In this insightful episode, Eric Woodard, CEO of Win At Work, shares how you rethink dissatisfaction, stop chasing entrepreneurship as an escape, and find alignment by focusing on real needs and human connection. If you feel stuck, frustrated in your work, or tempted to start something just to “get out,” you won’t want to miss it.
You will discover:
– How to use curiosity and market needs to find work that actually creates momentum
– How to identify whether your dissatisfaction is situational or a sign you’ve stopped growing
– Why starting a business to escape a bad job sets you up for failure
Episode Transcript
Scott Ritzheimer
Hello, hello and welcome. Welcome once again to the Start scale and succeed. Podcast, the only podcast that grows with you through all seven stages of your journey as a founder, I’m your host, Scott Ritzheimer, and you’ve heard it like just about every founder’s story out there starts with a bad job. We hear it all the time, so often that something unusual has happened, I think, over the course of history, and that is that we’ve started to think that maybe the only way, or definitely the best way, out of a bad job is to start our own organization. But I think that could be a huge mistake, because getting out of a bad job is a bad reason to become an entrepreneur. I believe that with all my heart, I believe there’s a much, much easier way to find fulfillment in your work. And my guest today is going to be able to help us find the way.
I’m really excited about this. Today’s guest is Eric Woodard. He is the founder of win at work, where he helps founders, leaders and professionals build careers and businesses that actually work for their lives. He’s known for turning complex career and leadership challenges into clear, practical steps people can take right away through coaching, workshops and content, Eric helps people get unstuck, build trust faster and create momentum without burnout. And His work focuses on clarity, confidence and human connection, especially during moments of growth, change and reinvention. Eric believes success should be should feel sustainable, not exhausting, and his approach blends real work experience with simple frameworks that stick, and he’s here with us today, Eric, welcome to the show. You’ve coached some folks through some pretty significant career transitions, and have made some remarkable career choices yourself. What does real job dissatisfaction actually look like, and how is that different from just having a rough stretch?
Eric Woodard
Yeah, well, Scott, first of all, so happy to be here. I just want to honor you for like, putting together this podcast and serving all the people that you do. It really makes a positive debt in the universe. And you’re exactly right about, you know, often when people are in a bad job and they don’t know what to do, they will one of, one of the things that some will do is they’ll be like, Well, I’m gonna start my own thing and look for some people that’s, that’s a great move. And unless you’ve got, but unless you’ve got that pitch, it’s, I wouldn’t say it’s necessarily an easier path. And so, so to answer your question, you know, some of the options, or some of the ways to make a job better, and I’m stealing this from from one of my coaches, the godfather coach, a guy named Steve Chandler, is the idea of agreement. So often, when people are in jobs, they’re just living in a world of expectation without agreements. And that can be a whole big, giant recipe for her.
Scott Ritzheimer
Yeah, yeah. And there are times in any career that it’s a little mundane, right, that it’s a little challenging. How do we know if that mundane is systemic or situational? How do we know if, hey, this is something that is a attention to be managed in this the course of normal life, or a problem to be solved?
Eric Woodard
Yeah, it’s a great question. And look, I think that happens in every arena, right there. There are seasons, even as an entrepreneur, you know, there are seasons of sort of ho hum boredom, and then there are seasons, seasons of sheer terror, and then there are seasons of excitement and growth. And the same thing happens in, you know, a w2 job. I don’t think that’s unique to somebody, you know, doing a nine to five. But one way, you know that one, one can sort of have a sense of it is, you know, like, like, how’s the learning, right? My experience is, is that people are in jobs that that sort of, you know that for sort of feeling stuck, that being in a rut really boils down to, like the sort of the learning curve has stopped, like challenge, you know, because when people aren’t learning and they’re not challenged, they’re often not really happy. And by the way, this is not unique to jobs. This is unique to, I think, any, any arena. So you know, if you’re in a job and you’re feeling that it might the job might not be the problem. It could be that, you know, you might not have been as entrepreneurial within your job as you could be or want to be, or it could be that you’re now overqualified for the job you hold, and it’s time to get it’s time to level up within your organization or another organization. But it may not necessarily be, you know, the next level. Could be entrepreneur, but it might not be.
Scott Ritzheimer
Yeah, so a lot of times when folks are frustrated with their job, I call them dissatisfied employees. But folks are frustrated with their job, it’s usually my boss, this, my pay that, you know, the compute, commute, this, it’s almost always some kind of external factor, but I just don’t think that adds up. What, what is the real driver behind dissatisfaction that you found in your work? And how can we diagnose it the proper way?
Eric Woodard
Yeah, so sometimes it, you know, I mean, I agree with you, those are, like, the bad boss. It’s, it’s not really the bad boss that’s making me upset. How we’re relating to the, quote, bad boss, and even the fact that we’re relating to them as bad. And it could be that, you know, we’re feeling, you know, gets back to, like the Maslow stuff, right? You know, we’re feeling afraid. At some level, we’re feeling threatened. And that can be our identity, that can feel, you know, we’re a social tribe species. If we want to go back to all the caveman wiring, right? There’s somebody, you know, here’s an interesting thing about jobs, by the way, and with all deference to our Native American friends, this, they could be an exception, but the closest thing we have to a tribe in the modern day is probably our work, and the boss is the closest thing we have to a chief, right?
And so we’re sort of wired that way to operate in, you know, that’s just, I mean, this goes back to, like, amygdala, you know, lizard brain stuff like to operate within a tribe and the social interactions within and if, for some reason, we feel disrespected in the tribe or positions not recognized, we have wiring that basically tells us that we’re about to die, because 100,000 years ago he might have been. And so if we can sort of glitch out of that and realize, no, I’m not, I’m not threatened here, it’s just that there’s, there’s something at work that’s a little dysfunctional, and rather than take my ball and go home or quiet, quit or sit in a corner and pout, we have these magical things, Scott, these magical things. They’re called requests. We can make mouth words. We can go to people and we can say, Hello, let’s co create an agreement around what’s happening here to make it gooder for everybody. And often, what happens is they say yes, and if and when they don’t, that’s when we can get really curious and replace judgment with curiosity, because my boss is a jerk. Is really a form of judgment. Whereas if we can replace that with I wonder what’s going on for my boss, miracles can unfold.
Scott Ritzheimer
Yeah, yeah, I love that, because there’s so much that we can do even without changing the job, right? There’s so much that we have control over, and that a bad job isn’t necessarily a bad job I love it’s the way that we relate to it that’s really profound. Now, there are some bad jobs and there are some bad bosses. There are some circumstances, maybe even not a bad job or a bad boss, but just something that we’re out of alignment with ourselves. How do you help folks get to the bottom of what a dream job would really look like? What’s the right work for them?
Eric Woodard
Yeah, well, I mean, the first question is, if and when we feel an upset, right? If and when we are angry about our job or dissatisfied or whatever, the first question to ask is, you know, where are we? Where’s that coming from? Are we? You know, are we? Are we reaching that conclusion on a Friday afternoon when we’re tired and we haven’t eaten and we haven’t petted a dog in a while, you know, like, like, if we’re like, already triggered, that might not be the best time to make this analysis. But let’s say, for argument’s sake, that we’re, you know, we’re sitting on a mountain in Tibet and we’re meditated and we’re eating and we petted a dog, and we’re coming from a place of neutrality, right? This isn’t just a panic, hangry sort of moment, and we’re like, kind of neutral, and we’re like, yeah, I don’t want to do this anymore. I don’t want to, you know, deal with this anymore. Then that’s a place where we can, we can be like, okay, yeah, this isn’t the job for me.
And then what, oftentimes, what I find is people will do is they’ll go into trying to explain it, right? They’ll start judging themselves. Well, you know, they’ll start shooting themselves right, and and they’ll be like, well, I should, I should, I should, I should. And I’m like, yeah, if and when you’re done, you don’t have to explain it to anybody, including your employer, right? If they’re like, why are you leaving? Because I want to, but why? Because I want to, right? That’s perfect. I mean, this is what I like to call my yay capitalism speech, there are things about capitalism that one could, you know, arguably debate the pros and cons. And one of the maybe good things is, is free movement of labor. They can often fire you at will. And guess what? You can quit at will, and you can change jobs at will. Yay capitalism. This is the way it works, for better or worse. So yeah, we don’t have to fret about it too much. We can just decide and take action and come from a place of efficacy and agency.
Scott Ritzheimer
Yeah. And so once somebody has taken that degree of agency, they’ve realized, hey, maybe this isn’t the best place for me. This isn’t what I want to do. There’s this big looming question there. There’s like, what do I want to do? And so how do you how do you help folks answer that question?
Eric Woodard
Yeah, Scott, do you know the Japanese idea of ikigai? I bet you do. You know what I mean by ikigai? Have you heard that? Okay, so
Scott Ritzheimer
I heard it from a car show. So yeah. Keep going.
Eric Woodard
that, for that, for your listeners who don’t know, it’s basically Venn diagram, four circles. The circles are, what do I want to do? What am I good at? What can I get paid for? And what does the world need? And what I find a lot is people focus on what I want to do. They make focus next on what can I get paid for. Then they’ll focus on what I what am I good at? And finally, at the end, they’ll focus. On, what the world, what does the world need? And my invitation to anybody who’s trying to figure out their career stuff is to flip that,
Scott Ritzheimer
Wow
Eric Woodard
ask the question, what? What’s needed out there? And my friends, the world is in need right now. I mean, just turn on the news. The world is in need. Like, only everywhere there’s plenty of need out there. So, so you know, if you can build a better mousetrap, people are going to beat a path to your door, and that that has never been more true today, whereas if you’re out there, just really focused on me, me, me, me, me. Let me tell you how I can be impressive. Let me tell you about my skills and experience. They don’t care. They don’t care because they’re only thinking about one thing employers. That is, they’re thinking about themselves. So let’s focus on them. That’s how we can create miracles in our career.
Scott Ritzheimer
Yeah, it’s, it’s really cool, because it gets into what a lot of entrepreneurs deal with, is, how do they find a market, right? And how do they present what they offer to the market? And so there’s, there’s so many parallels there. For for our audiences, you have to it’s not about you. And so this is a total soapbox space for me, but it’s like, it’s why jumping into being an entrepreneur because of a bad job thing sets you up for failures, because you’re doing it all for yourself and about yourself, and that’s not going to work any better there than it does in your current job, which is a real problem. So I’m going to set you up a little bit. We didn’t talk about this ahead of time, but this is a something that’s really important. I think we’re highly aligned on it. But one of the things that I’ve noticed is you’ve kind of oscillated between the word job and the word work, and you’ve done it probably in the same way that I would just quick definition. What’s the difference between a job and work?
Eric Woodard
Yeah, well, they’re a little bit synonymous, I guess that. Thanks for pointing out. I guess the way I’m using it as a job is like a w2 right? Like it’s, it’s maybe a container for work, or one type of container where we do work, right? We We trade our time for money, we trade our expertise for money, and we get a salary. And it’s, there’s a job description, there are hours, there’s hierarchy around it. It’s a dub, you know, in the US what taxes is tax season, right? It’s what we would call we get a w2 right? It’s a salary position. Whereas, you know, work, you know, we could be working in our yard, we could be working as an entrepreneur. We could be working, you know, cleaning, you know, making dinner. I think work is probably, and those would be other kinds of containers for, for the idea of work. And, you know, I’m blanking on, on, on his name, but the guy who wrote The War of Art has written a lot about about this, Right?
Scott Ritzheimer
Steve Pressfield,
Eric Woodard
Panfield, yes, yes, yes. Like, yeah. Pressfield, he’s written a lot about the idea of, you know, what’s a professional? And a lot of times, you know, we can be a professional in a lot of ways. That doesn’t relate to being that’s the other word we could throw in here, job, work, professional. You know, those are three ideas that can sometimes happen in the same time, in the same place, and not necessarily great question,
Scott Ritzheimer
Yeah. yeah I love that. I love that. So I have this question, Eric that I ask all my guests. I’m very interested to see what you’d have to say. But the question is this, what is the biggest secret that you wish wasn’t a secret at all? What’s that one thing you wish every dissatisfied employee out there. Listening new today.
Eric Woodard
It’s great. It’s such a great question, and we’ve touched on a little bit. But there is no greater opportunity in the world to replace self centered judgment with them centered curiosity, right? If we can, if we can make it about them and not judge them, but be curious about them, I mean, miracles will unfold in our work, in life every time.
Scott Ritzheimer
Yeah, I love that. I love that them centered. Curiosity is so good. Eric, there’s some folks listening who is just the right message, right time. You’re exactly what they need at this stage in their career. They’d love some help just working their way through some of the complexity here. Where can they find out more about the work that you do. Where can they connect with you?
Eric Woodard
Thanks so much, Scott. So if you want to find out more, go to winatwork.io that’s winatwork.io I run a free workshop, like every week. It’s free for anybody, and just come and you can learn a lot more about how to get hired fast. We’d love to have you there.
Scott Ritzheimer
Fantastic, fantastic winatwork.io we’ll put that in the show notes for everyone. You don’t have to go find it, just tap or click there. And yeah, Eric, fantastic. I loved this conversation. It was exactly what I needed today. It was a lot of fun. Thanks for being on we really appreciate having you here. And for those of you watching and listening, your time and attention mean the world to us. Hope you got as much out of this conversation, as I know I did, and I cannot wait to see you next time. Take care.
Contact Eric Woodard
Eric Woodard is the founder of Win At Work, where he helps founders, leaders, and professionals build careers and businesses that actually work for their lives. He is known for turning complex career and leadership challenges into clear, practical steps people can take right away. Through coaching, workshops, and content, Eric helps people get unstuck, build trust faster, and create momentum without burnout. His work focuses on clarity, confidence, and human connection, especially during moments of growth, change, or reinvention. Eric believes success should feel sustainable, not exhausting, and his approach blends real-world experience with simple frameworks that stick.
Want to learn more about Eric Woodard’s work at Win At Work? Check out his website at https://winatwork.io/
Connect with Eric through his LinkedIn at https://www.linkedin.com/in/ericwoodard/