Corporate Escape Secrets: Why New Entrepreneurs Fail—and How to Win
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[00:00:00] Welcome back to the Gen X remix midlife laughs and next acts. Let me start today with a question. How many hours per week do you spend daydreaming about making the leap from your corporate executive role? Into entrepreneurship, whether it's coaching, launching an online business or following another entrepreneurial path.
How often do you catch yourself drafting and redrafting and drafting again, your glorious corporate escape plan. If this sounds like you, you're in the exact right place. I'm your host, Tabitha Jones. And today on the Gen X remix, we're going to talk about the top six reasons. I believe most women who make the leap from corporate to entrepreneurship fail and how to steer clear of some of these pitfalls [00:01:00] using the lessons I've learned, because let's be There is a very smart way to build your business while you're still in corporate.
So you can leave with confidence, clarity, and a steady paycheck from day one. As you start your new adventure, buckle up, we're going to be diving right in. And I hope that you take a lot of notes today because I'm going to share some great action steps that can help you. If this has been your dream.
We're going to really help you start preparing for these changes. I'll be honest, I really underestimated what it was going to take to make the leap. Uh, and I was really well prepared as you're going to hear. So let's take these lessons and dive in. Reason number one that I believe entrepreneurs fail is they wait too long to start.
The lesson I learned here is that preparation beats perfection, but overpreparing is a trap. [00:02:00] So many new entrepreneurs, especially those of us leaving corporate, we think everything needs to be perfect before somebody is going to take us seriously. In our new role, let's face it, we're taking on a whole new identity and we tend to believe that we need a fancy website and a professional photo shoot and maybe a bunch of automated funnels and a billion Canva things.
If you haven't started, you're going to fall into the Canva trap, the Canva trap, trust me on this one. I don't want you to do it, but you will. And we do all these things before you even land your first client. I want you to think about that and kind of tell yourself, Nope, we want to focus on some other things.
First, the things that you need to really prepare and get ready to go with are getting your pitch really dialed in snagging a few paying clients, and then you can start going for the bells and whistles as the money is coming [00:03:00] in and your budget can handle it. An action step to help you in this space is just start small.
I know I say this to my career advancement job search people all the time. It's the same when you're taking the leap into entrepreneurship, start small, identify who you serve and how you serve them. And once you've proven that people will actually pay you for what you're offering, then you can invest in that bigger branding and marketing stuff.
Otherwise, you're just burning time and a lot of money on pretty stuff that won't move the needle. And trust me, when I say there are about a million people out there that will sell you every solution known to man and woman, uh, not all of those solutions are going to work for you. And you're just going to end up feeling really frustrated and burnt out.
So preparation beats perfection, but over preparing is a trap. [00:04:00] Reason number two that I believe entrepreneurs fail is. They don't leverage their existing strengths. The lesson I learned in this space is your corporate skills are your ultimate secret weapon. Not every entrepreneur has those, and many of your competitors do not have them.
So don't underestimate the power of all of your skills with organizing data and budgeting. Sorry, I am not a budget person, forecasting budgets. Um, negotiation, building relationships, being visible, doing all of those things that you've done again and again over the years. That experience translates perfectly into managing and growing your own business.
Your action step in this space is to write down your top 10 skills. What are you amazing at in your nine to five, especially if these are things you'd love to do, it could be something like team leadership or presentation [00:05:00] skills or color coding your calendar. I am going to say your calendar is always number one.
So make sure you bring that in. But it could be all kinds of different skills that you bring to the table. I want you to write down at least 10 of those. And think about how those transfer into the business that you want to build. Those skills are going to supercharge your job, which I would say at this point should be your side hustle.
The future state, it will be your dream job. The sooner you can start transferring those skills, the smoother your exit from corporate will be. Reason number three that I believe a lot of entrepreneurs fail when they make the leap from corporate. Into entrepreneurship is they'll stick to a bad idea instead of pivoting.
My lesson I learned here is that if you've lost your spark, pivot, just pivot wisely. Entrepreneurship can be tough. If you are thinking of getting into [00:06:00] coaching, like me, you don't go in an office every day and feel the energy of your team. And sometimes it can feel really lonely. It can feel really hard.
And that's normal. But if you feel like you're dragging yourself through the mud daily, and your spark is dimmer than ever before, it's time to reassess. Now, as I say that we don't want to fling the plate plate of spaghetti at the wall every other week and change direction every other week, because that's not how we move fast either.
But if you are not feeling things are right, and you're energetically not aligned, Make a pivot. I've had a lot of coaches along the way say you need to pick a horse and ride it, which is fair, right? Pick your niche, pick your offer, pick your thing and do it. The problem is sometimes as you've been riding a horse a really long time, you start to get some saddle sores.
You start finding out that certain things aren't quite working the way that you expected them to. [00:07:00] And that's when you need to take a step back and reassess. Is there something simple you need to change? Maybe you're just wearing the wrong pants. Or are you riding the wrong horse, which is kind of a big deal.
We don't want to keep writing it if it's feeling harder and harder. So think about that. If, if you need to hear it, this is permission to pivot. Um, I felt like I needed permission for some reason for a little while. It's a, it's a weird thing. And I know those of you who have started your entrepreneurial journey have probably felt this at times.
The action step to help you with this is write down what you love to do. And what you can't stand about your current direction. And then make sure that we don't have a lot of that. I can't stand to do this in your day to day work. Um, for me, I hate, I know people always laugh about this because I led technical teams so long.
I hate math. I hate numbers. So if there's going to be a lot of math or numbers, it is not my thing. So I [00:08:00] know that, but I also know there's going to be a little bit of it. So think about it that way. Right. Can I handle a little bit? Yes. Can I handle that 30 percent of the week? No. Make sure you clear that out and then reach out to a seasoned coach.
Someone who gets us corporate veterans who can give you a fresh set of eyes and help you pivot without blowing everything else up.
Reason number four that I believe a lot of entrepreneurs fail is they get trapped in perfectionism. You know that you felt that in your corporate job, so much perfectionism has held you in place. I see this a lot with my career advancers, um, definitely see this a lot in the entrepreneurial space. We will get stuck in that trap of perfection.
The lesson in this ladies is done is better than perfect. Always, if you are spending months, oh, uh, just obsessing over the perfect font [00:09:00] pairing or you're rerecording a 10 minute video 47 times, you're leaving the real opportunities on the table. Uh, early on funny story, I decided Instagram reels are the way to go.
Instagram reels are not the way to go for someone like me. I would spend hours working on six second reels. That's ridiculous. I know you're laughing right now. It will happen to you. Try to save you from yourself, but it will probably happen. Just, we have to get over the perfectionism. I've had friends that just say, uh, I'm still trying to record this video.
And I know that that video is, you know, maybe 10, 15 minutes long. Like, what's the problem? Well, I don't like the way I look, or I didn't like the way this was happening, or I could see that little chin sag. Ladies, nobody is looking at that except you. What people want to hear is the content you're sharing.
So get out of that perfectionism mindset. [00:10:00] Your action step here is honestly just pick a launch date, circle it and read on your calendar and honor it. Like you would honor your best friend's birthday launch, gather feedback, make changes as needed. You're going to learn more from your market and your ideal clients.
Then you will learn in a week of just endlessly trying to change and manage anything that could possibly be your client. Your ideal clients are going to give you language that you need. They're going to tell you what they want. So if you're working on that escape plan, pick up your calendar right now, pick a date that makes sense.
And circle it in red. Let's start marching towards something. Reason number five that I believe a lot of entrepreneurs fail is they burn through their budget on solutions that don't help. Now coming from that entrepreneurial world myself, [00:11:00] I get it. I totally understand how. You know, in the corporate world, we're able to just throw money at something and somebody will fix it.
We can hire a contractor. We can get some software for our teams. We can do all of those things to fix it. But in the real world, as you're building your business, there is no 10, 000 course, 12, 000 course, 27 course that will fix your business. If you lack clarity, ask me how I know there are some really great.
Coaches out there, especially business coaches. But again, not everyone gets that job from decades of conditioning and the corporate environment. Into entrepreneurship. And that makes you a really easy target when people are out offering and promoting their tools. Um, if you need a referral ever for somebody, for something you believe you need to know, let's chat.
[00:12:00] I've got, I've got a list of referrals, people that I trust, people who can help you, but there are so many people there that will literally sell you the moon until you're bankrupt. And not many of those will help you make money and not every one of those is going to work well for you. Uh, I've joined programs that once I was in, I realized they were all video.
Oh, this makes me crazy. It's my pet peeve. You get in and they're all video modules. Well, I didn't know early on to ask, are you actually coaching me? Or are there video modules that I'm expected to watch friends? We know we are not going from our busy corporate life into watching hours upon hours of video modules, whether they work or not, that's just not where our hearts and heads are.
So just be really careful. The action step here is just channel your corporate savvy, beautiful self. Do a risk benefit analysis before you invest in a glitzy coaching program, ask direct [00:13:00] questions about your situation and about your goals. And if the answers are vague or off base run, don't walk to someone who speaks your language.
There are a lot of times I wish I had done that run. There also are a lot of really shady sales tactics out there in the coaching world. And you just want to be really, really careful and really aware so that you aren't throwing money at solutions that don't help move you forward. Reason number six that I believe most entrepreneurs fail when they make that leap from corporate into coaching is they don't put themselves out there enough.
My lesson learned there is visibility matters. And this again applies in entrepreneurship, entrepreneurship, and career advancement. Interesting thing is, is I practice what I preach. I love being around people, but early days I was sitting at my desk working on certificates that nobody has [00:14:00] even asked me about.
I spent my time working on learning tools and how to link things between my, I don't know, my website and capturing emails, um, addresses. So I could send emails and, oh my gosh, I could give you a list of about 4, 000 tools. I feel like I've learned. If you're someone like me and you love learning and you love technology, it's really easy to stay hidden behind your desk, literally and figuratively, just continuing to work on all kinds of cool things.
I make the prettiest things in Canva. But I spend hours making something that I could pay someone to do in about 15 minutes. So we're all guilty. Let's save you from this, this feeling and save you from that failure and make sure that you're getting out there talking to people about what you do, getting feedback, sharing your program, sharing your big idea.
And, you know, be prepared. Sometimes people aren't going to understand it. That's one thing that I [00:15:00] struggled with a little bit when I was making my decision to leave my corporate career after a really long time. And it was that my friends and family didn't understand it. They didn't understand that pull.
They didn't understand why coaching was so important to me or why I felt like that was the right thing. And, um, when I've had hard days, it's been really hard to talk to some of those individuals because the immediate answer is, well, we're hiring or, oh, I know so and so is hiring or here, let me make an introduction to you shooting you right back and boomerang into your comfort zone.
Right. The reality is it's hard work and you've got to surround yourself with people who are like minded. And when you get out and you're putting yourself in front of people, you'll also start attracting people who are like minded and excited about what you do. So your action step here is to commit to strategic visibility.
When you are getting ready to go, I want you to pick one [00:16:00] social platform and one live method. Now, The social platform. I know everybody says, Oh, it's so easy. You just go to Canva and you can post on LinkedIn, Instagram, and Facebook. The problem is you can't manage that by yourself. And again, we're starting strategically, right?
So pick one. If you are going into the career coaching space, career advancement, career growth, career, anything, your people are probably on LinkedIn. The reality of a corporate executive female who wants to be promoted from director to vice president looking for a coach on Instagram, pretty slam. So think about where you would go to look for the service that you're offering.
Personally, I still only go to Instagram when I'm looking to stalk my son and see what he's up to, or when I'm looking at cute animal videos. So be really strategic about your social platform. You can't be everywhere. So pick the one that makes the most sense. [00:17:00] And then for showing up live, maybe podcasts are your thing.
I love being a guest on other people's podcast. I get to share information with their audience. I make a new connection with the podcast host. It's a lot of fun. You may be more interested in booking speaking gigs. I also love that because I love being in a room where the energy is there and my energy translates or there are tons of local networking events.
Find the ones where your people are and show up consistently. People can't buy from you if they don't know you exist. Shocking. I know. And kind of getting back to starting before you make the escape. This is the really great way to go out and test your plan. Bring it up. See what people say. Capture their language.
Capture their words. Because you're probably going to need those as you're building your business and getting ready for what's next. So friends, those are the top six reasons. I believe that a lot [00:18:00] of people making the leap from corporates into entrepreneurship fail and really struggle. But I want to remind you that failure is always a lesson.
We fail fast. We fail forward. Right? So. Take the lesson, learn from it and go do it better. The next time you can absolutely do whatever it is you want to do, but let's do it strategically. So when you make that leap slash escape, you're feeling good about it. You're not feeling stressed out and you got yourself enough runway to keep the momentum going.
So now that I've shared that, I'm going to share a little bit about what I'll be doing differently in 2025 because. Even as seasoned entrepreneurs, we're still learning, evolving, and sometimes face planting. And I say seasoned entrepreneurs in the world. I'm still a baby it's been, uh, four years. So, you know, still going, still [00:19:00] growing.
So a couple of things I'm going to be doing. One is making another pivot. Uh, shiny new direction is on deck and maybe you've already guessed it. I've spilled a little bit of the beans, so keep your ears open and let's connect. If you think you've got the answer and you're feeling as excited as I am.
Number two is aligning every goal and every dollar. If it doesn't serve my main objectives, it's a hard no. I am laser focused in 2025 done with the distractions done with the shiny objects done with the random spending. Number three, it's the 80, 20 rule, but we're going to make it fierce. I'm going to be dedicating 80 percent of my time to the things that actually grow my business.
So those high impact activities like speaking gigs, podcasting and working with my clients, the other stuff is going down to 20%, which is going to be admin, social media, and. Whatever else needs to be done in between. Um, another piece is I'm not really going to be offering a lot of free things anymore.
[00:20:00] People just don't show up or they show up, kick the tires and move on. So that's been an interesting part of my learning and somewhere where I probably spent about 80 percent of my time. Uh, the last, well, I probably stopped doing it the middle of 2024, but the year before that and the year before that so much time and energy.
And very little payouts. So that's the 80 20 I'm flipping that on its head. Um, number four, I'm going to be showing up in the right rooms. So intentionally stepping into spaces packed with brilliant executive women who either want to level up in their corporate job or plan their corporate escape route.
So if that's you, let's definitely connect in 2025. You know where to find me on LinkedIn. That's the easiest. I also always share my email address and contact details in the show notes show notes. And number five that I'm doing differently, taking more time to just breathe and enjoy the ride. Life is too short to run [00:21:00] on fumes every day or to feel like I'm spinning in circles.
So I'm really carving out time to reflect, recharge and celebrate those wins big and small. So we've covered those top reasons why new entrepreneurs stumble. I've shared my personal game plan for crushing 2025 and the moral of the story. If you're in corporate and you're making, starting to have those big dreams about getting into what's next, start building now.
So you can take that leap when you're truly ready and invest wisely, pivot when needed and show up where it counts. Transcribed Now, if you're a midlife corporate leader itching to leave, eventually be sure to tune in next week, we'll explore some practical strategies for juggling your nine to five and your side hustle.
So you can plan that smooth transition when you're ready to make that big, bold [00:22:00] move. Just final thoughts. I really hope this episode fired you up and maybe made you chuckle a little as you saw yourself in some of my stories. If it did, please leave a five star rating on Apple podcasts. I'm aiming for a hundred five star reviews in the next 30 days, and I know we can do it.
Are you ready to talk about your goals and how I can help you achieve them? I'm actually offering a 60 minute deep dive strategy session for just 197. I'll include the booking link in the show notes. And these sessions will fill up fast. They're a special rate for my podcast listeners, and I'd love to help you get on your path to success in 2025.
Um, and if you're serious about launching your dream business, the right way, let's absolutely chat. So until next time, stay fierce, stay focused and stay you. Let's turn that corporate daydream into your real life success story. [00:23:00] Take care.
