If you’re sitting on an idea because you don’t know whether it will work, you may be waiting for answers you can’t get yet. Some questions about a book, podcast, business, or creative project can only be answered by making a small version, putting it in front of people, and paying attention to what happens next.
Prefer to listen? Press play below.
Dr. J.J. Peterson knows how easy it is to live in the planning stage. He has books he wants to write, screenplays he wants to create, and projects he has spent plenty of time thinking and talking about.
Eventually, though, planning stops moving the idea forward.
Musician, songwriter, producer, author, and creative coach Jill Pickering has spent more than 20 years putting creative work into the world. Her advice for someone stuck between wanting to make something and actually making it is remarkably simple:
“You gotta stop talking about it and do something.”
That doesn’t mean recklessly betting everything on an untested idea. It means making a move small enough to learn from.
What Should You Do When You Have an Idea but Don’t Know Where to Start?
Make the smallest useful version of the idea instead of trying to build the whole thing at once. If you want to write a book, Jill suggests starting with a chapter or an essay and getting feedback. If you want to start a podcast, record one episode instead of an entire season.
“Start small,” she says. “You gotta just make the first move.”
That first move matters because action creates information that planning cannot.
An essay can show you whether the idea has enough depth to become a book. One podcast conversation can change what you thought the show was going to be. Feedback can reveal which parts of an idea connect with people and which need more work.
The goal of the first move isn’t to prove that the entire idea will succeed. It is to give yourself something real to respond to.
As Jill puts it, “Movement begets movement.”
Do You Need to Find Your Voice Before You Put Your Work Out There?
No. Your voice can develop through the process of making and sharing the work. Waiting until your ideas or style feel completely original and fully formed can become another reason not to begin.
Jill remembers being influenced by artists including Lisa Loeb and Alanis Morissette when she first started writing music. J.J. points out that this is a normal part of developing creatively: people often begin with influences before discovering what sounds and feels like their own work.
There is an important distinction between stealing someone else’s work and being influenced by the people who came before you. The problem comes when you believe you need to emerge, as J.J. describes it, “fully formed” before you’re allowed to create publicly.
Practice helps develop the voice you’re waiting to find.
“Putting things out there” and “practicing creativity,” J.J. argues, are part of how people discover their own voice. Jill agrees, which is another reason she cautions against creating an entire book or podcast season before testing any of it.
The work can change once you start doing it. That isn’t necessarily evidence that the original plan was wrong. It may be evidence that the process is working.
How Do You Know Whether an Idea Has Real Potential?
Look for evidence that other people want more, rather than demanding certainty before you begin. Jill recommends identifying markers that can help distinguish something personally fulfilling from something that may also have the potential to become a career or sustainable business.
For a musician, that might mean playing open mics and seeing whether they lead to more gigs. Are people buying merchandise? Are venues asking you back? For a writer, it could mean watching whether people find a Substack and subscribe. Online, it might mean people following, engaging, and asking for more.
“People will tell you that they want more,” Jill says.
That doesn’t mean everything has to become a business. Jill is equally clear that something can remain a hobby, and that there is nothing wrong with that. Creative careers can also exist alongside other work rather than replacing it completely.
The point is not to predict the future perfectly. It is to test the idea against reality and pay attention to what happens.
Eventually, there may be a point when the evidence is encouraging enough that continuing requires belief as well as data. J.J. describes that moment as seeing people buy, show up, watch, or respond—and then deciding, “I have to believe in myself and I have to keep going.”
Does Success Have to Mean Getting Bigger?
No. Success can include reach and financial sustainability without being defined only by audience size, money, or prestige. Jill’s own definition has changed over the course of her career.
She has performed on television and in stadiums. She has also performed in people’s living rooms. Today, she says, “For me, success is honestly connection.”
That doesn’t mean money and career opportunities are irrelevant. Jill is careful not to dismiss the importance of the larger gigs that helped her build a sustainable career. Financial realities matter if the goal is to keep doing the work professionally.
But those numbers are not the only meaningful measure.
One of Jill’s significant career moments came when Amy Grant, an artist she had admired since childhood, recorded a song Jill had written.
“That’s enough for me,” Jill says. “Whether I make a dollar from it or not, it didn’t matter.”
Defining success for yourself makes it possible to recognize value that comparison can obscure. A project can matter because it supports you financially, reaches a large audience, creates meaningful connection, fulfills you creatively—or some combination of those things.
What If You Put Something Out and It Fails?
Failure is part of making things, and learning to continue afterward matters more than avoiding every possible mistake. Jill learned that lesson in front of thousands of people while touring with Kelly Clarkson.
During one performance, Jill was supposed to play guitar with Kelly on a song Jill knew extremely well. Soundcheck had gone fine. But during the actual performance, something went wrong and the notes weren’t coming out correctly.
“I just bombed that song,” Jill remembers.
She apologized afterward, convinced the mistake might cost her the job. It didn’t. She continued performing, touring, and recording.
“I think failure is good,” Jill says. “I think you have to fail in ways like that.”
J.J. connects that experience to a larger problem with perfection. If everything stays hidden until it is guaranteed to be perfect, it never gets released—and you never learn that you can recover when something goes wrong.
“You have to risk failure,” he says.
The goal isn’t to enjoy failing. It is to stop treating failure as proof that you should never have tried.
Does Starting Something New Mean Starting Over?
No. A new direction can build on the experience you already have. Jill prefers to think of career changes as reinvention rather than starting over.
“You’re just kind of morphing,” she explains. “It doesn’t mean you have to burn everything down to reinvent yourself.”
The work may look different, but previous experience can still shape what comes next. Skills, relationships, perspective, and lessons learned do not disappear because the next project has a different name.
That matters because starting something new can feel especially risky once you have already built a career or identity. Treating every change as a complete reset makes that leap even larger.
A new project can instead be the next turn in a longer path.
When Is It Time to Stop Planning and Start?
It is time to start when planning is no longer giving you new information and making something would. You do not need to know how big the idea will become before taking the first step.
J.J. has wrestled with the questions that can keep a project safely hypothetical: What will people think? What if the timing is wrong? What if he has misunderstood his own talent? What if he has overestimated how much anyone wants what he is creating?
Those questions have stopped him before.
Now he is applying this lesson to one of the projects he has talked about for a long time: a book.
“It’s just time,” he says.
That may be the more useful question for anyone sitting on an idea. Not Can I guarantee this will work? or Do I know exactly where this will lead?
Do you know enough to make the first move?
Write the chapter. Record the conversation. Test the idea. Put something small in front of real people.
Then let what happens next teach you what to do next.
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Dr. J.J. Peterson: You've been professionally creative for more than 20 years. What do you tell people you do now?
Jill: Oh man, this is hard coming from you 'cause I really need to like narrow it down. No. This is like your whole thing.
Dr. J.J. Peterson: It was not a test. It was not a test.
Jill: It's a test.
Dr. J.J. Peterson: Welcome to Badass Softie, a podcast for leaders who are unapologetically ambitious and want to lead with heart because you're allowed to chase big goals without losing what makes you human. I'm your host, Dr. JJ Peterson I don't know if you know this about me, but I have a lot of things I wanna do.
There's ideas I wanna pursue, there's things I wanna create. In fact, this weekend I'm probably going to get a whole bunch of gourds and decorate the front porch and the house. I might make even a centerpiece for my table. I, I mean, that's just kinda the fun stuff, but there's also, like, proj- like, books I wanna write, and screenplays I wanna create, and, uh, so many projects that in many ways I, I'm definitely going to start eventually.
But sometimes I think I can spend so much time thinking about planning or thi- or just planning the thing and talking about the thing that I forget that there comes a point that if I'm actually going to put something creative out in the world, I have to actually do it. And I wanted to talk about that with my friend Jill Pickering.
Jill is one of my favorite people, and she's spent more than 20 years as a working creative. I mean, she was a touring res- musician in her own band, Jill and Kate, and as well as touring with, like, huge artists like Kelly Clarkson all over the world. She is a musician, songwriter, producer, podcaster, author, and she's taken all of that and continues to do that for herself, but now she is someone who helps other people bring their creative ideas to life.
And so what we talked about was creative work, the vulnerability of putting something new into the world, how to define success, and how success sometimes changes through the process, and what happens when we stop waiting for the perfect time and just start. I loved this conversation. It was really encouraging and challenging to me, and I know for many of you who are out there thinking about putting a book out or a new product or launching a new business, you're in that same space.
You have something creative, and you wanna put it out in the world, and I think you are going to love this conversation with Jill where we talk about all things creative, launching new things, and just doing the damn thing. So I'm so excited for you to hear today's conversation with one of my favorite people, Jill Pickering.
Jill, thank you so much for being on the podcast. I w- have been wanting to have you on for quite a while 'cause you were, A, a part of me dreaming this up. You helped me kind of process... I processed out loud a lot of, like, "What is Badass Softie gonna be?" Yeah. "And how's it gonna look?" And all of that. But on top of that, you have been somebody in my life who I have watched g- uh, uh, dream up, create, build- multiple things over even just the, you know, dozen years that we've known each other.
You are one of the most creative people I know. You are a very driven person, but not in a way that steps on people or hurts people, and also continue to live out your life in a way that I think is all, kind of centers around creativity and helping other people be creative. And so I wanted you to come on because I truly believe that you are not only a badass, but you are a softie, and you are doing it in a very fun and creative way that isn't always fun, for you.
Jill: Yeah.
Dr. J.J. Peterson: And that's part of what I wanted to talk about today. So thank you for being on the pod- podcast, and thank you for being a badass softie.
Jill: Thank you. I think we're done here. That was so nice. Appreciate that.
Dr. J.J. Peterson: So-
Jill: That's all I needed to hear ... you- Okay. That is. No, thank you. That was what
Dr. J.J. Peterson: we needed
Jill: today, right?
I'm, I'm so stoked. I love your podcast. I loved it before you even created it, 'cause I love you, and I'm excited to be here. Thank you.
Dr. J.J. Peterson: So, uh, let me start with this. So you have been, uh, going back, you know, through history for you, you were a touring musician. You, uh, created a, a business to help people with their social media.
You have been an author. You have been a TED Talk speaker. You have been, uh, a, um, a book launcher. You have done so many different things in your life of being creative and helping other people be creative. So y- you, I would say you've been professionally creative for, you know, more than 20 years. Um, what do you tell people you do now?
Jill: Oh man, this is hard coming from you 'cause I really need to, like, narrow it down. No. This is, like, your whole thing. This was- You know?
Dr. J.J. Peterson: It was not a test. It was not a test. It's a
Jill: test. No, I help people launch creative projects is really what I do, and a lot of times it's not necessarily people who have been in the creative world that much.
It's like they've had this whole career and now they wrote a book or they're launching a podcast, or I work with younger musicians and stuff too. But just kinda walk alongside them and help them get their creative work out into the world.
Dr. J.J. Peterson: Yeah, which is so fun because you've done that. I mean, so give us a little bit...
I gave a little bit of the intro ahead of time, but, like, give us a little bit of your history of being creative, launching creative things.
Jill: I've always been a creative since I was a kid, but I really, at college and after I started writing music, I joined a band, started putting out music, touring, singing with other artists, started a podcast, did all of those kind of things.
Um, but it's like cre- creative work, but you have to also do the business side of it, so you have to learn that side, too, which has been a challenge for me, honestly, 'cause I am... I could live in head in the clouds and just write songs, you know? And- ... um, honestly, that's not how it works for most people. So that's been my journey, is figuring out...
The creative side sort of comes naturally for me, honestly, but then how do you make it a business without also making it icky, you know?
Dr. J.J. Peterson: Yeah, I g- I think that- I hope I do ... for a lot of people who lean creative first- Yeah ... I think the business side is so hard, and self-promotion is so hard- So hard ... 'cause it's just like, if I just wrote the song, I, I just wanna write songs and I want people to either like it or not.
Totally. You know? Yeah. I don't wanna, like, have to, like, promote on social media and send emails, and I just wanna write the book or not, and people like it or not. But if you actually want to have a sustainable life with it, you, you have to do more than that.
Jill: You do, and that stinks 'cause, you know, it i- like you work so hard on this.
I see so many people work so hard on writing a book or starting a podcast, whatever, and then it doesn't necessarily go as far as they want because they don't realize that's just the beginning of the work, honestly, when it comes to getting it out there, so... And they give up a lot because it's, it is hard to do, especially alone.
Like, I think creatives actually, and, like, people who are putting work like that out into the world, they actually just, they don't need information, they don't... I'm not... Like, they don't need an expert, 'cause you can just go on chat, you know, or whatever, Claude, get all your information, how to do it. But you kinda need, for lack of a better word, just a coach or, like, a partner there with you to be like, "No, that's good.
Keep going." And I think that's kinda what I've come to do. I mean, I do a lot of tangible stuff as well, but sometimes it's just being with them and being like, "You got this." You know?
Dr. J.J. Peterson: Yeah, w- what do you find, like, yourself saying to people over and over who are trying to just put something out in the world?
What are some of the, like, themes that come up, things that people struggle with when they're trying to launch something creative?
Jill: Yeah, that's a good question. I think the biggest thing is people, like, do one push and think that's enough, and I think there's so much information coming at us all the time.
You need to tell people about your book or whatever a bazillion times. You know? It's like, it's n- and then they'll see it the 200th time. It's basically like don't be afraid to keep saying the same thing and telling people what you're doing, because they probably missed it the first 10 times. And then I think just, like, honestly, be yourself.
That's so simple, but- People try to emulate other people or, "This is how this person did it." And I think we're just lacking those genuine people in the world, and that's who people are drawn to. So get on Instagram Stories and be you. Don't try to be professional or whatever it is.
Dr. J.J. Peterson: I really do love that, 'cause I think that a lot of us, when we start to launch something, it, it's, in the early phases, we do kind of emulate or mimic other people.
I would imagine that when you first started writing songs, you probably were heavily influenced by certain artists.
Jill: Yeah,
Dr. J.J. Peterson: for sure. Did, did you ever kind of, like, copy them? Did you feel like, "Oh, I s- I am copying their style-" Oh, yeah ... a little bit when you were starting?
Jill: Absolutely. Lisa Loeb, Alanis Morissette, yeah, of course.
You, and- Yeah ... you don't mean to, but you just do it. You're just like, yeah. That's all you know. Well, I think- Yeah ...
Dr. J.J. Peterson: yeah, and I think for creatives, they... I, I, I give people permission a lot of times to borrow from other people's voices until you really do discover your own. Yeah. 'Cause I think that's one of the hard things, is that you don't wanna copy.
You know, you don't wanna steal, for sure. But a lot of people think, "I have to, I come out of the creative womb fully formed, and every idea is perfect," is... You know, but if you actually... You mentioned Alanis Morissette. If you actually go back to Alanis Morissette's early stuff, she was, like, on stage doing choreography and the Running Man and doing-
pop music- Total pop ... before she ever- Yeah.
Jill: Yeah ...
Dr. J.J. Peterson: ever, she ever became angsty. So she actually... It, like, took her getting on stage and, you know, doing the Running Man and Roger Rabbit to figure out that, no, I am not a pop princess. I am more of an angsty rocker, you know? And so she had to do that, and I think for a lot of us, we're in that space.
Like, w- you know, we think, oh, we have to B, E- A, either be like somebody else, or B, have our voice completely formed when we get out there.
Jill: Yeah.
Dr. J.J. Peterson: And yet just putting things out there in the creative work out there and practicing creativity, I think allows us to find our voice as well.
Jill: I love that, the practicing creativity.
I think that's so true. I think that's another thing people do, is like, "I wanna do a podcast," so they record a whole season, or they write a whole book. It's like, start with an essay. You know, start with recording one- podcast episode and see where it goes, 'cause it might go somewhere totally you didn't expect
Dr. J.J. Peterson: And I think, too, the other thing that comes up with this is the idea of what, when, especially when we're looking at other people, of what does success look like?
Jill: Mm.
Dr. J.J. Peterson: You know, 'cause it, and, and so, like, for you, I would imagine, I mean, you obviously a- as part of your career, I know you sang in back rooms in restaurants with five people there.
Jill: Mm-hmm.
Dr. J.J. Peterson: And I also know that you sang on, uh, in stadiums that were full of people, and, uh, also on national television. Right? So, like- Yeah
you've had the gamut of what most people would look at and call success over the years. Sure. And I imagine that even for you, that when you are starting to launch something, your definition of success over the years have changed. Ta- talk a little bit about that. What is, how has success changed for you?
What, or the idea of s- launching something successfully, how does that change for you over the years?
Jill: Yeah, I think it's, you have to define success for yourself, for sure. Because, I mean, yes, the big things that, like, I've been able to be a part of, being on TV or big stadiums, that is successful to most people.
Like, it's gonna get you even in other doors, right? But is it fulfilling? Does it, you know, does it make you wanna keep doing it? I think there's been shows in people's living rooms that I find way more success in You know, because it's connection. For me, success is honestly connection. If I can connect with someone through a song or a podcast episode or something I write or whatever, that's what I'm looking for.
Now, that being said, that is sort of a, an answer that you also need to, if you... I don't wanna say you need to, but you need to have that other success where you can keep funding it and keep, you know, getting in those rooms. And so, I don't know. I think it's easy for me now to say success is connection, but when I was starting and getting those bigger gigs and stuff, that was important.
So I don't wanna negate that either, 'cause I think, you know. But now that I'm, you know, a couple decades into it, I do have different success, like, markers, and it's mostly connection for me.
Dr. J.J. Peterson: W- and with that, I think 'cause f- when it comes to creative work, I think a lot of us do creative work because it is fulfilling and connection, stuff like that.
And I, like right now, the other day I just decided I wanna go make something. Mm-hmm. I was tired of thinking and processing, and so I told Jamie, I'm like, "I'm just gonna go and I'm gonna make something." And I drove around and I was just kind of wandering, and I found a bead shop. And I went in, and I just started wandering around and I found some beads, and I found, and I made these three key chains: one for me and Jamie and for Knox.
Now, that was very fulfilling for me 'cause I just needed to get out of my head and work with my hands a little bit and create something from scratch. But I pro- and it was very fulfilling. But I'm probably not going to drop my career and start selling beaded key chains- Yeah ... or start a bead store.
Jill: Yeah.
Dr. J.J. Peterson: So how do you know when you're talking to people, 'cause I know you work with even a lot of young artists and authors and different people like that, how do people know when something is just fulfilling and can be a hobby, and is fulfilling but also could be a job, a career? 'Cause I think oftentimes, especially when you're in the creative space, sometimes those overlap and w- they dom- one dominates the other sometimes.
But I think there's sometimes where something can just remain a hobby and something can then become a career. How do you know, or what would you look to if somebody's coming to you and go, "I wanna be a singer, and I wanna turn my musical career into... I wanna turn my musical hobby into a career"? How do you know what the difference is between hobby and career?
Jill: That is a really great question, and I think it changes sometimes. But I think you have to have some markers for yourself. Either it's a timeframe, like I'm gonna do this for three years, balls to the wall, you know? And I'm going all in, and I might lose money, but at the end of that, I'm gonna reassess.
There's sometimes that for some people. I think you can also, like, you have to test it out, so go do some open mics. Do they ask you back? Like, do they you know, do you get a gig from that? When you go do a gig, are you selling some merch? Are you... There's little bi- little markers, you know. And life is different now than when I was doing, starting music, 'cause I'm old.
But, like, TikTok, are you getting a great engagement on there? Are you getting people following you and commenting, like, "Do this song"? People will tell you that they want more, and I think that's a good marker for, even if it's like you have a Substack, are people finding it and then subscribing? You have to have some people willing to read your stuff or listen to your stuff, or else it's a hobby.
And that's okay to be a hobby. And I think a lotta times in creative work, it's a little of both. Like, most of my career as an artist, as a singer, I was doing some other stuff, too, you know, on the side or in between gigs. So it can be a little of both.
Dr. J.J. Peterson: Have you had moments in your career where you, like, at, in the moment went- Oh, I made it.
And I don't mean like the ultimate, you know, like forever, but was there ever moments or markers for you where you're like, "Oh, I did the thing"?
Jill: I see them more now looking back probably, but I think when we were, when I was touring with Kelly Clarkson, and we would, you know, I didn't have to have another gig on the side, and, you know, we might play Madison Square Garden and then fly private home or something.
I'm like- ... "Oh, that was kind of it," right? Like, that was sort of- You're like- Now, that being said, it's not- ... "Was that it?" Yeah.
Dr. J.J. Peterson: But
Jill: that's not my career either, right? Yeah. So I think for, that was me supporting another career. It became a career for me, but in my own, I wrote a song that, like, just a couple years ago that one of my favorite artists cut, and-
Dr. J.J. Peterson: Amy Grant.
I'm gonna say it. I'm gonna say it. Yeah. I'm gonna say Amy
Jill: Grant. Oh, Amy Grant. Yeah. I don't, I don't have a lot of, like, songwriting cuts. That's not... So for me, that was a moment of like, wow, my childhood idol is singing a song I wrote. That's enough for me. Whether I make a dollar from it or not, it didn't matter.
That was so cool for me. So yeah, I, I think money is not a great gauge, honestly. I- it's a big part of it. You have to be honest and look at numbers, which I hate to do as a creative. But does it fill you up? Like, is it gonna stick with you forever, you're gonna remember that? I think that's, I think that's nice.
I like that. I'm a dreamer
Dr. J.J. Peterson: Yeah, I remember... So I, I toured and did improv comedy for, I think, three years. So, like professionally, you know, that was... I was able to sustain myself- Oh, I know, JJ ... doing that. I know. Maybe, have I mentioned, have I mentioned that I toured and did improv- No, I mean, I love...
Jill: They're my favorite stories of you.
Well, some of them. Yeah.
Dr. J.J. Peterson: But what's funny about it is I don't remember a lot of the individual shows, other than the disasters. Yeah. So I do remember a lot of the disasters. But the show that... The only show that I ever remember that I was like, "Oh, I crushed it," was actually a show that I did before I started touring professionally, and I did, um, at ComedySportz in San Diego, and it...
I didn't... I think I got paid $10. We g- I think we got paid maybe $12 for the whole show. And it is probably even, to this day, one of the most cr- fulfilling creative experiences of my life. And I don't remember a lot of the big shows. We did, like, big, big shows, and I remember little things about those, but again, mostly the things that went wrong.
Jill: Yeah.
Dr. J.J. Peterson: But my career in that space started as a hobby, and then continued to grow until I took the risk to kind of jump to full time and go, "Maybe I think I can do this."
Jill: Yeah.
Dr. J.J. Peterson: W- when people get to that point of saying like, "Oh, I'm gonna jump to full time," like, "I'm ready to take this leap," and you are coaching them, what, what are some of those things even with them at that point?
Like, okay, they're getting ready to... 'Cause I think that's one of the scariest points, is where I'm like, "I'm letting go of my safety net, and I'm going all in on creativity." What are some of the things that you say to them or coach them through in that moment?
Jill: First of all, I have to believe in them as well.
I feel like that I have to be honest and be like, "I believe you can do this." I, I don't work with people that I don't think that, because I don't wanna f- give false hope to people. You know? Like, "You shouldn't be doing this." I don't... You know, I don't know. So that's a starting point. So I think I'm there to be like, "You're gonna doubt yourself through this," because there's gonna be days where, like, no one watched your reel.
No one came to your show. No one bought your book that you thought they were gonna the first week, you know? And... Or just your family did, you know? And it's like- ... you know, and that stinks as an ar- It's, it's gonna happen for most people. But I'm here to tell you, like, it's a really long journey, and this is, like, just a little blip in it.
It sounds a little cheesy, but I think it's true.
Dr. J.J. Peterson: I do too. I mean, I think that that's a piece where, again, when we... Es- but... It... When you look at what other people's success looks like and you start measuring yourself against that, it's like, okay, you know, yes, there, that's that. But- Y- you don't have to achieve that for it to be fulfilling or make a career or make an impact or connection or all those things.
And if you really have start- gotten some good feedback and, you know, people are buying your thing or showing up for your thing or you're getting views and now you're gonna slowly start building, I think you do. You... It comes a point where you just have to go, "I have to believe in myself and I have to keep going."
There are so few overnight successes. It's like everybody, you know, you'll f- see somebody who, like, even won New Artist at the Grammys, and it's like, you know, "I've been doing... It's funny to win New Artist 'cause I've been doing this for 20 years." You know? Like- Every
Jill: time, yeah ...
Dr. J.J. Peterson: it, they all say it because it never was, "I wrote one song," maybe if you're Billie Eilish, but other than that it's like, you know, "I wrote one song, it hit big, and now I'm winning a Grammy."
That's just not how it works. You've been busking, you've been working, you've been traveling out of the back of a van, and, and now you're starting to get some traction, and then you build on that traction. And I do think, though, for, you know, I'm a little bit older than you. You mentioned being old, but I'm older than you.
Jill: So you're really
Dr. J.J. Peterson: old. And-
Jill: No, I'm
Dr. J.J. Peterson: just kidding. I'm really old here. And, and it- it's just interesting, too, though, when you get to this point in life, I think starting over and starting something new feels even riskier and harder. And do you think that, you know, at this point even in your careers, like... 'Cause I've s- I've ev- you know, in the time that I've known you, you've started over a couple different times and changed different directions a couple different times.
You've always done music, you've always done creative, but you've, the way that that showed up has changed a little bit. Is starting over actually harder when you know what you're doing and what life is like?
Jill: Ooh, that's a great, great question. I think... I don't even, I, I think of it as, like, reinvention sort of.
It's like you've already, you're just kind of morphing. It doesn't mean you have to burn everything down to reinvent yourself, I think. You just kinda do the next thing on the journey, and all of the stuff you've done has built your character, it's built experiences that pour into the next thing. So- I, I'm not a big believer in, like, necessarily starting over, but just sort of taking turns and reinventing a little bit.
That's how I look at it, and that's how it's helped me, because I think starting over feels way overwhelming for me. You know? I'm like, "Oh, wait, I, I've built all of this, and then I have to burn it all down?" I don't think that's how it has to be. There... I, I do think there are, to qu- to quote Henry Cloud, Dr.
Henry Cloud, necessary endings of, like, this one's not I need to stop this and do something different, but it's gonna build on what you've, you've already done.
Dr. J.J. Peterson: Yeah, 'cause even now, you're s- you continue to produce. You just were in... produced for other people, as in album and music. Uh, you just recorded your own album, your own latest album.
Last week you were in the studio.
Jill: Yeah,
Dr. J.J. Peterson: I'm working on it. You also are continuing to write. You're continuing to... So you're con- you're building on everything. It's not like all of a sudden you stopped tou- being a touring musician completely. You still are in the music space. You're still doing creative things, and now you're just helping other people bring that to life.
And so I, I've y- I think that's really true. You're, when you're kind of starting over at our age, which some people I think- ... are looking to do even in this season-
Jill: Yeah ...
Dr. J.J. Peterson: feeling like you need to burn everything down and shut it all down, maybe you do. Maybe that is for you what you need to do. Yeah. But I think it's not always that way, even for me as I launch Badass Softie.
It's not like I'm letting go of the marketing space. It's not like I'm letting go of the teaching at Vanderbilt. I'm still doing those things, but I'm kind of launching some new things and building on it versus starting over.
Jill: Yeah, and even your comedy career and everything you've done up until this point- It pours into the next thing.
So I just, I look at them as building blocks versus like, "Oh, I used to be that."
Dr. J.J. Peterson: I do think I would be remiss if I didn't ask you about a Kelly Clarkson story. Mm-hmm. And it doesn't have to be about Kelly Clarkson, but about an experience that you had in the creative space. And what I want you to answer is not a highlight, but a disaster.
Jill: Oh man. I don't talk about this a lot 'cause it was just such a disaster. But I was playing one of my favorite ... We, she did a song every night that was like different in the set, and it would be a fan request. So people could tweet in or whatever. And someone requested this song that was one of my favorite songs of all time, and she was like, "Why don't you play guitar on it?"
'Cause I played acoustic and, and electric with her. Um, she's like, "Why don't you and I just do it together?" 'Cause sometimes it would be the full band. Sometimes it would just be a couple people in the band and her. So I was like, "Great. I love it." I, I knew, I know this song. Like verbatim I know this song. And we get up, we rehearse it and sound check.
It goes fine. We get, we get up on stage during the set and I don't know what happened. My guitar, I think something was wrong with my guitar, but like every note just wasn't right. It was like, and I was like, I'm looking at it going like, "Is the capo on wrong?" Like is ... And she's kinda looking at me like, "What are we doing?"
'Cause we pretty much trusted each other with like musical stuff, and I just bombed it. I just bombed that song. And I went to her bus after and I was like, "I am so sorry. I don't know what happened." She was like, "It's fine." You know, she's so cool. And she ... But it was a disaster for me. I was like, "This is the, I'm gonna get fired," and I just
It was, it was terrible. I felt bad for like years after that. Um, but you know-
Dr. J.J. Peterson: Did you ever get to redeem yourself by playing that song again?
Jill: I don't think we ever did that one again. We did other stuff and I did fine, so it's like whatever, but I think failure is good. I think you have to fail in ways like that.
I mean, I hated it. It was humiliating and I, I just hated that so much. But It, it does make you... No one's perfect. You know what I mean? And you're not perfect, and you're gonna screw up, especially in the creative world. You are gonna sometimes just bomb, or your voice will give out, or you'll write something that sucks, you know?
Hey, you can keep going.
Dr. J.J. Peterson: That's kind of why I wanted to ask you that to, to kind of as we're closing out here, because I think that's another big piece about being creative. If you're actually going to be creative, you have to risk failure- Mm-hmm ... and you have to fail. Like, if you hold back everything until it's perfect, it, A, it'll never get out there, and B, you- when you bomb, you'll never recover.
Like- Yeah ... you kind of... Like, that's, I think, the biggest thing about pushing forward creatively, is learning how to fail and get back up. Because, like, the, like, y- I know you got back on the stage after. I know you sh- continued to play guitar. I know you continued to tour, like, and continued to record. That moment did not define you, but how many people was that in front of?
Jill: Oh, gosh. Thousands. I don't know.
Dr. J.J. Peterson: Yeah. Yeah. You were... Like, we- we're not talking about- It was- ... a coffee shop performance here. This was- It
Jill: was, like, an amphitheater. Yeah. Yeah. I think it was an amphitheater. I don't remember even what city it was, but it was, it was probably 10,000. I don't know. Something like that.
Yeah.
Dr. J.J. Peterson: 8,000, 10,000. You failed in front of 10,000 people.
Jill: Yeah. So,
Dr. J.J. Peterson: like,
Jill: and- And I survived, you know?
Dr. J.J. Peterson: It's like- And you survived.
Jill: Yeah.
Dr. J.J. Peterson: And you got back up, and you continued to do it, and the people who were trusting you to succeed in that space also let you get back in that space. And so-
Jill: Graciously, yeah.
Dr. J.J. Peterson: That's so, when it comes to creativity, you know, especially when I was doing improv comedy, if I was trying to be perfect every single time, then I would never take any risks, noth- every b- thing would be the exact same almost every time.
It would not be funny. It would not be spontaneous. Nothing new would be created. You have to fail a little bit, and again, it's not that failure is feels good or you have to like it, but if you're going to be in the creative space, you have to learn how to fail and then turn right around and get back on that stage the next night and keep going.
Um- 100% ... that's the only way that it works. So if people are listening right now and they, like, are in that space of, like, "I don't know. I might try to do this. I'm thinking about doing this. You know, I'm, I, I wanna take my creative things to next..." And, and specifically, I think a lot of people in this space are talking about launching a new product, about putting a book out, about, um, releasing something into the world that probably is product-based or business, like launching a new business.
For the people who are in that space right now, what advice would you give them?
Jill: I think you gotta stop talking about it and do something. I think I fall into this, which is why I say it, but you, you gotta start small and do something. If you wanna write a book, and you have the idea and the vision and the book cover idea, like write a chapter and get some feedback on it, or write an essay.
Start small. Like, you gotta just make the first move, and then momentum, like movement begets movement. But I think a lot of people get stuck on planning it, you know? So just you gotta make a move.
Dr. J.J. Peterson: I think that's incredible advice 'cause y- you'll never get anywhere unless you do. Jill, how can people, if people are interested in following you and your creativity and some of the things that you're putting out in the world, where can they find you and follow you?
Jill: That's so nice. Um, I'm on Instagram @jipimusic. That's J-I-P-I music. And I have a podcast called Take a Jill Pill, and I have jip- uh, jipicreative.com if you have a creative project that you wanna... you're w- looking to launch and you need someone beside you to be like, "You can do it," that's, that's my world. So that's where you can find me.
Dr. J.J. Peterson: Love it. Well, Jill, I am so excited for all the things you have coming out. I'm excited for all the things that you're helping people come out with, 'cause I also know behind the scenes of, like, some of the other projects you're working on. So I'm so excited about everything that you're doing. I am so grateful that you continue to put creative and beautiful and powerful work out into the world, and that you lead with your heart in a way that inspires other people to do the same.
So thank you so much for being here. And again, I wanna thank you for being a badass
Jill: softie. Thank you. Can I say something about you, or are you gonna cut it?
Dr. J.J. Peterson: Probably cut it.
Jill: Okay.
Dr. J.J. Peterson: Probably cut it, but you can say whatever you want.
Jill: No, it's fine. Thank you, JJ. I...
Dr. J.J. Peterson: Say what, say what you wanna say. Say
Jill: what you wanna say.
What you wanna say. Okay. Thank you, JJ. I think you do such a great job of being creative and business-minded and doing... like melding the two. And I love your podcast, I love everything you do, and I really appreciate you having me. Thank you.
Dr. J.J. Peterson: Yeah, we're cutting that. But thank you. Kidding. All right. Love you, my friend.
We'll see you soon.
Jill: Thank you.
Dr. J.J. Peterson: Oh, I could have talked to Jill for hours, and I do. There have been so many nights where she and I have stayed up late talking about creativity and vulnerability and putting things out in the world. And I'm so excited to hear her n- her new album, which she just finished recording.
And the thing that has kind of stuck with me through this conversation was just the idea, I think, that she kinda said at the end of just it's time to just do it. There are so many times in my life where I have had these kind of grandiose ideas, and my fear of failure or my fear of not doing it right or it being the wrong time or not actually taking full advantage of the moment, a- all the things, have stopped me.
Uh, what are people gonna think? Are they gonna think I'm arrogant by putting this out there? Am, um, do I, have I misunderstood my own talents? Like, have I overestimated that people want this thing? And the reality is, if I am passionate about it, if it means something to me, and I'm starting to see that it means something to other people, I should put it out.
Whether it becomes this huge thing or a small thing, or I connect with a million people or one person, put it out. That's what I was reminded of today w- in my conversation with Jill, is that there are things in my life that I know it's time. It's time to start doing it. One of those things is a book. I am in the process now of starting to write a book, and it's just time.
It's time for me to do it. So if you're in that space, may this be the day that you say, "Okay, it's time to do it." It doesn't have to be big, doesn't have to be fanfare, and it 100% does not have to be perfect. It's just time to do it. This is your push. So let me leave you with this. May you have the courage to make the thing you keep talking about making.
May you stop waiting until you have more time, more confidence, a better plan, or some guarantee that it's gonna blow up and be huge. And may you remember that success doesn't always ha- mean that something has to be bigger, louder, or more impressive. Sometimes success is simply making something that feels like yours and letting other people connect with it in a way that then makes it feel like it's theirs, too.
Because we believe you can be both ambitious and kind, fun and driven, powerful and deeply human. I also believe you can be creative and successful. Your leadership can inspire, your success can have soul, and your ambition can make space for everyone. That's why you're a Badass Softie. We'll see you next week.
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