082: Tracy Cherpeski | Figuring Out Your “WHY” to Thrive Forward

Tracy Cherpeski, Founder of Thriving Forward Mastermind, is an executive coach, consultant, and leadership development expert. Tracy helps her clients who struggle with feeling like they have very little control over their time and energy, and who wish to create a healthy, fulfilling path to greater success. Her coaching and leadership training programs offer whole-person, integrated leadership, executive development, and mindset mastery.
In this episode, we get into the reason you should figure out your WHY. Tracy shares with us what it was like to lose 80% of her revenue as COVID hit, but what it allowed her to open up, and how one of her members in her mastermind is now following her dreams and making it in the world of music. Check it out!

[02:04 – 10:30] Tracy’s learning journey and Masterminds

The Mastermind Effect:  01:55

Let’s dive into it. Our ability to learn from different people has changed over the last 5 – 10 years. When you and I were younger, there were textbooks and teachers around us and eventually, family, friends, and co-workers. But that’s just a sliver of what’s possible. How is your learning changed from your early years versus today?

Tracy Cherpeski:  02:26

Besides the obvious, we have the internet at our fingertips. We can Google anything; It’s connecting with people from far-flung places. I have these great connections with people in Australia. I’ve met a few people virtually in South Africa, Canada, Europe, and all over the US without traveling. The biggest thing is being able to make those connections and learn from people and their experiences.

The Mastermind Effect:  02:52

Absolutely. I’ve said at the beginning of the show, the best way to learn is from other people’s experiences. If you can learn from someone that’s already seen around that corner or made that mistake, whether they’re in your industry or not, it’s pretty dang powerful.

As we’re learning from different people, we have access to more people, and we’re also able to take in more information than ever before it. They can be confusing at the end of the day with the amount of information out there. Some people learned from mentors, coaches, masterminds, accountability partners, online courses, and lots of ways to learn.  Who are you currently learning from? And more importantly, how did you find them?

Tracy Cherpeski:  03:33

That’s a good question.  The most recent thing that I have engaged in is a leadership course called World Legacy. I’ve just completed the first round of what they have broken into sections. I just did the first breakthrough. We’ll do a second breakthrough, and then we go into leadership. They’re not secretive. They don’t give a lot of information because they don’t want you to decide already whether this will work for you or not. You get to decide as you go.

I am quarter way through already. I got up Monday morning after completing the first round, and I’ve gotten so much done by 8:59 am. I remember this clearly.  I thought it must be lunchtime because I had gotten so much done. I was able to get into flow quickly by learning how to break down some of those mental barriers that keep us from taking action steps. I’m currently involved in two masterminds, which I’m leading. But let me tell you something I learned so much from the participants. I’m furiously taking notes to reflect back and because I think that’s such a great nugget, and I’m going to incorporate that into my thinking. I’m going to take this action step, or somebody might have a resource. Those are important. These are just everyday entrepreneurs who are doing great things and come into the mastermind. They are very humble, vulnerable, and willing to share. We learn a lot about our mindset. We also learn a lot about getting stuff done.

The Mastermind Effect:  05:06

We usually wait till the end of the show. You mentioned something like, “it was 8:59. And you’re like, it must be lunchtime”.  What was that nugget you implemented that caused the ability for you to sit there and say, “I’ve gotten so much done already”?

Tracy Cherpeski:  05:26

I teach this stuff. I’m good at teaching it to others. I learned that I wasn’t allowing myself to have it all the time. I was giving it to myself sometimes.  I would fill up my morning with a to-do list. I think that is almost worse than checking your email. It’s the kiss of death. For me, I got up yesterday. I have so many things I didn’t finish last week because I was in this course. I’m going to wipe those off my plate. I did not write anything down. I sat down and started firing off emails. Then I was like, “Oh, I wanted to work on this one thing for my podcast.” So, I went over, and I did that. Then I thought I need to do this other thing. What happened was I got up in the morning, and I asked myself, “What am I committed to today?” And I was committed to clearing the decks and clearing the way. I did that between 8:15 and 8:59.

Tracy Cherpeski:  06:25

I did it before, and I thought I need lunch now. I just need breakfast and coffee, and  I’m good. Now, what I’m going to get finished? So, I asked myself again, What am I committed to finishing today? What am I committed to? By midday, I had gotten a whole chunk of other things done. I had a series of calls, meet with my clients and meetings.

The Mastermind Effect:  06:54

I appreciate you sharing that with us early.  I’m going to ask you something else to share with us probably when we come to an end.

A lot of people get stuck, and they don’t know how to execute what’s in our head. We’re still going through a pandemic. It is creating a reset and how we can accomplish things as a society or as a person with the gift mentality. How have masterminds helped you when you’re looking to reset yourself and get unstuck?



Tracy Cherpeski:  07:30

When the lockdown happens in early March, almost all of my first quarter going into second quarter business diminished. All of my plans for the year and 80% of my business or potential business tanked. Normally, that would probably have put me in the fetal position and freaked out. But I thought I’m not the only person going through this; it was probably a good portion of the population. I’m fortunate enough to be married to somebody who is employed at a steady corporation.  We didn’t have to worry too much. I  decided to clear my head.

I’ve got these masterminds planned. I’m not planning on launching one of them until later, but I’m going to open it up now. The other thing I’m going to do is to waive the fee for anybody who really cannot afford it. I’m not going to ask them to justify it; I’m going to ask them to decide whether it makes sense. I was asking for the “cost” with a commitment of one year. I had eight spots open; I filled all eight spots by the end of the first week. I interviewed everybody and made sure that they were a good fit.

The second mastermind I opened a little bit later. I kept its original start date and also filled that very quickly. It was originally going to be for three months. I was testing out this concept of a three month and extended it to the end of the year.  It’s ended up being a nine-month. A couple of people dropped off because they couldn’t maintain the commitment, and they hadn’t planned for that.

This helped me get to work, do my thing, and show up for people. That helped me get unstuck through the process of facilitating these masterminds. I don’t have to teach anybody anything because that’s not what a mastermind is about.  I needed to show up in the right energy to bring people up or bring them in based on how I could read them.  We do it via zoom to at least see their body language. It helped me come back to service. All the fear that I had was still there. I’m not going to lie and pretend to be fearless because I’m not.  I was able to bypass that fear that might hold me in the same place and just charge forward and be there for people. Because in the beginning, the middle, and the end of the day, my goal is to be there for people and support them into their highest version of themselves and their businesses in life.

The Mastermind Effect:  10:02

The amazing thing is, when you’re there for them, they’re also there for you. You don’t even have to ask it. It’s the best support system. It’s awesome.

Tracy Cherpeski:  10:11

It is. I’ve learned so much. I don’t think of myself as any more of an expert than anybody else in there. I just have a skill set to manage a group. But where the mastermind was concerned, I wasn’t showing up trying to be anything; I was just showing up and creating this space.

The Mastermind Effect:  10:26

Create the space, be a facilitator, and guide the journey to where you want to go. Speaking of masterminds, they’ve been around for a hot minute. Probably the original mastermind, as I say, was the apostles. And then, Benjamin Franklin creates the Judo club or the Leather Apron Club. Then, you and I spoke about this guy right before we hopped on called Napoleon Hill.  He defines the world of masterminds and what it is.

[10:31 – 26:19] Self-Education and Tracy’s reality

The Mastermind Effect:  11:00

There’s been this huge boom in self-education moving away from standardized education. Where do you see the differences between self and standardized education going forward?

Tracy Cherpeski:  11:13

That’s a good question. I have multiple degrees. I believe that they’ve helped me get to where I am. They helped me in the corporate world. They opened doors for me and all of that. However, none of what I studied in school prepared me for what I’m doing now. I didn’t know how to start a business. I didn’t know how to ask for help. In an MBA program, they teach you how to do it yourself. I got great advice from my accounting professor in my MBA program. He said, “Tell me again, your background, what did you study?” And so I told him I have a degree in French. And he’s like, “here’s what you need to know about accounting; memorize and dump and hire good accountants. Just get through this class, get a bit better, so that looks good on your transcripts, and move on with your life. That stuck with me because there are certain things that we don’t really need. We may need to understand the functionality and the benefit of having that in our lives.

My kids are in public schools. They’re both in high school and on track to go to university. We have a lot of side conversations about school. I believe what will happen, especially since so many school standard school systems have been forced into a different way of educating right now; they are being forced to be more creative and more collaborative in the learning process. I don’t think this is universal. I believe we are very lucky to live in this tiny little bubble of university town and academics. We have this incredible system, but I believe that that’s part of the way forward.

I appreciate universities. We need to train people and help them grow into their potential. We might need to learn certain things to pass state exams. If that doesn’t change, then that’s not going to change. There has to be some measurement, right? What if we prepare people to be ready to enter the workforce or create something of their own when they’re done with high school, regardless of what they do afterward? I don’t believe that we do that now. People leave high school very unprepared, and you don’t have much choice but to work something or force yourself into something or tried to get into university.  I believe that all these tools that we’ve seen developed over time will start to cross over. As long as we can call it education to satisfy our state governments, that’s going to be the way forward.

The Mastermind Effect:  14:09

I hadn’t thought about, when you’re saying like, “are we preparing the students that are in high school, going forward?” Fortunately, I had a pretty good work ethic, and I had to get a job because I knew I would have to pay for continuing education. I listened to what all the business people were saying. But there’s a trade school, there’s college, and then there’s like, “Hey, whatever you were just gonna go do.” There’s nothing that’s filling that void and sitting while they’re in that that high school classroom saying, “Hey, listen, it might be something else, and you got to start focusing on that now.” If you don’t have the household that helps you with it, and so many students don’t know what is out there, that’s a scary thought.


Tracy Cherpeski:  14:55

That’s a scary thought. I’m not better off than my parents were, and they don’t have a college education. I have two master’s degrees, and I’m doing well. But my parents were multimillionaires. I’m not there yet.

The Mastermind Effect:  15:11

You have to find out what’s important to you. Is it becoming multimillionaire, or is it the lifestyle that you have? I have to say it’s the lifestyle because you and I talked about that off-camera; what you have there from DC to Carolina is like, night and day.

Tracy Cherpeski:  15:32

Yes,  I have nothing against DC; it’s just a hard place to live after a certain period of time. Money is not the thing for me. I strive to make more, invest more, and do all those things. I have my goals and all of that. I am better off than my parents in terms of my happiness and my connection to doing something that I love.

My father was a businessman who bought an existing business and then revamped it to be something solid and recession-proof. He took really good care of his employees. I paid close attention to that, and I’m thankful for that. He told stories about how he’d sneak out of the parking lot driving slumped down in his car. He would skip class most of the time.  He graduated by the skin of his teeth. He became a successful businessman by working hard and being extremely determined to create a financial legacy for himself and his family. I feel extremely fortunate to have grown up that way. I also learned a strong work ethic from him. My mom worked in the world of insurance, and she liked what she did. It was a default for her. She just did it because she needed to work. Then she did it because she wanted to.

The Mastermind Effect:  16:50

The work ethic is something you can’t learn from school.  It’s inherited, and that’s a big thing.

When people invest in their future, they have a better than vague idea of what they’re going to get and have an expectation of what the outcome is going to be. What should people expect when they enter your reality and your mastermind?

Tracy Cherpeski:  17:23

They can expect to be challenged. They can expect from other people in the group and me a lot of questions and loving pushback when they express limiting beliefs as if it’s the truth. They can also expect to be loved from the moment they enter the space. It may take a while to hit your stride in a mastermind, but the connection is instant. People can expect to come in and be challenged, be supported, and come up with great ideas. There have been a few collaborations through my two masterminds that I have. They have been really beautiful; some are still in progress, and they’re finding their way forward. Some people don’t know what it is yet but they want to collaborate. They’re letting that idea come as each week goes by and as they interact outside of our groups.

We don’t use the word accountability; we say harmony partners. It’s really the same thing but the punitive implication of accountability,I just wanted to wipe that off. Our goal is to create a sense of harmony in our own lives. Balance is a farce. If we work a lot, we’re not in balance but we might be creating something that feels harmonious for us, which is what balance ought to be  described when we talk about that. They have their harmony partners and they meet up. I don’t even check in on them to ask if they have their call. I stopped doing that. I just trust that they are, and if they’re not, they’ll know that because they won’t be getting the value they wanted. So there’s a lot of trusts. It’s not my intention to parent them and micromanage. I just come in, and I work on the assumption that they’ve done it, and if not, they’ll share. That’s been lovely because people are upping their game by being told that we believe in them. We believe in one another. It’s awesome.

The Mastermind Effect:  19:44

Beautiful. Love it. I feel the people in the rooms you’re putting together have a way of surprising us, whether it’s their willingness to learn or their drive. Give us a success story of someone who’s either currently in or has been through your mastermind.  What was the outcome because of that room you curated?

Tracy Cherpeski:  20:05

One of my participants came in a transitional stage. They are not sure if they wanted to apply for veterinary school or sing opera. They currently own their own business. They have a pet care services business and a background in veterinary medicine. We ask each other questions like, if you could wave a magic wand, and you got up in the morning, and your feet hit the ground, and you were excited, what would that be? And she said, “not being in school.” Through the process, she realized that she wanted to be a musician. She plays piano, sings, and composes music. She found a program in Italy to study under some of the most prominent opera trainers, and it was set for the summer. It went remote and worked out well for her because she didn’t have to spend the travel money, and she had a little bit of time on the outside of those things to explore over.

She joined a Facebook group. This is all from us asking questions. Now that you’ve created that feeling, what can you create from that? What can you do? All of these questions of digging into her soul, in a loving and supportive way, she found a songwriting program. She’s like, “I can’t afford that, but I want to do it.”  So, we asked her in one of the meetings, “how could you afford it?” She said she doesn’t know and she was really nervous. We kept asking, how could you afford it? And she said, “I’m gonna ask them a scholarship program?” She did, but they have given all the scholarships away. But she kept showing up for their free meetings anyway, and she kept asking. She pursued and persistent that they offered her a scholarship. She’s in the program. She’s collaborating, producing, and getting her name and art in front of people in the music business. I don’t know exactly where she’s headed, but she is now officially a professional musician in the music industry. I predict she’ll be making good money off of that in no time. It’s incredible.

The Mastermind Effect:  23:02

That’s amazing. The power of the right mastermind, right there.

Tracy Cherpeski:  23:09

Yes. Her business, career, and all this stuff are looking great. But for me, the biggest piece of satisfaction is that she is completely turned on. Her light is shining so bright. She still has the voices that say all kinds of really untrue things to her. But she is so determined to embody the person she knows is this musician, this creative person. She refuses to be a starving artist.

The Mastermind Effect:  23:50

I was on a call with Jim Kwik. He talks about ANTs (Automatic Negative Thoughts). Ever since he’s given us that ANTs, it’s been amazing. Anytime an automatic negative thought comes in there, and you start playing a scenario in your head, and you’re done. Get rid of the ANTs.

Tracy Cherpeski:  24:30

I love that. Automatic negative thoughts.

Tracy Cherpeski:  24:47

They don’t go away. We can drown them out with more positive thoughts and by taking inspired action. Nothing builds confidence better than getting clear about what you want and stepping toward it.

The Mastermind Effect:  25:01

It might not be the action that gets you to where you’re going. But if you overanalyze that analysis by paralysis, you’re not going to get anywhere. You might as well take that plane off and figure it out as you go along.

Tracy Cherpeski:  25:15

Exactly. I like to use the analogy of trying to get your car to start if it’s a stick shift car. You try to start pushing it, and it’s so heavy. Those first few steps are so hard, but you got to get your car started. You have to be at work or whatever. Not everything has to be slogging and really hard. But if you’re not sure where to start, start moving.

The Mastermind Effect:  25:51

Do something. Action, through implementation, creates results at the end of the day.

Tracy Cherpeski:  25:59

If you don’t know what to put it toward, you don’t have a project, or you’re kind of stuck, go take a walk. Call somebody you admire or do something that lifts your spirits and shifts your vibe because once you get into a more positive brain space, you create better energy. You can create something amazing from that space.

The Mastermind Effect:  26:19

Join a mastermind, talk about something near you.

[26:20 – 36:02] Creating Success

The Mastermind Effect:  26:21

I talk to my coach about success. In our solo shows, we talk about success and what it means. It’s a different definition for everyone. Once you define success, that means you’ve also defined failure at the end of the day. That’s why it’s scary. There are a lot of things that go into success, such as mentorship, getting a coach, experimentation, partnerships, and willingness to fail. As we have such a sensitivity through social media and all the other things out there today, what is a step you feel is in the right direction in being successful?

Tracy Cherpeski:  27:02

I would say, ask yourself what you really want over and over again. Follow up that question. If you’ve run out of answers, you’re probably there and asked tw more after that. Once you’ve asked that question and answered it until you’re exhausted, now ask what would be possible once I achieve it. There are more steps but keep going. It’s a Socratic method. You just keep asking until you run out of answers because we bury a lot of our desires with other people’s expectations, with what we’ve been taught, and with what we might have looked at somebody else’s success and decided we wanted to try that on. Go ahead and try it on. But keep asking the questions.

The Mastermind Effect:  27:57

Ask it over and over again. Don’t just accept the answer.

Tracy Cherpeski:  28:04

Right. Like the lotus flower, we don’t get to the pretty picture until we’ve put our roots down in the nasty muck and dug through it. Even that can be pleasurable if we’re finding our way toward what we want. It’s not to paint a picture of grueling, horrid, and difficult, but we have to do the work. We can do it with a sense of gratitude, joy and anticipation but the work still has to be there. If anybody enters your field and acts like they’re an overnight success, they are bold-faced lie.

The Mastermind Effect:  28:45

It’s tough when you look at someone else’s success. You don’t know what it took to get there. The ugliness and the gut-wrenching hours are the stuff you don’t see. You only get to see the final pretty picture. That’s why we’re creating the Success finder because we don’t want that mastermind to show up. My analogy is this. I rented the camera, the photographer, the fancy car and I got the money gun, but I spent all my money and couldn’t afford to put real money in it. It was Monopoly money shooting out for my social media post. Is that who you want teaching you? Probably not?

Tracy Cherpeski:  29:28

I’m very turned off by that. I appreciate nice things. I drive a Toyota, and I couldn’t care less. It’s a good car, and it does what I need it to do. That’s not where my thing is. I love nice cars, but my goal isn’t there, right?  I’m not knocking if somebody’s like, “I want a Lamborghini. I’ve always wanted a Lamborghini.” Go for that Lamborghini. Just recognize that that’s not really what success is. Success is the pleasure of getting there. Success is the journey toward goals.

The Mastermind Effect:  30:27

Well, there’s always new ideas brewing in times of prosperity. It’s easy to win when the world is winning. I think ingenuity and creativity come when we feel the squeeze. And we’re feeling the squeeze still. What are you working on right now that’s going to take place over the next 12 months that excites you.

Tracy Cherpeski:  30:46

I’ve got a couple of things that I’m doing. One is a podcast, which I’m launching on January 13th. It is called The Entrepreneur Mindset Reset. Right now, I’m just interviewing and having a great time. I’m excited to share that with the world. So far, the interviews that I’ve done, it’s like everything else shuts down. We get into this energy similar to a mastermind, where we’re just we’re talking back and forth.

I do not currently have any masterminds booked for next year. I don’t know when that’s going to, but I know I’ll do. I’ll probably do a couple more next year.

I’m very excited to share about one of my clients.  I came out of a meditation one morning and said, “I want to be more involved locally.” I want to be part of something. And then, a potential client came through the pipeline, which was a referral. She is building a wellness clinic in Downtown Raleigh serving underserved populations. It will be everything from counseling services to acupuncture to physical therapy to other medical needs. I’m putting together a team for her for grant writing and marketing. She’ll have two different marketing campaigns for this and whatnot. People who have money can come in and spend it on their wellness. That’ll generate the funds to support the underserved communities. Her heart is in helping people have a better life by improving their health.

The Mastermind Effect:  33:43

You handled so much in 2020; you’re going to have so much more in 2021.

The Mastermind Effect:  34:12

Last thing, what is a tip tactic or actual item that if someone listening today implemented it, they’d see real results over the next 30,60, or 90 days, whether it’s in the personal or business life?

Tracy Cherpeski:  34:31

Get incredibly clear about why you want to do something. Get really in touch with that “why” and don’t censor yourself. I’m going to go back to the car analogy. If it’s “I want a Ferrari,” then hang in there tight. Why is that Ferrari important to you? Keep asking that “Why?” Why do you want that luxury? What does it mean to you? It’s not just status; it’s something else, right? If you get really clear on that “why,” you become the best kind of bulldozer ever because nothing will stand in your way. You just have to reconnect to that every day.

The Mastermind Effect:  35:16

I love it. Get clear on your “why.” It is important no matter what it is. Tracy, I appreciate the time you’ve spent with us today. I look forward to our future collaboration and what we’re going to build going forward. We’ve got Tracy Cherpeski, Founder of Thriving Forward Mastermind. Tracy, thank you so much.

Tweetable Quotes:

“There are certain things that we don’t really need, but we need to understand the functionality and the benefit of having that in our lives.” – Tracy Cherpeski

“Nothing builds confidence better than getting really clear about what you want and stepping towards it.” – Tracy Cherpeski

“If you’re not sure where to start, just start moving.” – Tracy Cherpeski

“Success is the journey towards the goal.” – Tracy Cherpeski

Resources Mentioned:

Connect with Tracy on Linkedin, visit https://www.tracycherpeski.com/ 

Be one of the early adopters of The Success Finder! Download it from the App Store or Google Play Store

You can connect with me, Brandon Straza, on LinkedIn, Instagram, or send me an email at brandon@thesuccessfinder.com. I’d love to get in touch and talk more about personal development and how you can move beyond your limits.

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