The B2B Podcast Index
Make Music

Our Biggest Regrets as Independent Music Artists (Learn From Us)

Make Music · 2026-04-06 · 19 min

Substance score

18 / 100

Five dimensions, 20 points each

Insight Density3 / 20
Originality3 / 20
Guest Caliber5 / 20
Specificity & Evidence3 / 20
Conversational Craft4 / 20

Ian Austin, William Toll, and Haddon discuss their biggest regrets as independent artists with 700,000 combined monthly Spotify listeners, focusing on how doubt, lack of confidence, and delayed commitment to music prevented them from pursuing their artistic careers earlier.

Key takeaways

  • Delaying commitment to your primary passion for 6-8 years due to doubt and lack of confidence costs you years of potential progress and skill development.
  • Having backup plans (Plan B, C, D) dilutes your focus and commitment; going all-in on your primary calling is more effective than hedging with safe alternatives.
  • Shame from others' reactions and negative feedback can create seeds of doubt that last for years; you must actively reject doubt and embrace pushback as part of an artist's path.
  • Indirect paths in music (session musician, producer, worship leader) can prevent you from pursuing your true calling as an artist until you fully commit to that identity.
  • Learning from peers who have actually achieved success in music is more valuable than content from untested sources; community and belief-building are critical for sustained motivation.

Topics in this episode

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

3 / 20

The episode is almost entirely personal anecdote about self-doubt and indecision, offering no actionable tactics, frameworks, or non-obvious ideas for indie artists. The sole recurring 'lesson' is to reject doubt and go all in - a platitude repeated multiple times with no added depth.

doubt is not from God. It's not, it's not a good thing, um, ever
we just want to advise you to get ready for the pushback and embrace it and just accept it as just part of the life of an artist

Originality

3 / 20

Every idea in the episode - believe in yourself, reject doubt, go all in, learn from practitioners - is generic motivational content that circulates everywhere. There is no contrarian framing, no first-principles reasoning, and nothing that challenges conventional wisdom about the music industry.

Reject doubt. Reject doubt. It's not a good thing. It never is.
you have to have some sort of tolerance for potential failure or, um, the willingness to go against the odds and just work really hard, outwork the other people

Guest Caliber

5 / 20

The three hosts are modest indie artists with a combined 700,000 Spotify monthly listeners - real practitioners but not operators at meaningful scale. Prior to music, Speaker B was in material management and Speaker A tried carpentry; neither background adds cross-domain authority relevant to a serious music business discussion.

We are a team of independent artists with, give or take, 700,000 monthly listeners combined on Spotify
I was doing, like, material management

Specificity & Evidence

3 / 20

The only concrete figure in the entire episode is the combined 700,000 Spotify listeners; everything else is vague personal narrative with no named artists, platforms, revenue figures, or growth timelines. The 'four month plan to quit' is the only other quasi-specific detail.

give or take, 700,000 monthly listeners combined on Spotify
I made like a four month plan to quit and then do music

Conversational Craft

4 / 20

This is an unstructured co-host roundtable with no interviewing dynamic, no challenging follow-ups, and no productive disagreement. The single notable 'question' is a basic clarifying prompt, and the hosts openly validate each other's identical stories throughout.

Wait, what did you do?
This is so funny because mine is the same exact thing as you guys. This is kind of funny how it lined up

Conversation analysis

Computed from the transcript - who did the talking, and the verbal tics along the way.

Share of words spoken

  • Speaker A43%
  • Speaker C32%
  • Speaker B24%

Filler words

like134um62so36you know32uh29kind of13actually9er5I mean5basically2sort of1literally1obviously1

Episode notes

In this episode, we get honest about our biggest regrets as independent music artists - and how you can avoid them. Looking back, a lot of it comes down to lack of confidence and waiting too long to fully commit. We talk about how hesitation, second-guessing, and playing it safe can quietly hold you back and what happens when you finally decide to go all in on your music. If you’re an indie artist trying to build momentum, this episode is a reminder to trust yourself, take action, and stop delaying the path you know you want. Indie Roots is a production company started by Haddon, William Toll, and Ian Austin. We're all independent artists and have approximately 700k combined monthly listeners on Spotify. If you're on your own journey as an independent artist but struggling to navigate the road, we would love to help guide you in our coaching program. For a free intro call, send us an email at ⁠⁠indierootsllc@gmail.com⁠⁠

Full transcript

19 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Hi, I'm Ian Austin. I'm joined by my co hosts, William Toll and Haddon. We are a team of independent artists with, give or take, 700,000 monthly listeners combined on Spotify. And today we are talking about our biggest regrets as independent artists. Okay, who wants to spill out their heart for all the people first?

Speaker B: Yeah, I don't mind going first. Um, so I think I got started with music fairly late compared to some people. When I see artists who are like 18 years old and have a million listeners or something, I didn't really start until I was like 18. Excuse me. But, um, yeah, I got really passionate about writing songs and producing and, you know, um, street performing and, you know, I was like a freshman in college and I was actually studying biology. Um, but a lot of my friends in college were in music. Um, so I'm kind of like the opposite, uh, like case of someone who started in a science and then ended up in music, you know, whereas I. It seems like a lot of people, they'll go to school for music and then end up in something unrelated. But, um. But yeah, I, uh, got really passionate about music. But, um, I just had a lot of fear and, um, doubts and I just had really low confidence and I just thought, there's no way that's me. You know, I always play it safe. And so basically that mindset, I would say, plagued me for, um, probably like six years.

Speaker A: Um,

Speaker B: and it wasn't till I graduated college I got a job, like a standard job. And then two years after that, I was. I met my wife, we were dating, and things are getting serious. Also, the company I worked for went bankrupt. Um, I still had a job there, though. Like, they got bought out. But, um, I just thought, okay, if I'm ever gonna try this full time, you know, now's the time. I had some money saved up and I had some ideas for how to make money. Um, so, yeah, six years after I really got, uh, the true passion is when I really, like, went for it. And, you know, I know that time was spent building up the craft and the skill level. Um, but even then I never really, like, went all in. Um, and, uh, I don't know what. So this is what really changed my mindset is y' all might know the story, but my boss and I were working till 10 o' clock 1 night. I mean, it was horrible. And, uh.

Speaker A: Wait, what did you do?

Speaker B: I was doing, like, material management. Um, and so we were like, making a budget for the company with all the materials that we, uh, Like a materials budget and, um, if my boss, which there's like no way she's listening to this, but if she is, you know, she. It was not like she was a great boss. But, um, so nothing against her. She taught me a lot. But she said, because I guess I was like, had a bad attitude about it. But she was like, if you're not willing to do this, then you're not cut out for this career. And I remember driving home and I was like, I'm not willing to do this. And so that night I was actually driving to the beach because, uh, Jimmy and I and our brothers were doing a beach trip that night. I decided, like, I'm not willing to do this career. And so I made like a four month plan to quit and then do music. But basically I just wish that I, if I had just made that decision like six years earlier and just not had the doubt, I could have been so much further, you know, or if instead of paying four years worth of tuition, I, you know, just went all in on plan A, man, I would just be so much further. So really it was just a mindset thing. I wish I had the confidence sooner. Um, and you know, obviously my, My path was my path and I don't know where I would be if I didn't have my. The path I ended up going on. But, um, if I was to do it all over, I wouldn't have had plan B, plan C, plan D. I just would have gone all in on plan A. Because now that I've done it, I know that I can do it. And if I can do it, anyone can do it. And so, um, yeah, that was, that was long, uh, winded. But, uh, um. What about y'?

Speaker C: All? I mean, I guess mine, mine is very similar. I think that the number one regret that I have is, uh, doubt and just misdirection. Pretty much the same thing. Um, I think when songwriting became by far the number one passion in my life, it was. It wasn't for another, like, I don't know, eight years that I decided, no, like, I need to just accept that this is my calling and go for it, like, fully. I mean, there was like, I guess, I guess like two years after I realized that I did. I did have that moment where I abandoned shit, abandoned everything and just went for it. And I think I've talked about that before where I just, I did it without a plan, um, without any skills or plan or mindset or any, any preparation knowledge. Um, um, and. And I'm glad I did for a lot of reasons, mostly Spiritual, um, to kind of hit rock bottom and get in God, to like, just shake me awake. But, um, but like, really the, the thing that like, I, I ended up retracting, you know, from, from music and just being like, you know, I'll just put it on the burner. Um, I just shouldn't have done that. You know, it was. I, I pretended. I, I convinced myself that, oh, uh, you know, like, I don't really care, but secretly, like, it was the only thing I wanted. And so if people were to ask me, you know, what I want to do or what direction I'm going in, it would never come up. But it was always in the back of my mind. Um, and a lot of that had to do with like, shame of not being accepted. Like, you know, lots of, lots of times you can get discouraged when like, you know, because I used. Because when I, when I first started to have those convictions, I really, I really, I hesitated. But I did speak my mind about it and I did tell loved ones that this is, this is like my primary thing. Um, but just like the reactions that I would get really discouraged me and they kind of fed, fed, fed me a lot of doubt and made, uh, me feel very silly. And so it just, it just, ah, it sowed, it sowed a seed of doubt that lasted for several, several years. And so, um, I'm not blaming, I'm not trying to blame others. Um, I think that that's, that's going to happen to anyone. And so if you're listening to this and, and you have those convictions and you're like, worried what people will say or think. Um, yeah, the. I guess it's not great advice to just tell you not to worry about that because what kind of advice is that? But like, but try to do your best to frame your mindset around. It's going to be rejected. There's no, you know, this is just the way people see the world. And uh, and it's something that you just have to brace yourself for and keep going. Um, and, and just fight the doubt. Because doubt is not from God. It's not, it's not a good thing, um, ever. And uh, unless, like, unless like you're thinking you can jump off a building and fly or something like that, then doubt's probably a good thing. But, but when it comes to like, pursuing your calling in life, um, that where there actually is a pathway, it's, it's, you know, you're going to go against the odds, like the, ah, you know, that that's something that you'll you have to embrace, but any. Any kind of real success and quality of life. You know, you have to. You have to have some sort of tolerance for potential failure or, um, the willingness to go against the odds and just work really hard, outwork the other people that are trying to do the same thing and, um, be smarter about it. Um, but don't let negativity get in your way when you know what your convictions are.

Speaker A: This is so funny because mine is the same exact thing as you guys. This is kind of funny how it lined up. I'm not as old as you guys. You guys are like, ancient. No, I'm just kidding, dude.

Speaker C: George Washington is my uncle.

Speaker A: I'm, uh, mid-20s and they're a little. Few years older than me. But yeah, mine is. I wish I would have been more just intentional and, um, decisive about pursuing, um, the artist thing earlier, because music's always been my thing. I mean, I started piano lessons at 5 years old, but I didn't. I didn't enjoy it. I mean, I was five, but also I just didn't enjoy, like, playing someone else's work. And then, uh, it's literally like Mary had a little Lamb, but it's still someone else's work. And, uh. And then When I was 10, I discovered songwriting, or I guess it was composing. I just created my own songs on the piano. And I wouldn't practice my classical, like, music I was supposed to do. I just, like, played for hours, just creating stuff. And it was like, this is amazing. And that was really the thing that I loved about music. And so I knew that about myself. But then I had in my mind of, maybe I'll be like, uh, like, you know, one of those piano players that plays at the hotel. They're like the background music. I was like, maybe I'll be that. Because that just felt like, oh, that's. I know people, or I know of, like, people that do that. So it's like, that seems like a safe option. And then. And then it became as I started to write lyrical songs and, uh, I was writing stuff like that, I thought. And I learned how to produce. It was like. It started with, I want to learn how to produce, because I'm writing these songs and I can't wait to show them to the world. And what if I got a song on the radio? This is like when I was a senior in high school, what if I, oh, I want to be a music artist. And there's kind of like that innocent, like anything could happen. But then it turned into now I know how to produce me, I'll just be a producer because that's a lot more feasible than being a music artist. And uh, so I was like, yeah, I'll be a producer. I can make it work that way because music's my thing. Um, but then I kind of gave up the music thing, um, when I went to college because I was like, well, I want to have a family one day and I can't be on the road all the time with a family. I would rather be a, ah, faithful father and husband than be a music artist. So I guess I can't be a music artist because I would just have to tour 24 7. And so I gave that up. I just didn't know there was another way to do it. And I gave that up. And I was like, I'm going to be a carpenter. And I, uh, remember telling my friend about that, um, in my early 20s. I was like, yeah, I just feel like carpentry is like the safe option. And he was like, dude, if you think carpentry is a safe option, that's probably not what God has for you. And I just remember thinking that and being like, yeah, I really want to be a music artist. I just don't know how it's going to work. And so, so then I was at carpentry and I, like, hated it. And it was just so misaligned with my personality. And I was thinking, I got to get out of this carpentry job and I'm going to learn how to produce for real and I'm going to be like a pro producer and I'm going to be a producer and. But then when I produce for people, I'm like, I want to be the artist. I don't want to be like, like a puppet in their hands. And they're just like, using me to serve their creative vision. I want to be the artist. And, um, sorry, this is so long, but there's more. Uh, and then I was like pursuing the artist thing and. But an opportunity for being a worship leader came up and I was like, you know, it's probably more godly to like, be a worship leader because it's like working at a church. And man, I just gotta, like, I just gotta do the hard thing even though I don't want to do it. So I was like a worship leader. But it was just, Even though it was music, I was like, this isn't none of the things I love about music. I'm not using any of those things in worship leading. I love creating songs I love, like, self expression and like. Like that and that I'm not doing that as a worship leader, and I kind of hated it. Um, and, uh, so just like, over and over being like, yeah, I know. M. Like, music's my thing, but not. Not like admitting, like, no, the. The artist part of music is your thing, not just being a session musician or a producer or a worship leader. It's like the artist part is the thing. And I wish I would have just, like, gone with that earlier instead of, like, back and forth. There's also a time where I, like, I wanted to be a pastor just because it was like, that's more spiritual than being an. But really, I wish I would have just been like, no, deep down, like, this is a crazy dream. Like, to me, it felt like me saying I wanted to be an astronaut, but, like, at the end of the day, if, like, you're. If you're supposed to be an astronaut, just be an astronaut. Who cares? Just do it. And I wish I would have just been that bold. And, uh. And it really helps. It really helps. Knowing other people that are doing it, like, that's been a game changer for me. I didn't know you could, like, make money off of streams or make money other ways. I thought you just two were. I thought you just tour yourself to death. And, uh, yeah, but it's really helped, like, knowing you guys and knowing there's just different ways. And that's actually one of the reasons we started, um, doing coaching is because we want to. We want to equip artists with number, uh, one, like, the belief of, like, you can actually do this. And here's what we've done, and we want to equip you to do it too. And we don't want just, like, artists off here on an island thinking, oh, you have to sign to a label or you have to tour all the time. Like, we want to provide, like, a, like, um, peer, like, uh, advice to you and shared experiences to, like, instill belief in you, to, like, actually go for this thing. And just like, we do think, like, the best way you can actually grow is you learn from people that have actually done it. Like, not learning from some guy on YouTube that he's never actually made in music, but he just makes videos about making it into music. But, like, we think it's so valuable. It's like, it's kind of like on the job training. Like, you're learning from someone that's doing it in real life and you're, like, coming alongside them. And so yeah, man, if I'd have had something like that, I think that would have helped me tremendously. But I just kind of spun my wheels and I was really indecisive for a while.

Speaker B: Yeah, we, like, we're just a bunch of like average normal guys too, you know. I m. Don't know about. I. I just, that was my thing is I, I'm. I'm just a normal guy. I, I can't do anything special, you know, so.

Speaker C: Yeah, but it takes. Yeah, I guess it's like, that's good. That's a kind of a good mindset too. On the other hand, it's like you want to have humility and not be like, I am. I am a transcendent God. And so people are going to love my music because I'm just oozing with awesomeness. Um, so. But yeah, I hope that was helpful. Um, you guys just, Just, uh, reject doubt. Reject doubt. It's not a good thing. It never is. Um, and so I guess that's kind of the key takeaway here. But decide in your heart. Just be convinced. Convince in your own mind. Know, know what you know, you know what you feel in your heart. And um, and just like pray, you know, just don't do, like, don't do anything foolish. But if, you know, if you know that you can make this happen, um, or at least take an honest attempt at it. It's. It's definitely worth all the effort and framing your mindset around it. Um, so we just want to advise you to get ready for the pushback and embrace it and just accept it as just part of the life of an artist. Um, but, um, but yeah, and then also on the production and business side too, we have, we have, ah, we have coaching services that Ian mentioned earlier. Reach um out to us for that. And it's also good like mindset, um, training stuff too. Just have a conversation about, you know, where you're at. Um, but yeah, you can schedule. You reach out. Reach out to schedule a free introductory consultation. We'd, uh, love to talk to you. Um, email us at ind inderoots llcmail ah.com to schedule that. Um, also don't forget to like and leave a comment and subscribe to the podcast and leave a five star rating and we will see you on the next one.

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