665: Letting go of the Executive Title: Creating your ideal job to fit your life – Katie’s Career Transition Story

(00:00) Katie Hyskell: I can't have boundaries because then I'm afraid I'm gonna get fired. I can't have boundaries because I'll never find another job.

(00:07) Scott Anthony Barlow: What happens when you base your identity around your job?

(00:10) Katie Hyskell: Hard work is not the only indicator of life success.

(00:14) Scott Anthony Barlow: It can be difficult to leave the executive job title that you worked so hard for.

(00:18) Katie Hyskell: I'm saying I'm just gonna walk away and decide it's okay to not have a title, like to not have that level of prestige, if you will.

(00:26) Scott Anthony Barlow: Here's the reality. You go through seasons of life and what's important to you changes along the way.

(00:31) Katie Hyskell: As I continued to grow in my career and then started having a family, it got harder and harder for me to maintain that pace.

(00:40) Scott Anthony Barlow: That's Katie Hyskell, a sales executive who worked in the tech space, and in this episode, you're going to hear how she created her own role that fit.

(00:49) Katie Hyskell: By July, I had actually created my own job function, which I'm doing now.

(00:55) Scott Anthony Barlow: Also, you'll hear the counterintuitive approach that she took to finding what was right for her.

(01:00) Katie Hyskell: When I started networking in the job search process, I said no to way more things than I said yes to.

(01:07) Scott Anthony Barlow: You'll even learn how she had to think differently to find work that actually fits her and the life that she wants to build.

(01:14) Katie Hyskell: So by 2024, when I hit that burnout and my health decided it was also going to burn out, I really took that stop and said, “I can't keep doing the same thing and expecting different results.”

(01:26) Scott Anthony Barlow: This is Happen to Your Career, the podcast that brings you real people, real transformations, and the courage to do work that truly fits. If you haven't already subscribed, click follow right now so you don't miss any new episodes. Here's Katie, taking us through what led up to her career change in the first place.

(01:43) Katie Hyskell: So I didn't go into college thinking I'm gonna be in SaaS, go to market functions, right? Like that's not something that a lot of people plan for. So I had had a plan. I had an undergraduate degree in psychology. I was gonna go into counseling, made a pivot, just knowing where I was at the time in my life that I probably wouldn't have had great boundaries in that type of role.

So I went back and got an MBA and when I graduated with that MBA, it was about 2009, which the economy was not good. So the only job I could get was in sales, really. So that's where I got into this career, and was very successful for me. I learned a lot. I grew a lot. I achieved things I never would've anticipated.

But as I continued to grow in my career and then started having a family, it got harder and harder for me to maintain that pace that I had been maintaining in software as a service startup as a sales leader. So, really, what led to me finally pulling the trigger, I had done a stint, I think from probably 2019 to 2024, of just 12 to 18 months at a company before I completely burned out, and that time period and that window kept getting shorter and shorter.

So by 2024, when I hit that burnout and my health decided it was also going to burn out, I really took that stop and said, “I can't keep doing the same thing and expecting different results.”

(03:13) Scott Anthony Barlow: Initially, you were looking for almost anything, got into sales, were incredibly successful in the sales area. And then if I remember correctly, you kept getting promoted along the way, too, and did very, very well through all of that time period.

But it sounds like there was at some point where you recognize that you wanted to spend less time, less energy in one way or another. And then through a series of, were they company changes at that point in time? How did that happen? Those, you said 18-month stints that kept getting shorter and shorter before you reached that burnout period. How did that work?

(03:53) Katie Hyskell: I can actually remember the first kind of moment where I just realized this is not gonna be sustainable. And I kept trying to make little pivots that might help. So the first time I tried this was actually back in 2019. I was at a company that was not based where I live, so I was working remotely, but traveling at least 50% of the time, sometimes more, with small kids at home.

And so I said, “You know what? I'm not gonna do this anymore. I need to take a job that is more local to me.” 'Cause I thought that might minimize the travel. So I took a job where I was gonna have a global oversight of a team, which was really, really smart. I'm like, “No, no, no. They're headquartered here.” So ended up making that pivot and was working all hours of the day, leading a team in Europe, leading a team in Asia Pacific, as well as North America.

So it did not reduce my workload at all. And after that, and truly I'd like to say that this was something that I thought out so cleanly and approached in a really planned-out way, but it really wasn't. It was just ongoing exhaustion, burnout. I wasn't bringing my best self to work or home. And so at that point, I got very opportunistic and said, “You know what? I am just gonna take a step out of leadership. Maybe leadership is the problem and I'm gonna go into an individual contributor role.” Which is still very generally highly paid in sales. And I'm just gonna go into this world because I had a connection at a company. I could get the job very easily. Because it wasn't really intentional and planned and well thought out, I realized that I just kept putting every bit of myself into every role I would take, 'cause I never actually changed the way that I was viewing my relationship to work. And so those burnout periods were just getting shorter and shorter. I was still highly performing at all of these roles. I was never getting fired. I just get really tired really fast.

(05:48) Scott Anthony Barlow: What you went through is something that so many people experience where something doesn't work. You know, I think you've had a lot of really wonderful jobs. There were so many great things about each of them. However, they also were not necessarily the greatest fit for you in their entirety.

And jumping from one to the next, now, it felt intentional at the time, making that single individual decision, but looking back it was less intentional and then doing the same thing again. I think that's really normal. It's really human, 'cause we're trying to solve the problem. And I heard you say just a moment ago, it was partially about your relationship with work. Tell me about that.

(06:29) Katie Hyskell: I've told many people, since I've gone through coaching, that was the biggest benefit that I got out of working with Roberta was defining what is my relationship to work and what does work bring into my life. And I was learning and, and part of it is just who I am. Part of it is certainly that I, at a very young age, landed in a very heavily performance-driven career field.

So I had gotten to the point where my value was my output. I felt for some reason that I controlled the outcome of these organizations just by sheer force of will, a number of hours I was willing to put into it, right? So it really was a step back of saying, “What do I get out of work? How do I relate to work? And ultimately, what is the ownership that I have over these outcomes? What is my accountability to the job?” And that was a huge, transformative moment for me.

(07:23) Scott Anthony Barlow: When you say that was transformative for you, how did that show up? What actually changed in your reality?

(07:30) Katie Hyskell: So I would say the first thing is it really changed how I pursued jobs and you know, and ultimately, when I went into another job, what I was looking for, because that whole practice of doing the ideal career profile, but also doing, you know, “What is your perfect day look like? What do you actually want your day-to-day life to be,” was really eye-opening, 'cause I had had this concept of A, I've gotta be in a certain level of pay.

So it was like, “Let's explore that and what level do I need to be in really to maintain the life that I want.” B, I had this concept and also probably kind of coming from my background, of there's not a lot of female leaders in sales organizations, when I went into it in the area that I was in, in software.

So I was carrying this flag like I have to be doing these jobs because I can. I know I can. So I need to maintain it and I need to represent and I need to do all of these things 'cause I'm capable of it. So as I started to kind of unpack that a little bit, I was able to take that step back and say, “Actually, how could I be contributing in a way that still feels authentic to me and doesn't burn me out?” And it really tactically changed how I approached my job search ultimately.

(08:50) Scott Anthony Barlow: So the goal changed? Yeah. That's the thing that I heard loud and clear. We're not just looking for a job that is a quote-unquote fit; we're looking for how you want to spend your time in many different ways is what it sounded like.

(09:08) Katie Hyskell: A hundred percent. Because previously, every time I would look at jobs, it was, “Do I have this experience? What's the title? What's the pay that I'm going to receive?” Like approaching it this way, I literally broke out. “What would I be able to accomplish in my day? Can I take my kids to school? Will I be there in the afternoons?” And when I started networking in the job search process, I said no to way more things than I said yes to because I was viewing it under that lens as opposed to just looking at the skills that would be required to do the job.

(09:41) Scott Anthony Barlow: What was that experience like when you were actively out in the midst of a job search and you have a much better idea of what you want at this point? Was saying no easy for you at that point? Was it still difficult? What was that experience like for you as you were going through it?

(09:59) Katie Hyskell: It was really still difficult. I was very lucky. I was on an eight-month career break when I did the coaching. So I planned, like, I'm not gonna be working for this time period.

I had other medical stuff going on, I was working through, but I said I'm also gonna be focused on making this change. So I had a ton of time to devote to it, which was, to your point, about how fast you can escalate the process and it, because it is a ton of work to do that introspection and try to dismantle some of these beliefs I had, like I have to be a VP to be successful, right?

Like to really start to dismantle some of those things was a big deal for me. And then as I started to approach it, I can remember very clearly I was starting to do my networking and I had an old colleague come back to me and said, “Hey, I think, you know, you should have this conversation with my peer. It's the senior director role. I think you'd be great fit for it. It's remote, but you should still have the conversation.”

And I had that conversation before I said no, even though it didn't fit any of my requirements that I had set, I still had to have the discussion because it was so difficult for me to turn down the opportunity to have a conversation.

But after that first one, I had a much easier time of saying like, “This situation doesn't fit what I'm looking for and I need to reprioritize.” But it was difficult on that first one for sure.

(11:24) Scott Anthony Barlow: I'd love to understand some of the nitty gritty. Let's go backwards for just a little bit here, and if you think about, first of all, as you were getting started trying to figure out what was a great fit for you. What was the hardest part about that, that part of the process, if you will?

(11:43) Katie Hyskell: There were two things that were really challenging, like unexpectedly challenging for me. I think the first was when I was taking that step back and going through an exercise around strengths and even taking the Gallup strengths finder, which I have done before, several times in my life and having to say, “No, I'm not just gonna answer this by what I was before or what I think I'm supposed to be.” I actually had to take the time to say, “This is what it is.” And as a result, my results were actually very different than what they had been previously. So that one was harder than it should have been, or harder than I thought it should have been, because it's like, “No, of course I know what my strengths are. Like, I do all of these things.” And to take that step back and really explore that was different for me and was challenging. The other piece of it, kind of at the beginning, was breaking down and I know it's the most simple exercise to just say like, what do you want a day in your life to look like?

It should be simple. It was not simple for me. It was really like, what do I actually want this day to look like and what kind of flexibility do I actually want and desire beyond the work that I'm doing during the day, because a lot of previously, when I've gone through these exercises, it's been, what work do I wanna do? What work excites me? It had nothing to do with what I wanted a day in my life to actually look like.

(13:11) Scott Anthony Barlow: What were some of the beliefs, because you mentioned a little bit earlier that you had to undo, for a lack of a better phrase, some of these past beliefs that were no longer serving you.

(13:23) Katie Hyskell: So I think, you know, not to go too deep, but I think this would be relevant to a lot of folks. I think really getting to look back into why did I feel like I had to be such an overachiever? And in my case, you know, my dad was an immigrant to the US, so you have that kind of story of, “I had to work really hard and build this for my family and now I've given you all of this opportunity, so don't waste all this opportunity.”

So when you start from that kind of perspective in your life, I think sometimes what that can build is, okay, like perfectionism, first of all, like I cannot waste the opportunity that I've had. So if I am capable of climbing the ladder and doing these executive roles and continuing to push that hard at work, then I need to. It's not a choice. You should do it because you can.

(14:16) Scott Anthony Barlow: You must.

(14:17) Katie Hyskell: So that was the first thing I had to unravel is like hard work is not the only indicator of life success. So that was, that was one. And I think the other piece was really more around ego, right? Of, I feel like, and I really did have to dismantle this, like if I don't have the title and look at all of these people that came up with me in my career and they're all VP of this or VP of that, are they doing all of these things?

And now I'm saying I'm just gonna walk away and decide it's okay to not have a title, like to not have that level of prestige, if you will. So like dismantling some of that ego and really leaning into what do I actually want? That was challenging. That was a challenging belief to walk away from as well.

(15:02) Scott Anthony Barlow: What do you think helped you have that level of structure to be able to draw boundaries once you actually get into an organization or into an opportunity if you haven't already defined some of those in advance? Like that's something that is very difficult for many people to do. What made that easier for you?

(15:20) Katie Hyskell: Rock bottom boundary failure. Yes. Like truly. And when I say like I burnt out, I mean I had to have like multiple surgeries last year for things that probably could have been avoidable had I paid any attention to my chronic stress levels and health levels. So this was not like a pretty, “Yeah, I just decided to do something different.”

Like I was really struggling to kind of maintain my life and what was great. And I will say, again, just pitch Roberta 'cause she's amazing, but really was her offering up resources. She offered up a lot around, “Here's some resources to read about boundaries. Here's some exercises with boundaries, podcasts to listen to.”

I just took in so much information around boundary setting and types of boundary setting and all of that. So I will say failure and then learning, but also, really, what has been challenging, and I would say is challenging for most people, is going into job search and how you relate to your job with a scarcity mindset, which was my problem. I can't have boundaries because then I'm afraid I'm gonna get fired. I can't have boundaries because I'll never find another job. Or if I don't take this job offer, I'll never get another job offer. And so being able to know like my skills have value, there's always another job.

That kind of feeling of abundance, I had to sink into a lot, and in this job market that is not easy to do for people at all, but that was really what I had to sink into.

(16:56) Scott Anthony Barlow: When you think about what worked effectively once we actually got to the job search portion of the work that you were doing, what worked really well for you as you got into the job search stage?

(17:10) Katie Hyskell: So I was pretty structured with my outreach and networking, so I made that very structured list around nonprofit, public company, a company in this particular subset of technology. And then I just went into basically an outreach cadence where I started with who are the people I actually know? And first-level connections who would recognize my name? And let's start there to reach out and just ask for a call. And when I asked for a call, it was really structured and very intentional to say, “I'm not asking you to give me a job or refer me to your company. I'm just asking to have a conversation,” around like, “what has it been like for you working at company X, Y, Z, or doing this particular job?”

So that initially was how I booked a lot of calls and that I would track myself. I was booking like five to 10, 30-minute calls per week, and then I kept sharing my metrics with my coach and she would say like, “Remember, you have time. This isn't a race.” So I would do prep before the call, which I would recommend to anybody in an interview situation as well. In this case, I was really targeting like, let's talk to somebody who's female-founded and female-led, and maybe that'll be a different culture.

(18:21) Scott Anthony Barlow: What made you decide originally that the organization was more important than the work itself that you were doing? Not that the work that you're doing is unimportant, but that the organization was more important for you.

(18:36) Katie Hyskell: That was a part of really my deep searching that I did initially of what did I not like about the jobs that I had. And by and large, I actually really liked a lot of the jobs that I was doing. I struggled with leadership, or I struggled with strategic direction, or I struggled with things that felt like, you know, gaps in integrity, in decision-making process.

So I realized that it's not the job, it's really what is the integrity was my number one. Does the organization function in integrity? Part of it just comes from being part of a software startup landscape. So I wanted to be sure that that was number one. And then leadership and what is the leadership structure?

And I even went down to what is their funding type and what is their exit strategy, because of a company as a startup and they wanna go to IPO, they're gonna be acting a lot differently in their sales organization. So I went to a pretty deep level of organizational structure. Also, partially because in a startup landscape, I know that my job could change every three months anyway. So as long as I'm working for people I respect and an organization I can get behind, there's a lot of different job tasks I could do.

(19:53) Scott Anthony Barlow: I think you mentioned something else that's important and you gave that example of even looking at what their exit strategy is. I think that's something that is overlooked. Not just the exit strategy, but looking at anybody, any group of people in this case, an organization that you're spending time with, looking at them, that group collectively as a partner, if you will, for lack of better phrase, and that partner, if you're aligning yourself with partners that are going to be beneficial to you in the long term, like they're heading the direction you want to head in the longer term, I think that becomes a much more strategic move. And I rarely see people talking about that or looking at it that way overall, but I found it to be so useful just as a strategy for almost anything that I do, not just searching for jobs.

(20:44) Katie Hyskell: Yeah, a hundred percent. And knowing that, like, I'm gonna be spending a lot of time with these people, virtually in my case, but still spending a lot of time with them. But yeah, I think really also part of this just comes from experience, truly, and kind of seeing based upon the goals and strategies of that organization, like what is happening at the top is really gonna influence that culture down low. So if I wanna be part of a good culture, I need to understand what that organization is moving to strategically.

(21:17) Scott Anthony Barlow: Hmm. Love the outlook. As we were, you're at the point where you are talking to many different people. You're getting lots of great information, which allows you to make better decisions.

And do I enjoy this company? Are they a good contender? Are they a browy culture that I want nothing to do with whatsoever? So I take them off the list. All good information. Yeah, but where did that lead? What happened next?

(21:42) Katie Hyskell: So as part of the conversations, there was an organization where. And again, I do feel very fortunate. Part of the benefit to having been at so many companies in a short period of time is I've got a very sizable network of people that are in a lot of different places, which was really helpful. But I had found an organization that I was aware of for a long time because I knew several colleagues that had gone there and ended up saying, you know, “Let me start talking to multiple people within that organization.” Because I thought, you know, maybe from an area of focus, perspective, they might be aligned. So I was able to start the conversation and identify, “Oh, it's an individual contributor level sales job.” I was like, “You know what? I know I can do that. I know the leadership that I'll be working for. Like, let me just go into this individual contributor sales job and then we'll see what this will grow into because I like the organization.”

So I started that in January. By July, I had actually created my own job function, which I'm doing now. That is a mix of a whole lot of different things that I've done in the past and am out of the sales quota-caring environment again. But I had to kinda get my feet wet before I could make that claim.

(22:56) Scott Anthony Barlow: So let's talk about that. You found this organization that aligned strongly with all the pieces that you're looking for. And then you said, “Okay, I'm gonna go ahead and latch onto this organization and it matters slightly less what role,” because you know you'll be able to get in there and obviously, as you said, you got in there and now you have created a role.

So take me through what happened from acceptance of offer to the point where it allowed you to be able to create your own role, modify your own role. What did you do to influence that along the way?

(23:33) Katie Hyskell: So some of this helps by the fact that I did already have connections within the organization that I had worked with previously and that had worked with me in a leadership capacity. So they knew a lot more about what I had brought to the table historically. But when I joined, I was very focused on, “I'm gonna do a good job at this individual sales level role. Like that is my job. That is what I'm accountable to, and that's what I'm gonna focus on.”

So I went all in on the training and the onboarding and all of those things. I didn't come in immediately and try to start saying, “I'm gonna solve all the world's problems.” But as I got a couple of, well, maybe two quarters in to this, I started having connections with my CRO, Chief Revenue Officer, because it's a very small company.

It's a very, there's not a lot of layers and started saying, “Hey, I'm seeing some of these challenges come to the forefront. Here's some of the themes that I'm seeing.” So it was very intentionally making connections with a lot of people in the organization. And then came to her and said, “I know that I could be contributing more than I am right now, but I'm not interested in being a manager.”

So right now, that is a really straightforward, but I know I could be contributing. And so she thought through it probably for a few weeks and then we co-created. So she came and said, “Are you open to doing what we would call,” I think they called it a gig assignment. “So can we sign a three-month agreement of what your pay is gonna be for the next three months, and here's the tasks that are very strategically aligned to things that the organization needs to do. Because you're so versatile, can you kind of gap fill?” That's why I called myself a professional bandaid. “Can you fill some gaps?” And so I said, “Yeah.” And I started tying it to hard revenue metrics and KPIs that I knew I could track. It was a very iterative process, but it was also, kind of to what we shared at the forefront, I really had to have a lack of fear about job security to do it.

Because I know even now. I'm bringing a lot of value to the organization, but I'm not in a traditional role. So there could be at any time if somebody wanted to come in and say like, “We're gonna cut people.” But I'm pretty confident that if that was the case, I'll find something else. So I was able to be a little more bold in taking that action.

(25:48) Scott Anthony Barlow: I love that. And you know, is there really job security? Maybe in certain circumstances, we could argue depending on how we defined job security. But really at the end of the day, no, probably not, right?

(26:02) Katie Hyskell: No. I mean, if anything this year should tell people that more than anything else. People used to work at the federal government that thought they had job security, right?

Like there's not, and so I've kind of come to this conclusion that like, I gotta make my own job security, you know? Which is why I just knew anything I'm doing, I need to tie to metrics. I have to be able to track KPIs. It's gotta be really clear in terms of what I'm delivering. Because ultimately, I might need to make this case to somebody else, not just the chief revenue officer that I already know. So yeah, I think we gotta create our own job security.

(26:36) Scott Anthony Barlow: What advice would you give to someone else who maybe has made a couple of changes, hasn't had them work out in the exact way that they planned? They felt intentional at the time, but realized it was less intentional than maybe what they thought and is interested in doing it differently this time around. What advice would you give to that person? Yeah,

(26:58) Katie Hyskell: I would say it's hard to do the same thing on repeat and expect a different outcome, first of all. So what is it that they say? That's the definition of insanity, but in truth, it really is. So I would just say you expect things to be different, you have to be comfortable making some real changes.

But for me, a lot of it was less external and more internal and kind of me having to determine like, what was I bringing to my career situation? What was I bringing to these environments and how was I controlling or not controlling my own destiny? So I would say be bold. At the end of the day, you're the only person that has to wake up and live in your life.

So whatever anybody else thinks about what path you're pursuing, you're the only one that has to live in it and it being miserable for 40 hours a week or 60 hours a week or more, is that what you want to look back on? For me, a lot of it too was the fact that I did go through so many medical things last year and just kind of taking that step back and nobody knows how much time they have. So don't spend your time being stressed out, burned out and miserable if you don't have to.

(28:09) Scott Anthony Barlow: When you look back, what else surprised you about this? Let's call it a journey. You go with the journey.

(28:16) Katie Hyskell: So when I did the outreach on reaching out to like friends and family and how would you describe me and all of that. That actually was quite surprising, and I say this only because I've spent my entire career life, sometimes doing like challenging, angry contract negotiations, occasionally having to fire people, like doing some of these things that are challenging. But in my personal life, a lot of people that didn't know me very well would assume I was a kindergarten teacher.

It was so incongruent and so doing that exercise and seeing from the people I've worked with what they thought my skills were and the people that just knew me from my personal life, it was really different. And so part of it for me was like, how do you combine those two things? Because I think that was part of the challenge that I had iIn my career was feeling like it was just I wasn't integrated as a person. So that one was surprising.

(29:16) Scott Anthony Barlow: I think something else that you said earlier on in our conversation really stood out to me because we've seen it over and over and over again, and you said something about, “Hey, I was, you know, one of very few women and I felt compelled to keep holding the flag and moving forward.” I won't presume to entirely understand that I see the theme in the pattern and recognize how hard it can be. So what allowed you to sort of step around that and realize that, “I need to do something for myself and my family first.”

(29:46) Katie Hyskell: It's still hard. But I think for me it was really just understanding what do I need to create that's the best for me, and if someday it is going back into leadership, then how do I do that in a way that's still really healthy for myself and for my family? Because I kind of, I got to the point, and I was gonna say I was having babies during the height of my career. I would have younger women all the time say, “Oh, you're such an inspiration because you're doing it all. And how are you always doing it all?”

It's because I never let them see that I was cracking it, you know? Like there was no vulnerability there, 'cause you had to prove that it could be done. And so I had to take that step back and be like, that's not serving them though. Because then when they get to that phase and they're trying to do it all or have families and they're struggling, they're gonna say, “It's not normal that I'm struggling. I should be able to do it all.” So I thought like, just the serving, if it's not serving me, ultimately it's not gonna serve them. If we can do this, let's build it in a space that is serving us and do it in a way. And so now I kind of still, I still see that as my role.

I work with a lot of women that are now entering baby phase. And I still see it as my role to try and be a role model, but now I'm really open of like, “Hey, here's all the struggles I had. Here's what I wish I had done differently. Here's what I feel like I did really wrong. And here's how I'm viewing things now.”

If you're ready to stop believing the stories that are actually keeping you stuck and start creating the career in the life that you want, drop me an email directly, scott@happentoyourcareer.com. Put “Conversation” in the subject line. We'll connect you with the right person on our team, and we'll figure out the very best way that we can support you.

Happen To Your Career - Meaningful Work, Career Change, Career Design, & Job Search