Permission to Start Over: Five People Who Got Kicked Out, Dropped Out, or Walked Away

Five guests. Five very different lives. One thing in common: every one of them dropped out, failed out, got kicked out, or walked away, and built something meaningful anyway. In this compilation, a deputy attorney general, a congressional staffer, an Amazon AI policy leader, a med-school admissions director, and a serial entrepreneur share how their worst setback became the start of their real path.

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Transcript

SPEAKER_01 0:00

Life is not like roads and highways and freeways. It it's like the ocean.

SPEAKER_05 0:06

I would just say just go through it, you know, give it a go. Try things, fail, amend your plan, and just give it a go. I mean, if you never try, you'll never know.

SPEAKER_03 0:15

What great advice. I wish I had it when I was in college. Was to just lean into your curiosity and keep exploring.

SPEAKER_00 0:22

I actually see imposter syndrome now. I was like, being light. I'm like, good. It means I'm unsure of myself. I'm putting myself out there.

SPEAKER_04 0:27

I catch myself saying it all the time, is just do the work. And then the other thing is it's okay to say yes to new things until you're ready to start saying no.

SPEAKER_02 0:37

Hi everyone, and welcome to Pathfound, the podcast about the real, messy, unexpected journeys that lead us to the work we love. I'm Monica Gandonia, and every week I talk with someone whose story proves there's no single right way to build a meaningful life. Today's episode is a little different. We're pulling together five stories from five very different people: a deputy attorney general, a congressional staffer, a tech policy leader at Amazon, a senior director who helps students get into medical school, and an entrepreneur in Cape Town, South Africa. On paper, these are impressive careers. But here's the thing they all have in common. Every single one of these guests dropped out, failed out, got kicked out or walked away. Stephen Kearns and Gus Orosco both dropped out of high school. Virginia Ross got kicked out of college twice. Sean Walpole failed out of his first university. And June Kim was dismissed from UCLA over a rule he didn't even know existed, walked away from pre-med and spent two years as a movie extra before finding his way back. This episode is about what happens after the worst moments on your transcript. It's about turning points, the people who open doors, the leaps that look reckless from the outside, and the self-doubt that it turns out never fully goes away, even for people at the top. If you've ever felt like you blew your one shot, this one is for you. Let's get into it. Let's start where none of these stories were supposed to start. Stephen Kearns is a deputy attorney general at the California Department of Justice. He went to Harvard Law, but at 17, he was a high school dropout sharing a three-bedroom house with five other people.

SPEAKER_00 2:15

So interestingly enough, I was a high school dropout. So I grew up in Long Beach. I joked that I was raised by wolves. So learned how to bend for myself fairly early on, have like a kind of fierce independent streak. Sometime around seventh grade, and my parents split, and I went from like very focused academically to like, I don't care. So I became a terrible student in like the span of a semester. And when it came to high school, I remember I had this big chip on my shoulder because I would do really well on tests, but I would do very poorly in class because I refused to do any kind of project or homework or anything like that. And my perspective at the time was like kind of cutting off your nose to spine your face, but you know, you're a teenager, so you think you know everything. And so I had this view that if school exists for me to understand knowledge and I can show that I know the knowledge because I do one on the tests, like the rest of it is theater. Why do I need to do this? And I didn't have the foresight to be like, okay, it's to get you to practice and build discipline. I pretty much dropped out out of spite at that point. I was like, this is a BS system. I don't agree with education.

SPEAKER_02 3:29

Gus Orozco grew up in Long Beach, the son of Mexican immigrants, translating for his parents and carrying pressure no kid should have to carry alone. Today he works in the United States congressional office. Back then, college wasn't even a concept.

SPEAKER_04 3:45

I already knew that that was the direction that I was gonna go. College really wasn't in my path or in even in my siblings' paths, just because we didn't understand how to apply for college, you know, we didn't have money for college. So so for me, I knew that really joining the military was going to be a way for me to create something more than just, you know, being the handyman working for my dad's plumbing company or or whatever it might be.

SPEAKER_02 4:10

Jun Kim was the model child of a Korean immigrant family. Honors classes, 15 to 20 AP courses, biology pre-med at UCLA. He did everything right. And then it fell apart over a policy nobody had ever explained to him.

SPEAKER_01 4:25

I was actually dismissed from the university due to a violation of an academic policy that I was not aware of. I had met with my advisor and she advised me to take W's. For those of you that aren't friendly, and W is a withdrawal it's where you drop classes in college, and instead of getting a letter grade, you get a W on your transcript. And so it was the summer of 1995 that I was dismissed from UCLA.

SPEAKER_02 4:53

Was it because you had too many W's?

SPEAKER_01 4:56

No, it's when you're on probation, you can't take, you can't withdraw. That's the policy. When you are when you are on I didn't know that because you know, I'm thinking, well, my advisor's telling me she's recommending I take the W.

SPEAKER_02 5:08

How come you didn't appeal it?

SPEAKER_01 5:10

I didn't even know about appealing. What is an appeal? Appeal is like the outside of a fruit. Remember, I I did learn English and I speak the language, but in terms of my understanding of how things work, how systems work, how do colleges work, how you know, these types of things I just did not know. And so also coming from my culture, you listen to what authority says. And so if you have an academic advisor who tells you they recommend you drop and take W's, I I I obey and I and I with true.

SPEAKER_02 5:41

Virginia Ross now leads Amazon's state and local AI policy portfolio. Her college transcript tells a different story.

SPEAKER_03 5:50

Oh, your girl didn't declare a major until her third year because I kept checking undeclared. I had probably like 200 credits by the time I graduated, and I got kicked out twice. When I first started, I think getting that taste of freedom after living under such a strict household, I didn't know what to do with myself. And I had fun and just had a lot of fun. Woke up late, you know, had all 8 a.m. classes because I didn't know. My parents didn't go to college like my mom did, but you know, and it's not their fault. They just like didn't know how to guide me. They didn't sit me down, like go, hey Virginia, like by your second year, you're gonna want to know what you want to do, and then you're gonna declare a major. And that just wasn't something that I felt I didn't have that self-motivation to do that. I was literally checking a box.

SPEAKER_02 6:36

And Sean Walpole, who has built businesses across two countries, flamed out of his first try at university in spectacular fashion.

SPEAKER_05 6:44

So my first year I did quite a lot of partying, but I didn't build any of those good study habits. And the wheels came off for me very quickly on my second year at college. Because all of a sudden I I did have to do some work. I ended up mostly ended up failing, failing university in the middle and having to go back home, which was a really big inflection point in my life.

SPEAKER_02 7:03

So what changes? For every one of these guests, there was a moment when the old path became unbearable and a new one cracked open. For June, the two years out of school taught him something he didn't expect. And then a letter from UCLA gave him a second chance.

SPEAKER_01 7:18

But ironically, those two years that I was out of school was when I realized I really wanted to be in school. But fortuitously I received communication from UCLA that, according to their records, that I did not graduate, which is true. I mean, I I got kicked out. So I did not graduate, but they had a readmission program that if I were to take five classes and get a certain GPA, that I could be readmitted. And so I took that as a sign that it's my second chance. First thing I did was change my major. I was no longer biopremed. I switched to psychology and education because I I was just really fascinated with people's motivation. Why are some people really motivated and others not? And then why is it also that some people learn more effectively than others? So that right there was probably the impetus for going into education for me.

SPEAKER_02 8:14

For Gus, the turn came after he left the army. He was home from Iraq, stalking shelves overnight at Home Depot, sleeping on his brother's couch, and feeling himself slide backward.

SPEAKER_04 8:25

It was scary. It felt like when I got home, I was I think 22, maybe 23, it felt like I just time traveled from high school. And I kind of forgot all of my military stuff. I I got like an overnight job, stocking shelves at Home Depot, and I was sleeping on my brother's couch for a little bit while I kind of got on my feet, and I started to feel like I was turning back into that high school kid that that really didn't have any purpose or direction. And so yeah, I definitely felt like I was slipping back into something that I really wasn't happy with. I feel like it kind of reignited or re-sparked something in me to, you know, completely change everything that I was doing. So I quit my job. I joined the Army Reserve and went to do training. And as soon as I got back, I enrolled at Longie City College and basically started school in the Army Reserve at the same time. And it I think it was the the kick in the butt that I really needed.

SPEAKER_02 9:21

Sean had to fail twice, first at university, then at making it in London before he was ready.

SPEAKER_05 9:27

And that led to yet another inflection point, I think, in my life. Because after that, I went back home to Zimbabwe, having failed to make it in the big world of London, and decided that I really did actually want to go back and pursue my studies. My parents were amazing enough to continue to fund my education. And I then applied to the University of Cape Town, and that's how I ended up moving to Cape Town, South Africa. Enrolled at UCT, started a new degree, but this time it didn't I really took it seriously.

SPEAKER_02 9:58

And Steven discovered something surprising when he walked out of the army on a Friday and into Long Beach City College the following Monday.

SPEAKER_00 10:06

So when I got out of the army, I started at Long Beach City College, and I remember I got out of the army on Friday, started City College on Monday, and was like borderline having a panic attack that Sunday night. Because I was like, oh my God, like this is gonna be like college, people are gonna be in like the quads puting Shakespeare like cold, and it's gonna be like incredible intellectual superpowers, which you know, I was in the army for the last four and a half years, I'm not equipped for this. And then I got there and I realized I had built the discipline and the practice that I refused to engage with as a high school student in the army. And so it was really easy for me to take like the ability to retain information in my curiosity, couple that with the discipline and the habits I had built in the military, and actually become a very good student.

SPEAKER_02 10:52

Here's the part of these stories that nobody puts on a resume. Almost every turning point ran through another person, a mentor, a friend, a professor, or in Stephen's case, a stranger who almost said no. He'd been rejected from a National Science Foundation research program in Costa Rica. Most people stopped there. He sent one more email.

SPEAKER_00 11:14

I actually was rejected initially, and this is a kind of bottled lightning, I got lucky moment, but I followed up and I was like, hey, you know, understand that I got rejected, and but I'm grateful you reviewed my application. What could I do better? You know, I just want to keep at this and I want to like take learning experiences when I can get them. The woman who was the head of that specific grant was a wonderful mentor of mine named Daniela Shepitz. She's um, I should say Dr. Daniela Shepitz. She's an ethio botanist, and she, I guess, was at a conference and just happened to pull up her phone at that time, was reading emails, had a bunch of them, picked that one, was like, oh wow, that's a really nice email, and like read my application. She's like, we need to get this guy. I don't know who screened in, but like, I think we should get this guy. Had it not been for the polite follow-up, I would have been that would have changed the arc of my life because that gave me research momentum to apply to more difficult science programs. So it really reminded me the importance, and I've used this lesson throughout my life. Professionals are busy, politeness goes a long way, and it's okay to be like, hey, look, sometimes your inbox is buried. I get it. Mine gets buried too. But to follow up and just be polite, show that you actually really care about this, and be thoughtful in your pursuit of it.

SPEAKER_02 12:32

June will tell you that mentors changed the entire trajectory of his career. As a biology advisor at USC, he'd hit a ceiling. Two mentors from his master's program told him to keep going.

SPEAKER_01 12:44

So this is where mentors are very important, everybody. But you already knew that. And I mean, if you're watching this video, you know the importance of mentors. I had two mentors from my master's program. I went to each of them separately and I sought their advice on my career. And then my mentors both said, Well, why don't you get your doctor?

SPEAKER_02 13:00

Virginia will tell you straight out that relationships are the through line of her entire career. Her first real job, the one that started everything, came from a friend who barely explained what it even was.

SPEAKER_03 13:12

And I had a really good friend from high school who worked at Booz Allen Hamilton, which is like a management consulting firm out here, and they do government consulting. There were like there was a day when they were one of the big five out here with Lockheed and like Bering Point and Accenture. And she was an EA there and she was an executive assistant. And she said, Hey, there's this like business analyst role open at the at the FDIC. And I'm like, What's the FDIC? She's like, I don't know, I'll just go apply. And I'll tell my boss you're a good person and you'll get the job. And Gus puts it more bluntly than anyone.

SPEAKER_04 13:46

For me, I've been lucky enough that I've had incredible mentors who who have shown me or who have who opened those doors for me. And so, you know, for a college student that m doesn't have the military background that I do, I think it it is finding those mentors. I mean, you're you're an incredible mentor to me, and and there's no real military connection here. But I think that's another thing is is get to know the old people because they're smarter than you are.

SPEAKER_02 14:11

Thanks. It was all going well until you you said that. At some point, every one of these guests did something that looked irresponsible from the outside. For June, it was the most unexpected leap of all. 20 years old, just dismissed from UCLA, and instead of hiding, he answered an ad in the student paper.

SPEAKER_01 14:30

I decided to do something very different, very out of the box, something just completely on my own. And so I started my career as a movie and TV show extra. So that's why, you know, while there's always a curiosity of what would have happened had I been dismissed from the university, but I also think I'm very grateful that that allowed me the opportunity to really do my own thing and adventure into something that I don't think any of my high school friends and classmates would have ever anticipated. In fact, that's exactly what happened. A bunch of people saw me on various TV shows. Hey, isn't that June walking in the background? And you know, people reached out to me, like, what are you doing these days? So why did you even think to do that?

SPEAKER_02 15:12

Sat acting.

SPEAKER_01 15:14

I think I like novelty. I like things, variety, I like changes. And I recall specifically seeing in the UCLA newspaper there was an ad for extras needed. And it's the most important words were no skills necessary, no talent necessary. I don't think it said no talent, but it just said new faces needed. And so I said that could be me, you know? And so I just went and got myself registered. This was way back before all the technology, so everything was Polaroid and paper. And so they took a picture and then they had all these different questions asking me about my talents and skills. Can I juggle? Can I play sports? Can I ice skate? And basically a full inventory of my abilities because you know, when they're filming, they do need people in the environment, right? If you have a main actor, Mary, main characters in the storyline, they could be at a shopping mall, they could be at the gym. There's gotta be people around, so it was fun.

SPEAKER_02 16:12

Virginia's leap started with a trip to the Grammys.

SPEAKER_03 16:16

Yeah, I saw the Pacific Ocean, which I had seen before, but I don't know what it was. I was in Palos Verdes visiting a buddy of mine, and I was like, Well, I need to see this every day. I'm gonna move here. And I came home and I broke up with the boyfriend I was with at the time, and I said, I'm moving to California, you can't come with me. I'll probably move, you know, when this lease is over in a month, I'll move into the second bedroom. And then I left, packed my dog up, and we moved to Los Angeles.

SPEAKER_02 16:42

And when Sean graduated with no idea what came next, his dad gave him the advice that became the engine of his whole career.

SPEAKER_05 16:49

I really, really struggled with what am I going to do next. And my dad said, well, don't just sit around, do something. And that was great advice. So I did. I started the computer company and I just lived from day to day and slowly but surely built up momentum. You know, you know, once you actually start with some momentum and moving, you can then say, Oh, well, this isn't working, and you pivot to the next thing, and you pivot to the next thing. But it's definitely much easier to go and do something great once you've gotten going. The hardest thing in the world is to take that first step, but you don't have to see the whole stairway to take that step.

SPEAKER_02 17:22

I want to be honest here because these leaps were not painless. June eventually had to admit to himself that acting, however much he loved it, was never going to be a realistic career. That kind of honesty is its own kind of courage.

SPEAKER_01 17:36

But I think I was honest with myself that, you know, it it is very, very difficult because of the sheer numbers. You know, there's so many people, not just in California. You have to understand people move to Southern California from all over the country and even the world.

SPEAKER_02 17:53

Right.

SPEAKER_01 17:54

Just in hopes of making it now.

SPEAKER_02 17:56

Here's the part I think every student and honestly every adult needs to hear. You'd assume that once you make it to Harvard law, the self-doubt goes away. It doesn't. Steven tells a story about one of his professors that has stuck with me ever since he shared it.

SPEAKER_00 18:11

She puts her cell phone number up on the whiteboard, then notoriously private person, Professor Freeman, puts her cell phone number up on the whiteboard. She goes, This is my cell phone number. Please don't save it. But text me what you're afraid of. Text me what you're afraid of. And, you know, give the room a minute, 90 seconds, whatever. And then she just starts reading them out. No numbers, just hey, you know, here's what it is. Here's what it is. And it was just so damn consistent. It's like, I'm afraid I'm not good enough. I'm afraid I'm not good enough. I'm afraid I'm not gonna be good at my job. I'm afraid I'm not gonna get a job. I'm afraid they're gonna find out I'm not good. I'm afraid they're gonna find out I was a really good student, but not a good practitioner. And it was just, I'm afraid I'm not good enough in some form, shape, and like, and it was it was just unique.

SPEAKER_02 18:51

What a great exercise.

SPEAKER_00 18:52

Oh, it's brilliant. It was brilliant. And but I was like, wow, like it really freaking is everybody. And so, you know, there's this kind of idea when if everybody's guilty, nobody's guilty, kind of thing, right? If everybody has imposter syndrome, then like you're just normal. And that's when you're actually growing, if you don't know. If you know, you're not growing. And so I actually see imposter syndrome now as like a green light. I'm like, good, it means I'm unsure of myself, I'm putting myself out there. Because once I started seeing like how low the bar could be, I felt a lot better.

SPEAKER_02 19:25

And then there's the strangest gift of all the failure that becomes the qualification. When June applied to be a biology advisor at USC, the very thing that had nearly ended him is the reason he got the job.

SPEAKER_01 19:38

Turns out when I asked my supervisor many years after, he said that was the reason why he chose me for the position. That I was very personally familiar with the whole bio major pathway and what it entails, the ups and downs, the emotional roller coaster. And so he was right. I was able to share and impart some of my own experiences, and my students benefited from that. And not realizing that negative event could actually return later in life to be the positive. And that's exactly what happened. And that's why it sounds so interesting. And when it's taken out of context, and people hear me say, I am so glad I got dismissed from college. I am so glad I failed as a pre-med. If you just hear that, that just seems odd. But if you know what I am doing now, which is I I've been working with college students, graduate students for the last 15 years, working with students to help them pursue medicine, getting into medical school. And so, yeah, it is full circle.

SPEAKER_02 20:41

So let's bring it home. I asked all five of them the same kind of question. What would you tell a young person or anyone trying to figure it out right now? Here's Gus.

SPEAKER_04 20:51

Understanding that doing the work isn't just about getting a good grade, it's also about understanding the processes in which you're in to be successful, you know, in those environments.

SPEAKER_02 21:02

Steven says to aim higher than feels reasonable.

SPEAKER_00 21:05

If you're in college, I would say take daring risks, right? Apply to the programs you think you're not going to get into, apply to the wild internships, shink for Congress, shink for you know presidential management fellows. Well, maybe not right now, but like that that the idea of like really glitzy things, you'll get rejected plenty, but you'll get really good at interviewing, you'll get really good at writing personal statements, so a skillful carry with you, and eventually you'll get something. Swing. Swing big and just see what happens. The reason you're probably not going to is because you're like, I'm not gonna get it, right? It's all worth my time. It is worth your time, even if you don't get it because you're practicing, and that's a life skill that you'll need for the rest of your life.

SPEAKER_03 21:45

Virginia's advice is something we should all do. What great advice I wish I had it when I was in college was to just lean into your curiosity and keep exploring because you just never know. Like I shot my I remember shooting ideas down so quickly in my head, thinking it was dumb or stupid, and not fully exploring what that could be. And so I would say that. I would say continue to to lean into that curiosity and continue exploring and just talk to as many people as you can, even though it's scary, we're not all that bad.

SPEAKER_02 22:18

And June brings us back to where we started the ocean. This is the heart of the whole episode.

SPEAKER_01 22:24

Life is not like roads and highways and freeways, it's it's like the ocean. There really isn't an established pathway. If you think of it that way, then you will only go down the roads that you think you can go down. Whereas serendipitously, my background is is the ocean. I could get to that island there, there's no set pathway. I mean, I could go directly or I could zigzag, I can maybe go around the island and go from the other side. There's no set way. And as long as you are learning and growing, I think that is the most important thing.

SPEAKER_02 23:01

Five people, five completely different lives, and one shared truth. The moment that looked like the end, dropping out, failing out, getting that letter sent home was actually the beginning. Nobody handed them a map. As June would say, there's no set pathway across an ocean. You just have to start moving. One email, one yes, one scary first step at a time. So if your path looks nothing like the one you were told to follow, you're in very good company. Thank you so much for listening to Pathfound. If anything we talked about today connected with you or gave you a new perspective, we'd love it if you subscribed, left a review, or shared the episode with someone you care about. You can also find us on Instagram at Pathfound Podcast. To explore more stories, resources, and ways to get involved, visit Keystoneetwork.org. This podcast is just one part of the journey at Keystone Network for helping young people and anyone figuring it out as they go build meaningful futures one step at a time. A huge thank you to my podcast editor, David Strutt. You can find him on LinkedIn for helping bring these stories to life, and to Elizabeth Minor at Silvermine Creative for the beautiful artwork and web design. And if you're on your own path, navigating the unknown, making a pivot, or simply figuring it out as you go, just know you're not alone. The route may not be linear, but there's always a way forward. I'm Monica Argandonia, and I'll see you next time on Path Found.