Why Do I Feel Lost In My Career?

Oct 21, 2025

The Secret Life of Walter Mitty

TRANSCRIPT

I wanted to talk about career and jobs and the feeling that we are supposed to kind of start to have it all figured out in this time of our post 20s, post, no, not post 20s, in 20s, post college era of our lives.

And this idea and the ideal that we're supposed to have some semblance of it figured out, like we're supposed to be on a path that is going in the same direction and have an idea of what we want to do because that's what we're told. That's kind of the idea and the convention that is pushed upon us and placed onto us.

before college, in college, after college, by people that we're surrounded by, by people who are above us at work, by people who are maybe even below us at work, by our friends around us. And I wanted to share kind of my updated perspective on career. And I'm not gonna call this career advice because I don't think it's advice. I don't think I know or claim to know more than you do at this stage of our lives. Like I'm 25 years old and I don't have

all of the advice I don't have. hopefully have some advice and I think even just hearing somebody else's thoughts on career and success and finding a path or starting to find a path and feeling like maybe I'm on it, maybe I'm not, might make you feel a little bit more seen and might make you feel a little bit more heard and

I am just going through this all alongside you. That is the purpose of guys set. Like that is what I wanted to do when I first started it. And by doing this type of thing, every week after week, like, and talking about different topics from relationships and dating to career and mindset and confidence and all of the different things that I talk about on here. I feel like I'm doing that. And I wanted to bring my perspective.

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on career onto here too, because I think it's changed lot and I think it's developed and I think it's supposed to over time. Like, I think what I said and what I thought after college and at 22 and 23 are now different thoughts than I have at 25 and going into 26 in May, which is like a year away. So I'm going to say 25. And I just like I'm going through this alongside you and maybe you'll

hear what I say and think differently about your situation because of it or apply something I said to your own unique situation to inform your perspective on what you do or how you feel about what you're doing. And after college, there's this perpetuated stereotype or convention that you get a job.

and then you try and do really good at that job because you want to get a promotion and stay on track and upgrade each time at that job. So you want to get a job and do well at that job. And then you want to get a promotion and keep on that path and on that ladder and build up and up and up. And that's what you see of people above you. And that's what you see of our dads and our parents and people who have you look up to as

role models of success, like that's what they've done. That is how that's what we know to be models of success of people who have done it before and what we think means done it right. Like that is what we know to be correct and to be good. And then there comes a time in that job where maybe you realize there's not that much left for you there. Like maybe you start to think

Huh, like I'm kind of stagnant here and I'm no longer really growing and there's nobody here that I think I can learn from and grow with and I don't really see a position that I can grow into and I'm just not feeling like this is still the thing for me and you get that feeling in your gut that like, you know what, maybe it's time to move on and maybe it's time to find my next thing and look for my next job. But it's before

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two years, which is the thing that I've been told I'm supposed to reach, which is like the conventional threshold of success. This two year mark that you're supposed to hit that you're supposed to just like wait out and stay until you get there because someone before us has decided that this two year mark is the mark of success that if you leave before the two years, you weren't successful at that position. You weren't good enough at the job to stay it out to stay the course.

to be there that whole time. And when you kind of decide that this thing is no longer really for you or suiting you and you're no longer learning or growing, you think that maybe it's time to start applying for a new job or finding a new job. So you go on to LinkedIn or Indeed or one of the three other job sites that are out there, probably all of them, you start scouring your connections for

somebody that might work in the thing you're you think you might be interested in because I don't know how else you supposed to know what you're supposed to do or what you want to do like there's no other way to figure it out beside being like hmm maybe I should experiment with that thing or maybe I would be good at that thing or maybe I want to try that thing and you put your resume together summarizing everything you've done in the past two years into three bullet points

Which I find to be the funniest thing, like, how can you summarize and condense everything you've done, everything you've learned, everything you've, I don't know, com- everything into three bullet points, so you try your best to figure out what's most impressive, the best three things you've done, or the best summation of the things you've done.

And you hope that that's good enough to make you look good and stand out above everybody else applying for the next opportunity, the thing that you're applying for. And then you start putting out applications and hope you get an interview and you're not going to hear back from all of them. Hopefully you hear back from some of them and that goes into a next round interview and an extra interview. And hopefully you get that next job. And then you have to hope that the next thing

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that you get is going to suit you and you're gonna wanna stay at that thing for the next two years of your life. But before that time, before that getting the job situation, you're gonna reach out to your network of people that you've hopefully created a strong enough connection with that they will stick themselves out there and say like, I think this guy Josh would be great for your position. And you have to hope that

they like you enough or trust you enough or think you're good enough to put themselves on the line or put them put their reputation out there as like a hey I vouch for this guy like I think he'd be good for you and you gotta hope you have a couple of those out there and this process could take anywhere from one month to six months or even longer like who is to tell you who's to know how long this is supposed to take especially when the job market is tough

And every time it sounds like somebody talks about the job market, it is always tough. Like I have never heard of a time in the job market where everyone someone's like, yeah, it's not tough. Like actually, this is a great time to find a new job. I've since college to now, and I guess forever and on like forever, far and beyond like to infinity and beyond it is always going to be a tough job market. I've never heard somebody be like, yeah, this is a good time. Like you should definitely look now because there's tons of people hiring like

That's never happened. I've never heard that sentiment shared by anybody that I've spoken to. And you also have to either start looking for another job while you're still in your job, which is like a very weird double agent situation that you have to navigate because you can't look like you're quiet quitting and you have to maintain all your relationships at work and keep that work. And at the same time, do this entirely other job of looking for another job and

There's a there's so many different things that play there. Like how how are you supposed to balance all of that? How are you supposed to figure all of that out? And during that time, while you're balancing two jobs, you also have to keep believing in yourself as hard as you can, because the tower of disappointment and rejection can start to look really tall after a while. And it gets a lot harder to maintain that belief in yourself after a long time and a lot of rejections and a continuous kind of like

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struggle to get applications out there and keep submitting yourself to people while also hoping that you get a response back in an interview and putting yourself out there again and again and again. And for all of those reasons, it is so much easier to stay where you are. For everything I just said, it is so much easier to stay put where you are.

Even if you feel like it is no longer suiting you, even if you feel like the industry you're working in is not the one you see yourself in long term and not the one you want to be in forever. Even if the job you're doing does not feel like it is a passion or something you want to wake up and do. Even if you feel like the coworkers around you are bringing you down, even if you feel like your boss is toxic and not helping and making you feel badly. Even if all of those things are true.

It is still easier to stay where you are because of all of the things that I have just said that like you have to do to find another job. Like it looks so daunting and scary when you think about the prospect of even looking for another job. And also because of the unknown, because the unknown comes with a lot of fear, fear of the what's next for me. What will I build for myself?

What will happen if I shake all of this up and decide to take a chance on myself and leave for something else? What's going to happen? Like what will be for me? So when you start to think through all of that and all that you're going to have to do and go through, when the idea of even starting to find something new comes into your mind, it is so much nicer to put that back into your pocket and be like, I will look at that next. Like I am not worried about that right now.

I can't worry about that right now because I have all these other worries. have all these other things and timing never feels right. Like this person's leaving this person's this this timing never feels right. So I'm just going to put that in my pocket and maybe come back to it later. And then maybe when you wash your pants the next time after five to 10 wears you'll find that thing in your pocket again literally like a dryer sheet or a receipt from the bar for the drink that you bought that you totally forgot about.

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or if you're lucky, like a $20 bill, that would be the best find ever. But you find it in your pocket again, the next time you put those pants back on, you're like, what is this in my pocket? You're like, there's that thought I had about leaving my job and taking a chance on myself. there's that thing that I had in the back of my head that says, this job feels wrong. It's felt, it has felt wrong for a long time. And I really want to try something new.

Because I know I have a lot of potential. know I'm really good at what I do. I know I can do so much more than what I'm doing right now. And I know I want to be more. I I want to do all this. I want to try this industry. I want to try this thing. I want to I haven't even applied for that thing. Like how will I ever know if I don't take a chance on myself if I don't ever try? That's all right here. I'm like, I just found that in my pocket. Huh? it's been a while since I've had that thought. Like, I haven't worn these pants in a month. Like I totally forgot that I had that thought. And when you see it again,

You have to decide what you're going to do with it. Are you going to take a look at it? Are you going to put it on your nightstand and keep it next to you? Are you going to write it in your notebook? Are you going to keep it out so you can see it every single day? Are you going to bring it with you to your job? Are you going to bring it with you every morning when you wake up? Or are going to throw it away? Or are you going to put it right back where it was, back in your pocket? Because once you find it, you have another chance for what you'll do with it.

And when that initial first thought comes on and you're like, this is way too daunting and scary to think about all of the different things that I'm going to have to do and think through and go through and emotionally and it's taxing, it's daunting. don't like the idea of even looking for something else. No, like, let me put that away. But when it comes back up again, you have a second chance with it. Will you put it back? Will you throw it away or will you keep it with you?

Will you send a picture of it to somebody and let them know like, I found this. Hey, I've been thinking about this. I want your thoughts on it. I want to just tell you I'm thinking about it. What you do with that is entirely up to you and no one can tell you what to do with it. You can ask five different people for advice. Hey, how should I spend this money that I found in my pocket? They're all gonna have different ideas for what you should do with it. Every single one of those people is going to have something different to say about that.

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Hey, I just found this receipt. What should I do with it? Should I keep it for my books and make sure that I'm tracking my money and my spending, or should I throw it away? People are have different ideas of what you're gonna do with what you find in your pocket every single time. I hope that reference is making sense. I hope you're tracking with me. I like it. And everybody, as I'm saying, is going to have a different idea for what you should do and how it should be done.

Everybody also has the societal impression for how it is supposed to go down. And what happens when you stray from that path? What happens when you go against the grain and you go against what the people are telling you to do or what all of the advice is telling you to do? What happens when you stray from the path of how it is supposed to be done?

and what happens when you leave that path completely. And that could mean hundreds of different things, right? Like it could mean leaving your job before the two year mark that you're supposed to hit because somebody has decided that that is the benchmark of consistency. It could mean leaving your job without another job. It could mean deciding that what you're doing and what you have been doing for the past four years does no longer feels like it suits you.

and that you want to shift industries or careers or schools or something completely. It could mean everything in between that and beyond it. And just because it's what you've been doing, it doesn't mean you have to keep doing it. And just because everybody else is doing it that way, that doesn't mean you have to do it that way too. I talk about the idea of comparison a lot.

the idea of looking around at what everybody else has and what everybody else has going on and thinking, why doesn't mine look like that? Like, why does my situation look so different than everybody else's? Why does it feel like they have it together and I completely don't? Why does it feel like they've had a promotion and a raise and they've climbed the corporate ladder to success or what I think success is supposed to look like or what they think it's supposed to look like? And I don't have that at all.

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Why? Why? And it gets hard, especially when you see someone finding what you might define as success, whether that's what I'm saying as a promotion or a raise or climbing the ladder, getting the next thing, the next thing and staying at a job and doing what they're supposed to do or conventionally is supposed to be done. Or somebody who seemingly has their kind of like career path in order and they're walking down that path tall and they look like they're happy and successful.

and it feels like you may be falling behind or running late. Because maybe what you thought was meant for you is actually not turning out to be what you thought it was going to be. Or maybe the people that you're surrounded by aren't who you thought they were or would be. Or maybe you start to get a little bit more realistic about what the world is really like and that has made you more of a cynic in your job and in the corporate world and in the startup world or whatever you're in.

that you're applying this sentiment or conversation to. Maybe you start to think that you're never going to find what's right for you or what you're meant to do. And maybe you're starting to feel like when you wake up every day and you kind of dread what you're doing, that that's how it is. And that's how it's always going to be. like, that's how it's been for generations and years and centuries. And for you, that's going to be the same thing too.

but you still have this idea in the back of your head or in your pocket that you want to change what you're doing before it is conventional to do it. Or that has happened for you and you've been laid off or you've been fired and your path now doesn't look like the conventional path. Whether this, I think this applies to all the situations, whether you're leaving a job, whether you're considering leaving a job, whether you've been fired, whether you've been laid off, any of those situations.

This is a this is like a blanket conversation for changing career path or changing job, whether it's on your terms or not. If you're in that mindset or that period of your life where you're feeling like it's not going, it's not working, it's not going well, and you're feeling like your options are limited, or you're going to have to stay where you are. And that is just how it's going to be.

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because you're either afraid of what is going to happen if you make the move to try or if you make the motion or the leap and take a chance of I'm gonna try something new or you've been forced to try something new. What I say to that is maybe it was never supposed to look like someone else's. And you are at what I am calling the unconventional part.

The part where you don't know what you're supposed to do, or what you want to do, or what's out there for you. You don't know if you're gonna find your thing, the thing that you're good at, or the thing that you're passionate about. This part is completely fraught with discomfort and inconvenience.

It's unpredictable and the bricks in front of you are no longer laid out for you to walk on. Like it is broken brick. You are at a stopping point, a halt. Welcome to the unconventional part, the unexplored part, the part that people don't talk about because it's hard to talk about because it's hard to be there. It's hard to put yourself there. It's hard to sit in that. It's hard to stay in that. And there are so many of us in our 20s

early late 30s like there are so many people in that unconventional part that are just left to like lay there that are just kind of left to hang dry because nobody's talking to them because nobody is nobody's giving that segment or that unconventional part attention because there's not a lot of advice to give there there's not a lot of things to say to that person

And that's why I'm attempting to. That's why I'm trying to. Because I have been there a couple times in the past few years. I'm there currently and it's normal. I think it is so much more normal than everybody thinks and everybody says and everybody talks about because how are you supposed to know what you want to do?

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How are you supposed to know that the thing that you're doing is the thing that you're gonna love for the next two years? How do you know that the thing you're gonna take a leap into and start doing is the thing that you wanna do for the next two years? Why this two year thing? Why all of this? I have so many thoughts and contradicting things to think about career and success and how it's supposed to be and how it's supposed to be laid out for you and why it's even laid out like that in the first place.

and why that is the stereotype that's perpetuated by everybody that's above us because what else, what, how else are we supposed to figure? Like, don't know. It's, it's kind of exhausting. It's really hard to have to wrap your head around that you're supposed to be happy in what you're doing. And at the same time, it's a job and you're supposed to make money and you're supposed to support yourself. And in that you're not supposed to complain too much, but you're, and you're also supposed to find happiness or figure out how to make yourself happier. But what if you're just not?

And what if the thing that you pick to do is just no longer suiting you and is no longer for you and you have to then figure out what to do next but you don't want to do what you don't want to have to figure out what's next because it's hard and it's uncomfortable and the unknown is a very scary place to have to sit and have to be. Well, welcome to the unconventional part. The part where you don't know, don't know what to do, what's for you and what's next. You might look at this and think, fuck.

and think all of the things I just said in that like crazy loop ramble that I just went to and get tired and depressed with even just the thought of it. Or you could reframe it, reinvent it, put on a different pair of imaginary glasses and try to see it differently. Maybe, just maybe, you could be excited about the unconventional part.

You could look at it with an excitement like a new found. I am so excited about what is coming next. I have no idea what it is going to be. And that's fucking thrilling. That's exciting. It's kind of fun to not know what you're going to do next or what you could do next because you have so much potential. You have so many things that you could do. So don't put yourself in a box. Think

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This is exciting. there's so many things I could do. There's so many things I want to do. This is the time you now get to think about all of those things that you have put inside of a box and put away and put it under a shelf and I've gotten dusty because you haven't even looked at them or haven't thought about them in so long because you thought that this was your path. The thing that you stepped into and have been in for the past two years or four years or six years or eight years or whatever. You thought that was it. And that was what it was always going to be.

But what about those other thoughts? What about those other things you wanted to do? Are those other things you wanted to explore and those pie in the sky that people call it? And I don't like that expression because I don't believe it's a thing. But those things that you thought would never come true because they were never possible. I heard a quote from the night at the museum that inspired my idea for this episode. Ben Stiller says to Robin Williams, I have no idea what I'm going to do tomorrow. And Robin Williams responds,

How exciting. And that absolutely reframed my entire mindset around what you can do with your life, with your career, with everything. Those two words completely reframed my mindset around the unknown or the unconventional part. How exciting. It completely changed my mindset. It completely changed how I'm thinking about everything.

That thing wasn't for me, and it didn't turn out the way I expected that it would. And that now gives me a chance to find something new that might just be that thing for me. It's not supposed to look the same as everybody else. So what you didn't follow the conventional. So what you left your job before two years. So what that this new thing doesn't feel like it's still right. So what you colored outside the lines and didn't paint by the numbers.

You actually don't have to. It won't be easy and it could look impossible at times. It might feel off. It might feel wrong, but you'll find it. And I know that and I'll find it. How exciting. We also don't have to spend so much time thinking about how it wasn't right and how we wished it had been this and that and blah and blah and

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We don't have to keep looking back and ruminating on what has been or what could have been or what we hoped that thing would have been. Because it's okay to move on and to move forward. Forward is a pace. Forward is emotion. We don't have to keep looking back. We don't have to spend all of our time thinking about what we wish that thing could have been because it had so much potential and if this had just been this differently this way and this had that...

We don't have to stay in that place. We actually can be excited about what's next. Be excited about our own potential. We have all of those abilities. We have the ability to reframe our mindset and the idea around what's next and the unknown and the unconventional. We don't have to look at it with such fear and with such anxiety and with such nervousness and with such like, I don't want to be there because I'm afraid to jump into it.

It doesn't have to be this never ending pit of doom and scary and horror. Like, what if it was exciting? What if it was a thing that you looked at and were like, instead of this dark pit of what will now be because I have to figure out what's next. What if we looked at it as all of the opportunities or all of our different potentials or all the things that we could be or the things that we want to be and just haven't taken the chance on ourselves to try and be yet.

What if that was the way we reframed it? I'm choosing to look at it like that. And I invite you to have that same perspective in this next step in your life, in this next journey, in this next thing that you're doing in the unconventional. I'm choosing to have that mindset for my next thing, for what is next for me. And I invite you to do the same. I invite you to step into that because

I don't think people talk about what's next and the unconventional with enough positivity and enough excitement. I didn't for the past 30 minutes because I think it's a scary thing to have to think about. But I am leaving that part of this behind. I wanted to set this up by saying, I feel all of that. I'm not better than any of that, but I'm now choosing to be because you can be because you literally can just say to yourself,

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applying for all of these jobs and having to make all these connections and all of these things and spreadsheets and having to add to my resume and all these things I have to do and all these things I have to be and the person I have to become and I have to do all of this shit. What if it wasn't that? What if it was I now get to figure out what I want to do next. I now get to make connections or look back at the network I've built and build a better network or build better connections or think back at the people that I've met in the past couple years and have conversations with them and pick their brains.

What if it was an opportunity and not an adversity? And I'll leave it at that. If you're in the unconventional, if you are in what I'm calling the unconventional part, what if it was an opportunity and not an adversity? That is the episode. Thank you so much. Listen to guys set a guy's guide to what should be talked about. I'm Josh. I'm 25 years old and I'm here every single week, every single Tuesday to talk about what should be talked about for guys in their twenties.

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