How Do I Transition from a Corporate Leadership Role to Entrepreneurship?

MURIEL WILKINS: I’m Muriel Wilkins, and this is Coaching Real Leaders, part of the HBR Presents Network. I’m a longtime executive coach who works with highly successful leaders who’ve hit a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them so that hopefully, they can lead with a little more ease. I typically work with clients over the course of several months, but on this show we have a time coaching meeting focusing on a specific leadership challenge they’re facing. Today’s guest is someone we’ll call Jane to protect her confidentiality. For the last 10 years or so, she’s worked in a corporate environment managing across different lines of business and regions. She and her team were revenue drivers and she had a reputation for turning around ailing parts of the business.

JANE: While I certainly have a lot of pride in the revenue and the results that I delivered, I have a ton of pride around the impact that I had as a leader on people. So, I had to balance my time between understanding the scenario of the business and start to create a really quick short-term strategy, but also be focused on the people side because as we very well know, if you don’t have the people portion correct, you’re certainly not going to have the productivity there that you need in order to deliver on the business objectives.

MURIEL WILKINS: That role created the foundation for where she is now in her career. She recently launched her own consulting practice, taking the formula she used internally to now help her clients grow their businesses. But the transition from corporate to entrepreneurship is new for Jane.

JANE: And I started my own management consulting business, hesitantly, I would say. I’m a corporate animal, for lack of a better word, and I truly love being in the corporate environment. I knew now more than ever, it’s going to be so critical that I manage myself, that I lead myself, and learn how to not shelve some of those what I feel are my superpowers really is the leadership piece. I’ve completely shifted gears in certain ways, and I’m worried that I’m not delivering on a value that I have to bring to them, and I just want to make sure that I’m leading myself to true success.

MURIEL WILKINS: Jane is now building her own business, which can be a pretty daunting shift for a lot of people. She’s looking for ways to build influence and be a leader outside of the structured environment she previously succeeded in. So, I started by digging in a little deeper to that success she had in her prior career to really define what she sees as the environment she thrives in. I asked her, what did success mean to her previously?

JANE: Certainly there were financial objectives and there were annual operating budgets that we had to hit. My team and I always devised a strategy ensuring that we could go back to the executives and even though we hit our objective, ensuring that we acted on all of the various strategies and tactics that we had mapped out that was very important, especially for my teams who oftentimes I found even in large, massive, like multi-billion dollar Corporate America organizations, oftentimes they’re not fully driven by the strategies, but the people piece was exceptionally important. Empowering people on my team from the youngest members, the most junior members I should say, so that they could start to earn and gain a very informal leadership experience before they even had anyone reporting to them. Peer-to-peer counsel and support networks were important to me. And then the development of each and every single individual on the team to ensure that they felt that we as an organization, we were investing in them.

MURIEL WILKINS: Okay, so it sounds to me like success when you were internal in the corporate world was being able to meet the business objectives while at the same time developing and leading people.

JANE: Exactly.

MURIEL WILKINS: All right, so it gives me, I don’t know. I have this picture in my mind of what that land looks like, right?

JANE: Yeah, exactly.

MURIEL WILKINS: Almost like a feel for probably what the energy of working in your organization was like. So what is the mindset that you think you had back then that enabled the actualization of the success that you had envisioned for your organization in terms of being able to drive for results while at the same time developing people? What’s the mindset that you had as a leader?

JANE: Well, there’s a mindset and there was also a runway. Just as I’m speaking to you about it, the questions are popping up, what is different? Why aren’t you doing those things? First and foremost, I would say from a business results point of view, I had an infrastructure of the organization where we had annual objectives and long-term objectives that we were trying to hit. It might be launch a new product line, for example, and so then I could take that larger corporate strategy and then start to define what our accountability would be in driving that. What’s absent in the new client based environment is some of them are operating in the absence of that strategy, and some of them are very entrepreneurial driven. They’ve had much success leading their organization without a strategy that it’ll take some time to help them exercise that muscle, to understand that at this stage of the life cycle of their organization, in order for them, because they might have been seeing stagnant growth, in order for them to catapult themselves to the next level, it’s going to require planning, and that’s universal. Then I had mentioned the runway in the corporate world, although we oftentimes mostly feel like we have the shortest runway ever, that runway feels that much shorter when you are working with a client with a very finite period of time to prove results before they make a decision to say yay or nay, we should move forward.

MURIEL WILKINS: So, on the one hand, what’s different for you now? One is there is no overarching structure or architecture or framework that is driving the work that you have to deliver on.

JANE: Correct. And if there is one that exists, because some clients are different from others, it’s a very loose, it’s not a formalized plan. It’s very loosely there and probably has some holes in it and needs some updating, needs some validation in terms of data, et cetera.

MURIEL WILKINS: Okay. And then there’s also this, how much time you have to get them to move. So you’ve now identified what’s different. So, how does that make you feel? What’s the difference in terms of the impact that it has on you versus the way that you felt in corporate not having that overarching framework and having a shorter runway?

JANE: Well, first and foremost, I’m definitely hitting the ground running in an influencer role versus a pure leader role. Because I’m an asset to the executive leadership team, I’m asked to help them possibly rethink their organization, but I’m not being brought in on day one with direct reports and that leadership responsibility. So, right out of the gates coming in, I feel as though I do spend… And I do this with any new role that I have. So, this isn’t necessarily different. I have to spend and invest a good amount of time to build trust within the teams that I’m working with. So, there’s a lot of listening and a lot of learning and observation. So, that’s not different. But the difference being is that through their lens of I’m a consultant is a little bit different from this person is my manager. I certainly feel as though how I delicately try to influence different people within the client’s organization, those individuals are not expecting a leader. Now I have over time with some of the individuals because I feel as though I roll up my sleeves and I do whatever is required to further while, whether it’s developing the relationships or mostly to get the job done.

MURIEL WILKINS: It feels to me as you’re talking like something is lacking and I’m trying to understand what is it that’s lacking for you?

JANE: Yeah, that’s a great question. It’s probably the leadership piece.

MURIEL WILKINS: In what way?

JANE: Having a direct responsibility and an accountability to impact the growth and development of other individuals. I think in a very formalized way, that’s not to say, and I as I was just mentioning, I do this in the informal way, it looks different. So it’s probably still really very much there, but it’s not formalized. So maybe the client won’t necessarily be aware of that impact that I’m having.


JANE: It’s hard to measure that, and that’s not something necessarily that those individuals are going to report back to the executives to say, well, this is the impact that I’ve had. And then I don’t necessarily think there’s anything missing. I think it’s the mindset. There’s a mindset maybe shift that needs to happen, and maybe this just naturally happens over time the more you are out of corporate environment and you are in a consultant role that you become less focused on the I’ve got to prove myself, I’ve got to prove myself. But truth be told, I think I was like that in the corporate environment as well, because every year was a chance to be promoted. Every year was a chance to smash another goal. So, maybe that’s part of leading myself is reminding myself that it’s all the same thing, it’s just disguised differently. And the other thing that I definitely had to really have some stern talks with myself about was it’s not the number of hours. Certainly there’s an expectation if you have clients that expect you to deliver the equivalent of 20 hours of work in a week, even if you’re on a retainer base, you’re fairly cognizant of that in terms of how you delineate your time. But it’s the results that you achieve versus the number of hours that you’re billing for. And I had to remind myself of that oftentimes throughout the last X number of months that I could bill out 20 plus hours. But if I achieve nothing in those 20 plus hours, that billing process won’t last very long with that particular client.

MURIEL WILKINS: Right, exactly. So, I think it’s really interesting because my sense is you’re grasping for what are the measures of success that a year from now, two years from now, whatever X timeframe you want to use, you can look back on and say, okay, I’ve done well, I’ve succeeded.

JANE: That is 100% me, 100%. Because even at the end of the week I’m trying to create that list to send it out to the client, but I think it’s almost more so for myself.

MURIEL WILKINS: Right. Right, exactly. And you’ve had that when you’re on the corporate side, it was very concrete. They hand it to you. They say, Hey, it’s January, here’s what you’ve got to do by December. And now it’s like nobody’s telling you what you have to do. Nobody’s telling you what the measure of success is. You have to define it, and it might be ambiguous for a little bit until you have some repetition to realize, oh, this is how I can measure success for my clients. So ,my sense is right now, because you place such a high value on leadership and you’re missing that in your role as a management consultant in the way that you’ve had it before, it makes you feel like, What’s going on? Am I succeeding? And I think one of the things that I would offer you is when you talk about leadership, I remember somebody said to me once, or I may have heard it, I can’t recall, but they were like, “there’s being a parent and then there’s parenting, and the two are very different. You can be a parent and not be great at parenting, and you can parent as a verb without necessarily having the title of being a parent.”

JANE: Very true.

MURIEL WILKINS: And I think what you have shifted from when you were in corporate, you had the title of being a leader positionally, and you were also able to lead. So, you did both. You were like the holy grail. You were a leader who actually led. Now, when you’re internal to your clients, you don’t have the positional title. And I think that’s what you’re feeling the miss of, right?

JANE: Yeah, exactly.

MURIEL WILKINS: They don’t see you as the leader. And so I think you need to sit with that. And I’ll ask you in a sec, how does that land with you that they don’t see you that way? But that doesn’t absolve you from the verb of leading. When I say that to you internally at your clients, they may not necessarily be seeing you as the leader, they’re seeing you as the management consultant. How does that land with you?

JANE: Well, yeah, it’s reality, that’s the current reality. And as we’re talking through this, just this morning, I identified to one of the executives, there’s an individual on the team that has these types of development needs. So, not necessarily in this exact moment part of maybe the accountabilities that I was signed up for, but definitely, I’ve been wanting to say something, wanting to highlight something, and I did do that and it was well received. And I’m almost wondering, as you talk about the whole differentiating the title versus the action verb, maybe I just have to carve out those moments as they organically come to light, and maybe in this scenario it’s a little more cushioned around what we’re trying to achieve in this partnership, the productivity, this might be in the way or the resources because the math and asked to comment on the required resources of the organization. Is there a better organizational design for a certain department? And maybe identifying where it’s not a matter of sweeping out certain individuals because they’re not performing, but it’s going a bit deeper. Were they ever performing? And just using some of those leadership muscles that I would have been flexing before, but trying to keep it again in an organic way. And when I think about that need, there’s almost like a fear that five years from now I’m called back to the corporate world. Does that get rusty or is it just I just have to dust it off a little and it’s still there? Because I, for the last 13 years, made a strong commitment that on a weekly basis I was doing something to elevate myself as a leader.

MURIEL WILKINS: So, I don’t know if it gets rusty.

JANE: Muriel, you’re supposed to say no.

MURIEL WILKINS: Because that’s what you want to hear, right?

JANE: Yeah, exactly.

MURIEL WILKINS: JANE is up against what a lot of entrepreneurs run into when they can no longer rely on clear cut corporate deliverables and metrics. She’s thoughtful and wants to do a good job, but is searching for how to define that and what it means in a different context from her previous career. She can jump right into the tactical with her clients and see what needs to be adjusted in their business, but she’s struggling in finding good leadership goals for herself in her own entrepreneurial venture. I’m curious about whether or not she’s ready to let go of the structure and familiarity of the corporate environment. Let’s jump back in as I bring this up to her.

JANE: Yeah, great question. I certainly have my ambition, even though I’ve veered in a different direction in this current moment. My ambition is C-suite. And C-suite I feel the most important skillset is that leadership piece.


JANE: Setting culture, empowering people, that all equates to high-level of productivity. I mean, there are other things in that equation, for sure.

MURIEL WILKINS: Yeah. So, I don’t want to read into it. So correct me if I’m completely off here. Am I correct in saying that you, having started your own business and become management consulting is not necessarily the end all? Meaning I’m going to start my business, this is it, right? As far as you know it really is a stepping stone or a bit of a detour and expansion, but still at some point you’d like to be back in the corporate path on your way to the C-suite? Correct?

JANE: Yes.

MURIEL WILKINS: Okay. So, that makes a difference. That makes a difference because I think in the same way that you mentioned, how do I leverage the skills and the knowledge that I gained when I was on the corporate side, how do I leverage that in terms of serving and seeing my clients? I think you have to think really intentionally about how do you use this experience in starting your own consulting business so that you’re learning some things and you’ll have some skills and knowledge that you’ll be able to leverage that prepares you for going back into the corporate side at some point.

JANE: Yes, that’s right.

MURIEL WILKINS: And I think some of the discomfort you’ve been feeling is, I’ve started my own business, I’m working with clients, and it’s like, where’s the end? You’re making this motion where I’m going in circles, but where’s the end? And is this really it?

JANE: Very much so yeah, those thoughts have definitely been popping up for sure.

MURIEL WILKINS: Yeah. Okay. So, it’s good to know that this is in context of this other goal that you have, because then that changes how you approach it. All right? And this piece around, is it going to go rusty? And I said, I don’t know, because it depends, it depends what you do with it.

JANE: Sure. Sure.

MURIEL WILKINS: I remember when I left my corporate job, corporate and I had been in strategy consulting and I moved into coaching and I hung up my shingle and it was just me at that point. But I remember always saying, you know what? Worse comes to worse, I can always go back to being a strategy consultant or go back to corporate because I know how to do this, this, and this. And then I remember a couple years in, maybe it was on year five or six, I woke up in the middle of the night and I woke my husband up and he was like, what is going on? And I was like, I don’t think I can go back. And he said, what? Go back where? I said, my fallback plan. Remember I could just go back to this. I don’t think I can go. And he was like, what are you talking about? I said, I don’t think I can work a spreadsheet the way I used to. Because I had let it go rusty. But the reason I let it go rusty is that even though that was my little fallback plan, it was a fallback plan out of fear. I didn’t really want to go back. So, I let it go. But if I really wanted to go back, maybe I should have taken actions there. So, what I’m going to ask you is, if your end goal, your uber goal is to be in the C-suite in a corporate environment, what are the skills and muscles… I’m going to put them in two categories. What are the skills and muscles that you want to maintain and retain and keep fresh that you already have? And what are the ones that you want to grow while you’re having this experience in having your own business and working with clients?

JANE: The second one, I don’t readily have an answer for. The first one, so what’s already in my existing wheelhouse?


JANE: The strategy component, the ability to come into a business, identify very quickly how it’s been working, what’s led to the current success or lack of thereof? What’s impeding growth? And what are some of the tactics that can be employed for some quick wins? Well, first off, I always say, I’ve always said this to my team, no one really, truly will follow or jumps on board if you don’t have a plan. It’s like I’m showing up to a house build and I don’t have the blueprints for the house, and I’m the architect. So, I’m always rapidly starting to devise that blueprint. But a couple of quick wins really gets people on your side and having the ability to confidently make bold decisions to chart a new course, it’s really hard when an organization or a division has been doing something for 10, 20 years, but to boldly say, We’re going to go in this direction and I believe these are the results it will achieve. And I feel that that’s a requisite in a C-suite role. And of course it’s a template. It can be applied to any business, any division of a company, et cetera, et cetera. And then achieving those results 100%. What do I need to develop? When I left the corporate world, I was in a fabulous organization. I’ve been in very big organizations that are very recognizable. I was very proud of that. I was very proud that they believed in me and they developed me, and I was able to excel, but I was pigeonholed. So, even when I tried to make a leap to the other side of the business, I was always kindly redirected. S,o learning other functional parts of the business I feel is really important. But also making a name for my myself and expanding my own brand to bust out of being known for X, this functional expertise, and that it’d always be my name, would be a little more synonymous with this type of function.

MURIEL WILKINS: So, there’s a couple of things that I’m hearing from you, all right? When you talked about the things that you can keep, right? Because I see this as what do you need to keep? What do you need to pick up? And what do you need to let go of? And I think they’ll let go of part is probably what’s going to be a little trick again, but we’ll get there. But the stuff around what do you need to keep, and they’re all related. What do you need to keep? The strategy piece, being able to drive to results, being able to lead people towards results and support the agenda of the organization.

MURIEL WILKINS: You want to be able to keep all of that. What I heard as an undertone is a sense of ownership, a sense of owning how we drive to the results. A sense of owning how you develop the people to get to the results. A sense of owning how you frame the vision and the strategy in order to meet the overall corporate strategy. And to what extent do you feel you have any ownership when it comes to the work that you’re doing for your clients in the way that you did on the corporate side?

JANE: Well, I definitely feel as though I’ve shifted to player more so than coach because I’ve had to. I’ve had to be able to say, “this is something that I have contributed in the last X number of months, and those have been quite tactical.” I mean, I have written strategy, but I feel that’s a communal document. I took information and data and input from various sources of the organization. And for me, in that particular instance, it matters more to me that it’s a communal paper versus this is mine. Because then I feel as though I’m trying to take something that I’ve authored and enforce it on people as opposed to it was a community collaborative effort. Let me ask, when you ask that question, is it because you feel that it’s important to me to be able to say I can put my stamp on that? Is that why you’re asking the question?

MURIEL WILKINS: Well, I don’t know why I’m asking the question. I just ask the question. I wasn’t going anywhere with it. It’s just something that I missed. And so I’m going to ask you that do you feel a need? And without judgment. The clients aren’t in the room here, right? No judgment. Does it do something for you? Does it give you more of a sense of confidence or value if you feel like you can point to something and say, “that was me?” There’s a direct line back to what Jane did.

JANE: Yes, and I don’t like admitting that because for the last 15 years, that’s exactly the opposite of what I was trying to do. I felt like I was being the opposite of the leader that I wanted to be if I had to take ownership of something, it was the team or individual on the team. But in this case, because it is self-preservation, and it’s also, as I mentioned, I started off the clients on a pilot program, at the outset, that was to give myself leverage so that when the six months were up or the two months were up, it was time to negotiate because a few of these organizations, they had never really worked with a consultant in my capacity, for example. And so I wanted them to feel comfortable with the retainer based model. And I knew that I would have a better ability to negotiate after showing some quick wins. So, yes, I had to say, boom, I delivered on that.

MURIEL WILKINS: Okay. And I think what’s key here is the way that you tee that up by saying, “I hate to admit that because that’s what I’ve been trying not to be in my past role, yet, here I am. And here I am having a need to be able to demonstrate what I’m bringing to the table, not only to my clients, but also to myself, because I came into this a little hesitantly,” as you said.

JANE: That’s right.

MURIEL WILKINS: And so, when we hesitate, it means there’s always a little something that’s saying, did I do the right thing? And so I don’t know, yes, you have something you need to prove to your clients, right? And it sounds like there’s something you’re trying to prove to yourself. So, what is it that you’re trying to prove to yourself?

JANE: I think what keeps me up at night is I know that I’m a fairly decent price tag for these organizations, and it’s very important for me that I deliver value on that. That there’s a real ROI and not a 1.5 times ROI, a 10 times ROI. But there’s also… yeah, I don’t want to break my winning streak. I felt like it’s really important that I’m always tracking the wins. There’s a great story around that. When someone asked me in the last five years, what have you done? I like to be able to pull up the, well, we achieved this, we achieved that. I have data points at the ready. I think that’s the way I’ve been brought up, is to always set a goal, and in almost every aspect of my life, set that goal, smash it, and set another one, an even bigger one. And that’s also how I also led my teams was we’re going to the Super Bowl and we win a title, and then what’s next? We want to win two Super Bowls. We want to go here. I feel motivated by that. And I like to look at my trophy cabinet probably, I mean, this is revealing my deepest secrets, but I do. If I was an athlete, I’d want to have a gold medal, I want to have won the Olympics, a world title. And it’s not about being the best of the best, it’s about setting that goal and then smashing it. It’s just ringing the bell when you close the deal. It feels so good and it feels so good when you’re in a team and you do that together. Those are some really emotional moments. And when you leave that leadership role and you’re an independent consultant, you have to be your own cheerleader, but you’re so used to doing it for the entire team, and then there are times when I have to tell myself, “I’ve got to get excited. I’ve got to get excited in these four walls here, and be the one to be like, ‘today we’re going to achieve this.’ I’m going to bring the bell.”

MURIEL WILKINS: Exactly, right? Oh my gosh, you are looking to ring the bell, but you’re using your old moments as the moments to ring the bell versus what does it take to ring the bell now?

JANE: That’s right. That’s right. Yeah. What does it take? And okay, there will be the we landed a client, that’s great. I have to set more of the micro moments so that there are smaller milestones to get excited about. And I think there’s doing that for myself and on my own, and then certainly doing that with the clients as well.

MURIEL WILKINS: Right. And I love the way that you framed that because we’ve been focusing our conversation, or you’ve focused a lot of your conversation around the client impact. And JANE, what I would say to you is you’re actually walking a parallel path. You’re wearing two hats. You’re a consultant, and we have to define still what does that mean? What’s the value in that? You can rename it to something else if consultant doesn’t feel right to you. There’s the work you’re doing inside the client, and that’s one piece of it. And the other path you’re walking is you own a business. So, you are a CEO.

JANE: True.

MURIEL WILKINS: You might be the CEO of one in a company building of one room, but you are a CEO. And I haven’t heard anything from you around what juices you up there.

JANE: Yeah, because I think as soon as I started with my first two clients, there were conversations around, well, how do we make this a full-time role? Almost like, how do we bring you on as an employee? And my part of the brain that craves security was like, yes, yes, yes, yes. And I had people offering to help me on the business side, Okay, we’re going to help you set up a website, you need a proper domain name for your email address. And I’ve been delaying and delaying that. And I don’t know what that means, but I think, like I said, that part of the brain that’s craving that just likes to be in the secure place. And I like to try to live by the philosophy that the greatest things can happen in the unknown when you’re in that seat of the unknown, that’s when you can dream up the most unbelievable realities, the things that you can make come true.

MURIEL WILKINS: So, let me just say something here. Okay? Because this notion of security.

JANE: Yeah?

MURIEL WILKINS: I’m glad you’re thinking about it that way because I think when people get to a place of, Should I start my own business or should I stay in my corporate gig? Which again, I can empathize, I was there. I remember over 20 years ago, do I keep the comfortable corner office or do I go to my walk-in closet and start working there? Truthfully. And a big piece of it was security, but I’m just going to plant a little seed about this word security. Security is all relative and it’s an illusion. Okay? I don’t know if you’ve ever experienced being in a corporate job and that security blanket being pulled out from under you. Either your boss changes, you lose your job, your people get laid off, big work change, et cetera. Or you’ve seen others go through it.

JANE: I have twice. So, you’d think that I wouldn’t know that is not as secure place.

MURIEL WILKINS: So, anything is as secure as you want it to be. Security is a feeling. It’s how you experience it. So, the person who’s the die-hard entrepreneurial, I-will-never-work-for, quote, unquote, “the big corporate, blah, blah,” their sense of security is not working there. And the person who’s like, I will never go start my own business, their sense of security is working in the corporate. So it’s all relative.

JANE: That’s right.

MURIEL WILKINS: So, there’s no judgment on whether, as you said, when you said that the best… I can’t remember the exact quote, but the greatest path is where the unknown is. Well, there’s unknown everywhere. And what you’re experiencing now is just another field to get comfortable with the unknown. But I think at the end of the day, you also have to ask yourself, what can I do to make myself feel secure in the chapter that I’m in right now?

JANE: Yeah. And I actually think that part of it is I almost feel like I need to shake everything off in this moment and shed some of the, I’m going back to corporate tomorrow because I really don’t think that’s where I’m supposed to be. Otherwise, why would I be doing this? Why didn’t I just spend X number of months and then look for a different job?

MURIEL WILKINS: Well, it’s not what you’re supposed to be doing. How about, what is it that you want? What do you want to be doing?

JANE: It’s crazy, but the word successful is going to come up. I want to be successful. I mean, we can define that in a million different ways. I need to lead myself through this, and I’m not leading myself through it. I’m being in it. I need to lead myself to get the most out of this situation that I can.

MURIEL WILKINS: And so, what does that look like? What does that look like to get the most out of this situation? How will you look back a year or two years, three years from now and say, I got the most out of this situation?

JANE: I have to stop living in this in between. I think there’s a part of me, and I’m not going to blame it on the client, but having planted the seed of, Well, maybe I need to accept that I’m doing it. I set out to start this management consulting business, there are people who are rallying around me and supportive, and I’ve had great clients that I’ve been able to set up. I owe it to them to fully be invested in the now, in what it is that I’m doing without being one foot in, one foot out. And then it’s just like I would for any other individual on my team, and doing what we’re doing right now is what’s my objective? What’s my objective for the next two years? What do I need to achieve not with the client? And whether it’s path A that leads me back one day to a C-suite. What does that look like? How do I lead myself through growth? Because I certainly led myself when I was in corporate, nobody told me to take leadership courses at Harvard. Nobody told me that I should be reading leadership books on a weekly basis. Nobody told me to put all these different things into play. So ,I know that I can lead myself, but I’m just not doing it. And then how do I ensure that I am growing outside of the growing that I’m doing with these individual clients? I’m not doing that.

MURIEL WILKINS: I think you have dove so deep into the client and doing the work, actually doing the work.

JANE: Yeah.

MURIEL WILKINS: That you’ve lost sight of the fact that you’ve started a business.

JANE: 100%.

MURIEL WILKINS: In losing sight of the fact that she’s also now a business owner, Jane is straddling. Her commitment depends on how she feels versus putting a stake in the ground and saying, “I’m all in even if it’s just for the next 12 months.” She hasn’t considered what it looks like if she doesn’t have an out, if she does plan to eventually go back to corporate. So, the mindset shift she is seeking is actually about moving to one of commitment. And here’s the thing, commitment doesn’t just appear magically, it’s a choice. It’s a decision. And that’s why it’s uncomfortable for her, because it’s a choice she has to make. She doesn’t have to be an entrepreneur. She can go right back to corporate if she wanted to. So, what’s becoming clear is that there’s nothing truly anchoring Jane in her new venture. My sense is that she lacks a north star with her own business. So, I asked her, how will she know that her business has been successful a few years from now? Has she laid out the strategy for her own business in the same way she does for others?

JANE: Yeah. The answer is no.

MURIEL WILKINS: You’re shaking your head. The answer is no.

JANE: That’s surprising to me. Yeah.

MURIEL WILKINS: So, what would that do for you if you just went through even the exercise?

JANE: It would be the blueprint. And I think that would allow me to commit to this because there’s a plan. But you’re so right. I’ve been so diving, I dug deep for it and I keep digging deep for the client, which is great. But I don’t want to be in a situation where I haven’t planned, There are no contingencies. Just like when I was in my corporate role, things will change. How do we plan for those contingencies?

MURIEL WILKINS: And I can understand why you dove right into the client because it gave you a hit. It gave you a hit of being able to point at the end of the day and say, I got a PowerPoint deck for the client. I’ve got it done.

JANE: Exactly right.

MURIEL WILKINS: I had two meetings with the client and they went well, I got it done. It gave you that hit of I’ve done something.

JANE: Yes.

MURIEL WILKINS: Which is, as you know, because you’re a student of leadership, leading is not just about doing, leading is also about being. And in being, what you haven’t been able to do so far yet is pull your head up and say, okay, where am I going with this? What does that look like? I mean, I don’t don’t know, you tell me. Have you set up sales objectives for you as you’re a business, how many clients you want by X period of time, how much revenue you want to generate by X period of time? Have you done all of that?

JANE: No. I set one revenue target.


JANE: Yeah. And what’s funny is, before I landed the clients, I was mapping out the process: Here’s what I need to do, I need a corporate sizzle to explain what type of services I’m going to offer, Im going to make four of them, I’m going to do a photo shoot, I’m going to work on my own branding. I had mapped that out. And you know what’s funny is this is exactly what I used to tell my team not to do. It’s the equivalent of having your head stuck in the email inbox. You’re just like what’s happening in the moment? What’s happening in the moment? And that is not a recipe for success. This has not been pulled together the way I would’ve expected myself to pull together my own business. And I actually don’t even call it my own business when I’m speaking to people.

MURIEL WILKINS: What do you call it?

JANE: I have clients.

MURIEL WILKINS: Okay. And I think that’s a big differentiator. You talked about, I think earlier in the conversation, sometimes it feels like you’re an employee.

JANE: Yes. Yes.

MURIEL WILKINS: You’re not an employee, you’re the owner.

JANE: I know.

MURIEL WILKINS: And there’s a difference between having an ownership mindset and having an employee mindset. And so you’re operating with an employee mindset, waiting for direction from the owner. And guess who’s the owner? You’re looking at her in the mirror.

JANE: Oh gosh, and it’s so true.

MURIEL WILKINS: Yeah. I think it’s time for you to put your owner hat on.

JANE: Yes.

MURIEL WILKINS: And it’s interesting to me, when you look at people who start your own business, sometimes they veer way to… They swing the pendulum on the other side than you. They’re like, I’m the owner and they do no work. And then they have no clients. They have a great revenue target, beautiful website, wonderful photo shoot, all the things. And it’s like, yeah, but how many clients do you have?

JANE: Right.

MURIEL WILKINS: Zilch, zero. And then there are those who you know better to start off with some clients and then play catch up on the, actually let me build this business, right? Because it’s an actual business that’s a little bit more sustainable to do, but it takes some intentionality to lift your head up outside of, as you said, the email and the client meetings and the deliverables to say, “Oh shoot. I’m actually running a business, I know how to run a business, I’ve done it before. It’s just been inside a corporate machine. How do I do it now here?”

JANE: Yeah, exactly.

MURIEL WILKINS: And I think in order to do that, the biggest thing, Jane, is it’s not because you should be doing that, it’s not because you expect that’s what you should do, it’s because it’s what you want to do. Okay? Running your own business is not for everybody, nor should it be. Only do it because it’s what you want to do. It’s like going on vacation. Don’t go to x, y, z destination if that’s not where you want to go. Don’t go to the beach if what you really want to do is go skiing, you can still have a vacation. Choose the vacation you want. And in this case, you can be a leader wherever the heck you want, but choose what container you want it to be in. Is it in the form of having your own business or is it in the corporate setting? I think that’s what you need to decide, even if there are time limits to it. And it’s okay to say, I want to do it in my own business setting, at least for three years. Or it’s okay to say, you know what? I’ve done this for a little bit now, I actually think I want to go back a little quicker to the corporate setting and continue to do my leadership thing there. Totally your choice, but you have to decide.

JANE: That’s the problem. I think I’m not convinced that I have made that decision. I do think I need to give it a little bit more time. We grow the most when we’re uncomfortable. And if you’d asked me in the last few years of corporate, I would’ve said, the only growth that I’m getting is I’m forcing myself to explore something that’s not even accountability. So here I am, I’m learning, I’m learning about all these different businesses, I’m learning about aspects of the business that before I didn’t have a role to play, I saw it from arm’s length. And so I think if I can just commit to it and say to myself, if tomorrow I wake up and I decide this isn’t for me and I’m not happy or excited because I’m the type person, I’m excited to go to work, then you can decide then. But at least you gave this a good old college try. How can you know if you love something or you don’t love something until you’ve really put your heart into it?

MURIEL WILKINS: All right. I feel like we can settle in. So tell me what… We’ve covered a lot, believe it or not.

JANE: I know. My gosh. We have.

MURIEL WILKINS: Tell me what your takeaways are.

JANE: Oh, there’s a lot there. There’s a lot there. I went backwards and we together went backwards, looked at what motivated me, what was empowering me then, and I think it’s important to go back to understand, Is that what’s going to make me feel empowered now in my current reality? I just have to say the emotional piece of leadership that kept coming up in the back of my mind is always talking. I think that’s the love affairs that I have with working is that piece. And having to admit it, that I’m not typically that person. I’m either white or black, I’m in or I’m out. I make decisions quickly and I’m steadfast about them. So, being in this gray zone of it’s hard for me to admit to that, but it doesn’t mean that it’s a fail. And so maybe I have to say that I’m proud myself to admit it. And so thank you for getting me there. And reshaping the win, that’s a big one for me. It really is. And I think putting in that effort, that’s going to be a challenge for me for sure, because I have to pump the breaks over here for a second on the client needs in order to take the time and invest in myself and this business that I’ve started that has a very nice revenue stream and understanding how I can scale this, what does that look like? And applying the same principles that I had in my old role, and to expand on that in establishing a business. So, yeah, we unpacked a lot. We definitely did. I feel like I just ran a pretty long race because you have to explore things and you have to be honest with yourself, and you have to admit what’s scary and is that why you’re coming in high? Or is it legitimately, you prefer something else? I think I need to, after this session, say to myself, I’m investing in myself. I’m investing in my business. And put your money where your mouth is because you’ve been talking – or, I’ve been talking  – about my brand is turning businesses around, starting things up and making them profitable and achieving those results. And I need to have that same story as it pertains to my own business.

MURIEL WILKINS: Exactly. Exactly. So, act like the CEO of your business.

JANE: That’s it. That’s right.

MURIEL WILKINS: I can’t wait to hear how this goes for you.

JANE: Oh yeah, yeah. I’m excited. I’m excited. We’ll need to do a check in for sure.

MURIEL WILKINS: Oh, we sure will. Well, listen, thank you. Thank you so much. Thank you for doing this with us.

JANE: Thank you.

MURIEL WILKINS: At the end of the conversation, Jane admitted that she felt that she had just run a bit of a race. Being in a state of ambivalence can definitely feel exhausting. But once you can be honest with yourself about what choices you need to make and what you’re ready to commit to, you can truly start moving forward toward your goals. On a personal note, I lived this scenario moving from a corporate executive role to becoming an entrepreneur and experience all the risks that come along with it. As a coach, though, I can empathize with Jane. But it’s important that I not confuse my client’s story with my own. And that’s why it was important for Jane to define what security means for her and not look to anyone else, including me, to do that for her. We create our own security, and it means different things for different people. Jane had to come to terms with that and choose what trade-offs she’s willing to make to achieve her goals. Only then will she get the most out of her entrepreneurial journey, however long it will last. That’s it for this episode of Coaching Real Leaders. Next time…

NEXT EPISODE’S GUEST: I’ve been able to show great value in areas that are not conventional or traditional in big law firms, and even in government service which I’ve had great experience with. I’m very good at building relationships and the law firms that I was at realized that there was economic value to me.

MURIEL WILKINS: Want more of Coaching Real Leaders? Join our community where I host live discussions to unpack the coaching sessions. Become a member at You can also find me and my newsletter on LinkedIn at Muriel Wilkins. Thanks to my producer, Mary Dooe; sound editor, Nick Crnko; music composer, Brian Campbell; my assistant Emily Sofa; and the entire team at HBR. Much gratitude to the leaders who join me in these coaching conversations and to you are listeners who share in their journeys. If you are dealing with a leadership challenge, I’d love to hear from you and possibly have you on the show next season. Apply at And of course, if you love the show and learn from it, pay it forward, share it with your friends, subscribe, and leave a review on Apple, Spotify, or wherever you get your podcast. From HBR Presents, I’m Muriel Wilkins. Until next time, be well.

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