E92: How to Know When It’s Time to Leave with Ben Fox

Most professionals stay trapped in toxic work environments because they don’t realize how much autonomy and self-awareness they’re giving up—until one moment of clarity changes everything. When Ben Fox left a high-paying tech startup after realizing how toxic leadership was eroding his well-being, he discovered a powerful truth: work is about remembering who you are and what you love. Now, he helps engineering leaders and tech professionals uncover their true path, whether that means quitting or shifting their mindset.

Whether you're in a toxic environment, feeling misaligned in your current role, or simply craving more autonomy, this episode offers actionable insights to take control and make work actually work for you. Perfect for tech leaders, software engineers, entrepreneurs, or anyone feeling stuck or overwhelmed by their work. If you're ready to stop settling for work that sucks and start creating a life that feels meaningful, this episode is your blueprint. Tune in now to discover how real change begins with awareness—and how you can turn your work into a tool for self-discovery, fulfillment, and freedom.

Guest Ben Fox is a career coach and mindset mentor for engineering leaders and tech professionals. His mission is to help you identify what truly matters, set healthy boundaries, and find the courage to shape a career that aligns with your values. Ben specializes in empowering clients to leave toxic environments and craft sustainable paths, rooted in authenticity and purpose.

Connect with Ben:

https://benfoxcoaching.com/

Want to be a guest on Work Sucks, But I Like It? Send Tony Tenaglier a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/worksucksbutlikeit

Transcript

SPEAKER_00 0:11

All right, welcome to the Work Sucks But I Like It podcast. Today we have Ben Fox. In 2022, he walked away from a toxic work environment with nothing lined up, no safety net, no perfect plan, just the realization that staying had become more costly than leaving. Today he is helping engineering leaders figure out what's actually next in their career. Ben, welcome to the show. Tony, great to be here. No, awesome. So, Ben, define work for us today.

SPEAKER_02 0:39

Yeah, I've been thinking about this. Work is about remembering who you are and what you love so that you can be of value to other people and be of service.

SPEAKER_00 0:53

So, what have you remembered in the work that you do? What are you trying to remember in the work that you do?

SPEAKER_02 0:59

I am an expert listener. I love creating this space of calm and deep compassion through listening to people. Uh and through that, I remember that I can be this big catalyst for people to make huge life changes for themselves.

SPEAKER_00 1:22

I love that. So did that sort of, I guess the catalyst of that toxic work environment, is that was that the catalyst that kind of set you down this path of deep listening or a little before that, or something else?

SPEAKER_02 1:35

I've been coaching for 10 years. And that was like the straw that broke the uh nine to five camelback. Love it. I love it, bro. I had been uh a full-time employee for a few years, and being in that work situation, I realized I am pretty miserable. Not because I don't like my work, even. I actually was enjoying the work I was doing there. It was a tech startup where I was um a talent agent, which was just I was getting to coach senior leaders in different sectors of tech, tech companies, figure out what was next and help make that happen with them. So I actually really liked the work, but the way the company was being led and the lack of autonomy and freedom, I just I realized I don't like how I'm feeling day to day. It's impacting my significant relationships in life. It's impacting my sleep and how I feel. I just can't be here and feel good. Um so I knew I needed to leave and it started me on the path to working for myself again.

SPEAKER_00 2:58

So I guess like a lot to unpack there for sure. I guess what's always interesting to me is, you know, when you have kind of a, you know, a crappy place to work, how much at what point do you say, okay, I'm going to say suck it up, but learn to work with it? Or you say to yourself, hey, wait a minute, this is not a good place for me. I need to leave. What were you sort of like going through? What was your thought process to say, wait a minute, this is not the path for me, I need to choose something else?

SPEAKER_02 3:23

I come from an entrepreneurial and creative household. So I grew up with this family culture of if you need a day job, totally get it, do it, but make sure you're still stoking the flames of your passion. And if it's really not working, you know, you're not going to be homeless. We'll we'll help you out. So I always had this uh sense of support and a different mindset when it came to work, where day job was really about paying the bills. It didn't have to be the passion, which fortunately for me oftentimes was the thing I wanted to be doing professionally. Um but yeah, being in that job, I thought when I got hired and for a few months or two months into that job, wow, I've I've found it. I'm getting paid more than I've ever been paid. These people are cool. I'm working in a tech startup in midtown Manhattan. Whoa, I've made it. And we went on this retreat. It's a company of, it was probably like 26 people. And I started to see some yellow flags, but I kind of brushed them under the rug. And on this retreat, it was like the veil was pulled from all of our faces. And the way that the company, the CEO, really wanted to run things was way different than the previous few months. Um, it was gonna get way more strict and intense. And uh when we came back from that retreat, I think six people quit on the spot. Whoa. So it was kind of like, okay, there's a the house of cards is starting to fall, and I need to get out of here. I started uh applying to jobs and interviewing as soon as I could at that point.

SPEAKER_00 5:24

So strict in what sense? I'm very curious. I guess like, yeah, without disclosing obviously too many personal details and names and things, but like, yeah, walk us through what was strict.

SPEAKER_02 5:35

So originally when I started, we had one work from home day a month, which was pretty low. Like I got that it was a mostly in-person job as a startup. Um, that got taken away. It's like if you're not here, you can't do the work. It won't count. Like it will count as a day off. And it went from, you know, if you're getting your work done, five, five thirty rolls around, yeah, go go ahead. Do your thing. To you have to be here at 9.30 to 6.30 Monday through Friday. Like, no, doesn't matter. It's like, what if I have an appointment to see a doctor? Take time off. Like, wow, this is um not what I thought I signed up for. And all of the interesting perks that we were given, like, hey, this is a there was a wellness room where people would meditate and stretch and all these things became like a storage closet. And and we were told, like, hey, if you're in here, it has to be very purposeful. Like, you can't be taking calls in here, you can't be working on anything else. Like it started to feel like I had entered the Twilight Zone. Like, this isn't anything resembling the reality I thought, and it was shared. Um, so before that retreat, there were 26 of us. This was July of 2022. By the time I left, there were 16 of those 26 people that had left, including me.

SPEAKER_00 7:26

So, what do you think changed in leadership? I mean, that's a pretty dramatic thing. Was there something in the food on your retreat that just like, I mean, I that's such a crazy thing to me, right?

SPEAKER_02 7:37

I think the yellow flags I kind of ignored was like it was my own ignoring of what was happening that made it such a surprise. Other people who were there longer, it didn't surprise them as much. I think what happened was this was 2022, things in tech were starting to shift a bit. Not as much as this past year or two, but they were starting to shift a bit. And I think the the bottom line of the company, like the profitability was was more in question, more in doubt. And I think the runway that the CEO had had gotten, like the round of funding, was was getting smaller. And I think out of fear there was a decision to us exert more control over people.

SPEAKER_00 8:36

I guess I'm just gonna say this. So how old is is the management team?

SPEAKER_02 8:44

Yeah. The the CEO was early 30s. Really? Yeah. But I think it was like there was really no team. It was really him. Yeah. And him like telling the board certain things that were maybe or maybe not so true. So no there wasn't a structure of of deep accountability because it was pretty much a founder-led company where he really did have all the power at the end of the day.

SPEAKER_00 9:22

I'm actually shocked that someone in their 30s would be thinking like that. Because usually the millennials, you know, I don't know how old you are, Ben, but like I'm millennial, I'm 38. And I guess like, you know, you were you mentioned the word autonomy, right? That's an important thing in our work today, however, you find that. And I just find it shocking. I don't know. So I guess not all millennials are made the same.

SPEAKER_02 9:42

Yeah. I think there's this vein of tech founder that runs through the US, specifically like New York and Silicon Alley, of you gotta work people hard, get the most out of them. It's okay if there's turnover, it doesn't really matter. There'll be people to replace the seats, the butts in the seats. And you need to build something. You need to build the unicorn, the billion-dollar company. It's gonna be great, but it has to be hard work and grinding. Um and I think he was totally okay kind of burning through people because he thought he could replace them. And to his credit, I mean, a lot of the big tech companies do that.

SPEAKER_00 10:32

But I guess it makes you wonder like what we're working towards, right? I guess how has this experience shaped the things that you're aligning? You know, you talked about you had the paycheck, you know, this great job in New York and all these benefits and whatnot. You know, I guess walk us through why you see what you're working towards today.

SPEAKER_02 10:51

Leaving that job gave me the courage to not be an employee again. I started contracting again as a as a coach. I was um working at two different companies, building my own schedule, telling them how many hours I wanted, started to get back some of that flexibility and autonomy. And I was doing that for two and a half years. And it was around the time of the 2024 presidential election, like the results from that, where I was on my roof here in Brooklyn and I had this moment of revelation for myself, where I realized there are so many people that are miserable in their work that really don't have to be. And by that, I mean they've got the privilege, financially speaking, to leave and figure something else out. And I in that moment I thought I can help them and I can do it by myself. When I started coaching, I I had my own business back in 2016 to 2018. Loved the coaching, didn't know what I was doing with sales and marketing and and branding. End of 2024, I thought, okay, now I need to find people who are going to help me do this and kind of off-ramp from these contract roles so I have some runway. Um in the past year and a half or so, I've been really focused on helping, as you said in the intro, software engineering leaders who are feeling misaligned in their work environment, take a step back, oftentimes quitting, but not always, and get healthy, figure out what they really want with their with all of our short time here on planet Earth. And then help them create the path to get there.

SPEAKER_00 13:06

So Ben, I'm very curious why software engineers, right? Yeah. So your position at the tech company wasn't a soft software engineer. So I guess like, what's your interest about software engineers?

SPEAKER_02 13:19

It was pretty random when it started back in 2019. So flipping back to earlier in our conversation when my ex-girlfriend was like, you need a job, because I was uh I was really failing with my business. Um I got hired at a coding boot camp as a career coach, helping their students get their first roles in tech as software engineers and data scientists, data analysts. And it was in that job that I realized these are people who are great at solving problems. They're not so great at dealing with the emotional stuff that gets in the way when it comes to um being in a toxic environment and figuring something else out. They're they're kind of oftentimes hard-headed, like I should be able to figure this out. They're professional problem solvers, but they're lacking something that I have, and I'm not super technical as a person. And it just felt like there's a really great chemistry between that group of people and myself.

SPEAKER_00 14:41

I love that. So, what's like one tip? One of the things I would say on the show is that success is not a matter of good luck, it's good skills. What would be the one skill that you've seen that you've been sort of like teaching over and over again to, I guess, build this emotional sort of muscle, if you will, with people?

SPEAKER_02 15:00

One of the things that ends up serving people the most in our work together is shifting their mindset from networking to relationship building. A lot of people will say, like, oh, I'm not so good at networking, I really hate networking. I'm like, Yeah, me too, because it's it's transactional. It's quid pro quo. What can I do for you? What can you do for me? And typically the people I work with, they're really good at what they do, and they've had emotional intelligence as far as working with their team, with their bosses. And part of the work that I do with them is leveraging the relationships they've built and creating new ones, but from a place of deep curiosity and wanting to be of service versus please help me get out of here and find a new job. It doesn't work like that. People aren't just going to hand over interviews. But if you can tell, like, hey, I'm actually curious about you, Tony, and when did you start being interested in rock climbing? And how'd you get into yoga? You feel there's a difference in how it feels. And I have a process that I walk people through that the more they do that, they actually start to enjoy the job search because they're having great conversations and leveraging, again, this um, these relationships they've built over the course of their career.

SPEAKER_00 16:38

I love that, Ben, right? So it takes a little bit of work, right, to build relationships. I think today we're so used to, oh, I friended him on LinkedIn. Oh, added another number to my list, you know, and it's kind of sad, right? But how we met was Jake Kennington, right? So Jake was on my podcast, you know, last year, and uh he said, you know, Ben would be a great guest. And I said, Oh, Jake was awesome. So here we are, Ben. I agree. I love that a lot. So I guess what are your thoughts then, you know, with social media, with the ways that we network today? How I mean we have to we live with it, right? So how do you balance the two? What are your thoughts with it?

SPEAKER_02 17:15

I'll uh I I don't think your listeners will be able to see this, but this is my my main phone. It's uh a light phone. Oh, that's amazing. Yeah. It's uh a not smartphone. I won't call it a dumb phone. My brother works at this company too. Um anyway. I think the unfortunate part of our reliance on social media is it's taken us away from present moment and it has become more transactional, has become more about adding to your email list and your follower account and the likes and all this stuff that it's a real dopamine hit, but we lose out on presence with each other. Um, it doesn't have to be in the same room, like the fact that you and I are talking right now and we're both present with each other and asking each other questions and having this conversation. That's great. But I I've I fear that social media has um really taken over our brain space where so many of us are just plain addicted now to it.

SPEAKER_00 18:35

It's also making us more miserable, right? Going back to your point of like people being miserable. I just picture people on LinkedIn, they're like, oh, my job sucks. Look at this person killing it here, right? So it's like, so I want you to walk through a scenario. Imagine like you're coaching this person. So person that they're nine to five, right? We'll use them software engineer, and they don't like their job. And I guess there's a lot of other factors I'd have to give you, but I'd like because a lot of the listeners on the show are nine to fivers, right? Some don't want to quit their job, some are intimidated by starting their own business, being coaches. What would you say to that person that is at their job and they're just miserable right now with the work they do? They've been there for a couple of years, they know the rhythm, they know the bosses, the good people. You know, what would you what would you say?

SPEAKER_02 19:20

One of the first things I do with everyone I'm I'm working with, whether they know they want to be entrepreneurs or they know they want the security of a paycheck and a nine to five, is take a magnifying glass to their current relationship to work. If we don't really look at how work is happening now for you, it's going to be really hard to have a new relationship to it. Um a big part of the work that I do with people is having them identify their own responsibility in how and why things are going the way they are. Because if if you're not looking at that, the real pitfall is that you'll end up repeating it in the next job, or by being your own boss, you'll repeat those same patterns.

SPEAKER_00 20:20

So, what's an example that sticks out for you, Ben, in terms of responsibility that we should be looking at?

SPEAKER_02 20:25

A lot of people I coach are high achievers. And oftentimes that's paired with people pleasing. You want to do a great job. You want to make people uh succeed around you and you want them to like you and you want them uh to see that you're doing a good job. So yeah, I'll put in, I'll put in the extra hours on Thursday night and yeah, it's Sunday, but sure, I'll put in a few hours. And the boundaries get pretty loose. So one of the things I'll have people do is let's take a look at what your current boundaries are. Are they in line with how you want work to go for you? Because, hey, if you're not closing your laptop at the end of your workday and you're like, why am I so stressed? Why don't I have time for dinner with my family? And it's like, well, because you're still working. And that's something that's in your control. Yes, you might have to have a tough conversation with your boss and say, Hey, I'll get work done by five. If you feel like anything's missing, I can pick it up later in the evening. But it's really you who's working more hours and saying yes when what you should be saying is, hey, I'll get my work done. I need to prioritize this time for my family, for my health.

SPEAKER_00 21:51

I love that. I feel like, you know, just talking about me, I guess, you know, when you say that stuff, I think of like there's this sense of when we're working that. There's like a finish line we have to cross, right? We were taught that it was retirement growing up, even with a business, right? It's like if you get to a hundred podcasts, Tony, you're going to be a great podcast show. It's like, I guess, like what is your thoughts, Ben, on kind of balancing this idea of like these boundaries? I guess I'm going into goals, if you will, because we do need a metric, right? We do need something to sort of guide us. But like you said, we can get very blurred with it and it can become our all of our life, right? I have to get a million dollars, then I'm going to be happy. You know, I'm going to need 25 clients, then I'm going to be successful. What are your thoughts with that?

SPEAKER_02 22:35

One of my uh one of my friends and and new colleagues, colleagues in the loose sense, we are in the same circles. He loves to ask this question of what are you optimizing for? What is it that you're looking to what like what's the result you're looking to have in your life? What's the experience that you want to be having? And yeah, if you're optimizing for, I want as much money as possible, I want to have as many followers as possible, yeah, you probably need to go beyond 100 episodes and you probably need to have more than a million dollars. But if what really matters to you is quality time with your family and your friends, taking care of your health, having this balance between work and fun, you're going to be asking yourself different questions. And it becomes less about uh more and more, and it's more about what is actually enough for me.

SPEAKER_00 23:44

But let's face it though, that quality time is like hard to see when you're fighting bills, you know, taxes and just commute and all these shitty things that happen in your life. I guess like how do you get, how do you develop, I guess, the discipline, the focus to say this is really what I want? What's that work to see that real thing that you're working towards, I guess?

SPEAKER_02 24:07

I often think this is pretty hard to do by ourselves. I think this is why I have work at all, is that we really need each other as humans to get clear on the things that matter most. Um I've felt really isolated and siloed, and like I need to figure out the answer to these questions by myself, I I have overworked. I have just felt kind of miserable and stuck. But the moment that I let my guard down a little bit and am vulnerable with it doesn't have to be a coach, it can be, you know, uh a partner or best friend or a trusted uh parent, mentor. When I've allowed myself to be like, hey, I'm pretty miserable in my work, and I'm kind of losing a sense of what matters, they're able to reflect back what's actually happening. Um, and it's through that kind of social that I've gotten clear and I've helped other people get clear on let's get you out of the stuckness and the mess of what sucks in your life, and have you remember what you actually care about.

SPEAKER_00 25:30

I love that a lot. So, Ben, this is the work sucks, but I like it podcasts. What is one thing that sucks about your work today, and what are you doing to make it not suck?

SPEAKER_02 25:39

Well, as a solopreneur, I am a marketer, salesperson, CEO. I'm I'm all these things. I don't love all these things. One of the things I've found to be sucky is I'm reaching out, I'm cold outreaching every day on LinkedIn to people who I think might benefit from talking to me. Um, and the way that I the way that I make it palatable is I quote unquote eat the frog, do it first thing in the morning, um, when I'm at my computer, send out the connection requests, write my post. I'm like, I'm done. Well done, Ben. You have been the salesperson for the day or the marketer for the day.

SPEAKER_00 26:31

Love that. So I guess how do you okay, cool. So to make it not suck, I guess you just do it first thing in the morning. Just to get it over. Just get it over with. I love it. Yeah. No, I love it. I feel you, man. Especially like with the podcast, like trying to promote it and stuff, and everyone's like, oh, you gotta repurpose your content. And I'm just like, it is so much to create these things. Like, and I love sharing it, and I love sharing people's stories and their work, and it's like, I gotta do more. I gotta create more content. It's like, oh man, like this is just crazy. But so, Ben, this has been a pleasure having you on the show today. If listeners want to, I guess, recode sort of their work, you know, and make it not so miserable, where's a good place for them to land?

SPEAKER_02 27:12

You can check me out at benfoxcoaching.com if this resonates. You can uh see a little bit more about me, even book a call. And if you want to see more of my thoughts and my writing, I'm on LinkedIn, Ben FoxCoing. Um, I'm on there pretty much every day.

SPEAKER_00 27:31

Awesome. We know every morning now, so absolutely. Ben, it's been a pleasure having you on the show. Thank you so much. Thanks, Tony.

SPEAKER_01 27:40

That blows the blades, and it's