488: Quitting A Great Job To Pursue Career Happiness

What happens when you quit a job that everyone else would love to have? That’s exactly what Bobby did when he felt a tug that he was meant for more.



Bobby Grimm, Engagement Manager at Resultant

Bobby was working for a great organization, doing meaningful work he enjoyed, but he still felt like something was missing from his career.

on this episode

There are certain criteria that people who work with us are looking for in their career: work that is impactful (or what we call meaningful work!), work that you’re great at because you’re using your strengths, and work that allows you to be around people you enjoy and a team you love working with. 

So what if your current job checks all of these boxes, but you still feel that tug like there’s something else out there for you? How do you justify leaving what many would consider a great career? And where do you even start?

Bobby was enjoying his job, but he had been at the organization for 8 years and had gotten to the point where he couldn’t stop thinking “what else is out there?”

It would have been really easy for Bobby to stay at his organization because it checked almost all of the boxes. Listen to how Bobby talks about knowing when it was time to put a stake in the ground and go after true career happiness in a new, exciting role.

In this episode, Scott and Bobby discuss how Bobby took the time to dig in and got really granular on exactly what he really wanted and needed out of his next role, and then how he made it happen.

What you’ll learn

  • How setting boundaries can keep your career change momentum going
  • The importance of following your gut feeling and how it relates to career happiness
  • How to use your personal network to better understand your signature strengths
  • How to know when it’s time to leave a “great job”
  • Exercises to better understand what fulfilling work means to you

Bobby Grimm 00:01

What it ultimately came down to was the idea of something new and different, even if I didn't know what it was, continued to be more exciting than staying where I was.

Introduction 00:17

This is the Happen To Your Career podcast, with Scott Anthony Barlow. We help you stop doing work that doesn't fit you, figure out what does and make it happen. We help you define the work that's unapologetically you, and then go get it. If you feel like you were meant for more and ready to make a change, keep listening. Here's Scott. Here's Scott. Here's Scott.

Scott Anthony Barlow 00:40

I think all the time when people find our podcast, they think about, "Well, I must not enjoy my job." Or "This is for people who don't really like their work and want to do something that they actually do like." And actually what we find is, that's not always the case. What about if you were changing careers, and you've had a job that actually was something that you really enjoy? And maybe you've even found that it's impactful? Or it's, what we might call meaningful work or more fulfilling work, and you're even great at your job because you're using your strengths, and you have a team that you love working with? Okay, so if your current role checks these boxes, you might wonder, why do you still feel that tug to make a change? Is it possible to justify leaving what many people might consider a great career? The short answer is yes. The grass may actually be greener on the other side.

Bobby Grimm 01:37

I think that was one of those moments that I was just realizing that being good at something, though, doesn't necessarily mean you're going to be happy at it, or that it's as fulfilling as something else might be.

Scott Anthony Barlow 01:51

That's Bobby Grimm. Bobby is a career change veteran. He started his career as an attorney and eventually transitioned to the nonprofit sector. After eight years in his nonprofit role, he wasn't necessarily unhappy. But he had gotten to the point where he couldn't stop thinking, "what else is out there?" Bobby did a great job setting boundaries around the fact that he needed to change. It would have been really easy for him to stay in one of his roles, because it was almost checking all the boxes. Here's Bobby, going way back to the beginning of his career.

Bobby Grimm 02:24

I often joke by telling people that I'm a recovering attorney. So I was finishing up college shortly after 9 11, job market was changing as a result of that tragedy. But from my standpoint, I had always thought about going on for something past College Law School had kind of been on the radar. So I went and really didn't enjoy just about all of law school. But I came out, and my first job was a judicial clerk. So I worked for a judge on the Indiana Court of Appeals. And so I did that for about a year and then went into private practice. And I was primarily a business litigator. So that's kind of the high level, but I did that for, I think I practiced law in total for about eight years or so. And during that time, I had just had kind of an interesting conversation with a friend about, "I'm not sure if this is what I want to do for the rest of my life." And that was just really informal, literally sitting around the pool talking. And maybe a year or so later, she called me up and was like, "Hey, have you ever heard of KIPP?" I said, "No. What's KIPP?" And it was, you know, KIPP is a network of nonprofit charter schools. We got talking, because she'd come across a role that she thought I might be interested in if I was truly interested in, like, a non-traditional path after practicing law. So I looked at the role, interviewed for it, the person that interviewed me ended up leaving the organization, so the things just kind of died there. But I was really fascinated with what KIPP was doing. I scheduled like a tour when I visited the local schools in Indianapolis, it was just really taken by what I saw. So I was like, "I got to be involved with this." I started volunteering there for about two years. And then fast forward a couple years, they got a big grant. And that executive director said, "Hey, this might be a shot in the dark, but you clearly care about our organization. I'm creating a new role. And I'm wondering if you would be interested in applying for it." So I started working there. So I wasn't in the charter school world then for about the next seven or eight years I think it was.

Scott Anthony Barlow 04:37

What caused you to decide that you wanted to move on from that role, that situation?

Bobby Grimm 04:45

Yeah. So I felt limited in where I could go. I felt a little bit limited in terms of like, I don't know that I want to be pigeonholed into education to finish my career, and I was already approaching that seven or eight year mark where it was like, "well, a lot of people would probably view me as pigeonholed", so to speak.

Scott Anthony Barlow 05:03

It's that eight year mark, by the way? Eight years where you spent in attorney land. And then eight years... it's the time period for change.

Bobby Grimm 05:13

I guess so. And honestly, that was part of it too. It's just, I think about like the world we live in, it's so normal for a lot of people to move on after a couple three years, it's pretty rare that people stay in a job for their whole career, let alone, or even just the eight years that I did, but I was ready for a change. And then I think I also just was, I can tell that the way I felt on a day to day basis over time was just not feeling fulfilled. I was concerned about coming home and carrying the stress, or the frustrations or the dissatisfaction, the wonder, or the wanderlust of like, what else could be next, and I'm not doing anything about it, and that's affecting the way that I come home and act with my kids or with my wife. So there was a part of that. And honestly, I didn't know what was going to be next. So I just knew that where I had been, or where I was, I had sat on it for long enough to know that nagging feeling of wanting to make a change didn't go away. So I finally just had to do something about it. And I put a stake in the ground. I gave nine months notice saying, "I'd love to finish out the rest of our fiscal year, if you'll have me." And that was done without knowing what was next, I was going to figure that out. But I felt like it was the right thing to do to give my colleagues as much notice as possible so that they could kind of work and I could collaborate with them to find my successor or successors.

Scott Anthony Barlow 06:32

I love that. That's actually a technique that I've used many times over, where putting that stake in the ground, as you say, causes it to become a reality, or for, in my case, I think about it causes me to make movements I would not otherwise make or more rapidly than I would make without it. And it sounds like that same thing was true for you. Was that something that was uncomfortable at the time? Or did it really just make sense for you and feel very comfortable? What do you remember feeling as you were doing that, as you were having those conversations with the leadership team, as you were talking to the people at your organization and letting them know, "I'm going to... here's the steak, I'm leaving in nine months" what was that like for you?

Bobby Grimm 07:38

Yeah, it was hard at times. I mean, and it was hard throughout, really, the next... until I found my current job. So I mean, I wrestled with it. And I'd say for a couple of different reasons. You know, when I had the conversation with my boss in October, and gave that nine month notice, part of his response was, "Help me understand why. Because you're really good at what you do. You're doing work that's impactful, and it matters." And he was saying this with all sincerity. And the third thing was, "you like the people you work with", like that's a pretty good combination. And all of that was true. And my response was like, "Yeah, you're right. I think that was one of those moments that I was just realizing that being good at something, though, doesn't necessarily mean you're going to be happy at it, right? Or that it's as fulfilling as something else might be, or something that comes naturally or that best leverages your signature strengths versus, right?"

Scott Anthony Barlow 08:35

Do you remember what you said at the time to your boss? Do you remember how that conversation went? Or what words you use as you're talking through it?

Bobby Grimm 08:42

Yeah. I think it was similar to... I said, "You're right." I said, "You're 100% right. And I don't know what's next. I just know that I've been kind of thinking about making this change. I've been sitting on it, I've been talking to my wife and friend about it. And literally just trying to figure out if this is like a temporary thing, or if this is... if I'm really ready for that next step. And so, I didn't make this decision lightly. There was a lot of, like, thoughtfulness that went into it." I think I just, going back to the stake in the ground, I think I just said, "I put a lot of thought into it. And that feeling hasn't gone away that I'm just ready for a change. And if I already know now that I'm going to be looking and leaving I'd rather just be as transparent and collaborative with you to help find my successor versus giving you some, you know, two weeks notice before I leave" and again, there's nothing, like you said, I don't think that it's wrong in a lot of situations to give two weeks notice, but I think for me, I just... I know that if I'm going to be leaving, let's plan for it. And I trusted that they would be right by me in that process, not showing me the door sooner than necessary and they did. So.

Scott Anthony Barlow 09:55

What happened next? Your dad had tragically passed away unexpectedly. And then the world was in this upheaval in some ways, as people were experiencing everything that came along with the pandemic. And you were adjusting to being a stay at home dad, which was a decision that you had made as well. So tell me about what that time was like.

Bobby Grimm 10:24

Yeah, so everything you just said from the environmental situation, like making the decision to primarily be a stay at home dad was not ever really in the plan. It happened because of the timeframe that you just mentioned, right? Dad passes, I'm gonna take a break, or wait to start figuring things out. And then when COVID happened, it was a joint discussion, really planning, really family planning discussion with my wife, right. So she had a great job, her company was positioning to sell or getting acquired. And long story short, they did. But because of the fact that I had already made this decision that I was ready to make a change, she needed to stay in order for the acquisition process to play out. And then when COVID hits and schools and daycares are closing, or you don't know what they're going to be doing from one day or one week to the next, like, we needed somebody with that flexibility to stay home. And we also had, just as a family decided, like, we don't know what this really is going to be. So we didn't want our kids out in a daycare setting. So we kind of had the discussion– I stayed home, that was my primary responsibility. Meanwhile, I would be figuring out what would be next whenever the dust settled. I think kind of in that process, too. I was a little bit fortunate that I had some former colleagues that reached out and said, "Hey, are you doing any sort of, like legal or consulting work for schools in particular?" Because they were at this point working for different organizations and like, didn't have the ability to have somebody in house like, and the role that I was in. So I was able to start my own business and do that on the side. So I would say I have this side hustle of being a legal and business consultant for schools. So I did that just part time. But yeah, number one responsibility in our house for me was to be the dad, the caretaker and all of that. And that was really hard. Because being a father, being a good father is something that is top of the list for me, from a priority standpoint, always has been and will be, but at the same time, like I didn't envision it happening by being a stay at home dad, right? So I really wrestled with this, I felt like this dichotomy of... this is the right place for me to be right now, and I'm getting to spend more quality time and more bonding experience with my kids than I would ever have gotten outside of a situation like COVID, but also really wrestling with like, I'm supposed to be figuring out what's next for my career and finding that next opportunity. And doing both was just really challenging.

Scott Anthony Barlow 13:02

What do you feel like it was that caused you to decide to seek out other help for moving back into a different type of role?

Bobby Grimm 13:14

I just found myself trying to reflect, trying to think about what I enjoyed, and I think I was doing some of the right things. But one day, I just literally got on and Googled– "how to make a career change?" or something like that. And I found Happen To Your Career, pops up. And I see that they have this eight day mini course. I'm like, "Okay, cool. This sounds great and it's free. This is an easy way for me to have some support to guide me through this process." While me being super detail oriented or thorough, and I think I enjoyed the reflective part of the process as well. That eight day course probably took me more like a month or two. I don't know.

Scott Anthony Barlow 13:58

I could really see you digging into it, for sure.

Bobby Grimm 14:01

Yeah, I mean, I literally would sit down and reflect and journal on those things. And then I just got to the point that I felt like... I had looked maybe at some other opportunities as well. But I felt like, if this is the kind of content that you have and use for free, I'm gonna give them a call. So I scheduled a call, talked to Phillip, and just from the time that I did the a day mini course to talking to Phillip to meeting you, I kind of, and other people in the organization just felt very authentic, like I said before, it's important to me, your normal people who genuinely care about helping people. It's not just the business and maybe if I think that all the other people are normal that means I'm the crazy one. It just felt right. So yeah, started working with you both and then after that.

Scott Anthony Barlow 14:53

Well, I have appreciated the opportunity to work with you. And you and I actually got to do something, I don't think we've ever done quite the same way. You and I got to work together for a couple of sessions– two three sessions at the very beginning– as you're getting started really defining your strengths and beginning to understand how to utilize those for what you want to do next. And I wanted to ask you about the process. After the initial work on strengths, what did you find to be the most challenging parts of making a career change for you, especially in the way that you wanted to do it?

Bobby Grimm 15:35

Yeah, a couple of things come to mind immediately. One was just that it took longer than expected. And part of that was driven by... maybe the, arguably the uniqueness of the type of opportunity that I was looking for. I was also... It took a little while for me, and part because of that, and part, I think, because of just some fits and starts again with COVID going on, and some of the changes with like my wife's job, I kind of had to run hard at times, slow down at times, deal with stuff with the family, the kids when they're sick, etc,. So the duration really wore on me and it was hard. I would also say along the way, this, I wouldn't say that we met and had a few sessions. And all of a sudden, I knew exactly what I was going to chase. And I never deviated from it going forward. I don't think that that's what listeners should really expect, right? I think you're going to start out in the process, discover some things that are important to you, and the types of environments or people and work that you are attracted to. And then you're going to chase that but probably pivot along the way. And it's going to be this nonlinear path, at least for me it was, right? So along the way, throughout this, I think I would think for a moment that I'm chasing the right thing. And I might be really excited about an opportunity even and maybe... and I had a few situations in which I was, I made it pretty far like to a finalist round of interviews, and then didn't land the job. And while that was hard in the moment, something that I subsequently learned from it was, the next time something came along, I was still getting excited about it. I was still... I was like this is actually better than the one before. And I don't think that's because I'm some eternally optimistic person. I'm pretty realistic and practical. But I think that what helped me understand was, there's not just like one dream job out there, there's not just like one path that I could probably follow and be content, or it's gonna, you know, there were multiple different opportunities, all of which checked a number of really key boxes for me. And so when I got to the point, you know, as this process drove on for me, and I started to realize that, I think both with that realization and then also just the conversations with me and my wife, where we had to, again, put a stake in the ground, like, "Okay, it's time for me to get back to work." We put a stake in the ground on July 1st. I need to either be in that new job or really close like wrapping up the final details of one. And once I had realized that there were a number of different paths that I could follow, and I was okay with just saying "yes" to an opportunity and seeing where the path would lead and what unfolded instead of frankly being as picky as I had been, things just... I got a lot more, I started getting a lot more traction. I had far more interviews in that last month or two than I had leading up to that. And then July 1st came and I was sitting on two or three offers, some that were better than others or better fits. But I ended up actually having this interview on July 1st, I remember it was a Friday. And this is the day that I'm supposed to write, I'm supposed to have all of this wrapped up. And I had this interview scheduled for a job I applied for and I had said, I talked to my wife and to Phillip and I think I had a long walk while I talked with my sister the day before, I was like, "Look, I'm sitting on these couple offers, I gotta make a decision." But my sister asked, "Do you have something... Is there anything else like any other irons in the fire?" I said, "Yeah, I've got this interview tomorrow. But I need to make a decision." Like this is the timeframe that I'm working on. And unless they're ready to move light and quick, and they see something in me immediately, I'm not expecting it to happen. Well, that Friday morning interview, the conversation was like, "Hey, we've actually got this other opportunity. Would you be interested in hearing about it? I think you might be a great fit for it." And long story short, that was the job that I'm now in.

Scott Anthony Barlow 19:51

Well, here's what I think is fascinating about your story. It is this really interesting, almost paradoxical set of directions, because initially, you had to put this very firm stake in the ground to get movement forward that caused you to stop looking for, let's call it the perfect thing. And then start looking for things that really check some of the most important boxes and just moving forward on those in order to see what happened. And then, at some point, that had to shift again, that type of mindset in some ways had to actually shift again, because it sounds like you had two or three offers there. And none of them were quite exactly what you were looking for. And you knew that, and you had to almost say, "Okay, well, in some ways going to be slightly less firm and continue looking", as opposed to saying, "Okay, well, these offers are here, the timelines here. And, okay, I just need to pick one of these and not worry about anything else." So it's almost like in some ways, you had to bounce back and forth from mindset. But I'm wondering if that's how you felt about it? How did you look at that situation? And what would you advise other people, as they're making career changes, how would you advise them to think about this type of process?

Bobby Grimm 21:09

I would just say, for me, by the tail end of it, when I started to see things really happening, it was... I'm sure part of it was a result of a lot of work, and preparation that went into things. And I was finally honing in on more of the right things, and approaching those opportunities in the right way or a more effective way, right? I better understood my strengths, I better understood how to articulate my experiences, I had a better understanding and handle on how to explain what I was looking for, and what was important to me. So all of that was real. But I also think that, as I said, part of it was just having the wreck when I finally recognized that there wasn't going to be just this one ideal job or at some point in the process, I had actually poured a lot of time and effort into creating my own job description, which wasn't a waste of time. But it's also, at least for me, creating my own job description again, after I did that, I would say, kickstarter me in the right direction. But I also didn't land where I thought I would, right? And that's okay. I think I learned additional things that were important. My criteria changed a little bit, so to speak. And so when I fast forwarded towards that tail end, I had a better understanding that I wasn't looking for just one thing. I was looking for a set of criteria and what was going to be the best fit, and I was just willing to... I was more open minded about saying "yes" to an opportunity that sounded, like, great. Phillip had to often remind me like, "don't stress about this one that you're not excited about. You don't have to say yes to it, right. But when there are other ones that are really good fits, you don't know, you never know until you're in it, whether it's going to be great, or maybe it's great for a while and then things change." So when I started to just go into it more with this open mind of being ready to say yes to a good to great opportunity, then all of a sudden, it seemed like I was finding more of those good to great opportunities. And yeah, trusting the process, I guess, like praying for things and literally moving towards that July 1st. And then on July 1st, the job that I'm in opened up, and I didn't see it coming from anywhere. To me it felt like it was meant to be. It felt right. It felt, I kind of felt like God had said, "yeah, here's what you've been working towards." That may not be the way everybody else feels, or you know, and I certainly didn't feel that way every day of the rest of the process, but that's kind of how it all came together. Really.

Scott Anthony Barlow 23:53

It's so fascinating to me how you put it, and I say you, but really, this is true of many of the people that we've been able to help guide through career changes in one way or another. Where you put in all of this work, and it's this process of tweaking and evolution and learning and being open to new things, and then changing your mindset and replacing these learnings with new and better learnings and all the things that you mentioned. But then only after that does this crazy serendipitous seemingly almost, like well serendipitous, or, like God put it there,or this was meant to be, or this... those things happen way too frequently to be able to ignore. And in fact, anybody who's listened to this podcast for more than 10 episodes has probably heard that on one or two of those episodes in one way or another. So it's this really interesting observation that I've seen again and again and again, where almost luck or external forces meet preparation. And I think that that is so fun to see. And I think that that's a big element that is hard to pin down for people, and hard to certainly it's hard to trust. It's even harder to trust for me. But we keep seeing it happen over and over again. And it's so fun that that's a part of your story.

Bobby Grimm 25:09

Yeah, absolutely.

Scott Anthony Barlow 25:10

If you think back to any of those moments where you realize that, "you know what, this is no longer as good as it was. This is no longer what I want anymore." And you're thinking about being right on the edge of that precipice where like, should I do this? Should I not do this? Is it time to create change? What advice would you give to people who are in that moment and they're trying to decide what's right for them for the next step in the future?

Bobby Grimm 25:36

Yeah, I have thought about this. And I think for me, what it probably boils down to, I mean, I think you kind of nailed it, in some sense. Like, there are jobs that I've had that I was in love with for a while, right, I felt like I had made the right step. It's okay for people to first recognize that things change over time, right. So that one's really fulfilling job, it's not an indictment on the organization, the people you work with, or anything that's wrong with you to decide that you're ready for a change at some point. You might have outgrown that job, it was once the stretch opportunity you are looking for, and now you have conquered it and you're ready for the next thing. But that next thing is just not there in your current organization, whatever it may be. But for me, I think, and I've heard this many times on the podcast, right, people, myself included, will often sit on the decision to make a change for longer than maybe then they should. I think paying attention to how you feel, as you're deciding, though, is part of the process. Like for me, it was, I think I touched on this when I told my boss, leaving my last organization like I had been sitting on it for a long time. And what it ultimately came down to was the idea of something new and different, even if I didn't know what it was, continued to be more exciting than staying where I was. So even though I was more like afraid of, I don't know what I'm going to do, I didn't have any answer for my boss when I left about what was next, I didn't have anything really negative to say about, like, my experience really, like I wasn't leaving because of something had gone awry. I was leaving because something, on the other side of the horizon, just felt like it was calling, right. And that remained true through the ups and downs after I had put in my notice, right? I had between my dad passing or COVID happening, I had opportunities to stay where I was, and decide to not chase the career change idea. But again, like what I often found myself, where I found myself landing was, the idea of staying feels more tiring or exhausting or just less exciting than making a change and chasing that, right. And I would say I've seen that in conversations with like, even just with some of my close friends or brother in laws, when I've described the change that I did make, some of them are doing great in their careers and they've been there for a while, but part of the response I got was how that sounds– that sounds really fun and exciting and almost like energizing to just go and do something different. And so paying attention to that, if you feel like that itch that you've been sitting with just isn't going away, then it's probably time to explore it.

Scott Anthony Barlow 28:38

Most of the episodes you've heard on Happen To Your Career showcase stories of people that have taken the steps to identify and land careers that they are absolutely enamored with, that match their strengths, and are really what they want in their lives. If that's something that you're ready to begin taking steps towards, that's awesome. And we want to figure out how we can help. So here's what I would suggest, take the next five seconds to open up your email app and email me directly. I'm gonna give you my personal email address– scott@happentoyourcareer.com. Just email me and put 'Conversation' in the subject line. And when you do that, I'll introduce you to someone on our team who you can have a super informal conversation with and we'll figure out the very best type of help for you, whatever that looks like, and the very best way that we can support you to make it happen. So send me an email right now with 'Conversation' in the subject line. Here's a sneak peek into what we have coming up in store for you next week.

Cindy Gonos 29:36

Maybe you love what you do, but you're not enchanted with the organization that you're doing it with, right? Or in reverse, maybe you love your organization, you love the team, you love the people you work with, you love the culture, but the role that you're fulfilling there isn't fulfilling you.

Scott Anthony Barlow 29:51

One of the toughest parts of the career change process is the act of getting started. Putting the stake in the ground saying, "I need a change." Often the way to take action on this is by asking for help, which can be hard to do, especially if you're a high achiever. High achievers are people who have been able to make things happen for themselves, and that's allowed them to get far in their careers using that particular method. So asking for help doesn't always come naturally. But if you find yourself at a point in your career, where you want to make a change, and you're considering taking action through career coaching, then this is the episode for you. Today, we're going to dive into all the reasons career coaching may or may not be right for you.

Scott Anthony Barlow 30:38

All that and plenty more next week right here on Happen To Your Career. Make sure that you don't miss it. And if you haven't already, click Subscribe on your podcast player so that you can download this podcast in your sleep, and you get it automatically, even the bonus episodes every single week, sometimes multiple times a week. Until next week. Adios. I'm out.

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