Corporate to Entrepreneur: Five Things No One Tells You Before You Jump

The next promotion can be the moment you realise you’re done climbing. Not because you’ve lost your edge, but because you can finally see what the next rung will cost your energy, your health, and your sense of self. I’m hearing this from smart, senior women again and again, and it’s why I’m sharing what I’ve learned from making the jump from corporate to entrepreneurship after 20 years inside the system. 
 
I break down five lessons that don’t come from a quick Google search: how to stop relying on external validation when there are no KPIs or gold stars, how to handle failure and rejection without taking every wobble personally, and how to avoid “shiny new toy syndrome” when you’re suddenly free to do anything. We also talk about the uncomfortable truth of modern business ownership: whether you sell services, consulting, coaching, or products, you are the product, and personal brand matters more than most corporate high achievers expect. 
 
The biggest takeaway is the one I wish I’d heard earlier: your business will never outgrow your identity. Money beliefs, worthiness, fear of being seen, and perfectionism show up fast, so the personal development work is part of the business plan. If you’re considering leaving corporate, starting a side hustle, or building something more aligned with your values, this will help you create runway, build resilience, and design a business that works with you instead of against you. Subscribe, share with a woman who needs it, and leave a review so it reaches the people it’s meant for.

The Balance & Beyond Podcast Hosted by Jo Stone, founder of The Balance Institute

For women who are already succeeding, but beginning to wonder if they're willing to keep losing themselves in the process.

We know high achievers, because we are one. This podcast draws on Jo's 20 years in global leadership and thousands of hours coaching executives and ambitious women: the patterns she sees, how to untangle them, and what it actually takes to keep your success without paying for it with yourself.

If something landed today, there's more where that came from.

And if you know a woman this would resonate with, send it her way.

🎙️https://www.balanceinstitute.com/podcast
🔗 www.balanceinstitute.com
💼https://au.linkedin.com/in/stonejoanne
📷 @therealjostone

Transcript

Welcome To Balance And Beyond

Jo Stone (Host) 0:27

Welcome to Balance and Beyond, the podcast for women who've outgrown the old model of success. The ones who look fine on the outside but know the way they've been living no longer fits. If you're standing in the space between who you were and who you're becoming, this is for you. I honor the space you've created today. Let's dive in. I've learned that when the same conversation comes up multiple times, to pay attention. And there is a conversation coming up again and again that I need to bring to you. Women in my world, smart, senior, successful, are increasingly telling me they don't want to climb anymore. Not because they've lost their ambition, but because they can see what the next rung is going to cost them. They can see the pressure, the pivot, the changes that are coming, the chaos, and they've clocked that, you know what, the job I'm in now just isn't giving me the fulfillment that I thought it would. And so these women are starting to look elsewhere, not necessarily for a new job, because usually they've got fees to pay and holidays to pay for and mortgages, but they're really searching for something more aligned with who they are and what they're passionate about. And because this has come up so many times recently, I've been asked directly what have I learned about making the switch from corporate to entrepreneur? Because many people who become entrepreneurs have never been in corporate. Maybe they've grown up in an entrepreneurial family or they started their own business from the get-go. But for me, it's been six years since I left corporate and I was in corporate for 20 years. So I was pretty well institutionalized. And I'm grateful that in that time I've enjoyed thousands of clients and I'm closing in on six million in revenue in six years from zero. No product, no audience, no clients. What's crazy is that puts me in the top 2%. Would you believe only 2% of women-owned businesses have ever crossed a million? But the good news is I am just getting started. Now, I have not had an entrepreneurial upbringing. So I have learned all of this myself the hard way. My dad worked for the same company for 50 years and rose up the ranks from being an electrician, repairing photocopy machines in the old days of those giant things that were the size of a room, to being in second charge of the company. That's how things worked then. And my mom was a stay-at-home m. So entrepreneurship was certainly never modeled, never discussed. It was all about stability and staying in the one place and proving yourself and working your way up. So I've very much broken that family mold here. What I want to share today are the five most poignant lessons that I've learned since making the jump from corporate to running my own business. These are things that I wish someone would have told me before I started, the things that would have saved me a lot of time, a lot of money, and a lot of heartache. Now, it was really hard for me to pick just five. So I will stick to my five. And I want to make sure that I've given you ones that you can't just get from a Google search. These are ones that, as a woman, juggling me all the things that I wish I knew. First up, gold star proof yourself. In corporate, you get loads of external validation, whether it's a paycheck, bonuses, KPIs, you know how to meet things, you've got benchmarks, you get occasional feedback. Although I did find that the further up the chain you go, the less feedback you actually get, but it's there. You can celebrate things with your team members. You've got that sort of consistent system in some way. When you start your own business, you've got nobody telling you what to do. Everything relies on you, which means you have to find new ways to give yourself gold stars. When I first started, my gold stars came in the form of money and clients. But when it takes you a while to get money and clients, and then it's lumpy, it's so, so difficult for you to actually find the fuel you need to go on. When I first built my first ever coaching program, I went and asked 15 different people for feedback on my outline. Because that's what I did in corporate. If I'm honest, I was scared. I didn't know if I was right. There's a really fine line between being collaborative and getting market intel and asking some powerful questions versus this incessant search for external validation where truly I was just looking for everyone to confirm what I already knew because I didn't trust myself enough at that point in time. Interestingly, when I real built Balance and Beyond version 2.0 three years later, I didn't ask a soul. Because I didn't need to. I was the expert in this space. So it took me a couple of years to really own that. You have to learn to find your own source of internal validation. If you are still chasing gold stars, then you are going to be on one hell of a ride that is full of cortisol, full of adrenaline stress, and not a lot of sleep. Now, this is one of the joys and the challenges of running your own business. The really important lesson that you are your own handbrake and your own accelerator simultaneously. In corporate, I was in financial services. So there was a whole amount of regulatory stuff, risk management, legal approvals. I was in very collaborative cultures. I was seizing the world. And so even though I was somebody who was always pushing the envelope for change, no surprise, I still had a lot of people telling me what I could do. I couldn't necessarily do something that wasn't aligned with the corporate objectives. Going on your own, you have to learn, you know what, I'm my own accelerator. And if I'm putting my own handbrakes in place, then I'm just robbing myself of what I've come here for. But to do that, if you don't want to bunny hop between the two, the one thing will give you a smooth ride is being okay with failure and with rejection. Whether it's rejection of your pricing, your proposal, whatever it is, clients leaving you, having to give people refunds, having disputes. When you take everything personally, then my God, get ready for the wildest bunny hop ride of your life. And this lurching, if you have any perfectionistic tendencies, which, full confession, I did, becoming an entrepreneur feels pours rocket fuel on them. Because you will so easily find yourself tweaking, reiterating, looking for certainty in all the places that you can't find it. I spent a lot of time getting some of my branding documents ready and not actually going out and selling because that was a little bit scary. So hence I would want to go out and do things, and then the handbrake would come on. You can move faster when it's just you or when you're in charge. You don't need 15 people's approval. But when you are your own handbrake and you find yourself underquoting or you find yourself over-delivering, then this can really dampen your journey. So the freedom that many people are looking for in getting out of corporate is often that same freedom that exposes many of your dysfunctional patterns. And it will also expose where you're outsourcing some of your momentum. So after you've learned to find new ways to give yourself gold stars, or better yet, require less of them in the first place, you're getting a smooth ride instead of bunny hopping, is you need to know what you actually want. Or becoming a squirrel will eat you alive. In corporate, you have company objectives, you have the good old one-page PowerPoint with three or four pillars and columns, and you then have to do your strategy, and it latters up to that. So, and while I was in rooms that set the strategy, we still had shareholders, we still had things. I didn't have free reign. But as an entrepreneur, scribbling or shiny new toy syndrome, oh my God, it's so real. There's because there's no one telling you what to do. If you aren't focused and if you don't know what you want, then it's going to be so difficult to stay on tasks. And the worst part is the distractions can make sense because you logic your way. Usually they can be great distractions, they're exciting, they're opportunities, but they're probably often not going to be the ones that move the needle. So you have to be clear on what you want. You have to really learn to tap into your intuition because those squirrels are so seductive. Learning to listen to myself, really getting clear on what matters to me, on what's going to move the dial has been a constant journey for me. But it is a skill and a muscle I wish I knew to develop further when I was in corporate. I would use my intuition in corporate, but there was this inevitability about things when it's yours, almost like your own baby, when you have a team, when you're responsible for somebody else's meal ticket, well, then you want to be damn sure you can trust what's coming through. So the more you can build that intuition muscle, the more you can learn to listen to yourself, the more you can be aware of some of those blind spots and where you do tend to squirrel over others, then that's going to make a really big difference to how far and how fast you can go. When you become an entrepreneur, most of the time you are the product and you can't outsource the discomfort of that. Even if you sell widgets, these days, more and more of selling the widgets is the story about the people who create the widgets. And where did the inspiration come from? And what was the journey of that widget being produced? And if there's you're selling any kind of consulting or intellectual property, or you want to be on a board, you are the product. You need to have a clear story. You need to know what a personal brand is. You can't hide behind proposals and faceless pieces. And any masks that you have up are going to very, very quickly be exposed. What always makes for the most compelling sales, the most irresistible offers is when you're fusing your expertise in it. That means you have to show who you are. You can't just hide behind a LinkedIn profile. You have to actually bring yourself into the equation. And unfortunately, these days, that usually means getting comfortable with social media, hearing your own voice, speaking on camera, all the things that makes you incredibly uncomfortable. But you can't outsource that to anyone else. No one else can show up on camera as you. And yes, I know AI can do this stuff now, but there's an energetic component to running your own business, unless you're doing a fun video and it's you masquerading as a unicorn or something like that, then my friend, go for it. But if you aren't comfortable being yourself, if you incorporate are still not posting on LinkedIn and not being seen anywhere, if you're still hiding, then if you want to go into business yourself where you have to show your vulnerabilities, where you have to be authentic, it's going to be really hard for you. And let's just put a general note out there to discomfort, because this is what many clients who come to me have spent their entire life avoiding. The discomfort of making someone disappointed, the discomfort of entering into conflict, the discomfort of letting somebody down or saying no or feeling anger and not being able to express it, you are going to have to tolerate more discomfort running your own business than you ever have before. Because you're the product. And so if you're not selling, if you have not found a way to detach yourself, and this is where the gold stars come in, the being okay with failure, then it feels like rejection. And you will shrink and you will hide because it can feel impossible, especially in the early days, to not take that personally. Having faith in yourself, knowing your worth, irrespective of the numbers on your PL, having a vision, knowing where you're going is so important. Otherwise, you'll shrink, you will hide, you'll put yourself back into a box. And I believe that if you have a calling to, or you feel being you're being pulled, or you really want to do something else in some guise, whether that's a side hustle, you want to renovate a villa in Sicily, whatever it is, then you want to be true to that. So don't shrink from something just because it's uncomfortable. But if you're thinking of making the leap, then make sure you're putting yourself in containers, places that make you uncomfortable before you do it. It's almost like saying, I want to run a marathon. Well, maybe you should make sure you've got some sneakers and maybe you should start running some five and 10Ks before you actually begin. I've had so many clients say to me, Oh, Joe, no, I'll wait. When I've left my job, I don't want to do it while I'm at my job because you know that's a bit murky. And so, no, I'm gonna wait and I'm not gonna do any of that work. I'm just gonna focus up on finishing. And that makes logical sense in some ways, but then you are a standing start. And now it's on you. You probably have to make some money. And now you're gonna go into fear and pushing and franticness, and all these old patterns are gonna come up when in reality you could have been building some runway. And by runway, I don't necessarily mean you're out there scraping clients. I mean you're starting to post places, you're starting to get more comfortable in front of a camera, even if nobody else ever sees it. But you are building these skills and building these muscles. And I, for a long time, have always been quite comfortable writing because that's been a skill set of mine. But talking, I hated my own voice for a really, really long time and would squirm anytime I heard it. Now, 150 plus podcast episodes in, you just suck it up and get used to it. I've used to seeing, got used to seeing myself on camera. And more recently, I've been pushing myself on Instagram. I even went and hired a videographer to come and get B-roll shots of me because I was sick of hiding. So that was incredibly uncomfortable for me. And so I'm continuously pushing myself outside my comfort zone, knowing that that is where my edge lies and that's where my next level of success lies. Which brings me to the ultimate piece of advice that didn't show up anywhere in anything of what I was reading about starting your own business. Scrap the business plans and the PLs and all that crap. Your business will never outgrow your identity. If you want to start a business, there is no greater crash course in personal development than going in alone. Understanding your blind spots, understanding where you sabotage yourself, where you hold yourself back, the upper limits that you are hitting. Because you leave corporate and there you knew the rules. You had an identity that was usually defined by your title, your hierarchy internally, the industry you were in, your external piece. And now, if that all goes, what do you have? Sometimes that can translate, sure, if you're going on boards and things, but often then it has this reckoning. Well, if I'm not that, what am I? If that job gave me the guardrails, it gave me the direction, now I'm responsible for finding my direction, finding my motivation. Stop the squirreling. I've got to find my own source of validation. I've got to motivate myself, I've got to manage my own boundaries. There is so much that you're going to have to do as part of that process. And I have found again and again and again, when most people hit a cap in their business, it's because they've hit a cap with their identity. Sure, sometimes it can be structural or systems-oriented or it can be a product piece, but more often than not, that's what it is. And I know personally, anytime I've hit a ceiling in my business, my first point of call is I've hit a limit. I've hit a limit of how much I can hold. Any limiting beliefs that you have around worthiness, money, being seen, taken a risk, being bold, leaving the box, they are all going to come to the surface real fast. Particularly anything around worthiness and money. If you have to earn it, if you have to prove it, all of those old wounds are just going to blossom. And it's really easy to just shove them down and pretend they don't exist and put your head down and work 100-hour weeks, but they will always continue to bump you. So committing and knowing that this journey to start a business is as much a personal development journey of your own as it is a journey into sales and marketing and fulfillment and delivery and IT and all those things. Yes, there's all those technical skills, but you can master those. You've done all of that. If you've been in corporate, you actually have a significant advantage over others who haven't been in corporate. As I started my business, I was working with people who were nurses or teachers or police officers, and they didn't have a lot of the structures that corporate has given us. So you have so much that you can bring with you, which is amazing. But don't forget that the work has to continue on you. One of the big pieces when we talk about doing the internal work or the personal development work is really understanding what are your strengths and what are your values. So, as an example, one of my number one values is freedom. It's really, really important to me. It's why I hate rules. It's why I hate being in corporate, really. It's what I do everything for. So the thought of not having a handbrake is really exciting for me. I'm like, let's go, baby. Like, let's go fast. And I don't mind failure because it means I'm learning. But my husband, on the other hand, would not really make a great entrepreneur because his primary goal is safety. He hates risk. He hates failing. And it's really challenging for him. He, if he was to start his own business, he'd probably be quite cautious and he'd probably be a lot slower than me. Now, it's not necessarily right or wrong. While there do tend to be more entrepreneurs who over-index into freedom and that's why they go down that path, that doesn't mean that if you are someone who values safety and values risk, that you're not going to be successful. If you don't know that that's the case, then I guarantee you you will fail. However, if you get to know yourself well and you know they're your blind spots, well then great, you're probably going to be more cautious, but there's a chance that you're going to build something that's more sustainable. You're not going to take risks. And who knows, you might even find that you can learn to take risks in different ways when you find ways to cultivate more of that safety within. So that's what I mean when you can build a business that works with you, not against you. It's in alignment with your values. It's in alignment with who you are and how you want to show up in the world and what matters to you. Because if you don't find that alignment, then you will constantly be at war with yourself. I found that alignment of who I am, what I want, where I'm going, who I'm serving. You start to get those right. And that can take several iterations. I know it did for me. Well, then that becomes a beautiful way for you to step into your power, to step up and to really take the hits that are going to come your way because you know you're doing it for the right reasons. I'm here for the long term. I'm not just here to make a quick bark. This is what I'm made for ultimately. And so many women who are wanting to step into businesses like this feel exactly the same way. They want to find that sense of fulfillment. It's not always just about making money. For some, it's pocket money for new clothes or a holiday or things like that. But it's finding somewhere where they can grow. They've got that sense of fulfillment, where they've got that excitement and they know that it's worth it. They're not selling their soul for someone else. They're doing something that matters to them. And so it's been seven years. It's really hard to believe. Six, six and a half, seven, six, seven. Anyone who's got a kid. And this entrepreneurial life suits me so well. I don't think I could ever go back. But I'll be the first to say it's not for everyone. If you are one of the many considering making the leap, whether you're still in corporate, where you're starting to tentatively put a foot out and you have more questions, then in the show notes you will find a send a text to Joe function. You can send me a text, you can ask me questions, and if there are enough questions on this topic, then I'll do a follow-up episode and we can go deeper. Here's two taking risks, having fun, and doing whatever the heck you want. I'll see you next time. Thanks for joining me today. If this episode resonated, share it with a woman who needs to hear it. And if you want to be part of the Ripple Effect, leaving a review helps it reach the women it's meant for. I'll see you next time.