There are a lot of strong feelings out there about AI, machine learning, and the future of the workplace. It seems like everyone is or will be experiencing major changes in their roles. But, do you know how to reinvent yourself?
Whether you’ve been laid off or personally decided to change careers, understanding the core aspects of reinvention can be helpful. In this episode, you will learn more about why reinvention can be necessary and how to move through any fear that might show up.
Our host and CEO Porschia, alongside our guest, Tracy Oswald, will share their insight on the best ways to navigate your reinvention and how to stay ahead of where things are going.
Tracy Oswald is the Founder and CEO of Women Who Lead. As certified coach and former corporate VP, she is committed to empowering women in the workplace. Women Who Lead helps high achieving women with leadership development, coaching, and community.
What you’ll learn:
- Why reinvention is important in your career
- 3 ways executives and professionals can start reinventing themselves right now
- Tips on how you can reinvent yourself even if you are apprehensive or scared of starting over
- The factors that influence how long your reinvention might take
As a thank you for listening to this episode of the Career 101 Podcast, we are sharing our FREE master class – Career 911: Solving the Top 5 Challenges Executives and Professionals Have! It’s a training based on solving the common problems our clients have experienced to reach their goals. You can get access to the master class here!
Episode Transcript
[00:00:00]
Hello, I’m Portia Parker Griffin, and I want to welcome you to the Career 101 Podcast, a place for ambitious professionals and seasoned executives who want an edge in their career. We’re talking about all of the things you were never taught or told when it comes to career growth, development, and change.
Now let’s get into it.
Porschia: Today, we are talking about reinvention 101, how to reinvent yourself with Tracy Oswald. Tracy Oswald, a visionary leader with a proven track record in driving business transformation is the founder and CEO of Women Who Lead. This innovative company and community focuses on revolutionizing the way women work, live, Grow and lead with over two decades of experience leading successful teams and programs.[00:01:00]
Tracy is acutely aware of the unique challenges that high achieving women face. Her mission is to help women advance in their careers without sacrificing their physical and mental well being. As a certified coach, keynote speaker, and corporate former corporate VP, Tracy has spoken across the country and hosted a business podcast for USA Today.
She has delivered keynote presentations and workshops for organizations such as Gong, the Texas Business Women’s Association, the Project Management Institute, USA Today Network, Florida Press Association, Dress for Success, and Innovation Media Enterprises. Tracy holds a certification as a certified professional coach from the Institute for Professional Excellence in Coaching and has completed various professional development courses through Dale Carnegie Training and LinkedIn Learning.
Hi, Tracy. [00:02:00] How are you today?
Tracy: Wonderful. So, so excited to be here, Portia. Well, great.
Porschia: We are excited to have you with us to discuss Reinvention 101, How to Reinvent Yourself. But first we want to know a little bit more about you. So tell me about seven year old Tracy.
Tracy: It’s so funny that this is a question because just recently I was going through some old pictures from when my brothers and sisters were really young.
So we’re talking like in the late 70s and there was this picture of myself. I remember. I was in second grade, so I had just gotten, like, two new big teeth, that looked so out of place in my mouth, and the picture was me outside. I had, like, a dandelion in my hand, really long hair, it was white all over the place, and I had this sort of, like, sly smile on my face, and my eyes [00:03:00] were super wise, way too wise for, like, a seven year old, and yeah.
I think back to that version of me, and
I think kids, especially before we get all of the programming about how things are hard and how life is scary and all of that, we have an inner knowing that life is magical, things happen that you can’t explain, and what was the picture, that’s what I saw in that picture, and that was the essence of who I was.
I had. Was much wiser at seven that I probably am. Yeah,
Porschia: I loved how you described that look. And I think you’re right. As children, there’s this sense of innocence. But I think also the ability to dream big and believe that anything is possible. That should really be nurtured and that most of us lose, I [00:04:00] think, along the way.
Sure. And we know that as coaches, right? We end up helping clients to discover some of those things again. But when you think back to seven year old Tracy, what did she want to be when she
Tracy: grew up? So I thought I was going to be a professional dinosaur person. I was obsessed with dinosaurs. I would write papers about dinosaurs that no one asked me to write.
And, memorize all of the names and, look them up in the encyclopedias at that time. That’s what we had. All right. Awesome. Huge reader. I wanted to know all of the things and life was super exciting. I would say it wasn’t very much an introvert when it comes to live a lot of my life in my head and I did back then.
There was a kindness that I don’t believe I lost. I understood [00:05:00] about love and community and wanting to be connected in ways that were more meaningful than just, small talk on the playground, really wanting to understand people. And so I spent a lot of time with adults because They could, we could talk to me that way.
So, when I, you asked me to reflect back on, on her I would think my goal is. Spend the rest of my life to getting to who
Porschia: that was. I love that. So what was your first job, Tracy?
Tracy: Oh my gosh, I was a newspaper girl. I was in sixth grade and I had a newspaper route and I, after school I would.
Drive to the bank, to the newspaper place where I got all my papers, do my amount collected on Tuesdays and Sundays, and I did it for a couple of years but it, it, I’ve always had this sort [00:06:00] of
industriousness where I wanted to be mixing it up or be doing to learn, that’s very much how I learn is by actually doing the thing. And it taught me so much about. People and about consistency and about, when it’s, 95 degrees and I don’t want to do it or 32 degrees and I don’t want to do it, but people are waiting for the paper to do it.
So, it’s a lot of fun, but also.
Porschia: Yeah, it’s, I was just thinking to, to your point, even before you said, the 95 degrees and that mental fortitude to keep going, I was thinking you had to be very disciplined with that newspaper route, right? Because there’s no one technically over your shoulder the whole time as you’re doing it, right?
So you, that tells me a lot about you and that you were very disciplined growing up. So great. Well, tell us about some highlights or pivotal moments in your career before. Before you started your business, Tracy, [00:07:00]
Tracy: so remember I was in sales for a lot of my career and being in a sales office.
It’s very different corporate is very different than being in the corporate office, then I remember when I made that transition from the sales office to the corporate office when I moved from New York to Texas, about 10 years ago I was late to the game inside of corporate and did was not prepared for all political.
Things were, and it was shocking to me because in sales is sales, you go out, you meet your client then grow and you talk to your, sales teams and you help your coach your people. And there’s not a lot of that kind of forth politics where, you have to talk to this one to get to that one.
And who’s trying, it was a shock to me, later in my life. To have to learn to navigate. So that was a big one. [00:08:00] I think another one was I was in my late thirties and I was in a sales leadership position. And up until then, I always thought that there was going to come a time where I felt like, so I always thought there was the people that in charge that were in charge totally knew what they were doing.
Like I thought. They had it all together. They were super confident. They had all the answers. And it was just, I was in a meeting and I can’t even remember what it was about. And we’ll just have this realization that. Like literally no one knows what they’re doing. Like no one knows what they’re doing.
Everyone’s making it up and doing the best they can. And there’s no one right answer to anything. And it was a huge understanding for me at that time. Because I was, I was brought up at a time where you look to authority to tell you how to do things. [00:09:00] And I was shocked. I’m really disappointed that I’ve been listening to so many people who…
No better idea than I might have had. So that’s a really big learning. Yeah. Yeah.
Porschia: I, wow. So a lot there that I can definitely echo and I’ve seen with our clients and even in my own career. I like how you touched on Really starting to see the political side of some offices and some careers in different settings.
That is something that comes up with a lot of our clients and depending on their background. It is a shock like you mentioned. And then I also love your point about how. You realized everyone didn’t necessarily have it figured all out. I had a similar realization and I have a sales background to Tracy.
And when I got into sales and I started selling to CEOs there were CFOs, but higher level prospects in companies. And I realized. [00:10:00] These people aren’t any smarter than I am. These people aren’t any smarter than some of the people that we work with. And it really shifted things in my mindset as well.
So it sounds like you might’ve had a similar. Oh, yes. It
Tracy: was, it was shocking. I was disappointed, but then also it opened up so many doors for me. Like if they can have this kind of role and do this kind of thing. Do anything, right? So, yeah.
Porschia: Absolutely. So, what has been your biggest career challenge so far before you started your
Tracy: business?
So,
I think
there was a time when we were, it was at the Pony and it was a, started as a startup and it was in its adolescent phase. And We were super successful and I was in a leadership role there leading a team and huge big media company [00:11:00] came in and bought us and, was part of working through the transition of how do we bring together this.
Small company in this company, while I was doing that, I saw the writing on the wall when it came to the team that I ran and the similar team on the larger company, they just had so much more. Technology and people and bandwidth. And so I was like that, they’re not going to need two leaders.
I had to make a decision. Do I want to decide to go for that role? Or is this an opportunity maybe for me to pivot and do something entirely different? A reinvention inside company. And so I decided that I wanted to because I have a very high risk tolerance and I like to take chances on things and I was [00:12:00] at a point in my maturity and confidence in career where I thought, I’m gonna, I’m gonna really go for something.
And it might pan out and it might not, but I pitched a really big idea to the CEO at the time to lead a whole different part of the business, client facing, going out into, different cities in the country and educating them and, to get a whole plan and, but I had nothing to lose.
And she said yes. And that was a, that was like a big clue for me that the more you show up with that kind of energy and say, well, what’s possible, like, what All things are equal, and I could do this, or I could do something totally different. Let’s try this different other thing.
Because the worst that could happen is, either they say no, or I try and fail, and I can then just try the next thing. So I [00:13:00] think that, that was a moment where I had to, it was challenging in the sense that, it was risking all of the safety and, Political capital and cultural capital that I had built inside of this team to totally strike out in a completely different direction.
Porschia: Yeah, the reinvention. Yes. What made you decide to start your business, Tracy? So I was,
Tracy: I was leading a talent development team, and I had an idea that I wanted to start a leadership coaching program inside of the talent development team for, directors and vice presidents, because there was really no support at that level.
And I put a proposal together to my boss and said, Hey, if you. Need for me to get certified, I can start this, we can do this for our company. [00:14:00] And here’s all the downstream benefits, the whole cost analysis, all of it. When they said, yes, it was great. And it was my first day, that the coach training took place over nine months.
And there were three times we had to go to the. Physical location for like a weekend and everything else was virtual on my 1st day, like, within the 1st hour of this instructor talking and doing the orientation and talking about what this was. I was like. Oh, no, I want to do this. For me, like, I want to be a coach in the business and actually do this, right?
And it felt weird, right? Because I was there on my company’s dime and I have this big life realization. And so I did something that was scary at the time and I did it for my company, of course, but I also started my own business while I was working full time as a corporate executive. And that was also [00:15:00] very scary and risky.
Yeah.
Porschia: Well, it’s well, one we went through the same coach training organization I’ll say. And I, yes. And I had a very powerful experience at what then we called mod one that first and as well. So I can definitely attest to that. But it’s also great that you found the courage to start that business while you were still working.
That is another whole thing that could be a different podcast episode, Tracy, that we might have to bring you back for on, another, at another time. But yeah it’s great that you had that knowing right from the coach certification training that, Hey, I want to start my own business.
Tracy: But can I, in all in full transparency, because I don’t want everyone to think, Oh, this was just so easy.
I stressed, like I built my own website, I think it was on Wix, I didn’t set it live. I was [00:16:00] stressing so much that the minute I set it live, like your mind plays games, the minute I set up live, like. Somehow, everyone in my company was going to find out, right? It’s logical. That’s not, that didn’t happen, but you, there’s this guilt that I had because of this inherited sense of having to be loyal to the company, right?
Disproportionately so. More loyal to the company than to myself, which that’s a whole nother topic that I delayed for days and days hitting that go live button. And you don’t happen when I hit the go live button, nothing, no one said anything until I brought it to their attention because I felt like, wow, if they find out when I don’t call them.
Like, I felt like I, so I, talked to HR and all of that, but there I had so much [00:17:00] drama and so much fear. And so if anyone out there is going through that’s perfectly normal. You are not alone. What happens?
Porschia: Agreed. So that’s a great segue, Tracy. Many of our clients who are executives or professionals get to a point where they decide that they want to reinvent themselves.
It could be in regards to their career or their business. Why do you think reinvention is important?
Tracy: So I think because this is 2023 and because technology is moving so quickly, I think it’s even more relevant than it’s ever been. But even if that wasn’t the case, Portia, but I would look like if we have time, I would love to get into what the future of work might look like because of how quickly technology is moving to biggest like life lessons that I ever learned.
And I said one of them already, everything is made up. We have made [00:18:00] up everything right from what things mean to me I like to describe, as we get older, we miss playing with. Kids in the playground. So we invent businesses complex systems as a way to playing with each other. Maybe with higher stakes and on different levels.
We’ve made all of this up everything we have everything we see. And everything’s always changing. That’s my rule number two. And because everything’s made up and everything’s always changing, I think reinvention at its core is simply trying to stay at priority or a little ahead of where everything is going.
And if in my opinion, if you are not To speed with where things are going, especially now with technology and how much it’s going to It’s going to be [00:19:00] really hard for you. So I think reinvention is simply Making a decision, redeciding every day about how you’re going to grow, and it can be in small and fun ways.
It doesn’t have to be this big, heavy, complex plan you put into place, but it can be going back to seven year old one of the things, give a, I give a couple of different talks for companies and one is about the future of work, And so many people, when I give that talk, it’s a challenge, they bring up this, I don’t have time to keep up.
Like, I can’t catch up with all of my work and catch up with how fast the world is moving. And I offer, like, you, you don’t have to catch up. You just have to remember how to play catch. You remember how to be a kid. You just don’t remember where the playgrounds are and the playgrounds are now where technology is taking us and we [00:20:00] have to bridge that gap between how we use that to deepen connection to each other.
Porschia: So from your experience, what are the main aspects involved with reinventing yourself? Yeah. So .
Tracy: I think with reinvention, whether it’s by, I think it’s different, whether it’s by someone else’s decision or your own decision.
So I’m going to, I’m going to talk about this through the [00:21:00] lens of what happened for me. That’s cool. Because what happened for me, right? It’s like, was this corporate executive coaching side, there was a big company that I worked for and I got laid off. And so we laid off in last September. And so that was defining talk about defining moments in your life.
First time I ever got laid off in my whole career. And I decided, okay, this is my moment. I have to reinvent myself. It was out of necessity. I don’t say it was necessarily out of bravery. I think there are three specific things that happen through a reinvention, whether you decide or whether. It’s thrust.
You find yourself in this place where you’ve got yourself. One is there are you are going to experience lots of uncomfortable feelings when you’re going to want to stop doing whatever kind of growth you’re doing [00:22:00] because you don’t want to feel those feelings. And when I say you, I mean me. In, in, in getting laid off and not having that support system, not having all of those people anymore and going full force into, my coaching business I had more time to myself than I knew what to do with.
And when you are faced with time to yourself. All the feelings you’ve been stuffing down because you’ve been so busy come up and you have a decision to make is either you’re going to ace those feelings and really feel them and understand them, or you’re going to make yourself busy doing productivity things to avoid feeling those feelings.
So I think number one is being very aware, but is can feel really bad. That’s okay. Can feel really bad. The second thing is
when it [00:23:00] comes to reinvention, think about it like you’re this mad scientist and you’re simply experimenting with things. Because what I did a little bit and what I’ve, in talking to so many women who are going through the same thing or want to reinvent themselves they think they have to pick a thing and stick with the thing because that’s going to be their new thing.
And we’re going to give them themselves a chance to experiment with things they never would have tried in the past. So think like a scientist, experiment, see what works, see what ingredients you might need to add a little here, take a little there, try a new experiment if that doesn’t work, and approach it not like, this is the only way I can go, approach it like, how many different ways could I go?
Or how can that be? How can that be interesting? How can that be [00:24:00] exciting? It was, if I was, incredible scientists trying to figure out living a life through experimentation. And number three, having, when it comes to reinvention, especially if you are, this isn’t categorically true. I’m a Gen X.
I’m, I consider myself Gen X, right? I’m on the high end of Gen X. So I’m closer to Boomer than I am to millennials. When you have been doing something for a long time in a career and you have this idea that you want to reinvent yourself and what do you go for it there is there can be and there really is this sense of wait I invested so much of my life doing this thing but am I Does it mean that was all for nothing?
Like, how do I start over at this point in my life? Where, wherever that point is. And we’re so invested in the [00:25:00] thing they do for their career that, they’ve talked themselves into the fact that it’s too late, whatever that means. I think if you’re still alive, it’s not too late. Right. They talk themselves into the fact that I put so much time for, maybe I got, I have three degrees in this thing.
I can’t start a new thing because then I would be a beginner again. And there’s nothing like something that your ego needs worse than being a beginner again especially when it knows you’re really good at this other thing to do that. That’s a big thing to be on the lookout for is sense of holding on way past the expiration date on.
On the thing, even though you have so many skills and so many contacts and all of that in this one bucket, but allowing yourself to be a beginner in something new and risky and interesting.
Porschia: I love those Tracy. I love those.[00:26:00] So to recap for the listeners, number one was, being aware of the uncomfortable feelings that you might have.
Number two was thinking like a scientist. And not being afraid to experiment and three was being a beginner, and not necessarily holding on to the past. And those are really great. It leads me again to my next question. So I want to get your thoughts on this. I’ve had some clients tell me that they are apprehensive about reinventing themselves because they are scared to start over.
Or start at the bottom. What would be your response to someone who feels that way?
Tracy: So
the core of my belief system and how I coach my clients is that life is always going to be 50 50 average 50% of the time you’re going to feel good and 50% of the time it’s going to suck. [00:27:00] No amount of coaching or therapy is ever going to really change that percentage. Sometimes it’s like six to 40 or something like that, but you’re always going to have happiness about things.
You’re always going to have fear about things. So my question to you is, would you, what would you rather fear? Would you rather fear making the change, or would you rather fear staying where you are and hearing what could I have become if I allowed myself to make the change? No, that fear is going to be present.
No matter what, because the reason that they are thinking about reinventing themselves, is there some measure of fear about, is this sustainable? Do I want to keep doing this? I’m afraid that I, I don’t put this mold anymore. There’s fear, there’s apprehension, and there is a sense of unhappiness.
But they already have, so you’re gonna have it no matter what, would you rather have it [00:28:00] doing something that is new and exciting and that you essentially love to do, or would you rather have it being the same as you are, fearing them? Fearing reinvention and also fearing the fact that maybe you’re in a role that is not going to be in existence in a couple of years because of whatever technology or the company is going to lay off.
So, so you’ve got to pick your fear.
Porschia: So how long do you think it would take for an executive or professional to reinvent themselves?
Tracy: I think that’s so subjective to the person and where they are and where they want to go. So I can’t answer that, but what I can say is when it comes to knowing what the right steps are, a lot of times when, when you get to the executive level or management level, [00:29:00] There is. You’re intelligent, you’re smart, right?
And you wanna make the right moves. And so what I tend to see so many people, especially high achieving women do, is they wanna learn their way, right? They wanna book, learn how to reinvent themselves, and they read all the books, and they listen to podcasts, and they make their lists and their plans.
People wanna say, that is not going to help you at all, because the minute you step into the unknown, into the space of new invention, All bets are off, old rules don’t apply, and things are going to happen that you never have imagined happening. So all of you, you’re just delaying doing the thing by learning about how to do the thing.
So, so that’s the piece of advice I would want to give people is. Do it a lot sooner than you think you’re ready for because you can study this and learn this and make this [00:30:00] incredible plan and you take one step forward and you’re like, wow, this is nothing like I planned for and now so you have to decide.
Am I going to lean on my ways of being as a corporate executive and plan risk assessment? Or am I going to start to think like a scientist and step into the unknown and start experimenting? You’re just delaying what, where you want to go. So, so I know that’s not the question you asked, but that’s the answer that I have.
Porschia: Yeah, no, I think it’s a great answer. And it definitely is subjective. And I’ve asked you some questions today that people ask me. I mean, I know you’re another coach, and I want to get your perspective on it. But you’re right. I generally tell people that, a reinvention, or sometimes people are thinking about that in terms of a career change.
A lot of that is subjective. And it’s going to depend on you, your industry, your geographical location, [00:31:00] your transferable skills, how it Far away is this transition or reinvention from what you’ve done before. So loved getting your feedback on that. Tell us more about your company, women who lead.
Tracy: Yeah. So, I transitioned my coaching practice and I’ve always focused on high achieving women. That’s just where I love to play. And I want to help women, not just with work because but a lot of coaching about the stuff that happens at work. The older I get, Portia, the more I understand that when you plan for career success, I think it’s a, it’s like this shiny object that they put in front of you to say, plan your career success, but all the while your life success is not.
Being cared for so I thought the paradigm [00:32:00] entirely and folk women plan for life success. And, there’s not this work life balance binary I don’t buy into it, I think. I think our lives are like an orchestra, right? And in an orchestra, when an orchestra is playing a symphony, sometimes the French horn has the lead, and then it goes over to the flute, and then the cello comes in and plays for a few bars, and we hear all of these different instruments have their moment.
It blends together seamlessly, and I think life is like that. Sometimes you’re gonna over index out because you have to. Sometimes you have stuff going on at home where that has to be the focus. And trying to achieve balance is just a recipe for disaster because balance only exists in the moment in time, in perfect conditions, without anything ever changing.
So, because everything’s changing, because conditions are imperfect I think that… [00:33:00] The focus on how can I craft a life and live in a way that supports me was the human first who can give to these different areas of my life and all the
Porschia: relationships. I love that. So we’ll be providing a link to your website and other social channels in our show notes so people can find you online, but what is the best way for someone to get in touch with you?
Tracy: Don’t want to just get in touch with me to talk you can, there’s two ways. You can email me at Tracy at women who lead. io, or you can find me on LinkedIn and just DM me because that’s where I hang out, right? That’s where I’ve got. Most of my videos and lives and posts and all of that. But I have been thinking about TikTok.
I don’t know what are your thoughts? , you guys on TikTok?
Porschia: I’m not on TikTok, but I’ve heard great things about it. I think for me, I’m gonna [00:34:00] stay more focused on the podcast, but I think it’s a, it’s
Tracy: a great outlet. Yeah. I’ve been thinking about yes, LinkedIn. Or LinkedIn or email. Be happy to talk with you.
Porschia: Great. So, Tracy, I want to ask you our last question that we like to ask all of our guests. How do you think executives or professionals can get a positive edge in their career?
Tracy: I think to become more successful, you need to number one, become a lot more vulnerable with yourself, with your people, with your feelings, the truth with what’s happening in your business, in your life.
You need to be a lot more transparent with your people. And when I say your people, I don’t only mean at work. I mean, at home, let people in, let people understand what’s happening for you and give messages to, if you have a team at work call them the truth more than you’re comfortable with. [00:35:00] And number three, always staying ahead of where things are going.
From a cultural, societal, and technological perspective, be, always be ahead of the curve in your understanding and knowledge.
Porschia: Tracy, you’ve shared a lot of tips with us today. I’m sure that our listeners can use it to be more confident in their careers and with their reinvention. We appreciate you being with us.
Thanks so much, Portia.
This episode was brought to you by the Brave Bird Career Alliance, the go to membership designed for seasoned executives and ambitious professionals with everything you need for career planning, strategy, training, and [00:36:00] support. Thank you again for listening to the Career 101 podcast. I hope you have at least one key takeaway that you can use in your own career.
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