connect with when the shelter in place first happened. I was like, you know, I'm not going to be able to connect with these communities that have been performing for, so that was kind of to be in touch with them. And yeah, so I did that 38 days straight and I think we had about 115 songs in there. So that was a different thing, but kind of the same premise though, you know, although I will admit there were a lot of, there were some retakes in that one.

Ray:
But still good, just kind of getting into the practice of doing something every day and putting something out there and, you know, seeing what people think of it. And we'll drop a link to this in the show notes. Of course, this is at, Jason's website at KeyPlayerMusic.com. And that was a web video series calledThe Daily Dose that you did for, you said 38 days, right?

Jason:
Correct. I just started getting burned out. I was just like, you know, I wasn't enjoying it towards the end. I was like, if I'm not enjoying it, I'm not going to continue doing it.

Ray:
Yeah. Well, I definitely enjoyed the snippet of it that I checked out. So I appreciate it. You had a song in there, I think it was called Sandals? White socks and sandals?

Jason:
“Sandals and White Socks.” Yep.

Ray:
So I’d definitely recommend that one for everybody who's listening out there.

Jason:
Thank you. In fact, I think that might've been the one, that might've been the one I gave to Steve. I can't remember which one I gave to him to tell you the truth. And to the point of kind of going back to what you were saying about which songs do you choose, which are good enough to ship. There was one song I put on the original cassette that I gave him, that the only reason I wrote it was I wanted to try to write something in G flat. And it just kinda sounded kind of like this, I don't know, it sounded kind of like a Broadway tune in a way. And that was the first song he wrote lyrics to. So that was the one he connected to. And for me, it was like a throwaway song. I just put it on there. So you just never know,

Ray:
You never know what someone's going to do with your stinkers, right?

Jason:
Correct.

Ray:
That's the beauty of art and creativity

Jason:
And business too. I mean, you have an idea that you think, eh, it's not that — and like, all of a sudden people start gravitating towards it and then you know, it’s like, okay, maybe this is something

Ray:
Right, so you gotta just put it out there and find out.

I wanted to ask you a little bit more about mentorship and whether you've had the opportunity to, or you just had encounters with maybe younger musicians who have struggled in a similar way with just getting their creations out the door. And, have you been able to mentor and support other musicians who've struggled in that way?

Jason:
Yeah. Some that I run into. There's one guy particularly that comes to mind that, he's a fabulous guitar player. Fabulous, fabulous. And he's like in his mid, late twenties and he was struggling with... there's a great, I just re-read it in The War of Art where Steven Pressfield talks about the... I can't pronounce it.

Ray:
The Bhagavad Gita?

Jason:
Right. But there's a great line in it that basically, it says you have the right to your labor, but not to the fruits of your labor. And this guy was kind of questioning what he was getting back in return. And I told him, was like, man, just keep doing it, keep doing it. And also to embrace the opportunities that you do have. And he had some coming up and I was like, you got to take the bull by the horns and just do it.

And the thing is, you can control— along the same lines, you can control your output but you can't control your outcome. I mean, no matter how you put something out there, you don't know how it's going to be received, but you just have to do it. I mean, that happens with art and music, it happens in business, it happens in life. You just never know who you're going to impact. So I think the other big lesson I learned is we all have gifts to give and we don't know how they're going to be received, and we don't know how they're going to impact and the ripple effect that that might cause.

Ray:
So where do you want to take your music from here? Do you see yourself playing in rooms with people again once this pandemic hopefully settles down? Where do you want to be in a few years and beyond?

Jason:
Yeah, I would definitely like to do that. I enjoy live performing. One of the things I've started doing is writing music for podcasts, podcast intros and things like that. And also just, video and, you know, movies and TV shows. That's kind of where I'm, I've kind of been looking into, along those lines, music licensing, where that comes from. Ultimately, I'd like to be a location independent. So we're finding now with all the different technologies that I can potentially play anywhere and people can listen, although there — nothing beats having the direct feedback within a room.

Ray:
Is there any other advice that you would give to young Jason or maybe just someone else who would find themself in a similar predicament to the one you found yourself in when you were trying to pick songs for Steve Allen? Is there anything you'd say to them or to young Jason?

Jason:
Yeah, I would say the same advice I had is to relax. It's just another recording. The other advice I would say is there's not one thing… At that time I was also betting on the quote, the big break. I remember telling my wife at the time, I just need one big break, just one big break, one big break. The thing is, there's just all a bunch of little breaks that lead up to it, you know? And it's kinda like going to a casino and putting all your chips on one roll or one hand. It's all about the little breaks and maximizing on those. And also, nurturing those little relationships you have, because those are what feed onto, you know. Yeah, you might meet Steve Allen or Jeff Bezos or somebody like that, that you think, okay, that one connection is going to be it. But very, very rarely is that ever the case. It's cultivating and nurturing the relationships that you do have and building off of those. That's what I would say.

Ray:
Awesome. Awesome. Well, and you mentioned, yeah, you do music for podcasts and we'll see, maybe there's a way we can work a little snippet of your music into this episode, perhaps. But yeah, for everyone listening, you can go check that out at KeyPlayerMusic.com and we'll obviously drop some links in the show notes here. But wanted to thank you so much for joining the show and sharing your story. We know that sharing experiences of failures, it's not always an easy thing to do, and we're just really appreciate your being willing to come on and talk with me today.

Jason:
Well, thanks so much for having me, Ray. I really appreciate it.

Karen:
Well Ray, Jason's story really resonates with me because it's so painful to have such a great opportunity, and then because of your own perfectionism, have it suddenly disappear. And I've experienced that some in my own creative work. And I know that some of it was out of his control, but I can see where it would be really hard not to beat yourself up for missing such an amazing opportunity.

Ray:
Yeah, yeah. Well, and speaking of amazing opportunities, there's a lot that has been written and talked about around this myth of the so-called big break. The author Cal Newport talks about why it's important for people to try to be doers rather than schemers, so you're not waiting for that one big opportunity that's going to take care of everything for you. And Newport has a framework that he shares in a blog post that we can link to. He encourages people to think about any project in your life as essentially a two-step process. So step one, get started. Step two, keep going. And that's it.

Karen:
Yeah, that's really great advice, because it's so action-oriented and I think creative people can get stuck in their own thoughts and ideas.

Ray:
Yeah.

Karen:
So I think that is really great advice, and it's just so simple.

Ray:
Yeah. And now, you also mentioned not beating yourself up for perfectionism. But I think for Jason, there was honestly also just a lot of bad luck going on.

Karen:
Yeah, yeah.

Ray:
I mean . . . Steve Allen died.

Karen:
I know.

Ray:
I don't know how statistically likely that was to happen based on how old Steve was, but it seems pretty unlucky. And I can understand what it might've felt like for Jason to, in the same short period of time, to have this huge figure in the songwriting world, Steve Allen, say he wants to work with you. And then around the same time, Liza freaking Minnelli comes along and says she likes your songs. I would be running pretty high on those fumes, that's for sure. So I have a lot of sympathy for Jason, that was a pretty big rug to have swept out from under him.

Karen:
Yeah, and it must've been a lot of pressure too.

Ray:
Oh yeah.

Karen:
But I admire that he has been able to pick himself up and move on, and start to find some peace about it. And I think that's a lesson for us all.

Ray:
Amen.

All right, we've got another special guest here today to help us close things out. Joining us on the show is Jillian Benbow, who is SPI's community experience manager. Hey, Jillian. Thanks for joining.

Jillian Benbow:
Hello. Thanks for having me.

Ray:
It's it's good to have you, and we understand that you have a failure story you were willing to share with us, is that correct?

Jillian:
That is very true. I do.

Ray:
Awesome. Well, can we hear it?

Jillian:
Of course.

This was probably in, I'm trying to think, the early 2010s. I was really into trail running, where I live is perfect for it. I was actually training for a really big race called the Imogene Pass Race, which is, you basically run over a 13,000 foot mountain. You run from a town called Ouray to Telluride. So you go up, up, up, up, and then down. It's really intense. It's 17 miles. It's not a marathon, but I'm pretty sure after that a marathon would have been easier because the vert is just crazy, the gain.

So anyways, I was training for that and I was on a pretty popular trail near where I live. And so I was doing a training run and I'm on my way back. I'm probably a mile to the parking lot kind of thing.

And I'm coming down, feeling good, going slow, because that's what I do. And I passed this older couple. It was, what I'm assuming was a married couple, probably in their seventies. And I usually kind of just give people a nod and keep going. But the gentlemen of the party looked at me with this huge grin and he's like, "Look, honey, it's a jock." And I just smile. I was like, "Oh my God, did he just call me a jock? Me?" Especially because I'm not and so like, the fact that anyone would identify, that was just... It felt amazing. I had a little pep in my step.

Ray:
A spring in your step.

Jillian:
Yeah. And I thought it was just so sweet. It made my day, it made the run, which was brutal. I think I'd turned around early. I was just not feeling great. He flipped it around and it was just so sweet. It was just one of those things. So I'm going and I go around the corner and I hope they didn't hear it, because they were close enough. I just exploded. I don't know, I tripped over my own foot, and I managed to Superman for what felt like forever. But I mean, it was probably a foot, but it felt like I just slid for like 10 feet, arms out, hit my head.

I actually, I was wearing a visor and it dented my forehead, and just completely just slid, slid to home-base kind of situation. And then I just laid there for a second. Still, these like emotions of "you’re a jock" were quickly being replaced with like pain and embarrassment.

Ray:
“You're a jock.”

Jillian:
Yeah, “You're not.” It was kind of the voice in the back of your head, it was like, "Ha ha. Told you." So my little blip in being a jock was short-lived and I was bleeding everywhere. I had... Well, this might be TMI, but for anyone who runs, often you have the little shorts that have the built-in underwear. I managed to scoop a ton of dirt and pine cones and stuff into my shorts. Yeah. I was just a mess. What wasn't covered in dust was covered in blood. I looked crazy. I actually still have a couple scars still from this.

Karen:
Oh, wow.

Jillian:
So I had to hobble home because it's a trail head with a parking lot, but I lived in town, so I just ran there and I couldn't... I stopped running obviously. The run was over. I have blood dripping down my leg and just like hobbled home with my amazing jock body thinking like, "huh."

Ray:
You still had your jock cred.

Jillian:
I don't know. Definitely, the gravity was definitely still on. I tested it and it was there. It always wins.

I had these super deep gashes that I had to deal with. I also then had a race that I had to do and I fell again and broke open my hand, which was starting to heal.

Karen:
Oh my gosh.

Jillian:
And I had to —

Ray:
You're on a roll.

Jillian:
I was falling a lot. I did find out I actually have a labrum issue in my hip. So I think all the falling kind of makes sense in hindsight sort of thing.

Ray:
Fair enough. Fair enough. Well thank you for being so forthcoming and sharing your flops with us today. We appreciate you being willing to spill the beans.

Jillian:
Of course, of course.

Ray:
And the blood, as it were.

Jillian:
Yeah. I mean, if ever, I think part of my life purpose is to make people feel better about themselves by telling them things that have happened to me. If this helped anyone... I hope it did.

Karen:
Well, you're welcome to come back at any time to tell us any of your other flop stories.

Jillian:
Sure. I mean, suddenly now they won't be so bad because I'll be like, "Now I have good content for the Flops podcast."

Karen:
Yep.

Jillian:
There's purpose behind these clumsy moments I have.

Ray:
There's a reason we hired you.

Jillian:
“Let me see your running scars. Yep, you'll work.”

Ray:
Awesome. Well, thanks again, Jillian. And that'll do it for this episode of Flops. We'll see you next time.

Thanks for listening to Flops. For more information on today’s episode, including links and show notes, please visit SmartPassiveIncome.com/flops.

Special thanks to Jason Myers for joining us on today’s episode. Learn more about Jason and his music-focused business at KeyPlayerMusic.com.

Join us next week for a swim with the sharks that went wrong for reasons you might not expect.

Your hosts are me, Ray Sylvester, and Karen Beattie.

Flops is a production of SPI Media.

Our executive producer is Matt Gartland, and our series producers are David Grabowski and senior producer Sara Jane Hess.

Writing by Ray Sylvester and Karen Beattie.

Editing and sound design by Paul Grigoras.

Theme music by David Grabowski. This episode also features the songs "Hoagie for Dave" and "Whap Blues," written and performed by Jason Myers. "Whap Blues" also features guitar by Brian Kane and bass by Paul Breslin.

See you next time.