Regular Career Checkups for a Healthy Career

Episode Transcript

Kelly Callahan-Poe: What if you treated your career like your health, conducting regular checkups before symptoms get serious? Welcome to the Marketing Moms podcast. I’m Kelly Callahan-Poe, and today’s episode is called Regular Career Checkups for a Healthy Career with Wes Ehnert.

Wes is the founder and principal coach at Vertical Path Coaching and Consulting, where he helps people and teams live and work with intention. With a background in high-performing sales leadership and executive coaching, Wes brings behavioral science and emotional intelligence to his work with mission-driven organizations, helping professionals unlock clarity, confidence, and real results. Thanks for joining me today, Wes.

Wes Ehnert: Well, thank you, Kelly. That guy sounds interesting. I should meet him myself.

Kelly: He is interesting and the interesting part was a connection point. Now you and I know each other from our advertising days way back when the world has changed a lot since then. But when I had a chance to review your podcast, I found something, a little nugget of a commonality that we have and that commonality is that we are both Rush fans.

Wes: Yes, and I was knocked off my proverbial horse. Not that there’s grown women Rush fans these days. It’s just that, you know, we’ve known each other for so long and that never leaked out.

Kelly: Well, we’re gonna leak it today because it’s fun. And so my question to you is what is your favorite Rush lyric or lyrics and why?

Wes: Well, let me just preface that by saying it’s difficult for me because, for the obvious reason, there’s this brilliant lyricist with so many great, deep lyrics. And I also am a person who doesn’t initially pay attention to lyrics. I usually discover them much later after I’ve been mouthing them for years. I’ll say, oh that’s what they’re saying. But mine right now, top of head top of mind and you and I actually already pointed to it is the one in Free Will because I get to use that often and because I love the idea of personal agency and so Free Will has that quote “if you choose not to decide you’ve still made a choice” which is in a way kind of maybe a preface for our topic, which is if you choose not to take a look at your career, it’s going to happen anyway. It’s not going to wait for you to take a look at it. Same thing with free will. Choose, don’t choose—either way you just made a choice. So I do love that lyric.

Kelly: That is an excellent choice. Mine is a little longer, so forgive me. But my favorite Rush lyric is from the song Closer to the Heart. And it goes like this: And the men who hold high places must be the ones who start to mold a new reality closer to the heart. The blacksmith and the artist reflected in their art. They forged their creativity closer to the heart. Philosophers and plowmen each must know his part to sow a new reality closer to the heart. So these lyrics aren’t just poetry to me, they’re a manifesto. In a world increasingly divided by and driven by non-human intelligence, divided by political factions, Rush wrote the antidote back in 1977—that real change starts at the top, but is built by everyday people who take pride in their work. So there you go. I’m one of the very few and proud women waxing poetic about the Canadian band Rush.

Wes: Yes, I love it. That was a great one. You know, and I’ve known that song since I was a child, but I didn’t apply it to today. And it’s so necessary today. It’s perfect for today.

Kelly: All right, well, let’s start with the idea about getting a regular career checkup because I love the idea when you and I chatted about going to the doctor on a regular basis for your body, but you don’t necessarily do that for your career. So talk to me about what a regular career checkup entails.

Wes: Well, we could think practically, technically, and we could say that anytime you decide to stop in your tracks—because of course we’re all going about life—I’ll say this quote now because if I don’t it’s definitely coming and it’s not a Rush quote, but it’s John Lennon who said, “life is what happens to you while you’re busy making other plans.” And I love that lyric because it’s just such a basic truth that while we’re just hustling and bustling and being so busy and being so consumed by the flow and the momentum of our lives, our life is happening. So later you’ll look back in the rear view mirror at your career in retrospect and you’ll see that it’s been playing out just because you didn’t stop being intentional. So at a very simple, practical level, you can stop. Take a look at your documents, your resume, your LinkedIn profile, how you’re speaking about yourself in public settings, networking moments, and just take a snapshot of where you are right now exactly—and what about the materials that represent you? How are they representing you right now?

I’d say that’s more practical. I’m gonna point to something deeper, which will lead you to more profound ways of doing an assessment like this, a checkup. And that is to remember—this is a model that I use—it has you take a look at your life from the core: you, the core identity at the center, playing roles on the periphery. You’re a mom, maybe you’re a friend, a daughter, a boss, an entrepreneur, a club member. You’re all these roles. You do these things. But you are the core identity at the center of that. And that means that you mentally hold this picture of your career and how you’re actually functioning in your career. And if we don’t disrupt those ideas, we may not even realize exactly how our career is happening. So let’s just say we have a role in the job we’re in and maybe we’re headed for some promotion. That’s just a tiny sliver of where your core identity is at, what you may want for your entire actualization of your professional self. This may only be scratching at some of the things you may want and care about, but if we don’t have a stop at the career doctor office to say, let me check my vitals, we’re not going to have agency. We’re gonna keep just being on autopilot, floating on through—or as I made the pinball reference, you’ll just be bouncing around.

Kelly: So the basics are your resume, your LinkedIn, your cover letter, your posts, your website, your portfolio, any training and certifications that you’ve received that might be relevant to demonstrate that you are savvy in AI, for example—what are the things that are hot right now? And for me, as a marketer, I would be looking at branding. How are you branding yourself as an executive? Does it all look and feel the same way? Is the tonality the same? Do you talk about yourself in the same way? Do you have the same catchphrases?

Wes: Yeah, the way I like to frame this with new clients—I work mostly with career clients, mostly in transition, which tends to lend itself to this kind of conversation. I talk with them about becoming aware of their brand. Your brand, as I see it, is that quick take. This is why I can take this one over the next bottle of water, just based on brand. It means I know something by just what I’m seeing. So I talk with them about their brand, the value proposition—what makes me pick this brand, what do I know about it because of these labels—and then the messaging, the words, the images. I have to be aware of all three phases: the brand, the quick take; the value proposition, the nuts and bolts; and the messaging, the words. Because if I’m not consistent, then I don’t really have the brand I think I do. Somebody may perceive me in one place as one thing and in another place as something else. A typical version of that is you’re somebody in your career that someone would meet, they’d take in your brand. When they go on LinkedIn, do they have the same experience? Does it all line up? When they read your resume, does that all line up too?

So looking at all this and making sure it’s consistent—and it isn’t just your resume and your LinkedIn profile, but we’ve got to start there. Your basic portfolio, maybe you have a website that represents you. Start with the basics and then move more towards the internal, where we get to that more complex view: what’s happening from your center point and how you’re operating this complex self with all these roles. What are you being intentional about and what are you not being intentional about?

Kelly: So obviously we all have perceptions of what it is that we think our brand represents, but it’s also important to almost do like a mini 360 from your trusted colleagues, friends, and customers to confirm: does the value proposition that you’re putting out there match what you think it does?

Wes: Correct, you’re essentially having a gap analysis between what you think you are putting out there and what others say you’re putting out there, which is so important for that layer of objectivity. There’s an exercise out there called Real Best Self. All it really amounts to is you plug into this program and you end up sending 10 emails to 10 contacts that have known you throughout your life and various professional and non-professional settings, and you ask them to tell you when they’ve seen you at your best. It’s a really positive one. It’s really hard to go through that exercise and not discover new things about yourself and realize that you may not be talking about your own brand.

Kelly: So a lot of this is obviously outside your annual review because that’s only a piece of the pie. So you really have to create your own goals and make them measurable. Can you give some examples of what goals you might create—short term, long term—and how often are you adjusting and checking those?

Wes: I don’t mean any of these things to be too hard and fixed because I think it’s up to each individual. So it’s finding what’s right for you. That’s why maybe this means a quarterly review for a certain person who’s doing a lot of changing and managing a delicate or complex brand, or maybe it’s just an annual review. The self-check-in is where you get honest with yourself. This isn’t about how I’m performing for others. It’s how I’m performing for myself. Am I showing up the way I intend and want to show up? But the cadence can be whatever makes sense, and I like to work with clients to build a framework they would stick with and find valuable. Build from the ground up. Make sure it has the right amount of depth, the right amount of critical reflection, the right cadence—because everybody’s a little different.

Kelly: Well, let me throw out some things that might be in that framework. Job satisfaction—what areas do I need to improve on? That’s a big one, right?

Wes: Yeah, within a larger context of career satisfaction. You can measure the universe of your job. How satisfied am I with this job on a scale of one to 10? And am I here right now because I’m so satisfied and fulfilled, or am I here right now because it would be really uncomfortable to disrupt what I’m doing? That’s not asking you the larger question: how much career do you have left, and do you have longer term aspirations that you need to start thinking about? Because the runway gets shorter, not longer. Are you thinking about that, or are you going to wait until you suddenly go, my god, I wish I thought about that 10 years ago?

Kelly: Yeah, I just did a podcast with a woman named Nora Bouchard who wrote a book called Hidden Metrics. It’s really about the metrics that we hide from our bosses. And a lot of those things you don’t tell your bosses—those are things that need to be written down and that you need to be moving toward. And a lot of this changes based on life stage. I’ll be an empty nester this year.

Wes: Congratulations.

Kelly: Yes, I’m very excited, actually. I’m semi-terrified. But that’s a different place in space versus mid-career or early career. And so the types of goals that you have—you’re also kind of working on Maslow’s hierarchy of needs, where I’m really focused on self-actualization, the second mountain. Am I spending my time late in my career doing things that are my strengths, that give me energy, that make me feel fulfilled? And am I giving back to the next generation? Mentoring, that sort of thing. For me, those are a huge piece of the pie. But that changes based on your life stage.

Wes: Absolutely. And I think you make a really important point about self-actualization because it is different. If you’re fresh out of college, you’re trying to join the workforce. You have very different thoughts at that point about what it would mean to have personal agency, and what it would mean to do something fulfilling might just be to have a job where you can learn. Whereas later someone might consider introducing greater risk, perhaps much greater risk, for greater reward or better self-actualization.

I can tell you from a personal level—I was with a corporation for a long time, spent all my career in large corporations, and then six years ago got laid off. That was a huge disruptor, which is a gift, because if you’re not doing career check-ins, that says you are going to do one right now. And what’s good about that is you check where you’re at, and you realize that you might be ready for some risk you were never ready for before. In my personal case, I was ready for a level of risk and personal investment that I was never ready for before. I’ve now reached a certain level of competency and confidence. I’m talking about what I do now as a coach, as a performer, as a speaker, doing stand-up comedy, speaking, writing, podcasting—these are all self-actualization points that would not have really been realistic or even conceivable six or eight years ago. So the phase of life I was in was everything.

And one thing I encourage my clients to do is take a look at their core values and the priority order of them, because while they’re usually semi-permanent, they do change. At one point in your career, stability may be number one, whereas later, adventure starts fighting for that top spot and maybe even knocks stability down a peg, and suddenly you’re ready for different kinds of ventures.

Kelly: Absolutely. Well, this whole idea of planning for potential career disruption—I’ve always called it always have a Plan B. My dad moved around a lot when I was young for his work, so I was always the new kid. During my career I worked in LA, San Francisco, DC, client side, agency side. I’ve become very adaptable. And then COVID hit, had to pivot. I’ve learned that my superpower is actually all about navigating change and making sure that I am adaptable, anticipating what’s next, always having a backup plan because unexpected things do happen. If you’re in advertising and marketing, you will lose your job at least once. More than likely two or three times.

Wes: At least one. Yeah, I did that.

Kelly: Me too. And you need to anticipate that disruption in order to restart your career. At my wedding, my dad said, what’s your Plan B if the caterer doesn’t show up? I didn’t have a Plan B for that—Mexican. That’s really kind of been droned into me. But it’s essentially the thesis of my entire career and the reason why I started this podcast, whereby my Plan B has become my Plan A. And that happens a lot as well.

Wes: Plan B can end up being Plan A. Take the person who starts some side gig and then the side gig takes off—it’s no longer Plan B anymore. I want to draw a juxtaposition there, though. I think you’re absolutely a hundred percent correct and pragmatic and smart to think about a Plan B. On the other hand—I don’t know if you’ve ever heard this saying—what usually kills Plan A? Plan B. Because as long as you have Plan B as a fail safe, Plan A—you can sort of reason with yourself well enough to not really throw yourself down. If it gets tough or it gets scary, I have Plan B. And so sometimes, depending on where you are in your career stage, the very thing you may want is to not have a Plan B. Not a practical plan for if your basement floods, but the kind of Plan B that says I’m going to drive towards owning my own business—I’m going there. It’s not a question of whether I’m going there, it’s a question of whether the business can succeed or fail. Fail fast, try something else. Some things just require every fiber of your being to move towards them.

Kelly: I guess I would argue that frequently a Plan B is something that you’ve manifested in your head that may be part of what you truly want to do but never had the guts to do. Otherwise you’d be doing it. So I think it depends on your Plan B. Maybe there’s a Plan B, C, D. What if money were no object?

Wes: Absolutely. If it serves you to consider these optional plans—what I’m hoping to do with every client is enable them to go to a safe space where they can answer this question: what do you want to do? What do you wish to do? And I don’t want the Plan Bs or the fail safes to prevent them wandering over there to be able to answer that. You’re doing this podcast and I’m just guessing here, wild guess—the main reason for doing it is because you wish to do it, you want to do it. You’re probably doing this right now out of a sense of expansion from some part of you that has this to give. And it’s primary. That’s why it’s in the lead right now.

Kelly: Exactly.

Wes: I have clients that struggle to find the safe space to dream. Sometimes they need to imagine a world where they only thought about what they want and wish for. Then what would it be? Sometimes they don’t even know that there’s a ton of energy in that little spot, but they left it back there somewhere a long time ago or wrote it off. “Oh, that’s crazy, I could never do that.” But yeah, maybe they could.

Kelly: What are the warning signs that someone’s career is overdue for a checkup?

Wes: I like that question because it immediately suggests maybe we could have a checklist. Some of the warning signs I see are emotional. If I’m dealing with negative emotions—which may lead to a term like burnout; I don’t love that term, but we all know what it means—if you’re sad, if you’re angry, if you’re anxious, paying attention to what you’re feeling is a good signal to look at your life and say, am I running this thing the way I want to? Am I even running it? Is it running me? Your emotions are a key indicator.

Another is cognitive dissonance—something is just not feeling right. I see this often with people in transition. They come in with an idea of what they want to move toward, and then they find they have this resistance to the idea even though they’re telling me this is what they want. Or they tell me, “this is what I’d really love to do, I’m not going to do it, but it’s really interesting.” Something rubs the wrong way and they move away from it and avoid it. These cognitive dissonance moments usually trace back to your core values. What two values are not playing well together? Probably two core values are at war. You’ve always been taught to lean with one, but now in your current place in life, that’s just not as important as it used to be. And that creates that cognitive dissonance.

Kelly: I also want to mention—does networking fit into a career checkup? Should you be benchmarking your salary and your market value? And does a career checkup differ depending upon where you are in your career stage?

Wes: Let’s take salary and market value first. This one is highly dependent on your core values, because we first have to determine how important salary is. It may have been everything before or nothing before, but now it’s different. So first that has to be determined. Now I can say, this is really important to me—I’m not making enough or I want to travel in retirement, I need to build up a stockpile. Now I can work with that. On the other hand, if your core value tells me you’re really going for personal meaning—you want to do something with a nonprofit because that’s your driver—then market value isn’t going to help you as much as fit, cultural fit, purpose, mission. So I would put values before market value considerations.

Networking is evergreen. I don’t see when there’s a time in your career where networking isn’t a good idea. Let’s reduce networking to something more life-basic: community. We need community. Whether we want to belong in professional circles, or we want to surround ourselves with people who challenge us because they’re better, smarter, and further ahead than we are, or we want to share ideas, or we want to teach—those are three different phases you could be in. Networking is the vehicle for all of them. And the older you get, the more isolated you can be. Staying connected matters at every phase.

Kelly: In your consulting practice, you have a lot of tools you use to help people with career checkups. Can you go through some of those, and are there any tools available online for free or low cost that you’d recommend for people to do their own career checkup?

Wes: Absolutely. I keep mentioning core values. I use websites that I found that are excellent for doing a self-driven core values exercise—they give you a large sample to choose from and give you ideas for others. You can do a core values exercise for free just by doing something online. You don’t have to buy a thing. I’m always looking for those for my clients because I don’t want them to have to invest in something if they don’t need it. Take your core question and go to ChatGPT or Claude—let’s see what that’ll offer. Just always use your grain of salt with whatever you get from AI and the internet. But there’s plenty of free tools out there to examine what it means to be purpose driven.

I like to use Myers-Briggs, and I’m certified in it. I think it’s terribly misunderstood and has rarely been applied correctly. It’s based on Carl Jung’s theory about how we’re born with preferences, not traits, not skills or strengths—preferences. We either prefer introversion or extroversion. And then even those who teach that correctly often miss the latter piece, stage two of the MBTI assessment: how have you worked this out in the world? How have you developed the preference you don’t prefer, because you probably need that one too. Self-actualization would mean developing all your opposite preferences. So I love that tool. I think it’s very misused and underutilized, but that’s how I use it.

I use cognitive behavioral coaching. It’s based on cognitive behavioral therapy—you’re looking at how you’re interpreting activating events in your life and career. Something happens that you consider innocuous initially, until you give it meaning. And then you have a resulting feeling or emotion from that. This allows you to go back and decide if you gave it meaning with data that would back up that meaning, or did you just react? That could change everything.

There’s a fantastic tool that I’d encourage people to read about before they use it. The book is called Immunity to Change. The authors are Kegan and Lahey. They describe how people can build up an immunity to changing—it’s self-preservation, self-protection. We don’t want to change, so we build up clever mechanisms to protect ourselves from it. We may really want to change something consciously, but we will have some competing desire to do something else because we were taught that. They walk you through an “immunity map,” a five-step process, to discover the hidden assumptions operating beneath your behavior. Becoming aware of those assumptions allows you to make a conscious choice about whether you want to continue doing what you’re doing or not. You can’t change what you can’t see. Awareness brings change—that’s something I like to live by.

Kelly: I’m also a huge fan of workbooks. I just picked up one that I love—it has a personal manifesto, 2026 goals, a goal setting planner, an action plan, and a weekly schedule. And I also think about fitness tracking. For fitness, we track everything. I have a fitness tracker on my phone showing me my sleep, my yoga, my walking, my workouts, my meditation, reading. I track that on a daily basis. Why don’t we do that for our career goals? Where it’s front and center and you can see it right here on your iPhone. Goes back to your premise: we’re tracking our body—are we tracking our careers?

Wes: Let’s just drop the mic right there. Why don’t we do that for our career goals? Create the app, have somebody build you the app. I do have something in mind that I am working on in terms of an app, but you’re right on it. Our career needs our attention. Let’s be intentional and track.

Kelly: Well, I want to ask you one last question. You’ve worked with hundreds of executives and teams in your coaching practice. What are the biggest challenges that you see—the top two or three—with regards to maintaining, tracking, and transitioning careers?

Wes: I’ll give you the top two, they just popped right into my head. Number one, fear. Number two, limiting beliefs. Which are closely related. Take this basic premise: people move towards pleasure and away from pain. Fear is really uncomfortable, which means pain. So we’ll do anything to move away from what scares us. That’s the number one thing that might be keeping us from what we could be doing right now. When you get to your senior years and you’re in a rocking chair somewhere thinking about your past, it will be the things that fear stopped you from doing or being or approaching that you will wish you could go after again. You can’t get rid of fear—you have to face it. You can’t go around it.

Second, limiting beliefs. Wherever we might land on nature versus nurture in terms of how a person develops, we end up as human beings with a certain amount of limiting beliefs that I would suggest are about nurture—meaning we weren’t born with them as much as we were given things that caused them. So we kind of think, well, I could never do that.

Remember earlier you asked what’s a signal that it’s time for a career checkup? Here’s a third one, and maybe I should make it number one: if you’re fixating on what other people are doing and it’s getting under your skin, the problem isn’t what they’re doing. It’s what you’re not doing. You will find satisfaction if you start doing what you want to do, and you won’t care what they’re doing. But when you care what they’re doing and it’s bothering you, that’s a signal that it’s time for a career check-in—that you’re fixating on the other grass being greener.

Kelly: Very helpful. I think you’ve given a lot of good resources for people to think about in this podcast. So I appreciate your time today, Wes. We will provide links to your podcast as well as all of the resources that we talked about here and your website. You can listen or watch this episode on Apple Podcasts, Spotify, or YouTube, or on MarketingMoms.com. Don’t forget to subscribe and share, and thanks for joining.

Wes: Thank you so much, Kelly. This was an unusual interview. Thank you so much for an energetic, inspiring interview. That inspired me. So thank you. Alrighty, bye.