716: What Executive Career Change Actually Looks Like at $200K–$500K: Beyond Draining and Unfulfilling Work | Executive Series Part 1

[00:00:00] Scott Anthony Barlow: The higher you climb in title, the harder it gets to leave, and not just because it pays exceptionally well, but because the work becomes who you are.

[00:00:07] Katie Hyskell: I need somebody to get me off the hamster wheel. So I definitely don't think that it is always easy. There's ups and downs. You gotta pick your hard, but the structure for me was extremely helpful.

[00:00:21] Paul Ichilchik: We tie our identity closely into our role.

[00:00:24] Hayley Lowe: We often sort of rationalize our way into roles that, yeah, look great on paper, but feel wrong in practice. The more you ignore it, the louder it gets.

[00:00:32] Scott Anthony Barlow: What you're about to hear isn't career advice. It's the specific, honest truth about executive career change. This is for people earning 200,000 or 300,000 or even half a million dollars a year.

[00:00:43] In this episode, we'll cover why being stuck in this situation looks different, why the way out is different, and why nothing that you've tried so far is actually designed for the problem that you're in.

[00:00:53] I'm Scott Anthony Barlow. Welcome to part one of our three-part series on executive career change. In this episode, I'm going to walk you through some of the hidden elements that are currently keeping you stuck, including a trap that almost every executive falls into without recognizing it. And we'll cover three specific lies preventing you from taking action when it comes to your career change journey, especially if your goal is fulfilling work that also continues to pay well.

[00:01:20] We've been doing this work since 2013 with executives, and one of the things that we've learned is that we have to go backwards first to understand how you got here in the first place. And when we do, three patterns show up almost every time. The first, you fell into your career and may not have entirely realized it.

[00:01:38] Here's what I mean. Nobody sits down at 22 years old and says, "You know what? I wanna be a VP of finance at a midcap manufacturing company for the next 20 years." Not at all. Instead, you were good at something. You got promoted. You kept saying yes, because each time, the next step made sense, or at least it seemed to.

[00:01:58] Then somewhere along the way, this situation, which has probably been good for many years, started to feel differently. Maybe that was around year eight, maybe it was year 13. I don't know, but at some point you looked up and you realized that the version of success that you'd been chasing had changed, and you'd now outgrown your current situation, outgrown your company, and it had slowly become something that you would never have chosen in the first place.

[00:02:27] Paul Ichilchik: I think we're often conditioned, or I certainly was, to believe that as you progress, you become more of a leader and take on a management leadership role, and then that is success, so to speak. And I had leadership roles and led consulting teams and work streams, but I also found that I wasn't particularly fulfilling.

[00:02:41] Scott Anthony Barlow: Let's talk about the second pattern that we've observed. Again, the second pattern is that the environment around you has changed, probably gotten worse. Whether it's because of reorganizations, mergers, new leadership, whatever it is. You know, whatever you were willing to tolerate in the previous year has now become the thing that you can't anymore. It's changed. And again, you've outgrown this.

[00:03:03] The third thing is that by the time somebody reaches out to us, they've usually been trying to fix this on their own, sometimes for a year, sometimes for 3 or even 10 years. You know, sometimes that means that you've switched companies or taken internal pivots, or other times it means that you've done self-assessments, you've read career books, you've hired coaches.

[00:03:24] Now, a really interesting thing here is that differentiating between many executives and senior leaders that we've worked with, they often know themselves. They're not stuck because of lack of self-awareness or lack of self-knowledge. Usually, you're stuck because you don't have a great way to be able to translate that self-knowledge into specific, realistic, actionable next steps that move you forward.

[00:03:49] Katie Hyskell: I was still highly performing at all of these roles. I was never getting fired. I was just getting really tired really fast.

[00:03:54] Scott Anthony Barlow: That's Katie. You'll get to hear from her again, and that's what three years of trying to fix the wrong problem sounds like. Let's spend a minute talking about what's different at the executive level.

[00:04:05] Why is career change different for executives and leaders? The short answer is because most career advice out there, it just, it wasn't built for you. At your level, career change is a fundamentally different problem brought on by five specific factors. The first one is the identity problem, and at your level, the title and who you are have often fused.

[00:04:26] And it may not even be the difference between I work in finance anymore versus I am a finance executive. That's a little oversimplified. But after two decades, they start to merge together, which means walking away from a career feels like you're walking away from a version of yourself that you spent 20 years building.

[00:04:44] And the hard part is a lot of times it's difficult to be able to see, and this is one of the hidden pieces that is often holding you back from actual movement. A lot of times it tends to show up in how you think about what that movement looks like, and even the justifications around it, and this is partially because the thing that you're being asked to move away from feels like it's yourself.

[00:05:05] Katie Hyskell: Hard work is not the only indicator of life success. 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.

[00:05:17] Scott Anthony Barlow: Okay, let's talk about another element here, and this can be a big one, especially for high-income earners, and that is the income itself.

[00:05:23] It tends to work against you in a way that most people don't expect. When you earn, you know, 200 or, you know, $400,000 a year, USD, it often doesn't make changing careers easier. It seems like it should, but it makes it harder. These golden handcuffs start to get heavier with every promotion, and the salary that once used to feel like it's some level of validation that you were doing the right thing, heading the right path, well, it starts to feel like a reason that you can't do something different because it starts to feel unachievable as you evaluate that change.

[00:05:57] Now, an important point here is that that feeling of unachievability, that unrealistic feeling, is not coming from what is actually realistic. It tends to come from not knowing what else is out there and how it could be different. So our brains tend to fill in the gaps, and that's part of the reason why this is challenging.

[00:06:17] That gets into our third thing here, too, which is that the job market we're searching for doesn't really exist in the same way as other types of opportunities. At the, you know, 100,000, 150K range, the publicly posted job market is largely irrelevant. The roles worth taking are filled through relationships and trust long before a posting ever shows up online.

[00:06:41] Are there exceptions to that? Sure. But that's what we see over and over and over again. The executives that we're working with behind the scenes are rarely getting these opportunities. However, learning to apply to more job postings is the wrong skill set to develop at this level. Learning to have conversations that then lead to and create specific opportunities that don't currently exist is a much better skill set to develop, and it probably builds on skills that you've already begun to develop in your executive role.

[00:07:11] But the interesting thing is nobody teaches how to apply this to this type of format where you're changing careers, and almost nobody figures it out on their own.

[00:07:20] Now let's talk about the fourth thing that tends to be very hidden here. The same network that built your career is now the same network that often might be keeping you in the same box.

[00:07:30] Everyone you know is in the same industry or the same set of organizations, and every conversation you have with them reinforces the same narrow view of what's possible for someone with your background. The people who should be your best resource for making a change are almost always the people who are most likely to keep you exactly where you are unintentionally, and even if they're caring individuals.

[00:07:51] Now let's talk about the fifth thing. The stakes aren't just yours. At 350K a year or $400,000, the entire life that has been built around that income, schools, the home, expectations, your spouse's expectations, kids, mortgage, it's in the equation in a real and much more immediate way. You're not just making a decision for yourself, and that weight makes every step toward change feel significantly heavier than it is, especially when we add a couple hundred thousand dollars on top of that.

[00:08:21] Okay, now it seems like all of these should be obvious, but they continue to show up in very hidden ways. These five factors are part of the reason why generic career change advice just completely falls apart for somebody who's in your situation. They were really never built to solve the problems that you're actually in.

[00:08:38] Now let's talk about one of those, 'cause there's one piece that begins to tie the other pieces together that we just talked about here, and it explains why even the most accomplished person in the room often turns out to be the most stuck. After more than 20 years of being excellent at something, you didn't just build a career, you built a version of yourself.

[00:08:56] We mentioned this earlier, right? Each one of those promotions, every high-stakes decision, every time you were the one called on in the room when something critical was on the line, it became a brick in the structure that eventually became indistinguishable from who you are. Your reputation isn't something you simply have at this level.

[00:09:13] It's the internalization and embodiment of who you believe you are. Now, your network knows you as the person who does this specific thing, and at this level, inside the organization or inside the industry, your title communicates something before you ever even open your mouth, and your income isn't just compensation anymore.

[00:09:30] It's become some level of confirmation in the story that you've been telling yourself about your professional life. All of these little tiny pieces rolled up together, we call this the expertise trap. The cruelest part of it is that the better you are at something that you don't love or that you have grown out of, the more trapped inside of it you become.

[00:09:48] Being mediocre at something you don't love is easy to leave. Being exceptional at it with the promotions and the team and the comp to prove it, well, that's the trap. Katie, who we met earlier, had to deal with this too.

[00:10:00] Katie Hyskell: I had to unravel is, like, hard work is not the only indicator of life success 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."

[00:10:14] Scott Anthony Barlow: Okay, that's what it sounds like from the inside, but the further in you are, the harder it is to put down. But the expertise trap doesn't just keep you stuck on its own. It keeps you stuck through three specific lies that almost every executive at this level tells themselves.

[00:10:29] The number one lie, "Well, I feel like I should just be grateful." This is the most insidious of the three, because it disguises itself as a virtue, and it usually is coming from a good place, right? After all, you have a good income, you have stability. People would line up for the role that you're in. But the truth is, you can simultaneously be grateful for your current situation and also acknowledge that it's no longer a fit for you.

[00:10:54] It's no longer the right situation for you. These things can both be true at the same time. The people who use the, "I should just be grateful," as a reason to not change are almost always defining gratitude as staying in place. And often, those same people, after they're going through not being able to get rid of this feeling that something's off, that something is no longer a fit, and they go through several cycles of that, they feel like, "Why can't I just figure it out? Why can't I just be grateful for this?"

[00:11:22] Turns out this is not gratitude at all. It's avoidance wearing a moral disguise. Let's talk about lie number two, "I just need a better solution here." Now, this is the most expensive of the three, because it generates action that looks and feels like progress. It causes you to do things like updating your resume.

[00:11:39] You go take a handful of conversations or, you know, recruiter calls or you know, whatever else. Sometimes you eventually move to a new company in the same role or the same type of industry, but maybe with a slightly better culture. Maybe it has, you know, higher comp. And you might do this for 6 to 18 months, and sometimes it actually feels a little bit better because the change in scenery resets the discomfort enough for you to feel better for that little while.

[00:12:07] Then it stops working again, because what you moved was the environment, not necessarily the overall underlying fit. Here's Katie again.

[00:12:16] Katie Hyskell: It's really easy to just say, "Well, this time will be different." And I've done this in my career so many times. I still know what some of these things entail, and if I'm not willing to do those things, then I still need to say no.

[00:12:29] Scott Anthony Barlow: Here's lie number three, "I'm gonna do it for just one more year." Whether it's one more year, you know, one more quarter, you heard me say this at the beginning of the episode. It's one of the most common phrases that our team hears from leaders and executives and high income earners in general that have been thinking about making these types of moves for a year, two years, a decade, sometimes even more.

[00:12:53] One more year of vesting, one more year till this payout, one more year of building financial cushion, one more year to find the right moment that never actually arrives. Here is what the one more year sounds like in the words of someone who finally got out.

[00:13:06] Hayley Lowe: I wish I had taken more risks and done kind of crazy things and made more lateral moves. I'm kind of doing more of that in the second stage of my career, but I wish I had done more of that in the first.

[00:13:17] Scott Anthony Barlow: That's Hayley, and you'll actually hear more about her story in episode two. But I think the really compelling thing here is that almost every executive who finally makes this move ends up saying the same sentence in a different version.

[00:13:30] They wished that they had started years sooner than what they did. Katie says the same thing.

[00:13:35] Katie Hyskell: I will say the biggest thing I got out of this now, like in my balance, my husband will comment that this is noticeably different. When I'm in the weekend now, I'm in the weekend now. So that wind down period, like, I can turn it off and on now better.

[00:13:49] Scott Anthony Barlow: Now, if you've seen any of these parts in the conversation that you've been having with yourself over and over again for the last year or two or three years or ten years, then here's what I would suggest. Well, number one, I would encourage you to listen to part two of this episode, because we're gonna get into Hayley's story, and we're gonna get into Katie's story, both of whom you met.

[00:14:11] And we're going to do a deeper dive, helping you understand how they transition and what were some of the additional considerations that most people never consider for career change at this level. That's what part two in this series is actually about.

[00:14:25] And by the way, if you resonate with anything in this episode, from the expertise trap to the three lies to preventing career change, and you're ready to gain strategy, guidance, and support for making a change like this, just drop me an email, Scott@happentoyourcareer.com, 'Conversation’ in the subject line, and I'll connect you with a member of our team so that we can ask you about your goals for your change and figure out the very best way that we can support you. Until then, I'm Scott Anthony Barlow. Adios. I'm out.