Navigating Career Crossroads: When to Leave a Job

Podcast episode from the Ally from Corporate podcast (host Alli Peck) discussing how to know when it's time to leave a job. Hosts recommend generally having another job lined up, note exceptions for severe mental-health impacts (medical leave), and outline reasons to leave: outgrowing a role (no upward mobility), toxic workplace culture, better long-term career opportunities, startup instability, and lifestyle or family changes (commute, remote work needs). The episode also touches on career-stage differences (learning/do/teach) and the social aspects of late-career work.
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Welcome back to the Ally from Corporate Podcast. If you're interested in learning more about career development, job searching, and growing as the badass professional I know you are, you've come to the right place. So sit back and relax. Let's get into it. All right, today we have an interesting topic that an Instagram follower asked us. The question is, how do you know when it's time to leave a job?
And if you want, also ask a question, message us on Instagram, shoot us an email, and we're really looking for guests in 2024. So let us know, and we will answer it.
Let me know if you're a special person who has special things to say, and we'll have you on here.
Yeah.
All right, so today's how do you know when it's time to leave a job? I've left 10 jobs. How many jobs have you left?
Three.
Okay. So between the two of us, we've got some. Some experience with leaving a job. I'm going to say the first piece of advice I'd give somebody if they want to leave a job is have another job lined up. Like, job search first. Like, if you decide you want to leave a job, job search, get another job lined up, then you can leave your job.
Yeah, I'd never leave and not have something else lined up.
There's a situation where you could. If your mental health was taking such a toll from your job that it was causing you to have health issues that is very serious, especially if you have an emergency fund saved up and you can financially support yourself and have a little gap on your resume, by all means.
But usually you can medically tap out.
Yeah, absolutely you can.
But I would still not quit. I would actually say get a doctor's note and say, I'm so stressed. I need a doctor's note.
And medical leave.
Medical leave. Take the medical leave. Find a new job. I would never tap out and. And leave a job without getting another one. Yeah, I wouldn't do it. I wouldn't do it.
So, okay, so let's back up. So how do you know it's time to leave a job? There can be a ton of different indicators to tell you, okay, Allison, it's time to leave a job. So one of them, I would say, is you've outgrown your role, and there's no ability to. For upward mobility. You've heard of companies like that where there's. It's kind of a flat organization. You're not going to be getting a raise or a promotion. You're not Going to become a manager of a team.
Yeah. And those job roles, you're only staying one to two years, and then you gotta say, yeah, if I'm not getting a promotion and a pay raise, it's time for me to.
Skedaddle.
To skedaddle.
Yeah. And what that could feel like is you've been there for a year or two and you're thinking, okay, a year or two ago, when I started this job, I was challenged. I knew, like, I was growing my skills, learning things every day. But one or two years later, I feel like I know everything already. I feel like nothing surprises me anymore. I'm good at everything. I not learning anything new. So that could be one reason to leave a job. I heard a quote, and I don't know who it's by. Don't hate me. The quote is, at a job, you should either be earning or learning, preferably both. But if it's neither, leave.
Yeah, I agree.
So what does that mean?
So either you're. You're a master at your skill level and you get paid accordingly, or you're learning and you take a less paycheck. So. So you can actually learn all the skills necessary.
Yep.
But I would actually say that it's not a hundred percent that you need to learn or grow. It's just depending on where you at in your life. So let's say you're 55, 60 years old, and you just want to have a cushy job. You don't need to learn till retirement. Yeah. So there's Ma. Jack. Ma. I think his name is from Alibaba, the founder of Alibaba. He said you split life up into three categories. Learning. In your. In your 20s and 30s, you learn. In your 40s, you do, you become. And in your 50s, you hand over the torch and you teach other people.
I love that.
So in your 20s and 30s, you observe. In your 40s and 50s, you learn, and then you hand over the torch and you teach.
No, no, you said do was the middle one. Yeah, you learn, then do, then hand over the torch. Yeah, I love that. Yeah. So that's true. If you are. I'd say if. If you are less than eight years away from retirement, six years away from retirement, you should maybe coast at your job and not try to make any risky moves, because unfortunately, there is such a thing as age bias.
Yeah, but ageism. I was just in Florida with you, and I've met somebody that was working at Home Depot, and he said all his neighbors also work at Home Depot.
How old was He.
No, not Home Depot. It was Bass Pro Shop. He said he was, like, 67.
I remember that guy. Yeah. He was, like, in his late 60s. Older dude.
Yeah. And he said he works two days a week, three days a week. His buddies also work there. And he said, it's cool. I have something to do. Starting to get bored at my house. And now it makes some. He's like, I don't need the money. I'm fully retired. I have rental properties, but I need something to do, and my neighbor does it. And. Cool. I get to talk about barbecues, about guns.
I remember this guy. He was in the barbecue section, and.
He'S like, I got to talk about all these cool people that want to do barbecues and whatnot.
And so he probably makes friends.
Yeah. And he's like, you know, the social aspect when you're in your late 60s and early 70s is a thing for him, for him to, like, look forward to something.
Wow.
And he says, I can take time off. I can tell my boss, like, hey, you know. Because he said all his friends that are in the same neighborhood as him also work there. So he's like, I have a bunch of friends there. I don't do heavy lifting. It's not physically really, like, draining.
Demanding.
Yeah, demanding. So he's like, I'm inside. It's cool.
In the summer, I have a prediction to make. I am seeing a decline in birth rates. Stay with me here. This is related. I'm seeing a decline in birth rates all across the world. People in their 30s and 40s are not having kids. 20s, 30s, and 40s are not having kids like they used to. I would predict that more and more people, like, when Millennial is at the age of retirement and even Gen X is at the age of retirement, if they don't have kids, they will turn towards something like that to fill their time, because they won't have kids. They're not going to have grandkids. What do you do in your 60s and 70s without any kids or grandkids? That's what he said.
He says, I don't have. I have a wife, but I don't have any kids. So he's like, I have friends, but they're also working. And he says, I love it. I have five days or four days to recoup from, recover from a long.
Day of Bass Pro shop at the barbecue joint. And.
And he said, you know, he's also said, if somebody needs the hours and somebody's, like, really struggling, I don't mind giving them my hours. Then I have no work for two weeks.
But he did a nice thing for somebody.
Yeah. And he helped him out. It's like, I don't need the money. I just, you know, just want to do something interesting.
Okay, so that's. That's one scenario where you wouldn't leave a job when you're that age and you actually want to work. Let me talk about another scenario. How to know when it's time to leave a job. What if you have an incredibly toxic work culture and you. But you like what you're doing, you like the company, you know, the product.
Leave.
Really leave. So you don't think people, an individual, can change a toxic situation.
No, because it comes from the top down. Toxicity is like, oh, is it toxic? Is a toxic thing that spreads from the top down? Because you can't just have, oh, my team's not toxic. The whole organization's toxic. Yeah.
I think company culture is the worst behavior that's tolerated.
Yeah. And so if they don't put the kibosh on, you know, people. People saying stuff from the top down.
Yeah.
You're not gonna. From the bottom up trying to get the organization to be good because it needs to come from the top where they don't tolerate stuff and make the rules. And so then it trickles down to the bottom. And. And that. What helps the culture out.
Okay. So if you are listening to this right now and you're like, oh, my God, they're talking about me. I have a toxic work environment. There's gossip, there's conflict, there's backstabbing, there's throwing people under the bus, there's stealing of other people's work. Yeah. I would advise you to leave your job.
Yeah. There's nothing else you can do. I mean, you're not there to fix it.
Yeah.
Because that's what Deloitte does. And these high, you know, these McKinseys and whatnot, they come in and they look at the organization, they make cuts, they, you know, do an analyze thing, and they. They come in and, you know, see where.
Yeah.
Where it's going. But leadership should never tolerate toxicity.
Yeah, I agree. Okay. So know when it's time to leave a job, if it's a toxic culture, that's a very good indicator that it's not the right place for you. Somebody else might thrive in that environment. Some people love drama. We know a couple people that love drama.
Don't we love it.
Do you love drama?
No, I think it's. I think drama is when you have no problems. When you have no bigger problems.
Oh, you just create them on your.
Own when your company's flourishing and you have all the clients in the world, and then you start creating drama so.
You have something, something interesting to talk about.
Yeah, but when your companies, you know, that's why it's so important to have, you know, you know, KPIs that everybody knows, so they can, they can set on a goal and instead of them, you know, doing, doing stupid stuff, I get there's businesses that are more prone to it. Like when you're in the TV business, you know, like selling Sunset, those are like drama centric. It's. It comes with the territory. And that's what Netflix wants.
So you're right, it is appropriate in some situations.
Yeah, yeah. But it's, but if you're not, if you're, if you're not in that situation where you need to create drama for views or whatnot, you don't stay away from it.
Yeah, good point. Okay, all right. Uh, how to know when it's time to leave a job. I have another hypothetical situation for you. What if you like your job, it's okay. Pay, you're doing good. No, no. No drama, no toxicity. But what if there's another opportunity that presents itself, maybe at a different company, and you're like, oh, I wasn't looking for a new job, but that's actually an interesting idea.
Does it come into pay, raise better benefits, then take it.
Well, what if those things are not important to you?
Then why leave then? Why chase an opportunity that's not important?
Because, and you answered this in the very last episode, if you have a long term career strategy, and this is a stepping stone for you to maybe not necessarily have higher pay, but get to where you're going longer term, you could do that.
Yeah. But then you have a strategy and you have a goal, so you need to take the risk.
Okay, so then your point is, you know, it's time to leave a job if you have a longer term career strategy, and this is just, you know, you're good where you're at, but like, you're working towards a longer term, bigger thing, and an opportunity presents itself as a stepping stone to get through that final door that you're trying to get through?
I would say so, yeah.
Yeah. Can you think of any other reasons why it would be strongly advised for somebody to leave their job if they.
Get accused of stuff? If that happened to me once, yeah. If you're, if your manager just doesn't support you, has your back, you can always do in organizational changes. But it's. I think. I think nowadays, if you're not growing, you're dying.
Yeah. If you're not ripe, you're. If you're. Let me see. If you're not green and growing, you're ripe and rotting. Yeah, yeah, yeah. I mean, so you're saying, like, if you're bored, leave.
So, yeah. Job Hop. So if I'm talking to millennials now, just to clarify, millennials and Gen Z years, and they're not talking about boomers that are about to retire and be like, we do it this or Gen.
X, who are, like, almost at the executive level.
Yeah, yeah. And I think the boomers need to be gone and. Yeah, yeah, I think boomers. I think it's time for them to step out of their executive positions and.
Let the younger people take over.
Yeah. Because I feel like. Because I feel like they're so in. So into their old ways, and I think we need new. We need new leadership. We need fresh blood. Yeah. Because I think when the boomers grew up, they didn't even have Internet, so. And. And I've seen. Sorry. Yeah. And I've seen executives that are pivoting, that are fiddling around with Zoom when.
This can't even save a Word document as a PDF.
Yeah. And then I'm like, how did you make executive? Who did you have signed sex with to get an executive position? You're. You're. You're out of your mind. Yeah. You might have knowledge, but nowadays with the. With, you know, AI, I can have the same knowledge as you have. Probably even better, because I know how to use Zoom. So what are you doing at your executive position?
You're so right. Let's get some fresh meat in there, who's tech savvy, and let's see where we can take this organization. Yeah.
And it's time for you to just enjoy golfing. Go. Go buck the golf. And, you know, go bug your caddy at the golf course and say, back in my days, this is how it was.
You know, go smoke your cigar, grab your Prius. Okay, I've got another situation. I just thought of how to know when it's time to leave a job. What if you're working for a startup and you're anticipating that the company is heading downhill towards a ravine?
Startups are interesting startups. Startups can make you millions, but it can also be busts. And if you were. If you know that you're on track, might change anything.
On track for what?
Of it going.
Oh, if the company if it goes.
Belly up, if it's going to get.
Acquired, sometimes leadership does not tell you.
And sometimes it's an inch of way of either going belly up or being purchased. So you're like, yeah, yeah.
You and I worked for a certain startup that we didn't think had a long Runway.
It's Funny, Oscar on LinkedIn, he came to Oscar Garcia. Yeah, he gave a talk once and I watch it, and he said that all of his startups either went closed doors or got acquired. And so one time was like in the elevator with the cfo and he says, well, Oscar, we're gonna let you go. The company got acquired and we're all, we're all fired or something like that. And it's like, yeah, you just never know. So you gotta trust your gut.
Yeah, trust your gut, but it's also your career. So I'd be on the more conservative side. And if you think there's a chance I would leave because I was just a part of a company shutting its doors and then I was. I suddenly found myself unemployed and I'm like, oh, if I would have read the writing on the walls, I would have been job searching. Well, before that. Yeah, yeah. Can you think of any other scenarios for when it would be time to leave a job?
I just think you gotta listen to your. Listen to your lifestyle. Listen to what your family, you know, like, not like what your cousin, like.
Your wife and kids.
Yeah, because you might, you know, like when you have a huge commute for two hours every day, it might not be beneficial, you having that job. You might take a pay cut and run the numbers really deep. And you can do a job from home, make less money and still have more leftover.
Ah, so you're bringing up another situation. If it might be time to leave a job. If your life starts style or life situation changes. Maybe you have a child and you don't want to be in the car for two hours wasted every day. Maybe you want to have a job closer to home or work remote. Yeah, Interesting.
Cool.
Well, this was a shorter episode, but I think we covered a lot of good hypotheticals for how to know when it's time to leave a job. Comment below. If you are in any of these situations or if you've been thinking about quitting a job. And yeah, if you want to quit your job and you just don't know where to start, send us a message on Instagram. Just maybe we can help you kind of navigate where to go next. But yeah, thanks for listening. This is the ally from corporate podcast, obviously. And we'll catch you next time.
See ya.
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