Second Act, First Steps with Tabatha Jones

Thinking about leaving a stable corporate role but not sure how to do it without blowing up your life? We sit down with Tabatha, the Corporate Escape Sherpa, to chart a grounded path to a fulfilling second act that honors your paycheck, your benefits, and your sanity. No beach hustle myths here—just a clear, tested plan for building a coaching or consulting business while you’re still employed.

We start with clarity, walking through Tabatha’s Freedom Framework: why you want change, what skills you’ll bring forward, who you’ll serve, and how you’ll reach and help them. You’ll hear how to separate work you’re merely good at from work that lights you up, and how to validate a real problem clients will pay to solve. We unpack confidence hurdles that stop many high-performing women—perfectionism, comparison, and the identity shift of leaving a big company—and reframe confidence as the byproduct of aligned action rather than a starting requirement.

Money and time are the real constraints, so we go deep on both. Learn how to audit money leaks, build a financial runway, and partner with a financial advisor to model timelines and reduce fear. Then reclaim one focused hour a day for needle-movers: client outreach, offer iteration, delivery, and networking outside your employer. We skip the logo rabbit holes and highlight the habits that compound: small experiments, consistent conversations, and gratitude practices that keep your attention on opportunities instead of obstacles.

If you’re midlife and wondering whether it’s “too late,” you’ll find encouragement and a practical blueprint to build before you bounce. Tabatha also shares her free Corporate Escape Starter Kit with actionable steps on finances, networking, and early client growth, plus where to connect with her on LinkedIn and Instagram. Ready to design work that fits your life instead of squeezing your life around work? Follow the show, share this conversation with a friend who’s plotting a second act, and leave a review with the one step you’ll take this week.

Transcript

Welcome And Guest Setup

SPEAKER_00 0:01

Hello there and welcome back to the next episode of Overcome Yourself the Podcast. I'm so excited to be back to you today with Tabitha. And Tabitha is um, if I remember correctly, if I'm putting it correctly, I'm probably not, but you can expand on it. A second act coach. And so if you have worked in corporate and you've been wondering, can I do this on my own? Can I have my own thing? Can I have my own business? But what would I even do? Tabitha is here to help us out with that. So please, before I butcher what you do, Tabitha, go ahead, take it away and let us know a little bit about who you are and who you help.

SPEAKER_01 0:41

Oh my gosh, you did such a great job, Nicole. I appreciate that. Thank

Defining The Corporate Escape Sherpa

SPEAKER_01 0:45

you. Uh so I call myself the Corporate Escape Sherpa, basically here to guide and support women who are ready to take that bold leap into their second act, which looks like building usually a coaching or consulting business on the side while still in their nine to five job. And I tell you, I've had people challenge me on this. They're like, oh gosh, I work this busy job, I don't have time. I'm here to tell you, I know it sounds hard, but it can be done. I did it myself. I worked in a corporate career for many years, leading corporate teams for more than 20 years for a giant telecom company. My teams were situated across four time zones. I had vendors in other countries and still managed to spend four years building my business before I left. Um, so you can imagine uh

Building A Side Business While Employed

SPEAKER_01 1:35

it can be hard, but it can be done. Um, I took the leap out at 50 and have been working in my business full-time since then. And initially I started helping women who are more in that midlife, wanting to grow their career space. Um, what I learned is a lot of women just want out. So I thought, well, let's let's focus there instead because it's absolutely a fun journey and so rewarding. Um, so that's absolutely what I do. Really help women take their expertise, take the gifts that they've been given, the gifts that they've honed over the years, and help them turn that into a purposeful, heart-led business that actually makes a great profit.

SPEAKER_00 2:17

That is amazing. That is so smart. Um, and can you tell me a little bit more about that? Um, I know I read the confidence code, and one of the things that they studied is how women are overly competent, um, but maybe they don't have the confidence. And so they need to work on that confidence piece. And I feel like that might play into um, you know, like what is your expertise, right? And so you're probably already an expert at your corporate job, whatever it is that you do. You have something that you've got way more than 10,000 hours of experience in, and so you're amazing at it. How does someone figure out what that is and how do they use it?

SPEAKER_01 2:59

You know, there's a couple of things. So confidence

The Freedom Framework: Why What Who How

SPEAKER_01 3:02

is key and it is critical. And we know as women, sometimes it ebbs and flows a little bit, right? We get ourselves stuck in that perfection paralysis. We get to a spot of, oh my God, I can't do it because look how well she's done it. I'm not like her. And we get into the trap of comparison. So that confidence is so important. Um, a couple of ways that I like to help women start getting positioned before they take the leap. And I'm gonna say before they take the leap many times, because why leave and have fears or concerns or worries about money and can you make it when you could stay and keep that paycheck, keep the benefits, get your finances in order, and start building. So, my framework, I call it my freedom framework. We start with your why, your what, your who, and your how in that exact order. So, your why is start digging into your skills and your areas of expertise. Uh, I'll use a client of mine, for example. She is a tech leader, also, somebody that I worked with in my former life, super smart at making quick decisions, finding ways to automate things, um, coaching her employees and helping them get prepared for what's next in their career. She also creates a lot of dashboards and digs into a lot of data and builds a lot of spreadsheets. When I had her work on her exercise of for her what. Sorry, let's back up. We start with our why. Oh gosh, I got all into the what really quickly. Starting with the why. Like, why is this change important to you? Why is it important? Why do you want to coach? Digging that information out takes a couple of hours of journaling sometimes and getting really clear. Then we move into that what. So, the what, what we did with this person, I'll call her Sue, um, is dug into all of her skills and then really separated which ones would she be excited and inspired to wake up every day and use? And which are the things that she does that she really doesn't want to do so much? They're probably fueling her to prepare to leave corporate. Once we're really clear on that, we can dive into then what problems do you like to solve? What solutions do you like to offer that other people can't? Because we all have different perspectives. We've all had different experiences. And getting really clear on that. Once we've got that, we move into the who and getting really confident in identifying your audience. Who do you want to work with? I'll tell you personally, I did a lot of experimenting with this before I left my corporate job. I would work with anyone who came my way. And we know, as entrepreneurs, you can't talk to everybody or nobody hears your message. So I would work with graduates, uh, recent high school graduates. I've worked with college students who were applying for internships, college students transitioning into the workforce, midlife women who had been laid off or who wanted to get better jobs or get better at the presenting themselves. And really started honing in. And what I found is I loved working with women who were just a few steps behind where I was a few years ago. And then being able to see, you know, this is the impact I can have on these women's lives. They're realizing it's never too

Choosing Skills And Ideal Clients

SPEAKER_01 6:20

late. They already have everything they need. We just need to package it up and get it out into the world, which is where the how comes in. How are we going to offer these services? And how will we find our ideal clients? How will we let them understand why we stand out and why we're the best at what we do? And it's a lot of fun. Um, it takes a bit of work and concentration, but it all leads to building the confidence it takes to know that you can do exactly what it is that you're being called to do in this world.

SPEAKER_00 6:52

That is that is awesome. That is amazing. Um, and I love the framework. It makes a lot of sense, all the steps that we take. Um now, when you talk about starting your own thing and you're working, that sounds like a lot of work. So I imagine that you break it down to just a few fundamentals of things that actually need to happen in our business that actually move the needle, right? Um, and so other than fulfillment, which is actually doing your thing, like showing up for the client and actually getting the thing, your magic done, what are some of the other things that um the audience can concentrate on on getting done right now while they're still working to help them get to a place where you know they can do this full time and they do have enough clients um to replace all their income and all their benefits and all the things that they have, like you mentioned, you know, like health insurance and all those things that don't automatically come when you work for yourself.

SPEAKER_01 8:00

Those are fun facts. Yeah, absolutely. So it is hard. It's hard to find that time. And something that I recommend is you sit down first off and really

Confidence, Comparison, And Identity Shifts

SPEAKER_01 8:10

assess where your time's going each day. You've got commute time, maybe you've got kids to get ready for work, or you've got to check in on your mom or whatever it is on top of your day job, right? Then where can you find one hour, whether it's in 15-minute increments or 30-minute increments, just one hour a day to focus on one task that will move you forward towards your building your business? One of the most important things that I think about, and you kind of alluded to it in your question, is financial. Women in leadership, we've worked for corporations that have a lot of money. We've learned to throw money at solutions and just get the right solution, get it done, move fast, and we're spending someone else's money. So it's amazing. When we get out on our own, everybody seems to be coming out of the woodwork, wanting to sell you something, telling you why their solution is the thing you need. And we will lean into that old habit if we're not careful and start throwing money at all kinds of things to see what sticks. It's important to have a financial runway. And the best way to do that is to sit down and assess your finances honestly. Uh, I always joke, I have a White House black market addiction, and it was really bad when I was in corporate. I would just go in and drop $700, $800 and just be like, oh, I look so pretty. And then I realized, you know, I'm sitting at home, people see me from my neck up. Like it's not really gonna matter if I have 17 pairs of pants in my closet. I'm probably not wearing any of them because I'm gonna go out in the backyard when I'm done working today. So, you know, that was one of my biggest cuts. Like there was money bleeding there. So, really looking for those revenue leaks, I like to call them, or money leaks, subscriptions you're paying for that you don't use, all those auto charges that sneak on every month. Um, are there bills that you can pay off? Some smaller maybe credit card bills. Maybe you've got a Macy's bill you use every now and then, pay it off, get get rid of the card, get rid of it, put it in the safe, do something, stop using it. Um, but look for things like that where you're just wasting money. I was recently working with a client and when we did this exercise, found out she had three gym memberships. Well, one membership was for a gym where she used to go to work, one was for one close

Time Blocking And One-Hour Focus

SPEAKER_01 10:22

to her house, and one, it just was such a low promotional rate, she just kept it. Like, okay, well, which one are you really using? Let's cancel at least one, maybe two, and start funneling that money either toward another bill to pay your debt down or into a savings account for your dream job, which is your new business. And just with that exercise, she was able to find about $1,200 a month that she was able to secure, which then you can pay down other debts. You can invest in coaching, people like me who can help you with the guidance that you need to help move your business and your dream forward. But that financial piece is such a big thing. Once you've got your spending and your revenue leaks aligned and you understand where those are at and have started plugging them, schedule a call with your financial advisor. If you've been in corporate for decades, you should have one. Uh, whether it's the company that administers your 401k or whatever that is, get on the phone with them and assess where you stand. What does it look like? How is it going to look if you were to start collecting that at 59 and a half versus 65? Are there any shortfalls or things that you need to think about? Because that's going to help you just get even more clarity and feel even more confident when

Financial Runway And Money Leaks

SPEAKER_01 11:35

it's time for you to leave. And there's no pressure to leave. You can build the business and maybe decide, you know what, I like doing both. I'm going to stay here for a bit longer while I take care of whatever it is. Or, you know, maybe I want to circle a date on my calendar and I'm going to plan to leave on that day. Whatever it is, when your money is in order, your finances are straight, you have a lot less fear. Um, I'll tell you full transparency. Even with all of that handled, even with a second income in my home, there were days when I found myself looking at LinkedIn jobs. Not because I needed a job, but because I felt so uncomfortable certain times, because it's such an identity shift and such a change from being in a company with 100,000 employees where I was talking to people all day, every day, and running around in a panic with two cell phones and two laptops to this, oh, things are so calm. I can go hop in the swimming pool or go play pickleball in the middle of the afternoon if I choose, or if I can work it around my clients. So there is a big change, and there's just so many things we can do to prepare for it financially, really mindset, start building your network outside of the company that you work for. Because one of the biggest surprises to people who have left, um, this also happens when you're laid off from a company, is you get on the outside and you realize you don't really have a lot of people to talk to anymore because the people you were talking to are busy at their day jobs still. It's not that they've forgotten about you, it's that their priorities are still completely inundated with all of their to-dos at work. So I'd say finances first, building that network before you take the leap, and just making sure that that strategy is really clean before you pull the trigger and make the leap.

SPEAKER_00 13:20

Love that. Um, I think it's so important taking inventory, right? Um, is like the beginning of everything that you mentioned. Take inventory of what you have, um, and then take inventory of what you need, right? And that's where I start with all my clients is taking inventory. Because if you don't know, like same thing with food or you know, with like even if you're gonna clean your house, the first thing you gotta do is like, okay, what do I have to organize? I need to know, you know, what is like the the size of the container that I need for holding these things. Because if you don't know, then how can you decide? Um, and so I think that makes a lot of sense. Um, and that's so smart. So um, can one of my big things is gratitude? Can you talk to me a little bit about what role gratitude plays in this whole process?

SPEAKER_01 14:17

Oh my gosh, with you, gratitude is so important.

Networking Beyond Your Company

SPEAKER_01 14:20

So just waking up every day and thinking about the things you're grateful for. And sometimes you're grateful for the future that maybe hasn't happened yet. I know that sounds a little bit woo. I always say I'm not woo-woo, but I am a little woo. I dip my toe in. But you know, grateful for the clients whose lives I get to change. Uh, grateful for the clients I haven't even spoken to yet. Um, I have a friend who taught me, she calls it her PP meditation, her PP gratitude meditation. She's like, every morning when I get out of bed, the first thing you got to do is run to the restroom. I'm like, yeah, she's like, and as I walk, I put my feet on the ground and I say, thank you, God, for two feet that work. And then she's like, and I stand up. And I'm like, thank you, God, for having a body that can support, can support me in the things that I do. And so she says, even just walking to the bathroom, um, getting that gratitude out. And I've done it, and you feel so much better than you do when you're kind of grumbly first waking up in the morning thinking, oh, what's on my list? What do I gotta do? You're just gonna happen think about the good things, and that energy sticks with you all day. So it's so important.

SPEAKER_00 15:22

Yes, and for the days when we can't walk to the restroom, because I've been there where I literally could not walk to the bathroom in the morning. Um focusing on being grateful for you know, having a tool, maybe we have a wheelchair or being able to crawl. Like the floor is clean enough that you can crawl to the bathroom because that's what I had to do. Um, and even in those moments,

Gratitude Practices That Fuel Momentum

SPEAKER_00 15:45

being able to find anything, anything at all, that you could be grateful for because um I know how how tough it can be. Get out of that bed and then poop, oh, I'm on the floor, my legs are not working today. Let's go to the bathroom. And so it's a whole process, it is. Um, and so yeah, even the small thing, and it's not woo, it is very scientific. I know it sounds very woo-woo, but like there is science that it helps in our healing, um, it can help reduce blood pressure. And when I'm talking about practicing gratitude, um, and so like this is bona fide science. And I swear by practicing what you said, um, practicing gratitude for the things in the future, like for future casting, for um bringing it to you. It's a it's an important part of manifestation. Um, and it's kind of almost like a red car syndrome. Because like now your brain is on the lookout for that, right? And so it's like, oh, let's make this happen. And you get to see new opportunities and new things you might not have um otherwise. So I love that. Thank you for bringing that up. Of course.

SPEAKER_01 16:54

Yeah, I think so many of us overlook it, or you know, we have a little bit of a hard time or a stumble, and that really can get us down. Gratitude just moves you back to that more positive state of realization that maybe there's a lesson in it, right? Maybe there's a lesson in the hard thing you're going through. And maybe you don't see it right now, but even being grateful for that hard thing. Um, I went through that a little bit uh toward the end of last year. And at the time I was working with women who still midlife, but wanted to go after that promotion, advance their careers, or find new jobs. And I just was feeling like a little bit burnt out, but I thought, oh, what's going on? And then I sat there, I'm like, what is the lesson I'm being taught right now? What's what am I not seeing? And the lesson I was being taught is that I hadn't really opened up my eyes or my mind to the fact that I was having a lot of fun helping women make that corporate escape plan. And I wasn't really thinking about it from a business perspective. I was thinking, oh, this is just something I do for fun when I'm talking to my friends. And I was like, oh, wait a minute, this is the lesson. And I'm like, oh my gosh, I'm so grateful

Lessons, Pivots, And Finding Alignment

SPEAKER_01 18:05

that I finally got that message and realized what I needed to be doing. I actually gave myself a full 30 days to just sit down and think. And a lot of that was gratitude, grateful for the things that I got from my corporate career, grateful for my journey, even though there have been some hard times. I've definitely stubbed my toe. I've probably pissed a few people off here and there. Um, but absolutely, like, you know, every single thing has been a lesson and it's been a step forward.

SPEAKER_00 18:31

Yeah, and we have to be willing to make some mistakes, because if not, that's like asking for perfection, and that's like impossible. So, like, why would we even set up, you know, set ourselves up for that? And so the fact that you're courageous enough to make mistakes and to keep going after you do. I know I've been there too. Um, and so I commend you for that. So I think that's amazing. Thank you. Yes, you're very welcome. Um, so when we were talking earlier, you had mentioned to me that you have a very special gift for the audience. And so I would love if you could tell us more about that gift because it's it's a part of your program. So give us a little glimpse of what that looks like.

SPEAKER_01 19:20

Absolutely. So it is my corporate escape starter kit, and it has those first initial steps that you need to be thinking about as you're planning your corporate escape. Um, I call it corporate escape for fun,

The Corporate Escape Starter Kit

SPEAKER_01 19:34

because why not? Um, but it's things that you really need to be thinking about. There are a lot of coaches, I'm sure you've seen them and met them yourself, Nicole, that are out there that are like, you can make a million dollars a year sitting on a beach and working two hours a day, which you and I both know where that's going. Um maybe somebody had a miracle one day, I don't know. But you know, for most of us, there's definitely a learning curve. Um, so there are Some actionable strategies, including the financial piece that we talked about and building your network in that starter kit. And it's absolutely free. One of the reasons I created it, and I actually had this conversation with another coach who does some similar work, but her audience is a little bit younger than mine. One of the things she said is, you know, I tell my clients, you know, just leave your job and start your business. It'll be fine. If it doesn't work out, you can always go back to a corporate job. And I kind of hesitated a minute and then I said what I needed to, because that's how I operate. I said, well, that's great in your 30s. If you're 30, 35, sure, you can take a leave, go do your thing. And if it doesn't work, come right on back to a different type of job or whatever it is that you want to do. When you're in your 50s, it's a lot more difficult. When you're in your 50s, the hiring process, the, you know, just the uh salaries that we've earned after being in corporate for, you know, three decades-ish. Um, I say ish there. Um, you know, just the salaries we've learned and the things we expect, it's not as easy to get back to that salary. It's not as easy to get back to the level

Build Before You Bounce Philosophy

SPEAKER_01 21:12

of job that you left at. And so it can be really stressful, which is why it's so important. And my message, I'll keep saying it and let people tell me I'm wrong. I don't care. I know I'm right. That it is important to build before you bounce. So build it, get it going. You don't need to fully replace your corporate income necessarily once you do your financial work, but you absolutely need to be at a place where you feel secure enough to leave and take that step because we want this to be there for longevity. It's you may shift, you may pivot as you go, but we really want to set you up for longevity.

SPEAKER_00 21:48

Yeah, absolutely. And if you're focusing on the fundamentals, you you don't need 40 hours to do all the work for your business, right? Um, you can focus weekends and then after work, and you can have focused time where you're doing you know your business stuff. And so it's not like you're gonna be working, you don't necessarily have to be working two full-time jobs. If you are very intentional, like you're saying about taking inventory, what are the things that need to be done? And you focus on activities that are actually gonna, you know, do something in a business, not spend 45 minutes, you know, uh in Canva, like trying to choose a font. I've been there.

SPEAKER_01 22:31

Canva. Canva's the worst.

SPEAKER_00 22:34

You know, like going to the room like, oh my god, it's been five hours. Like it doesn't have to be like

Focus On Fundamentals Over Busywork

SPEAKER_00 22:40

that.

SPEAKER_01 22:41

Oh, you cut off after five hours. Good job.

SPEAKER_00 22:44

Right, exactly. But then having having if you if you have your job, you have your salary, well, you have the option of maybe paying someone to help you with those nitty-gritty details. Where if you just jump ship and you're like, peace, I'm out. Well, you might not have the, you know, like you're it's the hierarchy of needs, right? Like you're worried about filling your fridge before you're worried about your logo. And so now you're in a position where it's just it's not fun. And um, I think it's so important that the process be fun, that we actually get to enjoy what we're doing. Um, because then if not, what's the point? Like if you're just white knuckling in and like you're scared to get up every day, like what's you know, like what are we doing here? Like, this is supposed to be about fun and freedom and doing it the right way. And so I commend you. This is absolutely incredible. Um, and I think it's so important what you do and how you're helping women um, you know, really take control of what they do and how they do it. And so, yeah, that's amazing. I appreciate it. You are very welcome. Thank you. Yes, of course. Now, can you let the audience know how they can stay in touch with you on social media?

SPEAKER_01 23:56

Absolutely. Um, the easiest way is on LinkedIn. I seem to be there more than anywhere. Um, I'm Tabitha Jones, Tabitha with all A's. I'm also on Instagram at coach underscore Tabitha. And um

Where To Connect With Tabitha

SPEAKER_01 24:08

would love for you to connect and definitely let me know what questions you have. I love answering questions and supporting women wherever they're at in this journey.

SPEAKER_00 24:16

Yay, that's amazing. Thank you so much. Um, and as we're signing off here, um, can you share one of your big tips? Like what's a good tip that gives

Final Tip And Closing

SPEAKER_00 24:26

like a really big transformation for the audience.

SPEAKER_01 24:30

Wow, so many tips are in my head right now. Uh, you know, honestly, I'm just gonna say, get out of your own way. Stop overthinking it, stop judging yourself, stop worrying about what everyone else thinks, because I'll tell you they won't all understand it. Stop worrying about it and just do it. It's not too late. And this next chapter of our lives should be the absolute best chapter of our lives.

SPEAKER_00 24:54

Love it. And um, I proved mathematically in my book that not everybody's gonna get it. There's I'm I mean, I even made a whole chart in Canva and everything. So that is a hundred percent true. Um, that you know, it's just the numbers statistically, not everybody's gonna be on board, but you know what? Gotta make it happen anyway. So I love that.

SPEAKER_01 25:16

Thank you.

SPEAKER_00 25:17

Thank you. Thank you so much, Tabata. This has been awesome. Um, loved having you on, and we will catch you guys next time on the next episode of Overcome Yourself the Podcast. Bye. Bye.