The Cluttered Path
A Compass for Midlife: Our podcast helps listeners navigate the complex challenges of midlife through the collective wisdom of expert insights, real-life stories, scientific research, biographies, and historical narratives. Whether you're seeking deeper connection with others, navigating family dynamics, building financial literacy, planning a career transition, decluttering your life, or simply learning to enjoy life more—this is where we cut through the noise and help you craft your own roadmap to a meaningful life. Join us as we explore the human condition in search of personal growth and existential inquiry.
The Cluttered Path
#30 Rachel Spekman: Why Smart People Stay Trapped in Jobs They Hate!
What if your resume looks stellar, but your days feel hollow? We dive into the hidden costs of success (Anxiety, Insomnia, Quiet Dread) and show a measured way to pivot without blowing up your life. Our guest, career coach and therapist, Rachel Speckman, breaks down a practical framework for building a soul-aligned path where skills, values, and curiosity actually meet. You’ll hear how to translate vague dissatisfaction into clear data, spot the difference between a role problem and an environment problem, and make changes that protect both your well-being and your income.
We unpack the “three Cs” of meaningful work (Community, Contribution, and Challenge) and pair them with a simple Red/Yellow/Green task audit that reveals what drains you and what lights you up.
Rachel explains why identity gets tangled with titles, how to navigate the grief of letting go, and why calculated risk beats impulsive quitting every time. From industry-adjacent pivots to role redesigns to fractional work, we explore common outcomes and the mindset shifts that make them possible. Along the way, you’ll learn to build a backwards-facing resume that surfaces hidden wins and rebuilds self-trust, especially if imposter syndrome has been running the show.
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Meaningful Work, by Wes Adams & Tamara Myles: https://amzn.to/3MiK90b
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This is the Cluttered Path, a compass for midlife. You spent years building a career you're supposed to be proud of, but deep down, something's missing. The truth? It's never too late to pivot. You can redesign your career around your purpose and still create success that lights you up instead of burning you out. Our guest today is Rachel Speckman, a career coach who helps professionals who feel stuck in unfulfilling careers. She helps them go from high pay, miserable, and unhealthy in their careers to applying their gifts and talents in ways that still make great incomes, but in positions that align with their values and purpose. Rachel, welcome to the show.
Rachel:Thank you so much for having me. I'm so excited to be here.
Todd:So can we start with a quick bio on you? Can you tell us about yourself and your mission in life?
Rachel:Yes, I will start with my mission. My mission is to help as many people as I can in for however long I can to realize that they are allowed to want more for their careers and for their lives. And that settling serves a purpose in certain times to pay the bills, to get things done. And yet that is not a long-term strategy for living life. We want to go from, I want to help people move from surviving to thriving. And uh that is really my mission. My background is I was a teacher for seven years. I was in nonprofit and startup leadership for seven years. And then I went through a major life transition trying to have my children. And when I went back to work, work as usual, quote unquote, after I did have my first son, um, my first child, and I was just, I was in the wrong room. It wasn't filling me up in the same way. And I listened to that whisper for a long time. I started to experience a lot of what my clients experienced: self-doubt, unease, um, anxiety. And I started working with a coach and ended up making a major life pivot. And now I help others do the same.
Todd:Excellent. Yeah, super important conversation because a lot of people question success because I mean, we just lack full purpose and fulfillment. So glad to be talking to you. So let's let's just jump right into the hidden costs of success. Now, how does the story typically unfold for somebody who finds themselves in a career rut?
Rachel:One of the first questions I ask people is what percent happy are you in your career? And out of a hundred, most people find me when they're at about 20 to 40 percent. And I will jokingly say, would would you stay in a would you drive a car that was 60% broken or live in a house that was 60% broken? And of course, you know, it's it's a ridiculous question because we we can withstand quite a bit in our careers because we have bills to pay, reputations to uphold, fear, uh, we kind of feel like we've maybe gotten ourselves into this rut. And so making a change to your house or to your car might be a quote, quick fix. Whereas this is actually a bit more of a soul journey, uh a marketing journey, and a commitment to yourself.
Todd:So as a therapist now, what are the mental and physical health impacts of staying in a you call it a soul-sucking career? Can you talk about that?
Rachel:Yes. And I want to say soul sucking is such an individual experience. Something that you find soul enlivening might, I might find soul sucking, and vice versa. The best way I can describe soul sucking is a client, how a client described it, which is you head into work, into the turnstile, and and this client would say that they literally felt like their soul was leaving them as they entered the building. They couldn't be themselves, they didn't feel connected to who they were working with, they didn't feel excited about the projects that they were working on. And that's what I call the three C's, which comes from which comes from a book called Meaningful Work. Do you feel connected to the community, to the contributions that you're making, and do you feel challenged in the ways that align with you? And so to answer your question, uh, really the costs are everything from depression, anxiety, somatic issues, which basically means your body is starting to experience stress, panic attacks, insomnia. I see all of it, both as a therapist and as a career coach. And it doesn't have to stay that way. In fact, that's actually our body's system. That's our body's way of giving us data that something is off.
Todd:Yeah. Physical and mental impacts from just staying in a career that just is not a fit. So I can see it like we would have an identity crisis at some point and just have a have breakdowns. Is that common for people to have like mental breakdowns after spending too long?
Rachel:Yeah, I I would say it's often very private. I think there's this kind of uh, I don't know, vision of the Jerry Maguire kind of memo moment at work where you're screaming. And I don't think that I don't see that as often. I see that I see it more as my spouse is gonna kill me if I complain about work one more time. My friends tell me I need to really do something different, and you know, I put on weight, I have health issues or whatever the case is. And so from a from a therapeutic perspective, the stress of work is managing them instead of the other way around.
Todd:Right. Staying in that job is sometimes not a good option. So is there are there times where you do have people come to you and they're unhappy? And have you just helped them just make some adjustments so that they end up staying in their jobs?
Rachel:Very much. So when I work with people, I I ask how long they've been stuck for, because there's a cumulative effect to this. And so very often we work together for about four to six months to really uncover how did they get this stuck, not in a self-blame way, but in an exploration way. And then rebuilding, okay, well, what lights you up? Why? How do we get you paid for that? How do we get you applying to the right opportunities? And people generally have one of four outcomes working with me. And the first is they're like, actually, where I am isn't that bad. I'm just not using my natural skill set. Or, oh, I'm not on the right team, or oh, I don't I didn't choose the right project to be on. The second is they they they go a little bit industry adjacent. So I'm thinking of somebody I work with um actually today is her first day, but she's been in a in a kind of traditional banking role, and now she's doing a fintech role. Uh and so that's very exciting because it's kind of a pivot, uh, what I call a small, medium, or large pivot. She's doing a medium pivot.
Todd:Nice.
Rachel:And other people work with me and they say, I want to go fractional. I want to be my own boss.
Todd:Very cool. Yeah, so I mean, it's not like a one size, hey, you've got to totally uproot your life and you know, make this change and move to a different country or anything like that. It's sometimes it's it's just making changes right here where you are so that you can be more fulfilled.
Rachel:Yes, this podcast went out a few weeks ago that was the title is The Therapist That Helps You Quit Your Job. And I I thought that was funny, but not a hundred percent accurate because I help you evaluate if it's the right place to be, why, what are other options. And you know, the days, I don't need to tell you this or your listeners, but the days of staying in a job that you hate for 30 years are let's just hope behind us. And and also so many people who are stuck, you wouldn't want that for your children or your spouse, but we deal with it for ourselves.
Todd:This is true. So let's talk about the psychology of staying stuck. Now, what are some psychological barriers that keep people in jobs that they hate?
Rachel:I think I said it earlier, but I'll expand. The number one psychological barrier is fear of the unknown or fear of uh beginner's mindset again. And beginner's mindset, we we I'll kind of speak to this. I do have small children, but you know, you're watching a small child learn to do something and they they don't succeed, so they try it again, they have a lot of support. Well, as we get older, we're kind of just expected to know it, to be an expert at it. Maybe we are an expert at it, doesn't mean we enjoy it. So this fear of, oh my gosh, I'm gonna, I'm gonna leave something that I'm sort of quote, the top of my field for, um, or I'm gonna pivot it, and there's gonna be a reputational cost potentially, there's gonna be maybe a financial impact, all of this fear can get very loud. And I really try to bring it back to what I call a calculated risk. Yeah, because nothing changes if nothing changes, and so psychologically, we want to try to change a little bit out of time. So I I always like to give an exercise when I'm on a podcast. Is it okay if I give one right now?
Todd:Yeah, go ahead.
Rachel:Okay. So one of the exercises that I that I give very early on is I want you to write down the major activities that you've done for the last 24 to 48 hours professionally. And write those on an Excel, and then next to it, write what percent of your time you were doing those things. And next to that, write what your percent enjoyment was of that. You have to get honest with yourself, you have to get quiet for a minute. Just looking at your own data, you can realize, oh, I was on podcast all day. I hate speaking in front of a camera. Why was I doing I don't, I don't, but you know, well, okay. I mean, for me, I was I was giving, I was doing operations and budgeting and Excel for companies. It was fine, but I'm a people person. I was spending very little time in front of the person. And I realized there's really an imbalance here.
Todd:Yeah.
Rachel:So I call that the the red, yellow, green exercise. So you can get very clear very quickly around what what do I need to turn up a little bit and what do I what's really off in the red.
Todd:Yeah. I mean, a lot of times we just are unhappy and we don't we can't pinpoint things. So that little exercise of just putting things down, either on paper or an Excel spreadsheet, it's I can see that would be grilled. Very helpful. So good stuff.
Rachel:Yeah, I call it applied introspection. We have we have to, you know, we want to be, we want to be thoughtful about what's lighting us up, what's draining us, and then we want to apply it. And so let's just say I I this is such a bad example. I hated being on podcasts. Okay, well, I would I would say, could I be on one less? Or who on my team could be on another one? Or um wow, I really love doing this Excel. Maybe I can do one more and show my boss how useful this could be, because then you're doing what I call naturally opening your body up to what excites you.
Todd:Yes, very cool. Now I'm thinking of a psychological barrier that I've had in the past with it with a previous job, and it's identity. So really just identifying yourself with the role and the position and the company. And for me, it was the thought of leaving that company was devastating because of my identity. So that was a to me, that's I I mean, I I I'm looking back on that now and I can see that, but at the time it was it was miserable. But once I got free from that and looked back, it was like, oh, my whole identity was wrapped up in who I was as that role in that company. So yeah, that kept me stuck for a long time.
Rachel:I am so glad you say that. I that's actually what I focus on for therapy, which is identity shifts. And and I identity shifts from becoming a student to an employee. I focus on grief when you lose somebody you love, then all of a sudden your identity shifts very quickly, going through a separation or divorce. So there are all these identity changes, and work is a huge one. I joke all the time. I left, I was working with venture capitalists and angel investors and all kinds of people. And I said I was going back to social work school to become a therapist.
Todd:Okay.
Rachel:And I had people literally say, Are you okay? Like, what's going on? Like, you know, basically saying I was going through a crisis. And I said, I am beyond thrilled. I've thought about this for a year and a half now. I'm very into creating a calculated plan. I created a five-year financial plan for myself. Nice. I applied for every scholarship. I mean, I was very thoughtful. It was not impulsive. I want to tell everybody who's listening, please don't make an impulsive choice because you're going to be out of the fryer and into the pan.
Todd:Agreed. Yeah. And I like that you don't approach it from the perspective of you don't just have a cookie cutter approach. No. You sit down and analyze. Okay, where where are you? And from there, you're not telling you're not, you're coming, you're helping them come up with their own plan. So I appreciate that. Yeah.
Rachel:Thank you. Thank you. But definitely the identity is huge because we're social creatures. We I I mean, of course, I identified as an entrepreneur, as a startup person for so long. And the thing that I'll say is this is very kind of therapy session E, but that part of your identity doesn't go away. It just changes. And a new one, you take on a new one and you fold that into your evolving identity. All of our identities are are are changing.
Todd:Yeah, yeah. So what are some key indicators that tell us it's time to make a career change?
Rachel:There are the classic ones, avoidance of work, Sunday scaries every day, dread.
Todd:Um Sunday scaries, I love that.
Rachel:Yeah, I don't know if you heard it. Sunday Sunday Scaries on Wednesday, Sunday Scaries on right, feeling just purposeless in the in the role. Um, that's a major one, I would say, because people do crave, we crave a sense of purpose. Um, even if it's the purpose is I feel connected to the team, I feel connected to the end goal. And other other major symptoms, again, it can get very intense in terms of anxiety if we're avoiding something. I I give my example that I was crying in the bathroom. I was publicly giving presentations, but I was really, I call it asymmetrical. Asymmetrically, I was feeling very different. Wow. And and that um that can be a major place of of shame, of judgment to yourself. And when I started saying, wait, actually, it's okay. This is this is telling me that that my role is here, but my calling or whatever you want to call it is somewhere else. Then I started to allow that in a little bit more. But I really, the major issue people struggle with very early on, that's why a big part of what I do with people is mindset is giving yourself permission to make a change.
Todd:And then once you I think that that seems to me like it would be um once you get past that point, it's like, oh, is that what happens?
Rachel:It is, and it's like, oh God, now what? Like I always say, like 12 weeks from now when you actually know what you want to do and you have a plan, yeah, and you know what you're gonna maybe walk away from and what you're walking towards, that's actually the scariest time because you're like, wow, am I gonna leave in this economy with this and that? And that's why I'm saying we have to make these this you know calculated risk and we have to be really thoughtful. And and if if your level of enjoyment of your job is relatively high, absolutely there's no there's no need to make a change. For sure. I'm not convincing everybody or trying to tell convince anybody of anything. And what I do think is that at some point you were at 60% enjoyment and then 50% and then 40%. So if that is true, then the inverse is true as well.
Todd:So now let's let's talk about your framework for change if if we can for a minute.
Rachel:Yep.
Todd:Now you let's start with this. You talk about building that soul-aligned career. Can you dig a little bit deeper into that for us?
Rachel:Yeah, so I mentioned earlier the the three C's the community, the contribution, and the challenge. And I overlap that with the skills, values, and intellectual interests or curiosities. And so, and it's a actually a Venn diagram. So we want to be at the intersection of where our skills, I really feel like I'm growing in skills. I love the skills that I'm developing, I feel very value-aligned. This place values autonomy, I feel psychologically safe, I can make a mistake, I'm giving my own uh intellectually curious. Wow, I feel so engaged in the problems that I'm solving. When those three, let's call them cylinders are firing together, yeah, the center of that Venn diagram is you're generally in flow because you care about what you're doing, you have the skills that help that situation, and you feel respected, valued, seen, etc.
Todd:Flow state. I like that.
Rachel:Flow state. What happens is generally kind of earlier on, the skills are really leading our life. I really want to get that degree, I really want to get that promotion. I really, and then over time, our values start to change. And that's kind of where this identity transformation comes in. Oh, I had kids, I want to be home more. Oh, I have an aging parent, I need to reset my values. And so if there is a mismatch with any of those skills, values, or intellectual curiosity, then that's when we start to say, wait, okay, something is off. How do we get one of those back online?
Todd:Okay.
Rachel:So the way that I work with people is I say, is it the environment that's the issue? Uh, if so, are there can we find more value-aligned companies? Uh, is it the individual? Is it what you're doing day to day is not filling you up? So that's where we can be diagnostic.
Todd:Gotcha. Have you ever encountered someone where you were like, you know what? Maybe the problem is you.
Rachel:Well, what I will say is, and again, not everybody is this comes from a mental health framework called the system, circles of change, which is not a lot of people are in a pre-contemplation state. I think I have a problem, I don't know what to do about it. Then contemplation is I have a problem, I know I need to do something about it. And then there's action. I'm gonna make action. Yeah. Take action to make a change. Many people come and see me at a as sort of a pre-contemplation. I think I have a problem, but they're not ready to take action yet. And very often you will we will take action when we are forced to. So we either get laid off or um you have a panic attack, or something happens that thrusts us into the next stage.
Todd:Yeah, yeah. And you've got some very practical approaches. So that's the that's kind of like the framework, but you've also got some practical things you do to help people assess talents and skills. I think you've alluded to it, but can you talk a little bit more about those?
Rachel:Yeah. So I do a I everyone I work with, um, I do a forced ranking, which basically your top five to ten skills, values, and interests. And then we do a backwards-facing resume. When have these been online? And by online I mean alive and within you.
Todd:Um and when you say backwards facing, you're talking about looking back on past jobs and things to make sure. Exactly. See, okay, got it. Thank you.
Rachel:So I'll use myself, my very first job I was teaching. I will say, what are the things I was most proud of that nobody else saw? I call it your internal resume. One, I moved to a new city. I didn't know anybody. I'm so proud of myself. That shows risk taking, that shows initiative, right? These kind of things that we need to start bolstering ourselves with. And then I loved that I got to run a classroom. Great. What did I love about that? So we start piecing together, not just ran classrooms, right? The way that a resume bullet is, but what actually was happening within me that made me love that job? Um for some people, you know, they'll say, I love that job because I got three weeks of vacation. Okay. Yep. Well, all right. You know, I love those bumper stickers. I love bumper stickers. I teach a class at a at a university around here and career clarity and mental health, and I'll show a different bumper sticker each week. That's kind of one of my little quirks because I like taking pictures. And one of them said, I'm not living my life for three weeks of PTO or something like that. You know, because that's good. That's that's that's 50 weeks to enjoy two weeks.
Todd:Yeah, that's that means you die early. So that's so smoking.
Rachel:Those are some of the diagnostic tools I use early on because we haven't really talked too much about like imposter syndrome or burnout, but those things really take their mental health toll on you as well. And so we gotta almost let what I say kind of get back to the gym and start lifting some two-pound weights. Be like, oh yeah, I did do that thing at work.
Todd:Oh, yeah.
Rachel:And that's the thing I love to say is that I I my mission is to help high performing professionals. And I will have people come to me who run these large companies and big projects, and they say, Do you think I'm a high performing professional?
Todd:Uh yeah.
Rachel:So it's about your own self-identity.
Todd:Right. Yeah. So last question for you. Can you share an example of one of your clients and how they navigated that whole process, how where they started and where they ended up? Mm-hmm.
Rachel:So I have a client right now. Uh we are I start to work with people in executive functioning, I'm sorry, executive leadership roles as well when they've transitioned. Um, I have a client who was running her own business and was feeling very isolated, very burnt out, very drained. And so together we did exactly what I was talking about and realized her most exciting moments is when she's on a team, when she has a mentor. Um, we got her resume in top shape for that. And now she has joined and she's in a leadership role. Nice. And she's she's loving it and also having some challenges because she's worked for herself for so long. Um, and so now she's learning, okay, this is this is what's happening here. But she is so much more alive in terms of, oh my gosh, I'm not spending my day by myself every day, or I'm I'm helping with a team. And so again, that was a really value-aligned decision that took took about six months to get her, eight months really to get her where she went. And many rounds of interviews, different places. It wasn't automatic.
Todd:Nice, very cool. Well, I appreciate your time today. I know we've uh got to keep it short because you've got another commitment. So I appreciate your time, Rachel.
Rachel:Thank you so much for having me.
Todd:Rachel, how do people get in touch with you?
Rachel:So, my what so madeformorecoach.com. I have a free training on my site, and I'd love to connect with you there.
Todd:Excellent. So we'll include a description or a link in the description for people. And uh so appreciate your time. This is an important conversation, just my takeaways here, because all of us have been in jobs that we just absolutely find miserable. So as we're just navigating these passageways of midlife, sometimes you've got to take take a step back and make some changes. And sometimes we need a coach. And so folks like Rachel are there to help us walk through those troublesome times. But uh, if you do put in that effort and get through that scary part and find a way forward, I think uh we'll be very satisfied with the results. So, Rachel, thanks so much for for joining us and uh appreciate your time.
Rachel:Thank you so much for having me.
Todd:So now if you listen to this episode and you enjoy it, please consider leaving a review and sharing it with your friends. Until next time, see you on the path.
Music:This is the firefly.