Speaker 1: 0:01

People come to me regularly because they're like I just I don't know how to do this and I need someone to help me figure out how to do it. And inevitably in the very first session, the issue isn't really that they don't know how to do it, it's a fear. Whatever that fear is a fear of failure. It's a you know, it comes off as I don't have enough time, and it's like okay, is that? When you dig down, like, is that really what it is Right? Or time, and was like okay, is that? When you dig down, like, is that really what it is right? Or what's really underneath that?

Speaker 2: 0:28

Hi, I'm Becky. Welcome to Short Story Long. In this podcast, we discuss ways you can integrate who you are into how you lead. Sometimes we look back and have a hard time reconciling who we were then with who we are now. Over time, things change and sometimes we don't end up where we want to be. Listening to that inner voice that says I'm not on the right path is important. Today's guest shares an honest exploration of what happens when you decide to break free from the status quo and reach for what inspires you. She was willing to reimagine her path, which led her to a more authentic, fulfilling life.

Speaker 2: 1:11

My guest today is Toby Adamson. She's a founder, business owner and software leader, turned entrepreneur coach. With over 20 years of experience in high growth software companies. Toby has played a pivotal role in driving exponential growth, launching innovative products and facilitating mergers and acquisitions through strategic product positioning. Her career has been defined by a passion for invention, problem-solving and helping businesses scale. Now, as an entrepreneur coach, toby is dedicated to helping individuals uncover their best path, enhance their emotional intelligence and develop the skills needed to thrive in leadership or business. Her career coaching philosophy is rooted in the belief that applying fresh perspectives and innovative thinking to challenges leads to transformative solutions. Working with entrepreneurs, toby empowers others to break through barriers, reimagine possibilities and build a fulfilling future. Hi Toby, welcome to the podcast. I'm excited to hear about one of the inflection points in your life. You know that's what we're talking about today and I'm eager to get started and have our conversation.

Speaker 1: 2:23

Hi, Becky, I'm happy to be here too. Look forward to it so.

Speaker 2: 2:28

I know that there were some pretty significant life changes that were happening for you before this inflection point happened. So when you think about this big change that was transformational for you, what was your life before this decision occurred?

Speaker 1: 2:47

My life was just normal. I would get my kids ready Actually, I would wake up before they woke up. I'd go running, I'd get my kids ready, I'd get them to school, I'd go to work, I'd come home, get them from the bus, homework, typical suburban working mom life, and it was just sort of on remote control.

Speaker 2: 3:07

So, based on the fact that we're talking about inflection points, I'm guessing something changed for you. So what was the prompt that pushed you into a new phase?

Speaker 1: 3:16

I would say, if I were to go back, I was living a life that was expected of me but not the life that I wanted to create for myself. And there was a moment where I started reconnecting with my friends from college, from high school, from before high school, and you sort of realize who you were versus who you are, and I realized I wasn't living what I wanted to be. And so I started to look at my life almost from the outside in, if you were to imagine and started realizing how much I gave up of myself. And that became the beginning, honestly, of me thinking about working towards divorce. That was the catalyst, I would say.

Speaker 2: 4:09

How did that path go forward to the point where you were in a spot where you made a choice? I'm here and I'm no longer seeing myself as fulfilled. I'm starting to see the gaps and the cracks in how I am versus how I choose to be.

Speaker 1: 4:27

Well, I mean, the first step was the divorce, and getting to the point of I'm this isn't my life, to that was painstaking, because it's not just you, because it's not just you. I was trying to not be selfish. I had kids, but you know it's it's disruptive. So it took a lot of deep soul searching. It took a lot of getting used to it, getting used to the idea, accepting that the kids would be okay. So it took a while to get there. But that became the catalyst for all of the changes that happened after that and it propelled a whole series of changes that took me to where I am now, which is in a great place.

Speaker 2: 5:11

Professionally, what was that shift for you?

Speaker 1: 5:15

So the divorce was the trigger of everything. I actually don't know the stat on this, but I believe there is a statistic that shows that people going through a divorce are more likely to also lose their job Because, if you think about it, you're living in a lot of catabolic, negative energy, right, yes, in your life. So if you're constantly in conflict at home, you're going to likely come into work in conflict, and that doesn't usually bode well for you Right.

Speaker 2: 5:46

Yeah, employers don't like that. They don't like that Right.

Speaker 1: 5:50

Right. So the divorce is going on and that was a struggle. And I bought a house as part of that so I could move out and have a place for my children. And two weeks after I bought the house, I lost my job.

Speaker 2: 6:07

Wow.

Speaker 1: 6:08

Because I probably was not doing much work. I was buying a house, I was dealing with the doors. There was also a lot of other dynamics, a lot of like upper management shifting, that contributed, but nonetheless, actually I just I was just doing a, putting together a webinar and I did the Indiana Jones. You know, the ball coming down, the big rock coming down, the divorce pushed the rock like taking the gold idol off of the thing right, and the rock just kept on going.

Speaker 1: 6:41

At the very end there they were with. You know, guns pointed at me right.

Speaker 2: 6:46

Exactly, exactly, sprinting your way right into the guns. Yeah, not a great place to be. Yes, yes, yeah, exactly.

Speaker 1: 6:54

The good news is I had a great support system. Both my friends as well as the person who had owned this company before he sold it which is part of everything that happened trusted me because I had launched products for him and, when you talk about, that triggered mergers and acquisitions. I helped launch a product that was a tipping point to make the company more diverse, so that made it more attractive and he sold it and made a bunch of money. So there was a lot of trust built up between the two of us and so you know we chatted because I immediately when this happened you know I go into little financial security stress I call my realtor. I got to sell the house. You know I like I go.

Speaker 2: 7:38

We got to cut the budget. I need I like I go. We got to cut the budget. I need to unwind this thing.

Speaker 1: 7:41

I just did, right, right right, Cancel the lawn service, you know, whatever it was Right. I'm just like I go into reactionary mode, which I've sort of learned to calm down now, I think. So then I went into networking mode because I'm like I got to get another job Right.

Speaker 1: 7:58

And when we met he said you know, do you have any ideas? I'd love to partner with you. And he even said he would fund a lion's share of the business. And that's how much he trusted me, which was great. So I went through a series of ideas that I had had and I put a pitch together and that became the beginning, and so that took. You know, there's certainly a fear of going out on your own, a fear and that financial insecurity thing, and I wasn't going to take a salary for a while.

Speaker 1: 8:29

So, and I had two kids, one two years away from college, you know, I mean a house, that I had, a mortgage I now had to pay for. A divorce I had to pay for house that I had a mortgage.

Speaker 2: 8:42

I now had to pay for a divorce. I had to pay for, you know, and all of those needs for security were no longer obvious. How you were going to meet them at that stage. That had to be pretty terrifying, or at least frightening during that period.

Speaker 1: 8:52

Yeah, and you know the good news is there was a little bit of a ramp period because I had severance, so I had a little bit of a runway which helped and I always knew if need be I could, and which I did do. Actually, I found all sorts of ways to make money. I did a little bit of consulting so even though I was working full time in this business, I would take a day a week and do some consulting. I Airbnb'd my house and oh my god the stories I have from that because the rave that someone had at my house.

Speaker 1: 9:24

Unbelievable. That's a whole podcast in and of itself talking about that. But yeah, I was just looking for whatever I could to earn money.

Speaker 2: 9:37

Yeah. Just to keep that mortgage paid to earn money just to keep that mortgage paid. Yeah, so what prompted you to move into coaching in terms of that shift from sort of that extension of that other role right Finding this opportunity to partner with this guy, that you have a really strong relationship and, like you said, that strong trust between the two of you, and yet there's this change that happens that brings you into starting a coaching business.

Speaker 1: 10:05

So I started the company. We ended up in three years selling it to a major insurance company. We actually completely changed the industry.

Speaker 1: 10:15

That the whole monetization plan in that industry, kind of like think of what Uber did to taxis right, I mean sort of a shift like that Now it's a smaller industry, but a shift like that and so after we sold it I could have just stopped working when I wasn't really ready to. I didn't want to take the risk of a new company again because then I'd be taking this money that I just earned, which was going to fund my retirement, and putting it back in and risking it again, and that felt uncomfortable. So I took a job in my old career and it was great for a while and then it became not so great and I realized that what I really loved about my work now, versus what I had loved previously, was mentoring other people. Now I didn't know at the time that mentoring was different than coaching.

Speaker 2: 11:09

Right, Right, and yet again different from counseling right? Yes, absolutely yeah.

Speaker 1: 11:16

But I loved seeing people develop right, whatever the means of seeing them develop. So I think of it as my why changed my why. I used to love solving business problems using technology or whatever was necessary to use it and I switched to. I really liked seeing people develop and being a part of that development and I had had a coach for as part of my professional development at that company, we I had like four sessions with a coach.

Speaker 2: 11:48

OK.

Speaker 1: 11:49

And that was really informative and interesting and helpful. And so when I left that company I just thought about well, how do I, what do I, what do I do now? And I'm like I really like this, and I started formally mentoring, like with an incubator in town and even this 21 year old with financial, you know, with too many student loans that she was trying to figure out how to pay off, and helping her with the financial budgeting or whatever.

Speaker 1: 12:18

And so I looked into coaching and I talked to my old coach and then I talked to another coach and I said, yeah, I think that's what I want to do. And it also served me well because I could do it from anywhere and I could start to live the vision of what I wanted my later years to look like. I could start living it earlier than previously, than I might have been able to.

Speaker 2: 12:42

Right, that opportunity to say, look, I can have the lifestyle I want while also getting to do this really great work that I enjoy and supporting people as they move from maybe feeling frustrated and uncertain or whatever that might be, over to a place that they can actually see their own path forward. Right, I know that that's one of the things that's important to you and I wonder, when you look at yourself now we were talking before about you know when you think back to those times when you were reconnecting with folks you knew in high school and even maybe before, and the you that you were then, when you think about yourself now, what are the characteristics that you've kind of pulled through now that you get to bring into your coaching?

Speaker 1: 13:32

Well, I think I've developed a lot more emotional intelligence and a lot more understanding of just people like less judgmental. I think I was a lot more judgmental when I was younger and I accept people much more so as to who they are and recognizing that who they are is a product of everything they've lived.

Speaker 2: 14:02

Right.

Speaker 1: 14:02

Right.

Speaker 2: 14:03

Absolutely when it's. They have their own story and it's brought them to where they are now, whether they choose to stay there or not. Right, yeah?

Speaker 1: 14:12

And that makes me happier, because judging only hurts yourself, Right? Or I love the line you you're judged. You're telling more about yourself than you are about the other person.

Speaker 2: 14:23

Yes, it's like looking in a mirror and all the things that you don't like about yourself is what you're judging about that other person, and having that opportunity to help someone see themselves without you in it can be such a really great experience. When you think about developing that emotional intelligence, for example, how does that have you showing up differently in your life now compared to before that initial catalyst kind of came along and prompted you to even consider the divorce?

Speaker 1: 14:53

Yeah, Well, you should ask my children, but I think I'm a better parent now, particularly as they're aging, right? They're both adults now and you know no longer telling them what to do, letting them make the choices. Still being an advisor when asked, I don't throw my opinions, you know. I think I've just matured as a parent, which is good for all of us. Yes, I'm imagining that's also less frustrating for you.

Speaker 2: 15:18

Yes, yes, I think I've just matured as a parent, which is good for all of us. Yes, I'm imagining that's also less frustrating for you.

Speaker 1: 15:23

Yes, yes, I think I'm a better partner. I just recently got remarried, actually.

Speaker 2: 15:29

Congratulations.

Speaker 1: 15:30

Thank you.

Speaker 2: 15:31

I'm definitely more empathetic in life and I have a lot less stress and with that it makes me think about when we were talking about fulfillment earlier. That lower stress level seems like it would give you a little bit of space for other things to grow. And I'm curious about when you're working with the entrepreneurs who are your clients, how does that show up with them?

Speaker 1: 15:58

You get a lot of crazy ideas that people have of businesses they want to start and or even I encounter, you know, a lot of what I would call crazy, right, that's judgmental and I don't mean it that way, right, but things outside of the norm and it's sort of just an acceptance, right, and you just help them to the best you can of turning it into something that you know where they can make money and they can find their audience and they have a plan, right, and it's really they put it all together. You know I'm just asking questions and they're getting, you know, the aha moments, so it's, it just sort of shows up as facilitation almost right.

Speaker 2: 16:44

It creates that space for someone else to recognize oh, this is how I could monetize this and make it not just a hobby but actually an opportunity to develop and grow into a business, and who knows, then, where that might take them, and that's exciting. To your point earlier about being able to see it from that idea and blossom into whatever they decide to make. That and knowing that, while it wasn't your advice and it wasn't your support directly within their business, it's your support alongside them, helping them think through without having all of those mental blocks and emotional blocks that keep getting in their way sometimes probably.

Speaker 1: 17:26

Right, you know, people come to me regularly because they're like I just I don't know how to do this and I need someone to help me figure out how to do it. And inevitably in the very first session, the issue isn't really that they don't know how to do it, it's a fear. Whatever that fear is a fear of failure. It's a you know. It comes off as I don't have enough time and it's like okay, is that when you dig down, like, is that really what it is Right or what's what's really underneath that? So inevitably, our first session isn't about like oh, tell me what your business plan is. It's always something else.

Speaker 2: 18:03

Yeah, it's what is the presented issue versus what is the underlying issue that really comes into play. And you know, when you think about all of this transformation that you've gone through during this period that we've talked about, what are the things that are the most important lessons for you during that time?

Speaker 1: 18:25

Not letting fear get in your way right. That's definitely one of the lessons I learned. One day at a time, one thing at a time. My divorce took three years, so one day at a time was really important there. And I'm someone who I'm like, I'm a doer, I am like I get stuff done, and so the just the lags in the waiting and then the BS in between, I was just like come on, let's do this Right.

Speaker 2: 18:54

And I just shouldn't be this hard Right.

Speaker 1: 18:57

Right, and so I just had to, like you know, calm myself down and let it. I guess you'd go back to trust the process, right?

Speaker 2: 19:06

Yes, yes.

Speaker 1: 19:07

You know, another phrase that I think we all could use, which helped me on a daily, was they're not doing it to you because they're doing it because of them. Right Is the them Right Is the phrase right and to recognize and not helps you. Not take things personally, because we all our lens is it's about me.

Speaker 2: 19:32

Of course, because for us it is a lot about us, right, yeah, our survival first, yeah. You know, they even tell that to us in the airplanes. Right Our mask on before you help others.

Speaker 1: 19:46

Right.

Speaker 2: 19:46

So we need to make sure our mask is in place.

Speaker 1: 19:48

Yeah, so I mean, I even had an issue with a woman actually during coaches training. I said something pretty lighthearted to her and she reacted in a really negative way, and the coaches training at the time was really helpful. My first reaction was oh my God, what did I do? Right? That, of course, was my first reaction. Then I stood above it and I said wait, there's something else going on here. She's not doing this to me, she's doing this because of something that's happened to her. And it turned out that that was true.

Speaker 1: 20:17

It took a day for me to find out what that thing was. Then I started using my coach's training of what are some other explanations about what could be happening here, right, so? Take my lenses off, take my glasses off, try to see all the other. What does it look like with a red lens versus a blue lens versus a pink lens versus a yellow lens? Whatever right. And realize there's five possible explanations for what could be happening here, and let's let it play out and find out what those other explanations are, and then we could deal with it.

Speaker 2: 20:51

Yeah, yeah, because actually our experience isn't theirs right, and so there's an infinite number of opportunities that might be out there theirs right, and so there's an infinite number of opportunities that might be out there. And you know, one of the things that it makes me think about is you went through the professional aspects of losing the role and yet finding this opportunity to partner, and then you know, kind of doing the sale of that and moving into what you were doing, and really kind of saying, yeah, you know what, that just doesn't fit anymore the way that it used to, and now you're in this entirely different place. How does all of this and the learnings that you've had about this affect your choices going forward?

Speaker 1: 21:38

Well, I still, and this was in a book that I recently read. It was something about the 15 lies that are told to women, and one of them was one of the lies is you know, you have to have a plan and you have to work towards that plan, and there's so many I deal with so many people in my coaching that have that philosophy, and her recommendation was, and her recommendation was and this is how I really lived, my life was follow the opportunities.

Speaker 2: 22:03

Yes, I recognize that. Yes, I have also lived that life. Yes, I understand.

Speaker 1: 22:12

And you do have to evaluate that opportunity. Is that in line with where I want to be right? So if somebody gave me an opportunity to go open a Jimmy John's's, that's not really where I want.

Speaker 2: 22:21

That's not heading to a place I want to be I love I'll eat at jimmy john's you know, I don't need to have be participating in the franchise though right understood right so it's not like follow every opportunity you've.

Speaker 1: 22:35

You should be judicious about it. But if it's an opportunity that is serving you in terms of where you want to be in life, at least for the next five years, right then, follow it.

Speaker 2: 22:47

Right, that sounds like it really mirrors and ties into that idea of one day at a time in particular.

Speaker 2: 22:55

Because you have this chance to every opportunity that you see, Because you have this chance to every opportunity that you see. And it's interesting because when you're not feeling so rigid about but I have this plan and I have to follow this plan, opportunities are a little bit more visible and you can actually see of the things floating by that you might be able to choose. It makes me think about. There are like those sushi places, like the Japanese restaurants, and there's a conveyor belt that goes around and you can just pull the plates off and they just count the plates and if that particular food item doesn't seem appealing, then you let it flow right on by and let someone else who really is drawn to that take advantage of that opportunity and you just take what pleases you.

Speaker 1: 23:44

Yeah, that's a great analogy, Becky.

Speaker 2: 23:47

When you think about all of the things that you have experienced during this time, what are you the most thankful for?

Speaker 1: 24:05

for, certainly, the support that my children and my family and friends gave me throughout the process. You know there were times when you have your own business. I mean I was there, I was working from home, I was picking them up from school, but sometimes I'd be 10 minutes late because I had been on a call or I'd be in the car and somebody you know I was after hours and weekend support, and so sometimes I just had to be on a call and my family still to this day they'll say something like okay, go to here, press the little three. You know, like they knew the routine Because they had heard it.

Speaker 2: 24:41

Memory that won't unplug, right? They had heard it over.

Speaker 1: 24:44

So their patience and support, which you know, in the end paid off for everybody. But you know I'm sure that was hard. You know I was there a lot more, but then there were times when they'd want me to be there that I just I couldn't be Right, and so, yeah, that's probably the most thing I'm thankful for.

Speaker 2: 25:05

Yeah, I love that, the idea of that flexibility and that support and just that loving through all the change and it could be, you know, professional friend or children love, right, it's just that support network. With that. I'm just really excited that we've had a chance to talk through this part of your life and from where you were to where you are right now. Toby, thanks so much for the time today. I've really enjoyed our conversation and I hope you have too.

Speaker 1: 25:34

Yeah, thank you so much for having me, becky, it was fun.

Speaker 2: 25:37

Wow, quite the journey for Toby, wouldn't you say. As she reflected on who she was when she was young, who she was at that inflection point and who she would choose to be, a decision needed to be made. How often do we find ourselves at that crossroad? Am I living and leading as who I would choose to be, or am I adjusting based on what others want me to be?

Speaker 2: 26:01

Key life events have a profound impact on our priorities and goals in life. It can be personal or professional. For Toby, it was both. As she said, her challenging home life affected her work life. She believes that it resulted in her job loss. Her work life she believes that it resulted in her job loss. This was a catalyst for change in her life, as Toby describes it. She started looking at her life from the outside in and recognized how much of herself she had given up. It wasn't just about a single event, but a profound shift in perspective From living on remote control to actively choosing and creating her life path. It represented a fundamental transformation in how she viewed herself, her potential and her future. Toby developed greater empathy, reduced judgment and learned to see situations from multiple perspectives through her experiences.

Speaker 2: 27:06

Where's your opportunity to reflect on your choices. The most transformative moments come when we have the courage to listen to our inner voice and make bold, sometimes scary, choices that align with who we really are. For Toby, reconnecting with her authentic self wasn't just a personal revolution, but a professional transformation that changed everything. Her story is a powerful reminder that staying true to yourself isn't about having a perfect plan, but having the courage to follow unexpected opportunities that resonate with your core self. Are you interested in connecting with Toby to learn more about her story and the coaching she does? Find access to her LinkedIn profile in the show notes. Thanks for listening. If you found this episode helpful, share it with someone who could benefit from it. Until next time, I'm Becky Fraser, reminding you to integrate who you are with how you lead. Okay, bye.