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What happens when your career is technically working, yet you begin questioning whether it still reflects who you're becoming. In this episode, Ben Stein shares the internal season that preceded his move from executive leadership into purpose driven coaching. This is the Your Next Success podcast, and I'm your host, Dr. Caroline Sangal I'm a life first career coach and strategist on a mission to normalize questioning your career because I believe each of us is made on purpose for a purpose only we can fulfill. The longer we live out of alignment with who we are, what we do best, and why we are here, the more we miss out. And the more the world misses out on what only we can give. The Your Next Success Podcast is where we explore how to build a career that truly fuels your life. We talk about self-discovery, smart job, search strategies, professional growth, and you'll hear stories from people who have navigated big career transitions themselves, so you can create a life, first career and become your own version of authentic success. My guest today is Ben Stein. Ben is the founder of Purpose Up where he helps mid and senior level professionals navigate career transitions and land roles aligned with their strengths and values. Before launching Purpose Up, Ben built a successful career in advertising and tech holding leadership roles, including VP of Product and leading core cross-functional digital teams. Today he brings that executive experience into his coaching work, guiding professionals through meaningful pivots with clarity and strategy. Career transitions rarely begin with chaos. Often they begin with evaluation. In this conversation, Ben shares what was happening internally before his shift from corporate leadership into coaching. We discuss the difference between insight and action, how identity evolves during transition, and what it looks like when seeking matures into service. In this episode, we talk about what seeking feels like inside a functioning career, how identity shifts during professional transitions, why awareness alone does not create change, and how clarity becomes aligned. Now let's welcome Ben to the conversation.

Caroline 2:31

Welcome Ben Stein to Your Next Success, I am thrilled to have you um in this conversation today.

Ben Stein 2:38

Thank you so much for having me, it's an honor to be here

Caroline 2:40

Awesome. Okay, so as you know we're gonna talk about careers, career transitions that's also something that's near and dear to your heart you have helped hundreds of people with their own career transitions so we'll get to that very successful, successful author successful in so many author of multiple different books we will get to all of those things, and I'd love to kind of dial it way back help the listeners understand where were you born? Where did you grow up? What was life like for the you know the youngest Ben Stein?

Ben Stein 3:11

Going all the way back, so I was born in Washington DC and grew up in the DC suburbs and I actually just said goodbye to the house that I grew up in when I moved my parents down here um so we're gonna go back there every year, but yeah um youngest of three, dad psychiatrist, mom was a housewife and so growing up I was generally a introverted artistic sensitive guy and also just trying to vie for my place in the family because it seemed like my older sisters got the priority, so I was like all right I'm I'm I'm on my own here um and yeah, I mean I I had a kind of middle upper class upbringing and lots of advantages that other folks don't have and then also you know some family drama that and trauma that drives everyone with with pain and all of that too, so it was it was a good upbringing that also helped form the healing that I had to do later in life.

Caroline 4:18

Yeah, how much older are your siblings?

Ben Stein 4:22

So my oldest sister, Shauna who passed uh a few years ago from pancreatic cancer she's eight years older than me and Julie is uh is two years older than me.

Caroline 4:34

I'm so sorry, because pancreatic cancer is one of those ones that like by the time you figure out you have it then they end up saying like oh this is what it is and it's not looking good.

Ben Stein 4:47

Yeah no it uh it sucks um you know my sister was very brave and and positive through it all and we were optimistic because she got on a clinical trial for some immunotherapy Uh and that helped, but ultimately um yeah it's, uh it's a doozy for lack of better words.

Caroline 5:10

So sorry, so sorry. Okay, but at so but growing up you were saying she seemed to have it all together have the priorities and so focus was maybe on her and your sister and wait two sisters and then you're the youngest? Ah uh interesting. so how old was your how much older is your middle sister?

Ben Stein 5:28

She's two years older. yeah, ultimately, I think they were like by the time I came around it's like do what you wanted to do, my dad was a psychiatrist so one of the terms that he talked about in terms of child rearing philosophies was benign neglect, which was perfectly valid to like just let your kid do whatever your kid's gonna do and they only need so much and I wasn't abandoned as a kid, but I actually got a lot of free reign and so as I kind of grew from shy introverted kid into middle school trying to find my way and my people, I kind of adapted lost myself a little and kind of like survival, became a cool kid in that transition and that meant I was kind of running with the crowd that was drinking, smoking pot and that kind of informed my teenage years where it's probably more rebellious than I was programmed to be, but working to fit in find my tribe and um and survive the middle school high school uh years.

Caroline 6:28

And when did this artistic uh sensitive elements start showing? Like at in elementary school did you love art? Did you love drawing? where did that come into play and what did it look like?

Ben Stein 6:41

Yeah, I love drawing, I always loved it, I remember I had a teacher in the sixth grade who had been a cartoonist as a previous career and he was kind of almost one of my heroes and he would actually like draw these pictures every day cause we had um job where you know certain people were calling for the carpool lines and he would like draw a picture announcing who that was and and I remember collecting some of them I thought they were so cool, uh but yeah I loved cartooning and I loved drawing and that was just kind of where I could find flow and in in addition me and my sister Julie spent um hours and hours playing legos together uh when we weren't watching tv.

Caroline 7:22

speaking of tv what kind of shows did you like back then?

Ben Stein 7:27

So, I mean I watched so much tv, I mean it was just like bad eighties sitcoms, like and and it was everything.

Caroline 7:37

You want a car bed? Like some of those 80 sitcoms, right? Like was it Kurt Cameron had the car like the race car bed, right, I'm just saying like.

Ben Stein 7:47

Yeah, and that that reminds me of uh Silver Spoons with uh you know the kid that was really rich.

Caroline 7:52

Yeah

Ben Stein 7:54

Small Wonder, you know going back in time, yeah so I was born in 78 so I I I got you know the the brunt of the the eighties with my TV watching.

Caroline 8:04

Yeah, yeah. Okay, so school-wise were there any particular things that you enjoyed during actual school time?

Ben Stein 8:14

Yeah, I gravitated towards reading and writing I had some, I Uh they weren't necessarily learning disabilities but I was slow with my motor coordination, so like my handwriting sucks that was always like a struggle for me, um but I was always pretty um pretty smart, although I I went to a private school I got held back in third grade cause I started really early, so I kind of like corrected for my age and that was like a tough adjustment but then adjusted to that um but no I I liked reading a lot, math wasn't my favorite. I remember I always yeah so, math was a struggle and in high school, physics made math real so I enjoyed it a bit more and also had a really good physics teacher then, but yeah throughout my career I kind of avoided math where I could and and leaned into reading and writing.

Caroline 9:08

Interesting. And then that uh going from being one of the youngest in your class to now being one of the oldest in your class, how did that play into this perhaps getting into the the wrong crowd um and all that now you could drive first right, so how did that uh how did that play come to play?

Ben Stein 9:30

I just I just had a flashback, so I had my my mom's country squire station wagon uh and probably had about six or seven friends packed in it and we had decided to go down to DC to go see a show at the 9:30 and in DC there's like traffic circles and those are some of like the most stressful things for a new driver to navigate multi-lane traffic circles and like teenage boys are like screaming and I'm like oh my God I hope I don't die and um but yeah, so it was it was fun and I'm honestly lucky I'm still around with some of the bad decisions I made, um so I'm I'm fortunate to have uh come out relatively unscathed from all that.

Caroline 10:17

Were your parents aware of the decisions you were making or did they just think this is just a moody kid?

Ben Stein 10:23

They were aware, so yeah I mean I remember I got caught in ninth grade smoking pot, right, So um you know my dad would then like give me money to go out and he's like you're not gonna buy drugs with this are you? And I was like, Dad, I don't wanna lie to you, I mean and just like and he had respect that I didn't wanna lie to him instead of like really clamping down on me, so um there there was never like great repercussions except like one time when I got caught smoking in the house and then it was like okay we're gonna ground you and that time that I got grounded just for fun, uh I tried mushrooms for the first time, ate them and then came home for a family dinner and I don't recommend that to anybody but it was quite the experience.

Caroline 11:14

Okay, so high school um this experiencing life is taking all sorts of turns, did anything shift as far as were you still drawing and um reading at that time or mostly just hanging out with friends and enjoying and how'd that how'd that go?

Ben Stein 11:30

Yeah, I I was into computers and in middle school, I remember I did a like video editing camp and I got kind of into animation, so all of those I was kind of interested in in how things moved and and bringing art into the the digital sphere and I also found uh painting in high school and I went to a artistic school as well that that encouraged the art, so I still kept up with all of that and I remember I went to an art camp one summer and really kind of flexed um and and grew there artistically, um I I I didn't like want to become an artist but I still kind of found flow and enjoyment and um liked being in those places and and just kind of being in the zone with all that.

Caroline 12:23

And as you got to towards the end of high school, how did you decide what you wanted to do beyond that? Like, what what did you consider or what did you choose?

Ben Stein 12:34

So, I didn't have any ideas about what I wanted to do when I grew up at that point, so the idea was okay let's go to a good liberal arts school and you figure it out once you're there so let's just get into the best college possible, um so I ended up getting into Tufts up in Boston, um so I I partied a lot in high school but I also worked hard um and luckily was was smart as well, so did relatively well and I had some family um that helped me get into Tufts as well, I probably wouldn't have gotten in without legacy um and actually my nieces I think are like fourth or fifth generation there.

Caroline 13:22

Oh wow. Yeah

Ben Stein 13:23

So like my uh grandfather was an art professor there, my mom grew up on the campus and went there great-grandfather went to dental school there, um and now my now my nieces are going there and my brother-in-law is a teacher there. So,

Caroline 13:34

Oh wow.

Ben Stein 13:35

Rich history with that school. Uh so, I ended up studying Psychology I I was originally gonna start with computer science and then I started doing those courses and I was like my brain does not wanna spend time doing these things, this is too hard, so Psychology I was a interested in my dad was a psychiatrist and I wanted to kind of figure out why I was messed up and what I could do to fix it and I liked learning about Psychology both from a um kind theory perspective as well as I got into bio-psychology a little bit and then I minored in communications uh and was fascinated with um I took a a class on uh they they had the ex college at Tufts the experimental college, we could take weird classes, one of those was a television production class and I was like wow this can actually be a job, um and that really got me into the the children's television realm where I was like oh you could use TV and also kind of use it for good, so that the psychology were areas of interest that I gravitated towards.

Caroline 14:40

Let me understand this, uh this little passing comment of something about Psychology cause you wanted to figure out how you were messed up.

Ben Stein 14:54

Uh yeah, so I mean I felt, like you know growing up, so it was interesting, so I had a a dad who was a psychiatrist but he was pretty detached from what was going on in the house, like he wasn't that present and then meanwhile my mom actually you know suffered with depression all of that was like a very fascinating combination to kind of grow up with um and so I think growing up my coping mechanism was to kind of numb with the with the pain that I was experienced both with like the lack of presence of my dad and my mom going through it. So all that was like tough, so it was kind of like me checking out and kind of dealing with all that so I kind of felt like um I probably, not until my late twenties where I realized I was emotionally stunted because I hadn't figured out a way to deal with negative emotions like an adult and so I think you know I'd felt um yeah like like I hadn't fully matured as a person or wasn't on like the right track in many ways even though I was still like on the outside things were fine.

Caroline 16:10

Yeah, externally successful, Internally you're starting to be feel a little more like is this a problem or am I the problem.

Ben Stein 16:18

Yeah, I remember my first college girlfriend, you know that's where kind of my using marijuana on a regular basis kind of like became something where she's like do you always have to do that and I cared for her deeply and she was like an amazing young woman and I realized oh okay this is creating friction for somebody I care about and that was kind of like the first understanding of like this isn't I'm I'm not on the ideal path but I wasn't like ready to get help or address it at that point.

Caroline 16:51

Interesting. Interesting. And with your dad having been a psychiatrist was like mental health of not really like available but like I I mean I grew up in a household where like anybody who talked about like we had a lot of thoughts but we didn't have feelings um and you know talking about your feelings or something all that it's just a bunch of crazy people, right? So I imagine, like when your dad was there his perspective is different and but did did he help encourage your mental health you know and was that routine like a dentist appointment? Like or not you know, because just curious.

Ben Stein 17:29

Yeah, no I so I remember when I was struggling in fifth grade, like my mom was going through it, I was kind of missing school calling in sick and essentially I was kind of faking sick in order to get attention in the house and ultimately led to me uh being sent to a therapist and yeah, I I don't think I have like enough self-awareness from that time to see if that helped or not or probably did help at some point but I remember like I hated it and I was like I don't wanna be talking to this guy um so in that regards they're like oh he is going through some stuff, let's let's send him to let um therapy but outside of that there wasn't really kind of like much checking in or heart to hearts or things like that.

Caroline 18:26

Interesting. Yeah

Ben Stein 18:27

I mean, my mom was kind of like the emotionally intelligent person even though my dad was a psychiatrist, so if I did need it to confide in someone, my mom had the the sensitivity and the wherewithal to kind of be with me so I wasn't like totally abandoned, but um sometimes she had capacity sometimes she didn't.

Caroline 18:46

Yeah. Yeah. And did you know that? Like did you realize she was depressed? Did you know what that was or was it when you were later then finally able to be like oh that's what was happening with her.

Ben Stein 18:58

So, I mean I I realized it um cause it it was one of those things where you're you're constantly kind of like disappointed by somebody not showing up spending time in bed not being able to deal and then unfortunately um she went on some pretty hardcore medication in my teen years, which like essentially may for lack of better words mayor space cadet that like in your angry teenage years like when your mom is just like not fully there because of heavy medication that's super frustrating, um so that you know and I think you and going back to the psychology point I also kind of wanted to understand all the dynamics from like my mom as well to kind of like avoid some of those uh potential pitfalls for myself in the future.

Caroline 19:54

Yeah. Okay. So you uh go into psychology and you're wanting to try to like get deeper insight and info into how we think our thoughts, approaches, all of that um and did you love it? Was it just what did it always stay interesting or how did that how'd that go?

Ben Stein 20:17

Yeah, I enjoyed the different schools of psychology and like the I've I've always been fascinated by how we think and how we behave and that ultimately stretched into me being totally fascinated by coaching and personal development later on in my twenties and you know what was what was most fascinating to me was was bio-psychology and understanding that at a more root level um and how chemicals can affect our brain you know whether they're um endogenous or external, uh and cause I was also curious about the nature of addiction cause it you know, by that time I was hopelessly addicted to cigarettes and was drinking like on a pretty regular basis et cetera, so I was kind of curious about all of that as well.

Caroline 21:21

And were you interested in when you were still in undergrad, were you more interested in psychology to learn about yourself and just kinda like your own family or did you also have that seed or desire to help others too? Because I know it it transitioned into a lot of helping others but had you always had a helping others drive and desire?

Ben Stein 21:47

Well, when I was in college the two tracks for psychology were, A you could go the clinical route and about practicing and helping people and my point of view was like I'm too messed up and immature to think about that track so that doesn't make sense for me now uh and then there was the the research route and that seemed just incredibly boring and tedious to me uh in terms of living a life of a researcher, so I was like I don't think these are for me and learning about the the the kind of like television production track, it's like oh this is a great place where you get to utilize that creativity and apply it and and and also hopefully be able to make money cause I wasn't bullish about like becoming an artist or anything like that, so I tended to think okay the psychology will come in handy but I don't think I'm gonna practice it, let's see what I can do about you know making kind of bridging this gap between making money and being in a creative field and so that's kind of like where I um got out of college with.

Caroline 23:00

Did you do any internship or anything during college or what were some of your first jobs, paying jobs?

Ben Stein 23:07

I did a couple internships in college, so one of them that was funny was I worked at the local uh CBS affiliate In their news graphic department and that was hilarious because that was like one of the most jaded group of human beings, like if it bleeds it leads like creating graphics for you know murder blah blah blah and and so that was that was eyeopening, I was like oh okay this is interesting but this is not gonna be where I'm gonna end up and then the next internship I got was with um WGBH in Boston and they were the PBS affiliate and uh they made Arthur the kid show out of there, um so that that was a fun internship, um I got to be the voice of Arthur and email newsletters and I got to be the person who read through all the submissions for the Arthur Poetry Contest and which was hilarious, and like kids would send in like poo pee pee and swear words and all of that um and you know I I I got to learn more about what was involved with production and how it actually worked in the real world.

Caroline 24:14

And so this this vein starts to come in and then as you graduate college what did you choose to do?

Ben Stein 24:21

So, I was still with my college girlfriend at the time, she uh was was gonna become a doctor, so she got a job at the NIH in Bethesda where I grew up, um so I went to kind of back home to live with my parents. So I was trying to figure it out and so it was kind of like applying to like weird random corporate jobs just to get a job, but I was also looking for jobs in the television field and um you know this is where I learned kind of like I mean one of the lessons that I teach folks today about the power of networking like when I first got introduced to the idea of networking I'm like I'm gonna get a job on my own accord, like I went to college, I'm gonna put together a resume and then I'm gonna go in there and they're gonna like me or not I'm not gonna use nepotism to try and get me a job cause that's um but ultimately my uncle's neighbor worked at a documentary production company and I ended up uh interning with them and then ended up getting hired there and that was like my first of real job and it was great cause it was a documentary production company and we ended up working on this film Paperclips and it was the story of middle school children from Whitwell Tennessee who started a Holocaust Memorial project and they collected enough paper clips for um all of the 8 million people that were um killed in the Holocaust and it's a story about them learning about it and then becoming teachers to other kids in the area and this was like miles away from where the KKK had one of its biggest um uh beginnings.

Caroline 25:58

Interesting. Interesting. And and then what happened?

Ben Stein 26:04

So I I really enjoyed working there and I also realized like going up the production route was hard I also got this um part-time gig on ESPN2s Show Sporting Dog Chronicles as an associate producer where I was I was in the office helping organize the shoots and then I got to go out on a couple shoots and I realized I'm not an in the field guy, I I hadn't really gotten the training but I remember it was this husband and wife team and um I just have this distinct memory of being on set with these German short haired pointers which are a breed of hunting dog and there are some young ones and the direction I got was, go run these guys around to tire them out so they don't bark during filming and uh I distinctly remember I had these like big wide baggy jeans that were in style at the time and they were like falling down so one hand was like holding them up while I was running the other hand was like holding the leashes of these dogs and then I'm running them around being like this is what I went to college for and then I like turned over my shoulder and like everyone's laughing at me and I was like I don't know if this production roots for me.

Caroline 27:19

Interesting. Yeah, I was thinking like oh maybe you didn't wanna be like you know you still wanting to do the behind the scenes things kind of more aligned with you know being introverted but, no it's it's actually baggy jeans running dogs inter. Now had you had dogs growing up?

Ben Stein 27:34

I hadn't this was this was a random assignment and and I really I mean fascinating like I wasn't a hunter either but

Caroline 27:41

Yeah

Ben Stein 27:42

it was a fascinating opportunity I got to like go into Arkansas and some other random areas to see these breeders do their thing knew knew respect for for what those dogs do, but yeah uh I mean I I like dogs a lot but um I mean one of the best things was being surrounded by all these like Labrador puppies um during one shoot.

Caroline 28:00

Aw. Yeah

Ben Stein 28:01

Um so my girlfriend got a job um up in New York Well she actually she she started medical school and I wanted to move to New York anyway cause there's more opportunities in television I ended up getting a job at BBC worldwide and the appeal of that was a it was more about doing deals, so I didn't have to be out in the field and then b. uh the the boss that I worked for worked on children's television deals so I was like oh maybe this'll be a a good way to to kind of continue the children's television thread, so I got that job and so the first lesson I learned was networking, the second was storytelling and it wasn't intentional but my boss told me later that one of the reasons I got the job was because I was describing my previous job where I was sensitive to my boss who was a new parent and I knew whether to kind of like let him have his space if he had had like a rough night with a kid or um if he was ready to engage or not and she said like that or understanding really clicked with her, so that was one of the reasons that that helped me get the job and she only told me that afterwards and that wasn't intentional, but um storytelling can be important when you're telling the right story to the right person.

Caroline 29:18

Very much so, and and even that empathy that you were able to display there, I guess you'd learned that growing up as far as like how is your mom doing, what are you gonna do, how how are you gonna show up based on how she's able to handle the day and I and so much of that could correlate to somebody who is a new parent and now you're way more perceptive than other people about um how somebody's showing up and how you can show up accordingly. That's cool. And then what happened?

Ben Stein 30:31

So zooming out from all of this, I then got really bored there I mean starting a young life in New York was great, great that I didn't have a motor vehicle with the amount of drinking that I was doing at the time so that was a that was uh helpful for public safety, um but I got pretty bored and my ability to move up um was pretty limited and I wanted to get back to more hands on and closer to the creativity cause the pushing the paperwork wasn't exciting for me, so um I actually I forgot to tell you one of the internships I didn't get in college was at the Jim Henson company, so I always was a big Jim Henson fan and I remember getting that letter with Kermit on the um letterhead and saying I got rejected It was sad I'd gotten close but didn't get it, so any anyways um I I I remember interviewing for like another job with a muppet type maker someone who was in that and I chose between that and um this Noodle Soup Productions and this was a small animation company and, um the the roles for kind of a producer slash business development person, so I was trying to help them grow their business on the commercial side with ad agencies uh and then produce whatever we work that we got and that was that was it was an amazing experience um being next to all these amazing creatives and and as a producer I had the opportunity to kind of make more money than an artist which was important for me, so I was there for a number of years and got up to executive producer, ended up producing some great commercials um and I started doing interactive work there as well, Uh and that's also you know so I I was there from from my mid twenties to my late twenties and that's also kind of in my personal life where I was going through kind of like the dark night of my soul and I first decided to get help kind of hitting a couple different rock bottoms along the way, but in that experience it was nice being close to the work and being in business development and advertising then it was it was a great excuse to go to all these free open bar parties, so that was like fun for a while until it got like pretty empty and soulless um and then I finally realized like, okay, like partying is getting old I am getting older, my relationships with women weren't really um they were kind of gross in the way that I was treating them and relationships with friends weren't that um great because I wasn't like that present, so I I kind of things came to a head so I was always able to like keep work okay, but ultimately there was this like big gaping hole inside my soul and my heart where I was like I I need to change something and I tried to do it on my own for a while like listening to Tony Robbins and downloading things via Limewire trying to like reprogram myself and then ultimately um I made the call to get help in my late twenties um that I I thought psychiatry was the gold standard, so I first went that was my first line of defense and unfortunately some psychiatrists are there just to prescribe medicine, so I was there to,

Caroline 34:05

Yeah.

Ben Stein 34:05

My soul after holding onto like all of this baggage for years and then within like 15 minutes he's like what do you want prescribed and I was like it was like a gut punch and and I was one to experiment so I tried antidepressants but they just kind of like made me more numb, uh so I I went off them but I did go into therapy for a few months and that was cathartic to help get stuff off my chest that I've been holding on to, but it didn't change my behavior and I went into each sessions thinking what's wrong with me this week, so that seemed counterproductive and then ultimately an an ex-girlfriend gave me the gift of an intro coaching session, then I did a weekend intensive and then that turned into a six month uh client side program which then transitioned into a two year apprenticeship to become a coach uh and all of that was very transformational for me to give me tools to design my life intentionally which I hadn't been doing and also tools for changing my thought process, those negative voices in my head and dealing with trauma in a surgical way instead of swimming in it and how to alchemize that um, with some methodologies that really resonated with me in a way that therapy didn't and so I was really able to, I landed my first six figure job and I went from uh, the the studio side the agency side uh and I took over a year off of substances at that point at the challenge of my coach it was actually three months and I kept it going cause it felt great and I changed my relationship with substances I still there I mean there's more of the story there, but it was it was a great reset for me and I kind of grew up emotionally in many ways like going to weddings sober or dating sober and doing all of that and that allowed me to to grow up uh a lot and you know, I just kind of fell in love with being held to a higher standard and playing a bigger game and so at the end of that two year apprenticeship, I was like well if I'm gonna be a coach I gotta live out a dream and one of my dreams since I studied abroad in Australia and college was to travel the world, so I left my day job I left the coaching training program and I backpacked around the world for eight months and I started with Kilimanjaro and I ended with Everest Base Camp uh and just had some amazing adventures in between.

Caroline 36:35

And were you in a relationship at that time or was this like a fresh restart all all areas?

Ben Stein 36:43

So it's a good question. At the time I had met a Australian woman who was she was she was a doctor as well, I had a thing for doctors. But she was studying in New York getting a an extra master's, she was actually moving back to Australia and the idea at the time was that I was going to travel some and then moved down to Melbourne and I was actually I remember, I was in India interviewing jobs that had agencies in Melbourne and then I was like, I'm I don't want to do this I don't wanna do this, so I remotely broke up with my girlfriend and then I mean there's some funny details about the story, so they're not funny, but I remember it was Valentine's Day and it was right before I was going to do my Everest Base Camp Trek, she was taking some exams, so I didn't wanna break up with her before her exams to kind of like create emotional upheaval prior, but I remember I was like well so I sent her these like e-card for Valentine's Day knowing that I was gonna break up with her and I was like oh my God I'm a terrible human being and then I was doing the Everest Base Camp Trek knowing that I was gonna break up with her, so it was just like on my mind as I'm like walking for days on end and like the most beautiful nature and then knowing that I'm gonna have to break up with her her when I get back and then I break up with her when I get back over Zoom and then she's like well we have to meet and talk about this I'm like really? She's like yes, I was like okay Oh I'll give you that respect, so then she flew to Hong Kong and we had like a very bizarre breakup weekend. It could have been like a short film in itself uh but yes ultimately great woman it just didn't feel right for me to move forward with it.

Caroline 38:35

Yeah

Ben Stein 38:35

So we broke it off at that time.

Caroline 38:37

That's interesting. And and it's also kind of like um yeah like had you traveled a lot by yourself previously cause to I mean it's it's ballsy and it's great and everything anybody wants is on the other side of their comfort zone, so like there was a time a a few years ago where I intentionally just kept putting myself in uncomfortable character building experiences I couldn't quite you know leave kids and a husband and go around the world, but still that's a pretty ballsy move to make brave and transformational, but like what gave you the ugh to like actually go from the thought that would be cool to the action of yeah I think I I think I will do this thing that probably a lot of other people were like really? Leave your job? Go around the world, are you sure? That's is that a great idea.

Ben Stein 39:30

It was one of those things that was on my mind for years um I'm a big Tim Ferriss fan and he talks about the book Vagabonding by Ralph Potts and I read that and it inspired me, I was like I wanna do that at some point and I I kept thinking about it and I remember like talking about it with my dad he is like do you think that that's a good idea and you know I thought is this gonna be career suicide if I do that and ultimately what I what I loved about the the coaching container I was in was it was like okay let's design your life, like what do you want and I was like I do want this, so uh and then actually like making it happen the the accountability, so I think I had gotten accustomed to getting out of my comfort zone and uh I was like if I don't do this now I'm I'm not gonna do it.

Caroline 40:25

Yeah

Ben Stein 40:26

And and that was similar to you know later on when I had the opportunity to go coach full time after I got let go and we'll we'll talk about that, but um I was like if I don't do this now in my early thirties, I'm gonna have kids and I'm not gonna be able to get away, so like let's let's do this now, and I had had I'd heard a lot of people that had done Kilimanjaro and it was just like one of those things like when you feel envy it's like a signal, like go for it, right? Um and that was one of those things that I like wanted to do and I remember traveling alone in India was like a traveler's like scary thing, but I was like if I can do that it's like if you can be in New York you can make it anywhere It was like if you can travel in India then you're like you're a traveler so or a backpacker um so yeah I I kind of wanted to experience that while I could.

Caroline 41:11

And were you in shape?

Ben Stein 41:14

Yes, I mean, I had completed a couple of marathons by that point.

Caroline 41:17

Oh wow. Yeah

Ben Stein 41:19

Um and yeah I'd done the the New York marathon in 2010 which was an amazing experience and uh I remember walking around New York City with like a backpack in my boots breaking them in getting practice and there's this one Roosevelt Island subway station and I had like the biggest staircase and I remember doing that like up and down for a couple of hours um training. So yeah I was I was training for it.

Caroline 41:46

That's good. So even your pre character building experience you were mini character building. Although, I I've seen that staircase in pictures, one day I'll actually go there and I don't think that's a a mini, a mini character building especially with the backpack. Yeah

Ben Stein 42:01

It was it was for real, so uh yeah so I was I was in decent shape for uh for Kilimanjaro and um, yeah it was it was a challenge but it was it was beautiful, really enjoyed it and yeah had lots of lots of adventures in between.

Caroline 42:16

And then and then you come back from that and then yeah, let's catch back up on the and then what'd you do for your job after coming out back to that and then getting to those the later chapters.

Ben Stein 42:25

I wasn't fully aligned with the coaching company and going back to them I didn't feel fully aligned and I was scared to become a coach full-time at that point, so I went back into ad agency land um and you know became an executive producer, I remember I worked on the relaunch of ge.com started freelance and then got hired on and then I then went to another agency became a director of project management there um worked with clients like uh Samsung and uh and over there we worked a lot with uh Johnson and Johnson, but ultimately I was like I mean helping to drive bigger projects bigger teams and I was like okay but advertising was kind of a grind and I knew it like wasn't the thing for me but with the technical projects there was interesting things to learn and I like working with smart people especially the developers and the creative people, so I liked working in those team environments, ultimately uh one of the tech leads went on to small.com and he brought me a board to um be a leader in product management, so I had the opportunity to switch from like producing and project management into product management um and and kind of thinking about it more like software and that was a big pivot for me and I was scared about that, but I was like you know worst thing I can do is suck out it and I get fired but they paid me more money and it was a good opportunity to learn, so it was like Why not um and so that was at at Artnet uh which is a small.com that serves the fine art space and I knew it wasn't the thing for me, I wasn't like a natural great product manager, I was there for like four or five years and um it was kinda like golden handcuffs I knew I wasn't aligned with it and I wasn't adding the value that I would've liked to there and it was one of those places and I hadn't really experienced it before, it was like okay when am I gonna get fired? Because they weren't bashful about letting go of people and I knew my time would be up at some point, so I was kind of always looking over my shoulder, so in 2016 I was like what's my purpose? I need to figure this out, so I started the Purpose Up podcast, cause I loved podcasting and I started interviewing people living purpose-led lives to inspire others and to kind of get get medicine for me and then I started coaching as a side hustle at that point and getting some business coaching to help business build my business chops and so I had the best luck with helping people with career transitions cause I was trained as a life coach Um but I had this great corporate experience to leverage, so as I started on my coaching career I was like okay do I kind of wanna help people who are you know, abusing substances but not like full-blown addicts or do I wanna help people advance in their career and and ultimately it kind of shook out that trying to get clients who are struggling with addiction a lot harder than people who are I wanna get a new job and and I had a lot more success with that, so I I was kind of like my project management skills you know my advertising skills in terms of picking up, branding, copywriting, um and marketing and then invested in business coaching to help me learn how to build a practice and get clients and learn sales and all those skills to to do that, so I work as a as a side hustle and then my first son was born in 2018 and I go on paternity leave I get back and I'm and I'm at my computer the second day like a lot of my coworkers had got let go previously in a restructure and I thought I was okay um turns out they just wanted to gimme paternity leave which was which was nice of them um, and gimme a stress free uh paternity leave um and then the second day back I get the email from the CEO like come to my office and I'm like oh this is not good, like my heart drops and I'm like you know hearing my footsteps echo through as I go through like the big hallway to the CEO's office and then you know that kind of like out of body experience as I'm getting let go and I kind of like know what's happening but you're like processing and everything's in slow motion so yeah uh I got let go and I was like okay that sucks and as I'm so I was working in the Woolworth building in New York and as I'm leaving, I had my stuff In my hands and I get a call from this coach and he is like, hey you're in like you got accepted into this coach accelerator program, like literally as I was leaving the building and I was like okay this is a sign cause the choice at that time was to go for another safe tech job, they were easier to get in 2018 or um go for full-time coaching and I decided you know do I wanna live by example for my son or do I wanna play it safe and I was like let's let's live by example and so I I made the decision to go for it full-time and um and haven't looked back since.

Caroline 47:46

Awesome. And it was cool that like you explored and I think this is something that that you encourage people to do now and and and me as well while you're in that job even if you're starting to feel like hmm I don't think this is it you know you don't have to just make a rash decision and leave, you can leave by choice or by force, you kind of waited it out a little while but you were still building up skills exploring other things while having a little bit of a safety net and then when that was removed you were already a few steps ahead of somebody else who like just waits for the dire like oh I guess now I should figure out what I want to do.

Ben Stein 48:21

And I remember I'd also I was working with a purpose coach you know I I received of different coaches Uh one of them was a pur purpose coach um her name is Holly Woods and she's got a couple great books out Uh one's called The Golden Thread, but um she she encouraged me to look back at my childhood uh what I liked doing and one of those things was cartooning and part of me is like I'm an almost 40-year-old man at this point like why would I do cartooning. But um I remember drawing about the fear and anxiety of becoming a new parent and so I started drawing and then I started writing alongside that and I ended up making a a dad blog called I Hope I Don't Kill It and it never like blew up or anything but it was this really fun project where I got to draw and write in this irreverent voice and tapping back into my creativity was really freeing and knowing that I could do projects like that and that ultimately um when I was in a leadership container another couple years later, they were like oh what's what's a stretch goal that you wanna do that you wouldn't do otherwise and I had had a desire to write a children's book, so having that experience of the dad blog writing and drawing um empowered me to do this children's book uh and so I ended up writing Little Benny Piggy and Courage for the Win and it's all about feeling the fear and doing it anyway and I think that's the key you know we talked about getting outta our comfort zone, I think that is the key to finding successes is feeling the fear cause we either run away from it and that's what I did for years with numbing with um avoiding or we can we can step into it and um you know uh even as as recently as yesterday I was chatting with Claude, we were talking about my financial goals and plans this year and it's ultimately challenging me to raise my prices I'm like but no I don't wanna raise my prices and so um you know we constantly get to be in this space of of challenging ourselves and getting out of our comfort zone

Caroline 50:20

Absolutely. I get it I get it um and then you've got you went on after writing that children's book to to write something else uh what was that?

Ben Stein 50:29

Yes. So I wrote uh my first nonfiction book Purpose Up Break Free and Find Work That Matters and it's essentially the book that I wish I had had when I was in my late twenties trying to figure things out uh and and so I it it tries to encapsulate a lot of my methodology into a book um for people to understand how I approach things were we understand our vision we understand how those inner critics can run the show and how to rewire that and like a a big portion I think is healing some of those wounds from growing up and reframing them so that we can understand the gift in them and also once we kind of get rid of some of those lenses that we grew up with, we can see with clarity where we want to go more, so I

Caroline 51:19

think

Ben Stein 51:20

healing is an important part of the journey and then from there we can ask ourselves and we can be more in touch with our intuition, what does success would look like for me as opposed to what I've been programmed for and we can go on that exploration in terms of skills you know the the IKAGI where um we match up what the world needs with what you know we're good at and and our skills et cetera um and then from there what are the practical steps of selling ourselves, networking, connecting with people, building relationships and um how to tell compelling stories to enroll people

Caroline 51:58

Yes.

Ben Stein 51:58

and so it it it covers a lot and tries to introduce a lot of concepts in the way to help people where they're at.

Caroline 52:05

And and let's talk a little bit about that, like when you were growing up what did you think it meant Like what did you think success was? What did you think it looked like? Even if you hadn't bought into what your own personal success was going to be or what you wanted to do but you still had this view of yeah the world or what it was could be like if someone was successful, what did you think it was back then?

Ben Stein 52:32

Yeah. I don't know if I had really thought about success much to be honest um you know, I think both of my parents came from like a middle class background and there was almost a it it was like anti getting too rich or too much money, so it wasn't about like getting all of this stuff um you know I think so I I didn't really think about what does success look like I thought about, how can I find work that I can have fun with and that that was the first like like for me it was like make money have fun learn and grow and that was my criteria and then as I grew ultimately kind of um I like what Tony Robbins says about this It's like there's uh there's a science to success and you can follow steps, but there's an art to fulfillment and that fulfillment you need to figure out what that is for yourself, but ultimately there's a service component to that, so you gotta figure out how am I here to serve others and that that ultimately like with coaching served me I was like I really like this thought process and and a lot of therapy I think is great and I don't wanna discount em especially coming from my background and both my sisters became therapists but ultimately approaching was a lot more powerful for me and being able to challenge people, being able to be forward facing uh really resonated with me a lot more and so ultimately that became this like vehicle to live my best life and and serve others uh in the process.

Caroline 54:07

And so now how how do you define authentic success for you in this moment?

Ben Stein 54:11

For me it's am I being energized, am I serving and am I in flow often than not, so and also am I listening to those intuitive nudges about what's next, so for me those intuitive nudges that make me uncomfortable are around building real community and real life, um they're about speaking in public more uh and they're about ways to impact people less one-on-one and more one to many uh so those are those are those things that I'm being nudged towards that I'm excited about.

Caroline 54:54

And how do people find you? How do they work with you?

Ben Stein 54:58

Yeah, so you can check out my website purpose up.com I'm also Coach Ben Stein S-T-E-I-N on Instagram, so that's another way to find me and I'm also on LinkedIn I'm active there so you can look up Purpose Up Ben Stein um yeah so you can reach out to me via any of those channels and we can have a quick chat to see if it makes sense um you can also get my book uh it's on amazon Purpose Outbreak Free and Find Work That Matters uh so there's lots of different ways in and and if you want some free tools uh you can check out purposeup.com/gift and I've got some good job searching tools if uh if you're in the market.

Caroline 55:36

Awesome. Awesome. Well thank you so much Ben for telling a little bit more of your story and I I just wish you the utmost happiness success fulfillment and all of those things you do such amazing, beautiful work and you've helped so so many people. so thank you so so much.

Ben Stein 55:52

My pleasure. Thank you for asking great questions, definitely went a lot deeper here on my history but uh hopefully folks can can resonate with my story and uh I appreciate you holding the space.

56:04

Ben, thank you for sharing your perspective and the evolution behind your work. I appreciate the way that you articulate transition as a thoughtful process rather than a dramatic event. Your path from seeking to serving offers a grounded framework for professionals navigating their next success. Thanks for listening to Your Next Success with Dr. Caroline Sangal. Remember, authentic success is yours to define and includes aligning your career to support the life you want.