Episode Transcript

The Main Street CEO with Theresa Cantley

Episode: The Messy Middle: Multiple Pivots, Identity, and Defining Success on Your Own Terms

Format: Solo episode

Runtime: Approximately 26 minutes

Accessibility note: This transcript is provided so that deaf and hard-of-hearing listeners, and anyone who prefers to read, can access the full episode. It has been lightly edited for readability, removing repeated words and false starts. No meaning has been changed.

Speakers

Theresa Cantley: Host of The Main Street CEO, business advisor and author

Transcript

Theresa Cantley (00:01)

Hello, hello, hello, and welcome back to another episode of the Main Street CEO podcast. I am your host, Theresa Cantley, and I am so glad you’re here. I remember my writing coach saying, I am so glad you’re here. She said it to my friend when my friend went out to one of her workshops, and she said it to me, and I absolutely…

Just when she said it, it just made me feel so good. So hopefully, you know, me saying it to you while you’re listening made you feel as amazing as it made me feel when I heard her say it. So I am so glad you’re here. And in case this is the first time you’re listening in to the podcast, or maybe you haven’t listened in a while, we used to be The C-Suite Mentor and then we changed the name to The Main Street CEO.

And last episode I talked about why I changed the name and, you know, why we moved in the direction of The Main Street CEO. So as I said on the last episode, you know, people kept saying, C-Suite Mentor, but you don’t work with corporate. I’m like, no, I don’t. Not totally true. I take that back. I do work with, I have worked with corporate people. But the people that I work with the majority of the time are people who run multimillion dollar Main Street businesses. So, you know, it’s why we wanted to change the name to The Main Street CEO. So it’s a journey, which is what I wanted to talk about today, is the journey or journeys as an entrepreneur, which is something that I think, you know, a lot of people, a lot of experts out there and gurus don’t really like to talk about.

The different things that happened on their journeys. They either tell you the really, really bad, or they tell you the really, really good, or they don’t kind of touch on the in-between, or as my friend Andrea says, the messy middle. So I was in a business meeting the other day, and I’m sitting in this business meeting, and every time I go to this meeting, and I go to it once a month,

(02:25)

it’s networking, but then you also sit and they have roundtable sessions and, you know, you really get a lot of insights from other entrepreneurs. But every time I go there, like, I always get so choked up for some reason. I don’t know. I mean, I can talk to anybody. And for some reason I get in this room and I’m just like, I can’t get my words out right. And so I go to this meeting and it’s the roundtable session, and the guy who is the moderator,

he wanted to talk about journeys. And he is looking around the room and he said, you know, if you’re an entrepreneur, you have probably had quite a journey. And, you know, he threw out a figure, which I would probably agree with, that 90% of business owners, 90% of the people that own businesses have had or are having major struggles.

And if someone tells you that they’ve never had a struggle or that it’s been easy or that, you know, what you want to do is easy or what you want to build is easy, run the other direction, because it’s not. So he starts getting into this conversation and he starts, you know, talking about the journey. And he said, okay, raise of hands, everybody raise their hand

if you made a transition or had a journey from corporate into entrepreneurship. And, you know, there were 25 people in the room. People raised their hand. I raised my hand. And then he said, okay, those of you who went into entrepreneurship, have you made a pivot once? Raised my hand.

And he said, okay, those of you that have made the pivot once, have you made it twice? Fewer people raised their hand. I was one of the people that did raise my hand. And then he said, okay, those of you that have your hands raised, how many of you have made more than two pivots? And I was one of the only people, if not the only person, that kept her hand up. And he said, okay, he said, Theresa, he’s like,

(04:49)

would you like to tell your story about your journey? And I just sat there and I was like, oh my God, I was sweating. I got really hot. I’m sure my face was probably red. And I hadn’t slept much the night before because, full transparency, my aunt had passed away. And so I had like an hour of sleep. And I thought, you know what, I’m just gonna go down for the morning session and then I’ll come home. So of course I get picked on.

I was like, shoot. So I said, okay. So I explained my journey of moving from, you know, being in corporate America and kind of working my way through corporate America, ended up in a director’s role. And then we were burned out, tired, frustrated. If you’ve listened to the podcast before, you’ve heard me tell the story. My business partner and I, she’s my best friend,

we decided one day to go to New York City, and walking through the halls of a show, decided to open up a store. So we built our first store, our first business, which was a product based business. So when I was in corporate, I was in a product based business. It was actually product and service based, it was both. And then we built our store, which was a product based business, during the recession. So, 2008, when real estate,

forget it. Nobody was opening businesses. There was all kinds of stuff going on. And we decided to open up a business. So that was my first pivot. And then when certain things started to happen in corporate, and the company that I worked for, all the challenges that I ran into, while it was the most heartbreaking, frustrating, grueling, challenging, adversity-faced position,

company that I’ve ever worked at, it was also the biggest, it taught me the biggest lessons and learnings and gave me a PhD in navigating crisis and challenge. But I learned so much about business in that company. So I left when things started to go south in the business,

(07:14)

and the business was sold. And then when it was sold, due diligence happened, things unfolded. And my business partner and I decided, okay, I think this is our cue that we actually need to make the leap into entrepreneurship. So we did. And we had our store, but at the same time, saw the need for people to get help, because there were people who left corporate America

who launched a business, and they were struggling because they were trying to approach it with the same mindset and the same behaviors that they did when they were an employee in another person’s business. So we saw a bunch of people struggling, started the consulting business. And the consulting business had actually pivoted several times after the first.

Pivot I made was when I had to shut down the store after she was diagnosed with cancer, and then pivoted the consulting business. And what I found, and I said this when I told the story, I said what I found was that through all these hops that I had to make and all these shifts and changes that I had to make, I was never good at facing, like really facing,

the transition and the middle of the transition. I was really good at getting knocked down and getting back up. Really good at it. Like, I would get knocked down and I would say, okay. And then the next day I would just get back up and I would keep going. The part that I didn’t face was the actual transition. What I needed to do, like truly needed to do. Like, I knew that what got you here won’t get you there.

But I never really knew what that meant. I also never really knew what the word surrender really meant. People would say, you have to, like, just, Theresa, you gotta surrender, you gotta let go, you have to stop trying to force the result. And I was like, I’m not. And I didn’t really understand what that meant until more recently. But the bigger piece was that every time I was making a shift,

(09:37)

I wasn’t changing my behavior. I wasn’t changing my mindset. I wasn’t changing my attitude. So I was trying to build this new container, or I had built this new container, but I didn’t catch up from an identity standpoint. I didn’t catch up from really who I needed to become. I kept trying to hold on so tight

to who I was when I built that first business. And in some form, and I know a lot of people struggle with this, I was also holding on to being an employee, thinking that I needed to behave as though I was still an employee. And being a CEO of a business, I was the lowest paid, hardest working employee with a sucky boss. So again, I am telling this story to this group of entrepreneurs.

And, you know, that journey, what I realized, especially when I was recounting it, was that I got really good, or I really learned how to navigate difficult change, really difficult change, and truly where that resilience that you need, that radical resilience, comes from.

And it was something that I didn’t really fully embrace until that moment when I was telling my story. I mean, I knew it, I talk about it, I talk about succession planning a lot. But all of a sudden it started to dawn on me exactly how much change I’ve helped people to navigate, but I’ve also navigated myself. And I think the piece was, well, hold on, let me back up.

So after I was done telling my story, there was a woman that was sitting next to me and she raises her hand and she said, you know, I have a question. She said, I started my business, and I started it a little while ago, and it hasn’t been profitable. And I think this year is the first year I’m gonna turn a profit. And I was like, okay, well, that’s kind of normal. You know, most businesses are not profitable the first year. They’re not profitable the first several years. But she said, the thing that

(12:01)

I’m really struggling with is the success metrics. You know, what KPIs do I need to measure to realize that I’m successful? And I said to her, you know, one of the biggest mistakes that I made on this journey, through the different phases of this journey, is that I was trying to define success

based on everybody else’s definition, that I was working with or that I was talking to. And what I ended up finding was that that definition of success that I was defining was based on external results. And that completely ties to, through these different phases, not

having my identity and the internal piece catch up to what was happening externally. And then when it got to a point where all of a sudden, and I didn’t even realize I was doing it, I was slowing the growth of my business down, like subconsciously, like not even realizing I was doing it. I was slowing that container growth down because I needed to catch up here.

And once my identity, or once who I started to see I was becoming, was catching up, all of a sudden that container was too small for me to fit into. And that’s when the burning down happened. That is when being put back into the fire to be reshaped happened. And I see it happening with businesses, big or small,

all over the place, where we focus so heavily on the external results or the external pieces that need to get put into place and we forget about the internal piece. So I see this a lot when we talk about succession planning or we talk about selling a business. Everybody focuses on the numbers, the metrics, the valuation, the legal,

(14:28)

the documents, the agreements, you know, all of that. And nobody focuses on the people. The people, yourself included. Who do you need to become? Or who are you going to become through this transition? Or as your business grows, how can you grow and develop and evolve as well?

Because if you’re evolving and the business isn’t, there’s friction. If the business is evolving and you’re not, there’s friction. So we want to make sure that, and this is what I said to her, you have to define what success means to you. And defining what success means to you is gonna come from what do you want to feel like every day in life.

And then what kind of life do you want to live? And then you start to build the business to support the life, not the other way around. And it’s something that, I mean, she thought about it and she said, I never, you know, so many people that I’ve talked to or I follow or whatever, they’re talking about being a million-dollar business, you know, having 10, 15, 20, 50 employees.

You know, scaling it to multiple businesses, yada, yada, yada. And she’s like, I don’t know what, you know, I hear about customer acquisition cost, I hear about, you know, revenue, profit, like all this. She’s like, I don’t know what to measure and what would determine success. And she said, you’re saying to define it for what you want and what it means to you. She was like, that’s so helpful.

Because I was starting to get really stressed out about, oh my God, I have to do all these things. I’m falling behind and I don’t know how I’m gonna do this, and yada, yada, yada. So we talked through it for a little bit, and I think by the end of the conversation, she felt a bit better. And it was interesting, because what started to happen next was people sharing things, that they are at a point

(16:54)

where they’ve made some transition or they know they need to make a transition, and they’re struggling with understanding financials, or they’re struggling with, and their advisors are yelling at them because they don’t know their financials, or trying to understand, like, selling. Selling is a big problem that a lot of people have. And it was just interesting because all of these people started to open up and started to talk about what they struggled with or what they were struggling with,

and talk about things that they were afraid of, and talk about things that they, you know, didn’t know how to do and they know they need to do it, but they’re also like, they don’t know who to go to. And it was like all of a sudden, this conversation just started to evolve, all from me just sharing my transition, multiple transition story, and what

happened along the way, of getting knocked down and getting back up and getting knocked down again and getting back up, and then finally being thrown into the fire and reshaped to handle a bigger capacity. And I’m telling you this story and all these pieces of it because there’s a lot of transition happening right now in the world, in businesses, especially if you’re a Main Street owner. And the part, again,

that people get so wrapped up in is the numbers. We live in a society where people care about external results. They care about what people say about them, they care about what they look like, they care about what they have, they care about what’s in their bank account more than they care about how they feel every day. And the thing that I’ve learned going through the transitions that I’ve gone through, and having to navigate the adversity that I’ve had to navigate, is that it means more to have a life that is fulfilling,

and to have things and to be doing things that make you feel fulfilled, than to have a billion-dollar business or to have 50 employees. And I think that we miss that because we’re so focused on looking around at everyone else that we miss all of the magic that’s happening right in front of us. So

(19:20)

if you’re listening to this and you’re thinking to yourself, because you’re like, I’m getting to a point where I’m looking at what’s going on in my business and what’s going on with myself, and I’ve been so burned out and so frustrated and so overwhelmed and just overworked, and I’m thinking to myself, what the heck am I really doing? I encourage you to first start with, what is it

that I truly want? What is it that brings me joy every day? What is it that I truly love to do? What is it that I, you know, would love to do every day? I mean, ask yourself, start asking yourself a bunch of different questions to ask how you can live more fully, be more present,

build better connections, and ultimately achieve the growth that you’re looking to achieve. And I read something this morning, I read a post this morning, and I’m gonna butcher a little bit what their quote was, but it made so much sense, and I can relate to this. What it said was, you live life fully because you’ve sat in the front row at a funeral

for someone who didn’t make it to, in quotes, retirement.

And to me, because I know I have felt like this, is that you’re walking around going through the motions every day, doing what you think you need to do, doing what you think you should do, and not really saying, what is it that I need to be doing? What is it that I really want for my business?

(21:26)

What is it that I really want from my life? And then starting to build from there. That’s what I call building from the inside out, not the outside in. And I think in a time when we have tariffs, and I talk about this all the time, tariffs and rising costs and inflation. Every time you go to the gas pump, it’s ridiculous. Every time you go to the grocery store, it’s ridiculous.

And it is the world that we live in. And it’s very easy to get wrapped up in all of that and think to yourself, I’m never going to get out of this mess, or I’m never going to be able to make this work. Or I can’t hire the people that I need to hire because that’s going to take away from my profit and I can’t afford it. It’s very easy to go down that road and then feel like you’re in that front row.

So I encourage you to kind of let this all sink in and think to yourself, there’s a transition happening here. And in any transition, in any adversity, in any challenge, just like the company that I worked for that was full of adversity, there’s always a chance to learn something new. There’s always a chance to build, and there’s always a chance to recreate,

create from scratch, and to be reshaped. So I encourage you, if you’re feeling like that,

(23:04)

to really ask yourself, what is it that I really want to build here? And why do I want to build it? And who do I need to surround myself with? And what would this transition look like? And who do I need to become? I encourage you to ask yourself those questions and just see what comes up. Write some stuff down. Journal. Journaling is a proven exercise to

really help you to process through things, to become more aware, more self-aware, more aware of your life. And to really, like I said, to really work through some challenges, some limiting beliefs that come up, but even like just, you know, things that you’ve been struggling to try and get to the bottom of. Journaling is a proven way to help you to uncover where those insights are that you’re looking for. So I encourage you to do some of that. But

I hope that this episode helped you. And just so you know, you’re not alone. Transition, there’s so many people going through it right now. So many people. And with every change, there’s always the inside piece of it, and there’s the outside piece of it. Most of us want to just address the outside, but what we really need to do is start with the inside. So I hope that this helped you. Don’t forget,

if I can get my words out, I am opening up, or I have opened up, and I’ve already started to receive applications for the Main Street CEO Table, which is the year-long, advisory board style mastermind. I don’t want to call it a mastermind because, I don’t know, I just don’t like that term. So it’s advisory board style, six to eight people. And we are literally going to tackle all of these things

and so much more to really help you to get through these challenging transitions that you might be going through right now, and even to help you with any transitions that come your way in the future. So if you go to, we’ll link it in the show notes, theresacantley.com/the-main-street-ceo-table. Like I said, we’re gonna link it in the show notes,

(25:28)

and make sure that you apply for your seat today. I am taking applications for the next month, because I go through every one with a fine-tooth comb. We have a conversation before we actually get rolling, just to make sure that you’re a good fit. So it’s a highly curated group. If you are interested, make sure you go to that link and apply for your seat. But until next week, I hope you have a great rest of your week, and I look forward to talking to you soon. Bye for now.

End of transcript

Applications for the Main Street CEO Table, Theresa’s year-long, advisory board style group of six to eight Main Street business owners, are open at theresacantley.com/the-main-street-ceo-table.