Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs

Stop Waiting to Be “Ready”: How Pianist Michelle Lynn Built a Career on Action, Not Permission

Tonya Episode 22

The leap from conservatory to career is rarely a straight line. Pianist and entrepreneur Michelle Lynn joins us to share how she turned uncertainty into a full-time performance schedule and a thriving coaching community—without waiting for anyone’s permission. We dig into the early years of cold pitching in Europe, building community from scratch, and finding momentum by translating big dreams into small, scheduled actions that actually get done.

Michelle shows why planning and mindset have to grow together. If fear of rejection or a fixed identity keeps you from applying, posting, or pitching, no calendar can save you. We unpack practical tools—social media that serves presenters, brand assets that make booking easy, and websites that convert—while also addressing the inner work of reframing “I’m not ready” into “What will make me ready?” Her Fast Forward membership gives musicians and creatives a place to set goals every two weeks, stay accountable, and compound progress over months rather than moments.

We also get tactical about business models. Michelle explains why a membership creates recurring revenue and better outcomes, how workshops and a six-week social media program feed the community, and when a high-touch mastermind makes sense. On the personal side, she reveals the routines that prevent burnout: time blocking coaching and performance days, batching tasks to reduce context switching, and protecting energy with sleep, training, and boundaries. Marketing becomes less cringy when it’s service-led—help promoters fill seats, amplify partners, and show up as someone they want to book again.

If you’re a musician, artist, or independent creator who’s tired of waiting for the phone to ring, this conversation is your blueprint for consistent action and sustainable growth. Subscribe, share with a friend who needs a nudge, and leave a review to tell us the first small step you’ll take this week.

Get Michelle's Album: https://open.spotify.com/album/3XCoVEbwGpZuVQ92UTMwzp?si=Y3400HJETvuqd5rr9Zg00A

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SPEAKER_01:

Welcome back to Plan Like a Boss. I'm your host, Tanya Lawson, and today I'm sitting down with Michelle Lynn. Michelle is a Canadian pianist, singer, and entrepreneur who enjoys a wide and varied career. She regularly performs across Europe and just released her new album. As co-founder of the Fearless Artist Mastermind, Michelle believes that musicians have the ability to build their own successful careers and should not be limited by their own glass ceilings. She coaches musicians to reach their full potential and unlock the gold that is inside of them so that they can accomplish their purpose. Welcome, Michelle. I am so happy to have you.

SPEAKER_00:

Hi, Tanya. Thanks for the invitation.

SPEAKER_01:

Let's start by telling us your story, how you got here. Because I'm sure as, you know, a little girl or even a college student, yes, piano might have been something, but all of the entrepreneurship and all this other stuff probably wasn't on your radar. So tell us a little bit about your background and how you got here.

SPEAKER_00:

Yeah, absolutely. It's funny to look back, you can see glimpses of maybe things that you were good at when you were a child that then evolved into something you could have never imagined. So, you know, I was captain of the basketball team, I was very bossy as a child, I was in leadership classes, I was always, you know, in charge of something. And so then coaching just kind of came naturally. I I got interested in entrepreneurship around 10 years ago, I think. And I started by listening to a lot of Marie Forlio, Seth Godin, kind of a lot of power women speakers. So that kind of piqued my curiosity. And then tying into my piano career, realizing together with Deanna, my co-founder, that you know, musicians are completely unequipped for the real world, kind of evolved into the fearless artist and what we do now with musicians to coach and equip them to pursue their careers.

SPEAKER_01:

100%. And and you're right. Uh, I'm a musician as well. And we go through music school and they teach us how to play. They teach us how to teach, they teach us how to perform. They don't teach us how to run a business, and that's a big part of it. So when you first started out, what was the biggest surprise to you as far as running a business is concerned? Uh, what what made you realize, oh, wait a minute, this isn't gonna just happen. I have to make it happen.

SPEAKER_00:

Hmm. In terms of my own performing career, uh, I remember moving to Europe. I was 25 when I came over, and the plan was to be here a couple years, study with some different teachers, and then go back and possibly do a doctorate in Montreal where I did my master's. And so I then I think it was it was like, well, now what? Okay, I can start to build a teaching studio, and I got included into a church, so you know, all the kids started coming to my house for piano lessons. Thank goodness, because many expats don't know where to start in terms of building a community. So for me, church filled that need. But then in terms of performing, it's it's like, okay, I started to get connected to some conservatory students, but I wasn't at the conservatory, so I felt kind of like an outsider. And then, like cold pitching for concerts, nobody knew me. I didn't have a lot of recordings available. So, how do you pitch yourself even if you have nothing to show for it? Should I be doing competitions? Should I be working with so many, like, what do I do? And this is hard, and I don't have a teacher anymore to tell me step by step, like, do this, do this. And I think that was really hard. Yeah, there were some low moments in there. So then I kind of just, you know, then the leadership thing came in, or I got curious about other things and kind of started to fill my life with other things than just piano, which in the end has paid off. But if I look back, I wish that I could have had some kind of formation or plan to say, like, let's let's do this and commit and not have the ebb and flow. Um so I think that's where consistency is really something that I've had to learn.

SPEAKER_01:

I love that. And your membership is is this something you teach in there? You help people learn how to do all of this that you had to figure out on your own.

SPEAKER_00:

Yeah, exactly. So it's called Fast Forward Our Community. There's 55 musicians in there now, and it is really about um carving out steps every two weeks for like what am I actually pursuing? What is the goal, the vision, the dream? What am I trying to accomplish? Many people don't know, right? So it doesn't have to be this huge, wide life purpose plan. But it's like, okay, you want more concerts? Let's break it down, let's get it on the calendar. You've got the community support, the accountability to help you feel that you're not alone. Because I think that was one of the biggest things I felt. And also Deanna in Paris sitting there staring at the wall, saying, I went to Juilliard and nobody told me what to do now that I'm done, and I'm I'm just waiting for the phone to ring. So I think that element of small steps consistently is really what will make the difference if you're pursuing something. I love that.

SPEAKER_01:

And I think I think that probably spans the entire creative field. You finish college, you f have this degree, but nobody tells you what to do when you're done. Yeah. And that's something we all have to learn and figure out. So you've talked a lot about, you know, finding your goal and breaking it down into small steps to um accomplish it. And planning is something we talk about over here on the channel a lot. And I know you and you know me, and I'm a planning fanatic. Yes. So talk about, you know, we have a lot of musicians here, but we also have artists and business owners, creators, makers. Talk about what that might look like. Like if you, if someone was gonna sit down with you to kind of sketch out what they're gonna do, what might that look like for them?

SPEAKER_00:

Mm-hmm. You're right that this affects so many creatives, and I'm so glad that there are people like you teaching us how to plan. I know I have your uh workshop of the how to plan the last quarter of the year and getting tangible, getting practical, these steps are super important. But there's another element that ties in as a creative, and that is the fear of failure and the fear of rejection. So I think a lot of times when people come, I mean, the reason I back 25-year-old Michelle didn't want to apply for all the masterclasses, all the competitions, all the teachers was because I was like, well, what if they tell me I'm not good enough? What if they say you don't belong here? Um, what are you doing here? Who do you think you are? All of these terrible negative limiting beliefs. And even if there's some truth to that, a growth mindset would tell you, okay, I have work to do. I'm gonna get into the practice room with a plan and go after it. But unfortunately, I did not have a growth mindset back then. I had a very fixed mindset, and the fear of rejection and failure was enormous for me. So when somebody comes into something like our community, it's really about holding those two elements because it's sometimes people are like, yeah, okay, I can't just make a plan and say I'm gonna do it, because there are reasons why we don't do these things. So it's about unlocking what's going on underneath. What are your belief systems that are choosing these actions that you take every day? Because if you wake up and you believe that you can accomplish something, you will run straight down that marathon track. But if you wake up and you're like, I don't know if I'm good enough to do this, that's what will stop you from taking action. So for me, in terms of coaching or walking with someone, as you asked, it's really about unlocking the like what's what's happening on both sides of the spectrum here.

SPEAKER_01:

I I love that too, because yes, that that mindset is so, so important. And we we all have felt and probably still feel, I know I do, the imposter syndrome that kind of sneaks in. Yeah, you know, am I good enough? Are people gonna take me seriously? And I think what it comes down to is you have to try. You just have to do it because if you don't do it, you're not good enough because you never did it in the first place. Right. And I like that idea of reframing that into what do I need to do next to make myself maybe maybe I'm not good enough yet. What do I need to do next to make myself good about enough? Yes. Now from the business side of things, your membership, why did you choose a membership over one-on-one coaching? What what about the membership made more sense to you?

SPEAKER_00:

That's a great question. So when I first started dipping my toe into like the business world, uh, someone that I followed extensively was the Female Entrepreneurship Association. Her name is Carrie Green and she's in the UK. And she has a membership where you would pay a fee every month and get logged on to resources and community and kind of like a sort of Facebook feed where you can ask questions and discuss among other women. So it's your like-minded people community. So I think that was like ding ding-ding. Like all of our musicians were saying, I feel so alone. I thought I was the only one struggling with this. And we're like, welcome. We can make a low price point community for you where you can get connected to other people, ask questions, learn from each other. Um, and it doesn't have to be the price of one-on-one coaching. Um, that being said, we also have a mastermind that does include the one-on-one, which I absolutely love because then I have time with someone to kind of dig deep and say, like, you know, what's going on and how can we make sure that you are going after what you want. So uh in the Fearless Artist, we really try to um cater to all price points, all mindsets of either you come in for 57 a month and have the community of 55 people, or you come into the mastermind, which is uh different price point, different career strategies, different uh accountability. Um, and whatever people need, we can we can do that.

SPEAKER_01:

And this is something that they can kind of stair step up as well. They can come into the community first, and as they maybe their finances improve, or something else they can stair step up to the next level.

SPEAKER_00:

Absolutely. And like we have found in terms of selling to musicians, it's really hard to encourage them to spend money if they don't know what they're gonna get from it, right? Because the musicians typically have a poverty mindset. They think of everything as a loss. Investing in yourself in your career is kind of like, yeah, I don't know, I can just do it by myself. So we do bring in people at the low price point and then they trust and then they see, and then we have a social media program that's six weeks long, and then that seems more doable. So they'll join that. And then, you know, exactly as you said, having these other options for people once they see that they will get results.

SPEAKER_01:

Oh, I love that. I love the bringing in trust. Now, I'm guessing that this the fast forward did not just happen all at once. It's like, oh, here's my program, and we're starting with this membership, and then you have this, and then you can step up to this. So, how did that evolve? Because I know a lot of business owners and creatives out there are wanting to do something and they they look at people like you who have this built out and and they're they're thinking, I don't have the capacity for that. I I don't even understand how to make all that work. Can you talk a little bit about your evolution as you started building it? Because I know it didn't start all at once.

SPEAKER_00:

Yeah, absolutely. And maybe this is a good time to give a shout out to Nicole Ricardo, uh, our business coach. I've been working with her monthly for I think two and a half years. So this is really where I could come brain dump or just dump everything that was going on, all the frustrations, all the unknowns, not knowing how to speak to the audience. Who is my target audience? How do I convince people? And then of course, convincing became more about okay, how do I show them that we can help them? Um, so to answer your question, fast forward started with four people. And I think it was uh 30, 27 a month. We had a founding members rate. And yeah, I think maybe there were four to six people who joined initially, and we would have meetings of four people, and Deanna and I we looked at each other after and we're like, what are we doing? Like, this what is this worth investing in? Because it was taking a lot of whenever you start to build something, there's so much manpower that goes into just getting it going, the getting the machine to start to turn. Um, and then over time, uh, because I taught on faculty at uh university in entrepreneurship, I had a lot of curriculum around branding, networking, social media, marketing, all these things. So we turned them into workshops. And those we would sell as one-offs throughout the year at the Fearless Artist. And then we realized we should just combine them with the membership. And then we started figuring out ways to bring people in by offering them a free month. But then people wouldn't come to the calls because they were like, What is this? I don't know, is it therapy? Do we just sit around and talk and like complain about how hard it is to be a musician? So then we're like, okay, well, we'll bring them to a free call and then we'll show them how to get connected to the community. And then from there, we've really started to see that it's it's really growing. I love that.

SPEAKER_01:

And and yes, I we all, when we're developing something new, we're constantly changing it. We're constantly building it. Like you said, you you start out with four people and and four people at$27 versus 55 people at$57 now. That that's a huge growth difference. And then then also by doing a membership, you've got re regular recurring monthly income coming in. So another thing that I love to preach and to talk about is having multiple different income streams. Yes. So as a business owner, can you sketch out like we don't need details, we don't need numbers, but the the different income streams that you have coming in?

SPEAKER_00:

Yeah, as as me, Michelle, personally, I have my performing career. I play chamber basic concerts, solo concerts, and also with candlelight concerts, and they really have taken me to the point where I do not need to teach piano lessons anymore. I quit now two and a half years ago teaching piano, which was my main income stream back then. I also previously did a lot of accompanying, a lot of gigs, a lot of background gigs, working at a singing studio for three years just to give some context for people that now I have a full-time performing career, but previously I did not. So it was really about the, again, evolution of things. So that's my my performing career side. And then now on the TFA side, we have the membership, as we said. We have a six-week social media program that we run two to three times a year, depending on how if I can get my launch together on time. And then we have a mastermind which has 10 people in it currently. So those are the income streams. Then we do one-off workshops, as I mentioned. And what we'll do is people will pay for those. And then if they join the membership, we refund that workshop fee so that it they come into the membership. And you're right about the recurring revenue. And do you know what we found is that it works better for both sides because people will see results when, as we already said, they stay consistent over a long period of time. So if they come into the membership for one month and they try it and it doesn't work, yeah, I'm sorry, but like you didn't have time to implement anything that we're talking about, right? Because first of all, we have to try and change your mindset because we have to figure out where are you with your mindset? Do you think that you can get what you want? If you don't, we got to do some work there. That takes time. You have to overcome so many limiting beliefs about yourself and your identity. Then we have to implement the tools. How is your social media content, your branding, your your website, or your digital presence? Is that all aligned, right? So there's like a ton of time and work that goes into this. So we need at least six months with someone. So if they are giving us the recurring membership revenue, but that also means that we can actually make progress with them. So it's win-win. Oh, absolutely.

SPEAKER_01:

And consistency, like you said, plays such an important part. And all the musicians out here listening to this know exactly what you're talking about when it's when it's like you don't have to teach piano lessons anymore, you were doing gigging and freelancing and all that. Um, for those who are not musicians who may not understand that, it sounds like you were the the equivalent of your performing career was was your dream business and everything else was your day job. And through that consistency of pitching yourself, of getting your name out there, and probably a fair amount of rejection, you built it into where now your day job is gone and your dream job has begun.

SPEAKER_00:

Yeah. Isn't that fun? Oh man, it is really fun. And also I want to say the Instagram presence really helped me because I take Instagram really seriously in the sense of if I was invited somewhere, I was helping them promote it. I was reaching out to people, I was in the DMs, I'm talking to people, I'm networking, really using that resource rather than a lot of people are negative about it or they poo-poo it. And I'm like, you don't understand the power that you have by helping the concert promoter promote their concert. Do you know how much that means to them? That is a big win. If you can show that I have value by not just playing, but I will help you do your job, butts and seats, they're gonna want to work with you again. Learning a lot of people's skills and then the power of the self-promotion has helped a lot.

SPEAKER_01:

Oh, absolutely. And self-promotion, I know to a lot of people can seem cringy or icky, but there's there's a way to do it that works well, and it's just part of the job. It's it's part of the job for any entrepreneur. You have to sell and market yourself.

SPEAKER_00:

Yeah, how do you do it that you don't feel cringy? Because I know you do a great job.

SPEAKER_01:

Um, it took me a long time and a lot of mindset work. But I found the more I did it, the less cringy it felt. And I also tried to keep in mind that as I'm marketing myself, I am marketing myself as a solution to a problem. I am helping, I am serving my audience. And even if you're a musician who's promoting their concert series, you're serving your audience because they want to listen to what you do. And by promoting it, it makes it easier for them to find it.

SPEAKER_00:

Yeah, absolutely. I mean, we can't go to anything if we don't know it exists, right? So every time you see a billboard or you hear a radio announcement, I mean, how are you going to know about it if you don't hear about it? So we need to tell people what we're doing.

SPEAKER_01:

Absolutely. Now you're not doing the freelancing and the gigging and the piano lessons anymore, but you're still performing regularly and running an active membership. And, you know, I I took a glance at your performance calendar for December right before this, and it looks insane. So I haven't looked. Don't tell me. How do you balance it all? And how do you not burn out?

SPEAKER_00:

Great questions. Consistency in routine in the sense of I work with a personal trainer, I'm at the gym, I got more serious about eating well. Little little habits that I've implemented that have really helped me, like magnesium before I go to bed so I sleep well, practicing when I'm at home. Um I had to I had to work so much on my mindset around practicing too. So that's a whole other conversation. The other really big thing is time blocking in the sense of Mondays and Tuesdays. I'm working with Deanna, my co-founder, on Zoom on a co-working call. We have about two-hour block of work, and then we uh coach separately during the week. But my coaching is Monday, Tuesday for the most part. So Thursday, Friday, I really leave open for traveling, performing. And I think splitting my week in that way has really helped my mind of like, okay, I'm coach Michelle now. And like on a, you know, today's Thursday, typically I do have a couple of coaching after this, but it would be later afternoon. So the mornings are practice time, gym time, the afternoons are the coaching. And then I kind of try to do admin like at 11 p.m. on the last minute because I'm like, oh shoot, I really need to send this invoice. You know, though I'm not perfect with a lot of things. Ask my accountant. My taxes were very overdue. Anyway, but in terms of not burning out, I've learned not to push myself till I'm exhausted. I think that's probably been a huge revelation for me. I am way more self-aware of like, I'm feeling this. I need to pull back. And surprisingly, when I have pulled back, it's actually given a better result sometimes. Like I remember once in this coaching call, I felt like I had to show or give this person everything. So I was like coming with all the ideas and the energy, and I was like, let's do this, let's do this. And then I realized like she just really needs me to listen. And I can just sit here and be chill and save my energy. So it was better for both of us.

SPEAKER_01:

Yes, I love that. And hustle culture is overrated though. There, I said it. It's overrated. Yeah. It can do more damage than good. Yeah. And if you take care of yourself, you tend to show up better. So you can show up all the time, or you can show up less, but the best version of yourself. And it sounds like that's what you've you've learned and master over time.

SPEAKER_00:

Yeah, it's it's really, really changed for me to not push myself till the exhaustion. And uh yeah, pulling back. I sleep in the mornings. I'm not up at 6 a.m. jumping on the computer. Like, I don't have kids. So I watch my poor friends who are like getting not sleeping well at night. And I'm like, I'm just gonna enjoy this season of my life right now where I can lay in bed. Like not push myself at six in the morning. I like that.

SPEAKER_01:

I like that a lot. And and you you hit the nail on the head. It's the season of the life you're in. And it's going to change. And that's okay. There is nothing wrong with that at all.

SPEAKER_00:

I have one more thought. If I can add, I've I've learned how to batch what I'm doing because I did not recognize early on how much energy it takes to start tasks. So now once I'm in something, I stick in it. Like even three, four hours. Like, you know, after this podcast, I've got two hours of coaching, and that's no problem. It's gonna be fun and I'm gonna enjoy it. But if I had like one hour at 10 a.m. and then one hour at 3 p.m., like that would kill me because you gotta get into your coaching mindset, you gotta set up, you gotta sit down, like open your email. All of that is energy wasted. So I think I finally learned like that's why I mentioned like my mornings is one half of me, and then the afternoon evenings is a different version. And that has been the easiest way to like batch things. So if somebody needs an extra coaching call, it's like, okay, you can you can on Thursdays, but not Tuesday morning, because that's my gym time.

SPEAKER_01:

Yes, and boundaries. Yeah, these boundaries are so important. And it sounds like obviously, as entrepreneurs, solopreneurs, we all wear all these different hats. And by not having to change your hat all the time, it makes life a lot easier. So exactly. I like that. You've got your admin hat on, you've got your client call hat on, you've got your practice hat on, all of that.

SPEAKER_00:

Exactly. And and no when when I'm practicing at home, I look like a gremlin. Like I'm not made up, I'm not in my nice clothes, I'm like, I've got the hoodie on. It's like, don't talk to me. People wouldn't recognize me on the street, right? Like they'd be like, wait, are you that girl we see on Instagram? I'm like, yeah, but this is practice, Michelle. Like, she's a different person.

SPEAKER_01:

Well, I love that. I love that. And and yeah, I have, I like to call them my potato days. If I have just an admin day where I'm not gonna be on camera, although I did not put on makeup before this fall because I didn't have time. But you know, beautiful anyway. Well, thank you. I uh, you know, I have my potato days to where I'm in sweats and I, you know, I don't really care because I'm just working behind a computer or with a cup of tea and just yeah, enjoying life.

SPEAKER_00:

We don't have to be on all the time, and I think that's helped me a lot. Absolutely.

SPEAKER_01:

Well, if people want to find you, what is the best way they can?

SPEAKER_00:

Yeah, uh, this is Michelle Lynn for my Instagram, that's L-Y-N-N-E. And then the fearless artist mastermind is our musician uh community for any musicians listening. And uh those are the two best places.

SPEAKER_01:

Awesome. And we will link to Michelle's album in the the description and show notes. And and finally, if you could give one piece of advice to someone just starting out building their career, what would it be?

SPEAKER_00:

Don't let anyone tell you you can't. We listen too many times to these negative voices, whether that's coming from inside our heads or outside from an uncle who doesn't understand how a musician's gonna make any money or you know, whatever creative pursuit you have. Look for the people who are doing what you want to do and and figure out how they did it. Follow that.

SPEAKER_01:

Oh, I love that. I love that. And and I personally I take a hold my beer attitude to to anyone who tells me I can't do something. I love that. Hold my beer, I'm on it. All right, great. So thank you so much for coming onto the show. And I know my audience gleaned a lot from this. So do what Michelle says, get out there, be consistent, and keep planning like a boss.