Season 4, Episode 6: “I’m Not Feeling Challenged at Work Anymore. Does That Mean It’s Time To Move On?”

Do not adjust your speakers. This week’s episode of the Bitches Get Riches podcast does indeed start with chicken noises and saxophone mouth sounds. And we’re not even sorry.

Today we’re discussing a very good problem to have. What do you do with yourself once you’ve successfully aced your job and you’re out of challenges at work? Do you stick around, resting on your laurels? Or will that stagnate your career progress and turn your mind slowly into mush?

Anyone who’s stuck around here for long knows our thoughts on the matter. And they’re definitely more DTMFA than have-a-nice-cold-pint-and-wait-for-this-all-to-blow-over.

This week’s question

Today’s question comes to us from an anonymous listener and Patreon donor. Anonnymouse asks:

My dear sweet aunties. I work for a start-up that grew from 25 people to 250 in the last year and a half, since I’ve been with them. I have a generous paycheck, great benefits, and a vesting agreement that I’m halfway through (but I know those shares aren’t worth a dime if I can’t sell them), I like the work that I do okay enough. This is my first full-time job. I’m curious about what else is out there, what else I could be paying attention to, what other projects I could spend my time on. How do you know when it’s time to leave a position?

-Anonnymouse, beloved patron of the Bitches

We’ve written a lot of career advice on burnout, transitioning between jobs, and handling major questions about when to move on and how. So if you’d rather consume our advice on this with your eyes instead of your ears, here you go:

Our answer

This episode was unusually wholesome for us. We’re not addressing dire circumstances or solving unsolvable problems. Just helping a bitchling out with a win-win situation: how to know when it’s time to move on from a job you’re succeeding at. Which is good, because we were in far too weird a mood for a serious conversation. Listen to the full episode for our answer:

Or if you can bear the sight of us, watch us on the tubes:

This episode is sponsored by our partner Mainvest. They connect small business owners to investors through a crowdfunding model of investment. So if you want to dabble in a more wholesome, grassroots style of investing, Mainvest is a great way to get started. And if you’re a small business owner, Mainvest can help you crowfund investments to take your shop to the next level.

And as always, our podcast wouldn’t be possible without our Patreon donors, the question asker included! If you’d like to help keep the lights on around here and ensure we can pay Ducky a fair wage for her excellent, excellent production skillz… head over to our Patreon to officially join the ranks of Bitch Nation.

Episode transcript (click to reveal)

Piggy 0:00

This episode, like all our episodes, is brought to you by our beloved Patreon donors. So this week, we’d like to thank Rebecca, Linda, and Lucia. And an extra special thanks this week to Julia. Julia is a ballad to herself sung by Celine Dion at the peak of her career.

Kitty 00:23

Maybe we should try something less weird.

Piggy 00:25

We could talk about how I’m like, pecking at the microphone with my nose like a bird.

Kitty 00:30

[clucking like a chicken]

Piggy 00:32

[clucking like a chicken] Oh, that’s pretty good. [continues clucking]

Kitty 00:35

Thank you. [continues clucking]

Kitty & Piggy 00:36

[both clucking] [note from Ducky: no part of this transcript is a typo or an exaggeration]

Kitty & Piggy 00:43


Kitty 00:46

Our producer has informed us that we are weird. And she’s correct, so.

Piggy 00:53

She’s incorrect. She is incorrect. No.

Kitty 00:56

We’re normal! We’re exceedingly normal.

Piggy 00:57

[weird, high-pitched voice] We’re normal, we’re normal!

Theme Song 1:00

If you need some dough
 You don’t know where to go
 In this patriarchal capitalist hellscape
 Well here’s the ‘sitch
 We’re gonna help you, sis
 Because bitches get riches
 Bitches get riches
 Bitches get riches
 Bitches get riches
 And so can you

Kitty 1:26

[imitating the sax solo from “Careless Whisper”] Wait no, the sax is too long.

Piggy 1:35

[imitating the sax solo from “Careless Whisper”]

Kitty 1:36

I just realized it’s like 16 measures of just sax.

Piggy 1:39

[singing] I’m never gonna dance again! Guilty feet ain’t got no rhythm!

Kitty 1:44

Welcome to our podcast! It’s Saxophone with Your Mouth Sounds Hour. Hosted by us, Shirley Dingleberry, and my lovely co-host…

 Piggy 1:56

Bethany Blaylington.

Kitty 1:58

Yeah, I love Bethany. Beth. Can I call you Beth?

 Piggy 2:01

Um, I prefer Thany actually.

Kitty 2:03

Stop talking, more saxophone!

Piggy 2:05

[yet again imitating the sax solo from “Careless Whisper”]

Kitty 2:09


Piggy 2:10

Do we feel like we can pull anything from that?

Kitty 2:13

I think that was perfect, I don’t know why you’re not just rolling right into the intro. What do you think the people are here for?

Piggy 2:19

You’re right, you’re right.

Kitty 2:20

If not this?? Alright.

Piggy 2:21

I’m Piggy.

Kitty 2:22

And I’m Kitty.

 Piggy 2:23

And we’re the bitches in Bitches Get Riches.

Kitty 2:26

We’re two kids in a trench coat. Not human children. Goats.

Piggy 2:31

And we’re here to eat things you would never have believed were edible.

Kitty 2:34

Our time on this planet is limited.

 Piggy 2:37

So let’s get started.

Kitty 2:39

Today’s letter comes to us from a Patreon donor. Thank you blessed Patreon donor.

Piggy 2:43

Thank youuu!

Kitty 2:47

Our dear follower, who wished to remain anonymous, asked: My dear sweet aunties. I work for a start-up that grew from 25 people to 250 in the last year and a half. Since I’ve been with them, I have a generous paycheck, great benefits, and a vesting agreement that I’m halfway through (but I know those shares aren’t worth a dime if I can’t sell them).

Yes, correct.

I like the work that I do okay enough. This is my first full-time job. I’m curious about what else is out there. What else I could be paying attention to. What other projects I could spend my time on. How do you know when it’s time to leave a position? 

 Piggy 3:28

At time of recording, the news is all full of people who are just completely overwhelmed and burned out and stressed about their jobs. We’re hearing about things like slow quitting, which is mostly just people fucking doing their jobs without angling for a promotion.

Kitty 3:42

Yeah, refusing to have your wages stolen by working unpaid overtime.

Piggy 3:46

Yeah, exactly.

Kitty 3:48


Piggy 3:49

Weird. Crazy. So, I like this question ‘cause it’s somebody who is coming to us without burnout and stress. And I’m like, god bless you, honey. Like, somebody’s got to be over-achieving out there. Somebody’s got to be getting it done. And it might as well be you.

Kitty 4:03

I love that they are asking this question now, instead of, like, I am so burnt out and depressed that I don’t have the physical energy to do all the labor required to find a new job. So good. This is good.

Piggy 4:16

Yeah, we have like 9 episodes about that. This is very different. This is very different. But so this person has clearly like, they’ve gone through the burnout and they’re feeling pretty good about their job. And they’re like to the point where they’re standing around like, what else is out there? Alright, I want more challenges, I want more opportunities. They’re channeling their inner Little Mermaid. [singing] I want more!

Kitty 4:41

I want more. I want to be where the people are. I want much more than this provincial life.

Piggy 4:46

Way more than this provincial life. Absolutely. I feel like that’s kind of the answer here. Is like, if you—there are 2 answers here, I should say. Like one is, you know it’s time to move on to new job when you are overwhelmed, burned out, and feeling taken advantage of. But the other side of it is, if you are looking around and you realize that you have more to give, and you have sort of outgrown the confines of your job. Having been somebody who has switched jobs in the past—I had a job for 8 years and I knew it was time to move on because I was bored. And yet still somehow stressed because I knew how to do everything, I just didn’t have the time to do it. And I wasn’t feeling challenged, I was feeling stagnated and underappreciated. But that’s really when I kicked my job search into high gear is when I was just like, I’m wasted here. My talents are wasted here.

Kitty 5:46

Yeah, yeah. I think that, you know, it’s the kind of question that you will have to ask yourself throughout your life. When you are in a job, when you are dating someone, when you are living in a house or apartment, like this is fine, this is okay. But is there something better out there? It’s tough because in almost all of those situations, you can’t really like hang on to the sure thing while you explore. But out of all of them, the job is the easiest to try. So—

Piggy 6:22

Yeah, I wouldn’t try “exploring other relationships” when you’re like, in a monogamous relationship and you’re like, hmm, I think I’m ready to move on from this. I’m just, I’m gonna go—

Kitty 6:29

Just like shhh! Let me just tip-toe.

Piggy 6:33

I’m going to go fuck around.

Kitty 6:35

Yeah, like just downloading Grindr, which is how I find all of my dates.

Piggy 6:41

Oh yes. I thought that was a coffee app. Isn’t that a coffee app?

Kitty 6:42

That’s not the—yes, it is. I only date beans.

Piggy 6:48

Okay, good. Yeah, that’s what Rick Santorum told me.

Kitty 6:51

So, I think when you are in a situation where you’re like, overall pretty happy but you are just feeling kind of an itch to explore. I think you made a really good point about kind of following your instincts. If you’re asking the question, then that might be your answer. I will also say, sometimes you can come full circle and explore what’s out there and be like, actually, what I had was really rare and really great. So here’s the nice thing about it. If you’re working for a good company, there should be no barrier to you leaving the company on good terms and then one day returning. That’s more rare, I think, if you date someone and you’re like, actually I don’t know if this is what I really want, and then you come back 5 years later and you’re like, actually, you’re as good as it gets, can we commit please? Pretty please? I don’t wanna be out here.

Piggy 7:46

Let’s put a ring on it. I’ve seen the dating scene, and it’s grim.

Kitty 7:51

Yes, I’ve learned a lot about myself and others, and it terrified me, please, take it back.

Piggy 7:56

Please take me back.

Kitty 7:57

So, with a company though, and I have known individuals who have maybe say, a leader who says, I really want you in this senior management position, but you are so many levels below that I can’t justify that big of a jump to HR. They would make me interview a bunch of other candidates.

[thunder crashes in the background] 8:18

Kitty 8:19

So spooky.

Piggy 8:20


Kitty 8:22

Corporate America. OoooOOooohh!

Piggy 8:23


Kitty 8:25

So they say like, hey, go work for 6 months at another company in between those two levels so that then we can bring you right back and bop you right up. It’s a silly bit of bureaucracy, but that I have known that to happen. So it’s not crazy.

Piggy 8:42

That’s so incredible to me, ‘cause it’s such a risk for the employer, especially if the employee—

Kitty 8:45

It really is.

Piggy 8:47

Right! Like, especially if the employee leaves and is just like,um it’s way better over here, I’m not going back. So I mean, win-win for the employee, like either way they’ve got a place at their old employer or the new one but risky for the employer if somebody decides that they have it better somewhere else.

Kitty 9:04

Yeah and if your company wouldn’t consider hiring you as the same person with even more experience, even more education or whatever, further on down the road, they’re probably not as great of a company as you thought they were initially. So I think it’s worth it sometimes to take the risk and walk away from something good if you have that itch within you, but there is absolutely nothing! Nothing stopping you from discreetly exploring other options.

Piggy 9:35

Yeah, not not a damn thing.

Today’s Sponsor 9:37

Piggy’s Floating Head 9:37

[singing “Angel” by Sarah McLachlan in the background while Kitty speaks]

Kitty 9:42

Investing in giant, soulless companies can be disheartening. Who knows what kind of monsters are using your money to kick puppies or rip flowers out by the root? That’s why we like Mainvest, the crowdfunding platform that makes it easy to find and invest in wholesome small businesses. So if you’re passionate about supporting small businesses and hyper-local investing, use Mainvest to make sure your money is going to support sweet lil’ mom-and-pops and not Clubbing Baby Seals, Incorporated. Go to or click the link in the show notes to start investing in small businesses with Mainvest today.”

End of Sponsored Content 10:28

Piggy 10:28

One should never feel pressured to make this decision. Like, I’m reading this and our dear, dear Patron, who’s writing this is saying, you know, the company’s growing, I have a generous paycheck,I have a great benefits, I have a vesting agreement. Like they’ve got all these things, and they like the work okay. And I feel like they need to interrogate their own sort of reaction to all of this, because you don’t want to be like, oh, I’ve got all these great things but I feel like I should be thinking about moving on. Like I feel like I should be the climbing the corporate ladder. And it’s fine if you feel called to do that, but it’s also fine to be like, you know what? I’m pretty good where I am.

Kitty 11:12

I’ve got a good thing going. Yeah, absolutely. Contentedness in our society I think is very underrated and undervalued, but I think if you talk to people who have worked at a lot of companies, they are gonna be the ones who are first to tell you, if you find something that works pretty well, keep it. Because there really is an endless nightmare number of bad bosses out there in the world.

Piggy 11:39

Yes, exactly. Don’t feel pressured to move on, don’t feel pressured to angle for a promotion or a raise. I mean frankly, I think you should always be angling for a raise, but if you like where you’re at and you feel like it’s a good use of your talents, don’t feel like you gotta move.

Kitty 11:58

Yeah, I agree. And if you have that kind of like, ooh I think I want something new—is it necessarily coming from your sort of career self? Or could it be coming from your personal self? Are you feeling—

Piggy 12:15

Yeah, you might need to go join a pickleball league. That’s a thing. I’ve heard of it.

Kitty 12:19

[bemused silence]

Piggy 12:20


Kitty 12:21

I couldn’t begin to tell you what pickleball is and frankly, unless it involves kosher dills, I don’t want to know. It sounds—no, I reject this. But no, when’s the last time you went on a vacation to somewhere you’ve never been before? When’s the last time you went to some part of the world where you didn’t speak the language? When is the last time you made a brand new friend? When’s the last time you picked up a brand new hobby, or taught yourself a new skill?

Piggy 12:52

Like pickleball.

Kitty 12:55

Like pickleball. The important skill of knowing what pickleball is.

Piggy 13:00


Kitty 13:00

That’s a skill that I am open to developing, but am not actively working on.

Piggy 13:06

I mean, I guess my—your point is completely valid, which is that like, if you’re feeling this restlessness, it might not be about your job. It might be about some other aspect of your life. Some other pickleball-related aspect of your life and you need to start a new hobby, join a new club, like whatever, that’s fine. But just really like, sit with yourself and determine where the sense of ennui is coming from. You might be just fine in your job if you changed it up in some other aspect of your life.

Kitty 13:39

Yeah. And I think too, thinking about what is at stake for you if you—so the question asker mentioned that this is their first job. So they’re probably pretty young. If you are in your early to mid-20s, you don’t have a house, you don’t have kids, you ain’t married. You have a lot of freedom to explore. You may come to a part of your life, as I did, where settling in terms of my career was very much a conscious decision that I made. I found a job that was boring as fuck, where I got to work with people who are very nice and respectful of each other, and that had a company culture that was not toxic and the work was easy for me. And I was like, all right, this is it for me. Where I was in my life, I had just bought a house, I’d just gotten married. I wanted to focus on a lot of things in my life outside of work, and I wanted work to pay all of my bills while asking as little of me as possible. So you may come to a point in your life where you’re ready to settle. It might not be now. And again, like you can always—there are so many jobs in the world. You can always, always change. If you don’t like it, change again. If you do like it, change again anyway. We talk a lot about how job-hopping is an excellent, excellent strategy for building wealth.

Piggy 15:19

Great way to pad that bank account.

Kitty 15:23

Yeah, absolutely. You are far more likely to get a substantial raise when moving to a new company. Whereas many companies internally have either a spoken or unspoken cap in terms of how high you can jump.

Piggy 15:36

Those bastards.

Kitty 15:38

Usually that’s around like, I have heard between 4 and 10 percent, is just kind of the range. So if you stay with a company for a really long time, that can be fine. If it works for you, it works for you. But definitely be cognizant of the fact that you may be leaving money on the table. However, if you’re with a company that in a year and a half has grown from, what was it? 25 to 250 employees.

Piggy 16:09

Yeah. Yeah.

Kitty 16:11

Maybe they’re doing just fine. Maybe I would consider staying until those vested funds come through. I don’t know, that’s pretty interesting.

Piggy 16:22

I mean if they’re growing that fast, it might be the case that like, you’re gonna be reassigned to a new position within the company or your role’s gonna change.

Kitty 16:30

Talk to your boss, yeah. Tell your boss like, I love what I do and I love this team but I—

Piggy 16:35

I’m not feeling challenged.

Kitty 16:39

This has been my only job and I want to know what else there is. And you have to do some of this work, right? Like you have to know what it is that you want and tell your boss, so that your boss can make it happen.

Piggy 16:53

Yeah exactly, have that conversation.

Kitty 16:55

Yeah, don’t go in and just say, like I’m kinda bored. I just don’t know.

Piggy 16:59

I’m bored.

Kitty 17:01

Say something like, I would like more direct ownership over projects or I would like fewer client interactions ‘cause that’s wearing me out or you know, whatever, like come up with specific stuff.

Piggy 17:10

Yeah, I don’t want to talk to people ever.

Kitty 17:13

Don’t talk to anyone. Just don’t talk to people.

Piggy 17:15

Yeah, it’s true. It’s true. Or just saying, this anonymous asker says, I’m curious about what else is out there. Like tell your boss, I’m curious about what else is out there. And they might be like, oh my gosh, please don’t go. There’s a lot more you could be used for in here. Let’s put you on a leadership track.

Kitty 17:34

Yes. And I would also say, ask. You can ask your boss in more of a mentorship capacity. Like this is my first job ever. Can you be honest with me and give me an idea of what is it that you really like, you as someone with more experience than I have, what do you like about working here? What’s valuable about it compared to other companies? And ask that question of your boss, your co-workers, if you have mentors within your company, they can just tell you. And it may be that in your industry, people will say like, oh you can get a job like this anywhere. I’ve worked for a lot of companies like this. I have heard people say things like that. I’ve also heard people say, oh my god, never leave this place because it is a nightmare out there. And that’s very industry-specific. So ask the people in your industry and they will tell you who the bad employers are, who the good employers are. Especially if you’re at a company mixer, put like one drink in me and I will give you like a full letter grade for every company I’ve ever worked for and with.

Piggy 18:38

That’s why they call you the Kurt Vonnegut of corporate America.

Kitty 18:41

That’s right. [finger guns] Bing, bing! I give you an “A,” by the way. Wink, wink.

Piggy 18:45

Aw, thank you. That’s so sweet. I want to say something about timing, which is that you never know how long it’s going to take to a) find a new job and b) start at that new job. So again, if you’re asking the question, that’s a good sign that you might want to start that process. But even if you’re not asking the question yet, you should always be keeping an eye to what’s out there. You should always be applying to new jobs. You should always be practicing your interviewing skills if you can take the time off. But that’s going to be useful. And you might not feel ready to leave a place yet but then you interview for another job and you get really excited about it. And that sort of shows like, oh now I see what’s out there. Now I see what I’m lacking in my current role. I should go take on this other job. So I definitely think that there’s something to be said for constantly keeping your eyes to the job board and keep applying. And also it’s good practice. You know, you never want to get out of practice with that. Lord knows after the great funemployment periodof 2020 I am very well practiced in job interviews and it is a skill you don’t want to get rusty at.

Kitty 19:58


Piggy 19:59

So again, there’s no guarantee you’re gonna find a job within 6 months of starting to look for one. So start the process as soon as you get a little tickle that you might want to move on to something else.

Kitty 20:13

I like that, it’s good advice.

Piggy 20:15

Thank you. Thank you. I try.Are you good with that?

Kitty 20:18

I’m good with that.

Kitty 20:21

Listeners, if you want us to answer your question, go to and click “Ask the Bitches.” Our goal here at Bitches Get Riches is to help people, but we want to make a living wage for ourselves and our assistant doing so without being like a total piece of shit sellout. So if you believe in that mission and you want to help us achieve it, the easiest way to do that is to go to We also accept one time donations through if you need more of our spicy, spicy wisdom, you can read our articles and follow us on social media, and you can do all that stuff at

Kitty 20:59

Hey, is there anything else they should know?

 Piggy 21:01

Yes. Okay. I’m going to ask you a series of 3 questions and then I’m going to interpret the data based on your answer. Are you ready?


Yes, I am.


First question. What is your favorite animal, real or imaginary, and why?


Unicorns because they are majestic, they’re fast, they are free, and they are phallic.


Okay, and if you could be any animal, real or imaginary, what animal would you be and why?

Kitty 21:27

Oh, a house cat. A house cat! They just get to lay around all day. They’re so lazy. They don’t have to work. And when they’re hungry, they can ask for food pretty violently and people still think they’re cute. House cat, definitely. Easily.

 Piggy 21:40

Okay, okay. Last question, what is your favorite food and why?

Kitty 21:44

Monical’s Pizza because it is pizza so divine and so heavenly that it ruins all other pizzas in every geographic location for the rest of your life.

 Piggy 21:55

Okay, here is the interpretation. Your favorite animal is how you think of yourself. You think of yourself as a unicorn.

Kitty 22:03


Piggy 22:04

The animal you’d most like to be, a lazy house cat, that’s how other people think of you.

Kitty 22:10


Piggy 22:12

And your favorite food, pizza so good that it ruins all other pizza for you, that’s how you think of sex.

Kitty 22:19

Ding! Good to know.

Kitty & Piggy 22:24

Bitches out.

6 thoughts to “Season 4, Episode 6: “I’m Not Feeling Challenged at Work Anymore. Does That Mean It’s Time To Move On?””

  1. Patron’s situation sounds ideal to me! (Disclaimer: age 65 and semi-retired, working 2 part time gigs in completely unrelated fields.) A congenial job that pays well and is not soul-sucking leaves a person with enough mental and physical energy to learn and do awesome things in their non-work life. No need to buy into the American myth that your job has to be your primary source of fulfilment and identity. In a previous life I had a career that was my “identity” — it was good worthwhile work I was proud of (and still am) but it was incredibly draining and left me with very little time or energy for anything else. Not sure I’d want to do it that way again.

    1. Here here! We fully endorse the idea that your job is not your identity. That was a hard lesson for me to personally learn, but it got me out of a soul-sucking career and into something that serves me (and my mental health) better.
      Some people want a challenge, though! And that’s great if that makes them happy.

  2. I really needed to hear this right now. I have been at my job 6 years – six!! Before covid I was starting to wonder about moving on but then I got a whole lot of new challenges and I was certainly kept busy. Now though I’m starting to feel like I have done all I can in this role and it would be better to leave before I get bored/restless/something worse and leave this job that I’ve loved on a high.

    Job search starts in the morning.

    1. Isn’t it funny that two generations ago people regularly spent 40 years at a single company, and now we’re like “6 years? I feel stagnant!”
      We’re so proud of you for recognizing where you’re at and choosing to leave on your own terms. Attack that job search with all the force of the Amazon warrior you are!

  3. Yes it is important to remember nothing has to be permanent! If they decide to leave or if they decide to stay, they can change their mind again any time they want. I decided to take the leap to entrepreneurship because I had been at a job for 8 years, had gone as far as I could with the company, and was feeling stagnant too. But if I decide entrepreneurship isn’t for me, I can always go back to work for someone else.

    I would also pick to be a house cat, and people know I’m a cat at heart not because I’m lazy or good at napping, but because I am judgmental, have constant RBF, and need lots of head scratching from my husband.

    1. I think we can all agree that head scratches from a husband are the BEST.
      And you’re absolutely right! Career changes don’t have to be permanent. Life is long. Try different stuff.

Leave a Reply

Your email address will not be published. Required fields are marked *