Thinking about leaving corporate to do your own thing… but also low-key terrified? You’re not alone, and you’re not crazy. The work world is changing fast, and a huge number of mid-career professionals are quietly wondering:
“Could I actually become the CEO of my own life?”
In this episode, Todd and Chris break down what it really takes to move from a corporate identity to entrepreneurship in midlife – without blowing up your life overnight.
They walk through their 6 Tenets of Reinvention and apply them directly to the “corporate → entrepreneur” leap and you’ll also hear Chris’ personal story of going from a 20-year corporate career to coaching and building a business, plus the traps he wishes someone had warned him about.
In this episode, you’ll learn:
- The first kind of clarity you must get before you even think about quitting
- How to use mindset practically (not as a buzzword) when fear and doubt spike
- What “financial runway” and “emotional runway” really mean in a career reinvention
- How to start making money outside your job before you leave your job
- The 5 most common TRAPS reinventors fall into when starting entrepreneurship
- Several ‘entrepreneur-acceleratoring’ tips that will get you to success faster
*Subscribe, share this with a friend who’s “corporate curious” about entrepreneurship, and keep following along as we map out what your work reinvention really looks like.
Episode Transcript
Chris: there are people that we’re talking to right now where they might actually be making more money from the side hustle than they expected to be making at this moment,
Todd: The topic of today is about going from corporate to entrepreneurship because A lot of people, a pretty high percentage, are considering or have started becoming an entrepreneur later on in their career later on in life.
And that takes something, and we wanted to focus this episode to give real examples, real frameworks for how to think about moving from a corporate career over into being what we call the CEO of your own life or the CEO of your own future because it’s different.
At the end of the day and what reinvention is really about, is this idea that man, like the work world is changing big time. And the main notion is that your next step in your future could be even better than what you had before, if you would do the work to align yourself with that version that you wanna become.
yes, there’s a possibility that you could have your talents. Your purpose even aligned with your future moneymaking. For a lot of people that does require some form of entrepreneurship. And that just gives me a lot of excitement.
We’re also gonna cover what we’ve seen to be the common pitfalls when people are reinventing themselves and they’re not looking at, well, what is required to be successful in that reinvention, especially as it relates to becoming an entrepreneur.
And I know this is big for you because you did this, Chris, right? Like you went from a 20 year corporate career over into now being an entrepreneur, and look at us.
We’re doing this thing right now. So I know you have a lot to say on this one.
Chris: And I fell into some traps. Like you said before, I love the word reinvention too, something I say a lot as we talk about this is the concept of reinvention. The concept of the six tenets of reinvention that we have and some of the stuff we’re talking about today.
I wish that I had known these things. I wish that I had, the community that we have, I wish that I had coaches like us, back when I was first contemplating this, because I spent a lot of time in corporate, and I think you were alluding to this before, feeling unaligned with my work. Right? The work was not aligning well to who I was.
I even remember, I wish I had it with me right now, I can probably dig it up. I took one of those assessment tests of like your, personality, your leadership personality, and it was like creative visionary. And you know what I was, I was the head of technology procurement.
Is like, it’s not creative visionary at all.
I remember thinking, and this is how messed up the Stockholm syndrome of corporate can be, is I remember thinking, oh, creative visionary, that’s weird. must be something wrong with this assessment system. What it actually was is that is who I am. That’s why I’m so aligned to being a coach.
That’s why the work that I do now with people and in our community and with you is big picture visionary stuff. Helping people think in that bigger way that was that misalignment between my corporate work and who I was, that I had been feeling all throughout and sort of denying. So again, I just wanted to seed that out there in case there’s people that are listening or watching us that are in that, what we call phase zero of reinvention, where you’re thinking about doing something and I’m, I’m not quite sure what it is, but I know it’s not this.
Right. That might even be phase one for us, right? It’s just sort of like contemplating it and thinking about it and we just wanna open up that possibility that, yeah, maybe there’s a small action that you can take that can give you just a little bit of evidence that something else is possible.
Todd: Yeah. Beautiful. , I know that you went through this so clearly, and I love that you started off with this idea of getting clarity about who you really were at your essence, because when you’re thinking about this notion of reinventing your career. A lot of people, it brings up a lot of fear, right?
And in our community, we see it all time. There’s a lot of consternation, there’s a lot of fear, there’s a lot of doubt. There’s a lot of, I don’t know, uncertainty and that’s just part of the deal. But this notion of these six tenets and these six ideas, which we’re really gonna run through right now because they really do apply this particular lens of reinvention, which is moving away from a corporate identity over into an entrepreneurial one.
it works, The framework works for doing that. And you started off with the notion of seeing how misaligned you were before, and a lot of people realize that, that the work that you were doing in the world was not representative of who you are as a person. Right? And I’ve seen this for 20 years of coaching, Chris.
People, you know, they follow the path. They got the right jobs, they went to the right schools, like all of it. They made the money, they got the house, they got the all of it. Then at some point they wake up and they’re like, huh? Like, how did I get here? Because this isn’t really making me super happy.
And then they go through that proverbial midlife crisis. But what’s really happening right now and why we started this podcast is that a lot of this is now being thrust upon people because of the emergence of AI and the emergence of just the changes in the world. We are all now being forced to really think about how we’re going to make money in the future, what our careers are gonna be. And so while all that fear exists, I just always bring it back to this is opportunity, right? You have an opportunity to reinvent yourself. It’s not something that should be all scary and all fearful. It should be imbued with the idea that, oh wow, this is a redo.
I can actually start over in a sense. And I can start to think about aligning who I really am as a person, what my talents really are with my money making. And that’s gonna be the thing that draws you through to sustainable financial success and deeper levels of fulfillment. And so I think we wanna start there with that idea of getting clarity right?
No matter where you’re at in the stages of reinvention, getting clear. About where you’re at now and where you would wanna go is always the place to begin. I mean, you’re gonna hear me like a broken record on this because what I found in all these years of coaching is that most people don’t really know what they want.
But when you’re reinventing and you’re in a process of transition, start there. Take a moment in time to start thinking about what could you do? What would get you excited to wake up in the morning? Right Chris? Like for you, you found coaching. Like what is it? Think out of the box. It’s a moment in time in a practice.
Getting clarity is a practice. I don’t think people understand that. It’s an exercise where you free yourself from the trajectory you’ve been on and all the limitations that have been thrust upon you, and you just think, and you dream again, and you allow yourself to get out of your small trajectory and you free yourself.
And we start there, right? We gotta start with clarity when we’re talking about this.
Chris: And I’ll say this,, I found clarity on what I wanted to do, and I found my way to coaching, but it wasn’t the first thought that occurred to me, probably 10 years ago when I was really starting to come online to the idea of oh, this corporate career’s not working for me. In that phase that we see with people in our community where they don’t know where they want to go, they just know that it’s not here.
And they just know that they wanna do something different. Sort of that prec clarity phase, right? Maybe there’s, the clarity that’s being gained is the clarity that something has to change. That’s like the meta-level clarity, and then it’s change into what. Maybe this is my role in this conversation, is to provide a little encouragement to the people who are sort of curious about this concept to say it was a non-linear thing for me, the first things I started to explore, were consultancy, right? Consultancy in my field exploring some areas of interest in climate technology and green technology, and I was like, how can I contribute there? There were a couple of different things I explored and took action to experiment with that then informed my clarity, it’s always iterative. I do think that there’s some people, I mean, again, we see it in the community. There are some people who want the eureka aha moment, and I do believe that that comes to most people through the process. But you don’t just say, I want clarity, and then you wake up tomorrow and it’s like, *bling* you know, it’s not like that.
Todd: Look, absolutely. You know, it’s all iterative. And by the way, these six tenets that, that we’re gonna talk about today, you do them all, you play with them all, you take action, you work on your mindset, right? You do all the things and you start to form this notion of a new identity, that has the possibility to be aligned with what you really wanna do.
And we saw it recently, didn’t we? With, one of our members who has been saying. Very surreptitiously. Oh, there’s something new emerging. You know, in, in the back of my mind, it wasn’t really coming to the forefront, you know, of saying what it was.
But it eventually started to share about a new idea for work that is completely different than what she was doing before. Was coming from a completely different world, but then like this new idea is emerging and how I feel about it is. When you give yourself time to be truthful with yourself and dream big, like the answers are already there, you really do have senses.
You just don’t have words for it or you haven’t given yourself the permission. But like when you go through this process, it emerges in a very natural way and then you start to gravitate and then you can start taking action and starting to see if some of these things are real.
And I think that also leads into this next tenet of reinvention when you’re thinking about becoming an entrepreneur, which is mindset. And we talk a lot about this on this show, on this podcast because mindset just is not a buzzword any longer. Like when you’re in a process of transition and you’re reinventing and reinvention of your career is on the table, this is the time to turn fully into what can I do to set myself up internally to succeed.
And the way that we hold it is by looking at your optimistic self, your positive mindset as something to strive towards and set as your default orientation of going through life. Because when you’re positive and you’re excited and you’re optimistic, that’s when stuff happens. Right Now, this isn’t all pie in the sky because we both know that when reinventing, you’re just gonna, you’re gonna be dealing with fear, you’re gonna be dealing with doubt. It’s gonna come up like this is part of the process. But by having a goal with your mindset to be, you know what, they’re right, I wanna be in that state where I’m optimistic and I’m, positive and I’m looking at opportunity.
’cause I know that when I’m there is, when I make the right connections, is when people say yes to me is when like all of a sudden these serendipity start happening. And so we wanna start working on our mindset. With a very particular lens of, let me get myself into that frequency of being positive, and then almost as a backdrop, all these other things we’re gonna talk about can have a better shot of coming to fruition.
Chris: And you know, Todd,, I like to come from a more, what I think of as being, the rational thought mind side of this sometimes. And where I, say okay, is the universe working through us? I say, yes. But if you want to be more tactical in the way you think about that, it’s openness, right?
It’s awareness of the possibility. We talked about this in the group yesterday where it was like the things you notice when you’re open to possibility. When you’re open to what could be possible for you, you start to see things that are aligned to that, that were probably there all along.
Right? And it’s just that your brain is choosing and selecting because it can’t possibly process the millions of pieces of information all around you. So it’s choosing and selecting based on your mindset orientation. And I say that because I know that I was the type of person who 10 years ago probably would’ve been skeptical that mindset was that important. I would’ve probably thought, yeah, I get it. You have to be positive. You have to push through and whatever that means. But like, either it is or it isn’t something that’s gonna happen or something that’s available to me, and it’s like, no, you orient positively and optimistically and open to the possibility that you can change in the way that you want to, and your brain literally notices more, makes better connections, an offhand conversation that you have with someone.
You realize oh wait, did they just say that their cousin does the thing that I wanna do? Let’s continue this conversation. And just things like that. So I kind of throw that out there for the skeptics right in terms of a person who has reformed and grown from skepticism and cynicism to much more openness and optimism, my life has gotten a ton better because of it.
Todd: And I think especially when you’re looking to become more entrepreneurial and you’re looking to start side hustles the mindset piece, it’s not just about being optimistic, it’s more also about being curious, and listening as you said, being open-minded. The mindset is calm, steady, detached, positive, right?
Like no white knuckling our way through it. You wanna look at yourself as an experimenter. And that’s a really important part for reinventors that are looking to start new ventures. Give yourself time, which leads into the next tenet of this, which is what we call game planning.
And especially when entrepreneurial ventures are on the table, perhaps you’re looking to start your coaching practice or a consulting practice, or a lot of people are taking what they did in the past and are starting fractional work, right? That’s entrepreneurship. And it could be something completely new as well.
There’s a lot of people that do that. But for most people, when you’re reinventing, you’re not completely leaving everything that you did before behind. You’re bringing it forward to create a new trajectory for yourself that has all this wonderful possibility, and game planning is really important because you’ve gotta be tactical.
And the way that I talk about this with my clients well, game planning, these ventures that maybe aren’t solid yet, or maybe you have several different, ventures that are on the table. Is creating emotional runway and financial runway. Okay. And we should talk about that a little bit you’ve done a really good job as a reinventor to give yourself that financial runway, like you are smart.
And we’re gonna do an episode on this particularly about how to plan out your money when you’re in a process of reinvention. We need to be smart about money, let’s talk a little bit about those two things, Chris, financial runway and emotional runway.
’cause I know you have a lot to say about this.
Chris: They are related to each other, but Right. Just from a place of financial runway, I think something that we talk about all the time, and honestly, something that I have experienced firsthand is that just thinking, oh, if I start this venture, whatever your estimate is of how long it’s gonna take to get to the level that you wanna get to, you’re probably wrong. Now, maybe you’re lucky enough to be wrong that you get there faster than you thought, but most people, it actually takes longer than you thought. so when we have conversations sometimes with people who are like, Hey, I think I wanna try this new thing, I wanna stand it up. You know, it’s November now. by March I’d like to be replacement level salary or whatever it is. It’s like, okay, you know, pump the brakes. That’s probably not the way it’s gonna go for most people, unless you really catch lightning in a bottle. So having some financial realism around that, or having some realism around that, and then having the financial runway to give yourself the space ideally that you are not feeling the pressure to be like, I have to make this work by a certain date because that pressure, that really becomes the problem is now any sort of creative risk taking or, or networking. I mean we talk about this all the time, Todd, we’re long game players, right? And of course we want success fast. And of course, , we love to help people act at speed and get success fast. But it’s better to be able to make the long game decision 99 times out of a hundred, where you’re not just trying to jump to make the next buck and you’re actually staying. The whole point of reinvention is to find this thing that is aligned and staying aligned with who you are and what you wanna do, and giving yourself the financial space to make those choices in service of the bigger picture.
Is really beneficial. And then there’s the emotional runway
Todd: Actually, I if you don’t mind, I wanna stay on that
Chris: there for a minute. Sure. Yeah. Yeah.
Todd: Just for a minute. Because I’m just gonna be really transparent. I’ve helped a lot of people in this transition and there have been times, and I have a couple of examples where, that piece of having the financial runway and understanding that extending the time words out is so imperative because you may come into this situation with big eyes like, all right, I found my passion, or I found what I’m interested in.
It’s just gonna happen really fast. That’s awesome to have that feeling. That’s awesome to have that optimistic, positive feeling like we just talked about. But you also gotta be real. And my recommendation is for people to pretty dramatically extend their timelines for what they think is possible to replace the income that they may be leaving.
If you can build out a plan, and this may take, this is tactical stuff. That’s why this is game planning. You may have to talk to your partner. You may have to really do some work with your financial planner. You may have to really look at this.
But we want you to take it on upfront and not go into it on the backend deal with the financial running upfront. Because I’ve had situations with clients, even though I was very clear around this, where they’re like, this is so right on, and I’m just gonna be able to build, a significant amount of revenue from what I’m doing within the next two or three months because I need to. And very gently I’d be like, I don’t wanna set you up for failure.
Chris: Yeah.
Todd: I’m telling you as your coach, don’t do that. And if that’s the case, if you can build a longer runway, then you need to figure out, like we talked in the beginning about that study, that people are starting these side hustles while at the job you don’t jump ship.
This is not a time to be irrational. This is a time to be sober. And to plan out your financial runways. So that’s why I just wanna bang that point home because it’s different than the emotional runway piece of it that I want you to talk about, but really be smart. And we’re gonna do episodes here on this piece, giving a little bit more tactics about how to really think about your money and your financial runway as you’re reinventing.
But I just wanted to share that piece.
Chris: Yeah. I mean, yeah, that feeling of need is what squelches the creativity and some of the smart risk taking that is actually needed to grow, right? So you, you don’t want to be feeling forced By that need. I’ll also say just to maybe be a little bit, the more encouraging flip side of it is when we talk about financial planning, like there are people that we’re talking to right now in the community where it’s, they might actually be making more money from the side hustle than they expected to be making at this moment, but because they haven’t sat down and done the financial planning to know.
I think a lot of people start from the benchmark of replacement salary. So if I make X, then as soon as I make X I can quit my job and whatever it is, but that might not be the case, right? It might be that if you’re making X at your job that you hate and you can make 0.6 X at your dream that you love, then it might be okay for you to leave that a little bit earlier so you can build that up to two X or whatever the math is, but you have to do the math and you have to go through that process. Now, we’re not gonna walk through that all now. That’ll be a different episode when we talk about that math. But to sit down and do it, I mean, we tell people all the time, put some stuff down on paper, right? And really kind of work your way through it, because that way you have concrete numbers.
Now you might not be right about all the details, but it’s not just the nebulous cloud of, I don’t know. At some point, I guess I flipped the switch. That goes back to our first point. That’s a lack of clarity numbers. Doing the math on a piece of paper is clarity.
Todd: it’s bang on. I mean, just to go with that flip side, because I talked about a client that I was working with that had a challenge on this piece, more often than not, people start making really good money on their side hustles when they go through this process faster than they thought, and then they run into another problem of, well, I don’t really know how to run this business.
Like I’m not really set up to run this business in the way that I want to. And look, it’s a good problem to have, but let’s just stay, you know, on the thing. And then for emotional runway, right? This is a big thing, understanding that you are just in a process of change.
Even though we just talked about staying optimistic and positive, right? In our world, in our philosophy, there is absolutely space and time for you to allow and reflect. That’s what we call it, right? To allow and reflect and to just have the self-regulation piece of this, where the fear and the doubt and limitations come up and to have tools that allow you to process that information because there’s actually valuable information in your fear, okay?
But also let’s not stay there forever. And so building in right from the get go that you’re gonna go on a journey when you’re reinventing. And that’s totally okay, But let’s say yes to it and do all the things that we’re talking about here because this will help you get to the promised land faster.
Chris: And I’ll say, and maybe you can tell me, Todd, whether you think this fits right into the emotional runway category, but I do think that there’s an element here too, of something we hear a lot. Something I’ve experienced is, communicating this journey to the people around you, the people that love you, some of the people that are closest to you can be a really challenging area for people, right?
So people who are reinventors, we’ve been doing something for 10, 20 years, whatever it is, it was very easy to say in a prepackaged way. Like I was the head of technology procurement, or you were this, or you were that, and now you’re in this place where it’s like you’re kind of experimenting, you’re trying something new.
You know, even if it’s a side hustle. Explaining that to people and, people don’t really clock right away what it is you’re talking about. It’s important for us in the reinvention process to have an intrinsic belief and not even just that, but a comfort with the fact that people won’t understand it.
It’s different. It’s new. We’re reinventing it. We’re inventing it as we go, and we’re finding our way to something that ultimately is gonna be really crisp and clear, but it won’t be in the, messy middle. And the reason I think of it as runway is like that messy middle could be a couple years. So we try to create the strength and confidence to not be reliant on our partner, our spouse, our parents, our whomever, friends, understanding it right from jump. There’s also a little bit we can talk about where you kind of protect your gold in the way you communicate that. But just wanted to mention that. ‘ that’s something we hear a lot, where people who was really certain and really obvious in a way what they did.
Now it’s a little harder to communicate and getting comfortable with that. Untethered feeling, of what they perceive in the eyes of others.
Todd: It’s where the rubber meets road brother. I mean, this is what you’re talking about. Because at the end of the day, we can get people really excited about this idea of reinventing their career. Like the need is there. You need to think about this. You need to think long-term about your career. All right, let’s get some clarity.
Let’s get some excitement. What could you do? All positive stuff, right? All right, let me work on my mindset. I’m growing. I’m gonna take this on. I’m gonna start taking action and doing new things. And then guess what? You come home and you tell your partner, Hey, I’m doing all this stuff, and they’re like, huh?
Chris: *wah wah*
Todd: I’ve seen, yeah. It’s wah wah wah* and then you, you’re completely deflated because all of a sudden, you have all this energy and then it’s not being supported and that is a very real part of this process. Okay. So that’s the emotional runway, understanding that everyone is not gonna be understanding what you’re doing.
And is not gonna be a long for the ride from the very beginning. And so we’re gonna do several episodes on this, around how to communicate, giving scripts for how to communicate your transition to the people in your lives. This is really valuable stuff. We’re not gonna get into all that right now, but it creates.
So much ease when you know how to communicate clearly with people
And when, ’cause it changes as you go through the process, right? Very, very important stuff I really, really love that. But let’s go to the next tenet because when you’re reinventing a lot of this is about taking action.
And actually taking action solves a lot of problems, right? So when you start experimenting and you start side hustles and you start thinking, right, how am I gonna make money? What do I wanna do? You’re taking our advice, you’re taking this reinvention thing and you’re actually putting it into play.
Couple main points on this is number one, you wanna start before you leap, right? you wanna start taking some action. And wear that lens of being that curious experimenter of your future. Right, and you wanna start thinking about, well, how can I start making money in different ways?
Who can I connect with? You wanna start being fearless around using your network strategically. It’s another very important point with taking action. A lot of people that start reinventing don’t realize that they have this vast network of people that they’ve worked with that they know. And it’s not about using people or manipulating, it’s more about being really smart about.
How can I reach out to people and have conversations that can help me move forward? And that is action that is taking action for others that may be just actually starting putting out a shingle, you know, all right, I’m gonna start doing some consulting. That’s what you did. You actually started taking action with doing the new career.
But the most important thing about reinvention is, and the call that we have, is don’t stay stagnant. This is not a time to deflect the reality that the world is changing, your industry is changing, your job is changing, and that you’re probably not very happy at it anyway. And so the opportunity is for you to actually do these things and then start taking action because without taking action, it’s all just up here mentally and like we gotta get out of that.
Chris: Yeah, back to the network thing for a moment, right? I think that a lot of times, especially if we’re going from corporate to entrepreneur, yeah, so maybe you have a giant network of people on LinkedIn or whatever it is that you’re connected to or all the people that you’ve worked with over the years.
if your view of corporate to entrepreneur is I’m going from sitting in a full-time seat to, I’m going to do consulting in that exact same mode, but now I’m hanging out a shingle. It makes logical sense to say, well, this is my network. I’ve worked with them for 20 years. They know who I am and what I do.
Great. I mean, to me, people tend to make that connection, what if you’re trying to, do something completely different. I’m doing something quite different. I mean, obviously being a senior leader had coaching elements to it, but other than that it was really a different sort of genre of work.
But everyone in your network on LinkedIn or wherever you think of your network abstractly, they’re all 360 degree full-fledged people who do a bunch of different things in their lives, and they all have brothers and neighbors and cousins. And so when you start to communicate, when you get that clarity, when you start to communicate what it is that you’re doing.
That network, they’re connected to you, the person, they don’t only think of you in the context of the corporate career that you had that whole time. I think that’s a fallacy a lot of people sort of fall into is
Todd: Mm-hmm.
Chris: I’m a product manager. I can’t communicate to them about my new hardware store or like whatever it is.
And it’s like, do you think that they don’t need wrenches I think that’s one of those things that goes back to a couple points ago, the openness this, the seeing new possibilities and then layering that on your network of people. you talk about taking action, I started by sending an email to 40 people.
My coaching career started with me sending an email to 40 people, offering pro bono services.
Todd: Right.
Chris: I got a pro bono client and then I got a few of those, and then a couple of those turned into paid clients at voila.
Todd: I think that’s such an important point, Chris. I love this the people in your network it’s not just they see you just as very like one dimensionally, like maybe they do, but when you reach out to them, here’s what I found is when I’ve coached people to do this and they reach out to the network and they have an open conversation, people are so interested, wow, I didn’t know you were into that.
And then you start having different types of conversations. And that’s where the juice is. That’s where reinvention happens, is like in those conversations. So when we talk about, strategically thinking about your network. You do you wanna sit down, as you’re doing this, as you’re reinventing and thinking about what you can do next, or thinking about growing your side, hustle into something big and really write out all the people that you know and really start thinking strategically, like how can you reach out to people that can help you potentially grow these different lines that are in play right now?
Most people are not doing that. And so when you take it more structurally and tactfully, that’s where you start to see the results. Right? And then you start taking action
Chris: maybe this is kind of the old skeptics view that I’ll bring in for a second. A lot of times when you say networking or like using your network, some people interpret that as being exploitative in some way or some sort of what am I gonna tell ’em I’m selling something, or whatever it is.
But you got to the heart of it just now, which is that, when you’re trying this, especially something that’s aligned with who you are and what you actually want to do, these are just genuine conversations. This is excitedly talking about the thing that you are learning about or experimenting with or trying or doing to people who you genuinely think might be interested in it, right?
We’re not telling you to bait and switch through your network or something like that. Right. That is not what this is about. ‘Cause I always struggled with, when I was in a career that wasn’t well aligned for me, I would go to these conferences and have to network and I’d be like, what do we do in this room?
I don’t wanna talk to anybody about anything. But once I switched into work that was aligned, it’s like you kind of can’t shut me up about coaching. Right. I love talking about it. I mean, that’s how you and I met each other is like we just talking and shop basically. I love that.
So It’s like unnatural for me not to network now.
Todd: What we’re talking about is being human like, be human, let’s get out of this thing where we’re just like these drones, working at these things and, and the people that do this, by the way, if you’re someone that’s listening to this and haven’t really crossed over to being that fearless about who you really are and what you want.
This is a gentle nudge to be human. Okay. Because that’s actually where the juice is. And you’re gonna find even one conversation opens up doorways and you’ll be like, oh my God. And they’re gonna appreciate it. The people that you talk to, will appreciate you being human with them.
And then they will give you their humanity back. That’s what’s so beautiful about this. Okay. And so taking action, like such an important part, and that can mean many different things that as an entrepreneur. Very, very important to take action. And the next big thing, thinking about going from corporate to entrepreneurship, which I think is probably the most important in some ways, which is all around building new skills.
This is where a lot of people get stuck in terms of going from corporate to being an entrepreneur. Because first off, I want to say that. On the positive side, you have skills right now, no matter what your career was, you have skills right now that can translate into some form of entrepreneurial success.
Just know that upfront. Maybe you’re great at operations, maybe you’re great at financial planning. Maybe you’re great at marketing and sales, like you’ve already done things That are set up to have a benefit in whatever you’re trying to reinvent towards. And I think a lot of people don’t realize that. But at the same time, there are going to be things that you need to learn, okay? There are going to be holes in your repertoire because being an entrepreneur requires very holistic thinking. We call it being the CEO of your future, right? Be the CEO of your life like you need to think. And a lot of people will get pigeonholed in those skills that they have.
For example, we have a reinventor in our group who is a COO type. And so for him to now think about marketing and sales and being out there is different and challenging, but this isn’t a place to stop. This is an opportunity to learn. Okay. And some of the best ways to learn, I’ll give you one of my favorite, is to find other people that are doing that thing well and learn from them.
Invest in learning from them. Invest your time in following their podcast or read their book or take their course if they have one, or whatever it might be, so that way you’re getting out of your own way. So I just dropped a lot there. Chris, I know you have probably some more
Chris: well. Yeah, you’re on the money with that. And I think I’ll drop something a little tangent, but it’s something that comes up for me when you mention that, which is that sometimes some of us get into a space where we see somebody who’s got those skills that we need, and our visceral reaction is actually to run away from that because we’re sort of like, well, I couldn’t possibly. Whatever, that person already is doing that, or whatever it is, and this is not the time for that. This is the time to say, if somebody’s got the skills that you need, if somebody’s doing the thing that you wanna do, how can you learn from that person? How can you be open to that? How can you leave your ego at the door, especially when you’re going from corporate to entrepreneur? this Is something we talk about a lot in the community. You were at the top of your game probably, and you were expecting perfection or high quality in everything you do. You’re not used to being a novice, you’re not used to being the newbie. You’re not used to not really knowing how to do things.
So you have to drop that ego and be comfortable saying, oh good, that person who’s crushing it, who knows how to do all these things, I don’t know how to do, how can I get some of that? Not running away from like, oh, I just don’t wanna look at that. ’cause it makes me feel bad about how I don’t have those skills.
By the way, this is very self aimed because my orientation for years was I’d rather just put my head in the sand than actually lean in, lean in through the discomfort and say, all right, ego down. How can I learn from you? How can I benefit? And also of course, how can I support?
’cause I have skills that that person doesn’t have. Especially if you’re gonna make a personal connection with someone.
Todd: Yeah. It’s so bang on, man. I mean, I, I learned this as well, I never really worked in corporate. Our partnership is like, you came really from corporate. I’ve always been in the coaching world. But I really was stuck for years I was the guy in the back of these rooms, not engaging in the programs, or believing in the teachers that were just further ahead than me.
You know, there was almost like this self-judgment or like, oh, I should be there, I should have already done this. And something flipped in me and I was like, wait a minute, these people are doing what I wanna do. Let me learn from them. Let me buy their program instead of not buying it.
Let me like, learn from them and be a student. And as soon as you make that switch, which is like the biggest thing for reinventors, this is a time to become a student again in your life. This is a time to be new, beginning, fresh mind, right? And, porous and like wanting to learn. That’s how you reinvent faster, right?
So investing in yourself, investing in others, modeling other people. I say this all the time, no matter what you wanna do with your life, let’s say you get clarity and like you have this reinvention idea and you have this business that you wanna do, okay? there are already like millions of people that are doing that very thing successfully.
And guess what? Most of them are not nearly as good as you are. So what’s the difference? They took action, they got clarity, they learned skills. They did everything that we’re talking about here. That’s why this system that we’re talking about is so useful because it gives you a framework by which to grow, explore, and actually succeed in whatever reinvented career pops up.
The building new skills thing, we’re gonna do a lot of episodes on this as we move forward, is a really big thing. And then the sixth one is, accountability and self-assessment. And we don’t have to go too much into that today because it’s a, it’s a large topic. this came to me from reading, the Tim Ferriss book, the Four Hour Body, you know, which is a great guy.
Love Tim Ferriss. He’s amazing. And he said something that really changed my life years back and he said that the fastest way to change any behavior is to track yourself. then I really started to learn that when you track yourself, you can really change. And when you’re reinventing, having some system of self assessment.
And also having a community of people that are reinventing, and are doing the same thing, is just a massive accelerator for finding that new success.
Chris: in our reinvention community, we have a lot of conversations that are really about accountability and honestly, it just comes from the heart. We were having a conversation with somebody the other day where it’s just, I felt like I said this out loud. I said, I felt like I’m more excited about your idea than you are right now.
What are you taking action to move it forward? And we got into a real juicy conversation where he came away being like, yeah, there, okay, there’s like 3, 4, 5 things that I need to do that I wanna do. Again, these are things that people wanna do, but then they’re not doing ’em. And a week passes and two weeks pass and three weeks pass.
We talk about self accountability and group accountability, but the group accountability is really powerful. We see this all the time in reinvention where we’re rooting for you. Right? We won’t belabor it ’cause this is a topic we’re gonna spend lots of time on in another episode of the podcast.
But I know that I spent a lot of time. Theoretically wanting to do things, but then when I actually put them into a plan and put them down on paper and say, what am I doing to move the needle on those things, that’s when you start actually getting something done and moving it forward.
Todd: We talked about this earlier today, the people that are really close to you, may not understand your need or desire to reinvent, and that causes like consternation and it causes a lack of confidence and all kinds of stuff. Therefore, you also need to find groups of people that do understand what you’re doing, which is common sense in a way.
Find a community, find people that can support you in where you need to go. And that’s what this one is all about. So this is really powerful stuff, Chris. And I think what we want to do, close it out by sharing, what we set out to say, which was like, there’s a bunch of common traps that Reinventors must avoid when they’re starting to look at becoming an entrepreneur.
We can go through these really quick, ’cause they’re all pretty deep, but the first one is over planning. Instead of, selling, and I’ve just found this, there’s so many people that there’s a lot of planning and excitement and But you gotta get into the marketplace. You gotta take that action.
You gotta, at some point as an entrepreneur, you’re gonna be selling something. You’re going to be presenting people with an idea that you want their engagement with to some degree. And there’s fear around that. And sometimes we go to the default of over planning, but this is about taking action, right?
Chris: to be clear. Game planning. Planning is a tenet of reinvention, so we are not saying that you don’t need to spend time planning. What we’re saying is that many of us, myself included, feel more comfortable thinking, theoretically about what we could possibly do in this new space than actually doing it.
So it’s the balance of planning and taking action. And it’s a feedback loop where you do some planning and then you have to get some experimental data to support or contest whether your, thesis is correct. You can’t get that information if you’re constantly you know, sitting there with the notebook, just like writing out, here’s how I’m gonna solve everything.
You get the data from the real world and you have to take action and it’s going to be uncomfortable by definition because it is change. The discomfort is not a sign that it’s not the right thing. It might be a sign that it is the right thing actually.
Todd: Yeah. Second pitfall for people that are reinventing their career when they’re looking at entrepreneurship, trying to do it alone. The one way I’ll say this is that solitude is death in this. Do not do this alone. Do not reinvent your career, your life by yourself. Okay? I don’t even think we need to belabor that ’cause we’ve been saying a lot, but that part is just so very important. The third one, hunting certainty before acting.
it’s never gonna be certain, like you did this beautifully when you sent out an email to 40 people. You didn’t know if you were gonna have a coaching career, but you went out as an experiment. You’re curious
Chris: right? We’re so comfortable with certainty. Like I always talk about white knuckling, trying to steer to the perfect answer and like this is a completely new mode that you might be entering, so you’re not gonna know the answers. That’s okay, right? You’re not gonna have certainty.
We try to create belief and then we try to create evidence to support that belief. But if you want certainty for like, in five years, I’m going to make X dollars and it’s look like this. that’s a great way to stop yourself from taking any action before you even start.
Todd: Yep. And then the fourth trap that reinventors fall into, you just said it in a way, comparing yourself to a five-year entrepreneur on your fifth day of being an entrepreneur. This takes time, people. It takes time. That’s why we’re doing episodes on this again and again. You’re going to run into successes, you’re gonna run into limitations.
It takes time. To move from a corporate career over to being, a fractional CMO into a consultant, into something that is a little bit different. It takes some time so give yourself that humility. It’s really important. And then the last one, and I, we wanted to end on this one, is thinking that your freedom, this like idea of your reinvented self, making tons of money and all this freedom and creativity means that you don’t have any structure.
Uh uh, what Chris just said, this is absolutely a time to structure your reinvention. it’s like structuring your freedom. It doesn’t just happen. You need to think about it and plan it.
Chris: this is so key for me personally, right? This is what I’m very passionate about because I realize that, again, we’re talking about going from corporate to entrepreneur. In a corporate world, there was so much structure that I was plugged into, as in a more senior role, I was making choices about what meetings I went to and what work I did.
But still those choices were very minimal and within a big system that I was sort of a cog in this, giant wheel. But in terms of now as an entrepreneur, it’s all on me. And when it’s all on us. We need to create the structure. We need to actively, proactively create the structure of what we’re spending our time on, what we’re focused on, we have to build it all up from scratch.
So yeah, there’s freedom. There’s more freedom in my day, right? As to when I can go to the gym versus when I had a nine to five job. But to act like it’s just sort of libertine, there’s no structure, and it’s all freedom is, it’s really the opposite.
Todd: Absolutely. Yeah. Well said brother. And so we’re kind of at the end of this episode, and if you’re liking what we’re sharing here, on this topic, going from a corporate career over to entrepreneurship, make sure that you subscribe to us, follow us along because we’re gonna be going through deeper layers of this like this is the time for so many people to think about reinvention in a tactical way, and we’re gonna slice and dice this in so many different ways and we’re gonna bring in people that are gonna blow you away, really. Because we wanna have other people outside of Chris and I talking about these things.
So make sure that you follow us along and make sure that you subscribe because the fastest way to get there to that success and fulfillment is to turn towards it. This is not a time to distract. And that’s what we are doing is helping people turn towards it and take it on with excitement, with energy, with focus.
And look, we got this and you got this. and again, Chris, I always say this, but man, just grateful we’ll be doing this with you, man. It’s a fun journey that we’ve been on and we’re doing this as well. We’re reinventing, we’ve never done this before, so this is all new for us and let’s just keep moving forward.
Chris: I love it. I love it. Todd, thanks so much man. This has been great conversation.
