May 4, 2022

How Often Should You Be Applying For Jobs Even When You Have One? - Ep. 43

Should You Always Be Applying to Jobs?

It's A Big Yes and Here's Why

There are many reasons why you should keep on applying for jobs when you have a job. Watch the full episode to learn how often should you apply for jobs when you're employed!

Welcome to Degree Free, where we explain what you can do instead of going to college, and how to teach yourself, get work, and make good money.

In this episode, we talk about:

- How often should you apply for jobs when employed and why you should do it
- Why applying for jobs will help you learn your market value and how you can leverage it to earn more money and have more benefits
- What are the common misconceptions that cause people to not look for new jobs
- The best places to apply for jobs when you're currently employed

Hannah talks about why you shouldn't feel guilty when leaving a company for better compensation.

Ryan also shares a story about his friend that got promoted twice in 15 months because of this strategy.

Enjoy the episode!

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Links and Notes from the Episode

Episode Transcript
Please enjoy this transcript or our episode!

Please note the transcript may have a few errors. We're human. It can be hard to catch all the errors from a full length conversation. Enjoy!

Ryan: Aloha folks and welcome back to degree free. We are your hosts, Ryan and Hannah Maruyama. On this podcast, we share fundamentals we've discovered and the mistakes we've made, while self-educating, getting work, building businesses and making money. We'll tell you how to make it happen. No degree needed. 

Hannah: Hey folks, so we actually write a weekly newsletter and I promise that you want this newsletter. It has really cool stuff in it and it's something that Ryan and I work on every week, where we find really awesome courses, we find really cool job resources, we find companies that are down credentialing their job listings and really interesting degree free news and then we put it into a newsletter and we send it out once a week. Now you should run, don't walk over to if you want to get that newsletter and I promise that you do.

Ryan: Yeah. Right on and let's get into today's topic. Today, we're going to be talking about how often should you be applying to jobs even when you already have a job?

Now, this is something that is not written in stone, right? But the, I guess the impetus of this entire episode is that like the job market is changing and it's changing quickly. 

Hannah: It's a real weird right now. 

Ryan: Right. And so we went from, you know, pre COVID, some of the record employment rates, you know, in 50 years or something like that. To, fast forward a year later, two years later or whatever it was, I was like, unemployment's out of like a seven year high or something. 

Hannah: Yeah. And the span of, you know, five minutes, basically. 

Ryan: Exactly. And so, and obviously that's for COVID and COVID restrictions and other factors. But the fact of the matter is, is that the job market is just crazy right now. 

Hannah: Yeah. And it's also just people moving to different people in different industries and that fund boomers retiring to. It's just, there's just so many factors that happened all at once. 

Ryan: Right. And yeah, we think that every 6 to 12 months you should at least be sending out a few.

Hannah: Yeah. If you're already employed.

Ryan: Right. Depending on what industry you're in, right? I mean, some industries are changing more quickly than other industries, right? I mean, 

Hannah: Yeah. If you're in tech, you might want to be doing that every two weeks. I don't know. 

Ryan: Right. Exactly. So, 

Hannah: If you're in construction and development license management and maybe every, year?

Ryan: Right. I dunno. Yeah, exactly. So it really just depends on the changing landscape of the industry that you're in, right? I mean, If you're in hospitality. A lot of places got hammered because of COVID restrictions because people stopped flying, people stopped visiting. Yeah. So that's one of the first things is gonna be, depending on your industry.

The one thing I will say too, if you are applying 6 to 12 months, every 6 to 12 months, sending out a few. You know, just kind of pick a number, right? Like 10, I think 10 is reasonable, right? You don't have to be relentless about the applying as if you need it right? As if you're about to go homeless, because you don't have a job.

Hannah: Right. 

Ryan: If you do have a job, just send out 10, just see what the feelers are, right? 

Hannah: It's way more pleasant to send out resumes when you were employed than when you are unemployed. I will say that's something, there's a very different feeling to doing that and I think that sometimes you're gonna get better results when you apply. When you know that you don't have to do anything except for apply, you can be a little more objective because you're, you don't need right now. You just kinda want or maybe you're just curious then, so you can be a lot more selective and a lot more, you can do a lot more research I think when you already have job and you're just kind of, and you're just kind of looking, you're kind of browsing. 

Ryan: Right, exactly. And then also, it's easier, it's an easier experience because you're already employed and you're probably already taken care of the bottom line. You're not backed into a corner, right? So that's, that's also good, right? One of the things that we do have to remember that just because you're applying to these jobs, you know, you can go through the whole interview process or not interview, whatever. And if you go through the whole interview process and you get an offer, that doesn't mean you have to take it. 

Hannah: No. 

Ryan: Even if it is better pay or whatever, right? If you don't want, if you like the company you're at and you don't want to take it, you can always say, no. 

Hannah: You do what you want to do. 

Ryan: Right, exactly. And if you don't, if you like the job that you're currently at right now, and you don't want to apply for any jobs within 6 to 12 months, and don't do that. 

Hannah: Then do not. 

Ryan: Right, exactly. And so, but if you do start accepting those offers, one thing that you do have to keep in mind is that it is gonna affect your job history, right? So you're gonna have a string of places that you worked for for 6-12 months and then you jumped somewhere else, which in, depending on the industry you're in, 

You may not really not. 

It probably, it may not probably doesn't matter. It really depends, right? But that is something to, at least, having back of your mind and it's something that's important to you, your job history and, and how long you've been at jobs. Okay. Well then just take that into consideration, but you know just to kind of concrete this home because of the changing landscape and because it's tarred to price what labor is worth now because the market's so crazy. We know a friend that received two promotions within the last 15 months, right? And gets paid a substantial amount more, right? And that just comes from doing exactly this, right? He just applied. As he was like, well, I'm just going to, I'm just going to look around and he applied me interviewed and he got him. So 15 months ago, he wasn't making nearly as much money as he makes now, right? I mean, good for him for getting out there and doing this. 

Hannah: And it's made the difference too, and I'm sure a lot of it is the fact that he was already employed. So it wasn't that pressure's not on, you can be more picky. You can be more nonchalant too, because you're, when you're unemployed and you're job hunting it's hard not to tie in other things about yourself to that process to get, you know, it just, it's hard to do that. Whereas if you're already employed and you, your, your basic bills are taken care of, you can eat, you can, you have a roof over your head, you can kind of breathe a little bit and you can be a little more strategic about what you're applying for or a little more selective in that you are interested in this and this, you think you could do it.

Ryan: Yeah. And then also there's gotta be something to be said for whether or not right or wrong. And I think it's starting to get better, but there's still stigma out there with seeing a resume. And you know, seeing that person hasn't worked in X amount of months, that's going away. I feel with COVID. Right? Because a lot of people 

Hannah: Now have giant dots in their resume, 

Ryan: Have giant dots in their resume. 

Hannah: Through no fault of their own. 

Ryan: Right, exactly. Right. Through restrictions and shut downs or they felt like they weren't safe at work or whatever, you know what I mean? 

Hannah: Whatever it was. 

Ryan: Whatever, whatever it is, there's all 

Hannah: Family stuff, they had to go, they had to move. 

Ryan: Right. Exactly.

Hannah: And there's so much stuff happened.

Ryan: So it's a lot more, explainable now, right?

It's a lot more justifiable, even though 

Hannah: you shouldn't really have gaps.

Ryan: Right. Exactly. And, but right there, wrongly, it does still happen. You know, people look at you and say, well, why do you have this gap? Like, why are you not employed right now? Some people might see that as a detriment and they're just, eh, you know, it is what it is. 

Hannah: Yeah.

Ryan: Right. 

Hannah: If he gets somebody who's super worried about that, you're probably not gonna work for that company anyway. 

Ryan: Exactly. So you don't want them all. 

Hannah: Yeah. 

Ryan: Right. Then you didn't want to work for that company anyway. 

Hannah: Yeah. 

Ryan: So one of the things that's good about sending your resume out, kind of with this frequency is that you can see, you can gauge the market.

Right. See if there's any interest for your skills and see what you're worth. See if you can get a little bit more, whether that's benefits or different schedule or whatever, but then also. It might be helpful to get a reality check, too. Right. And 

Hannah: Yeah. 

Ryan: So like, some people are at companies where they're already doing well.

Hannah: And they've been there a minute.

Ryan: Right. Or maybe they haven't, but they're already doing well. And, they try to go out to different. And try to apply, try to go to different companies or go to different roles. And they're finding that, oh yeah, sure. We'll hire you on, but we're going to pay you, you know, if you were making a hundred dollars there it would be like, oh yeah, we're gonna pay you 85 here.

It was like, whoa. Yeah.

Hannah: I really like my job.

Ryan: Exactly. It could be a reality check, right. 

Hannah: Or just maybe instead of reality check, you could just be a one of those things where you realize, oh, I just negotiated really well this time I'm going to keep this deal. 

Ryan: Is a very positive,

I think so

It was a very positive spin to put on that situation.

Hannah: I think so, glass half full 

Ryan: That is good 

Hannah: That's what I think to myself.

Ryan: I, I should think like that more often. Okay. So yes, you could think you could absolutely think about it like that. Whereas this time you've negotiated.

Well, very true. 

Or you can think of it as rally checking and saying, Hey, I got it. I got great.


Hannah: Pick your poison folks 

All right. So there's a few reasons that you might want to look for a new job and you might want to be sending your resume out to see what you can get on the open market. Obviously number one is going to be higher pay. Two, is going to be more competitive benefits and benefits is an overarching word.

This could mean you want a hundred percent of medical covered. This could mean you want a better schedule. This could mean. You want more PTO hours? This could mean anything about the benefits, both paid by the company and just intrinsic to the company. This could also just mean you're looking for more career opportunities.

Like, you want to work for a company where they actively promote from within where they're really aggressive about their education, you know, about their education of their employees, or you just like the trajectory of the company. And you want to go into that industry and grow with it. Or number four would be you just don't like your boss or your coworkers or your team or something about the culture of the company that you're currently at.

Those are all valid reasons to want to look and see what else is out there to see what you can find that might suit you better. And now with the way that as we talked about earlier in this episode, the market is really weird right now. It's very strange and it's one of those, but the side effect of it being really strange is that it's also, I feel the most employee empowering job market that we've ever had.

Like, I feel, I feel like the workers have the most power that they ever have. And especially in certain industries, there's definitely, you definitely have more leverage than you have. And people of our age as well, people in the millennial age bracket have more leverage. Because, there's a bunch of retirees. And so now these jobs need to be filled knowing where you stand, as far as you know, where the labor market's at, how you're valued in it, because of the fact that you're in the labor market, when other people are leaving the labor market and then understanding where your skills square up with what people need right now is a really good thing for you to put feelers out and just see what's going on around you, because this might be closing. We don't know how long this lopsided job market's gonna last. So while you can go ahead and feel out what's what's there. 

Ryan: So yes, one of the things I want to talk about to just highlight real fast by the better benefits is not, could be, you know, some stuff having to do with like a flexible schedule or you know, remote work.

Like currently you might not work remotely and you want to work remotely or you work remotely and you don't want to work remotely. Something like that, or if you want to, to have like a four day workweek or something like that. Right. Or If you needed more health insurance, something like that, fringe benefits too the list goes on and on, but just let your imagination kind of mull over what is your current benefits packages, whether that's comp or whatever it is valuable to you and see where you can improve. 

Hannah: But that's great advice because a lot of people don't think about the other things, you know, like the scheduling is a big one.

But now, especially. As there is a big push from older companies and larger companies to make them employees go back to work. Especially tech workers, which is a risky move, I think right now, because I think that they don't realize that a lot of tech workers are just going to quit and they're going to go somewhere else because they're going to just find somewhere that will, that will give them that.

So. If you fall into that demographic, you know, that's a, that's a good thing to keep in mind if your company is, if you're starting to hear whispers and starting to get nudges to go back into the office and you do not want to go figure out, go figure out what your, what your other options are, because you might need to know.

Yeah, definitely. And the last thing tell me kind of want to talk about are just. Some things that don't really necessarily have to do with putting your resume out there, but more about like the execution of it and how you feel. So, a lot of people feel guilty over trying to find a new job while they have a job that they are currently at.

And that has quote unquote, like been good to them maybe, or maybe they haven't been good to them, but just because they have it. They feel bad about putting their resume out there and seeing what else out there?

Yeah. That's definitely a very real thing. A lot of people, a lot of people do feel guilty about that.

I think too, I think a lot of women really feel guilty about that too. I know that I know that that sounds like that sounds a little sexist, but I, I do think women tend to feel that a little bit more like that pull to stay and, oh, well they did such and such for you, especially if at some point you went on maternity leave or something, that's another one after you come back, sometimes people might want to find a new job, but they feel like they owe something to the company, even though that was part of their included benefits.

Ryan: Yeah. So I guess the key is to basically difficult to just say it. Especially if you're one of these people that like don't feel guilty you don't owe the company anything. I mean, in vast majority of the cases, I mean, Maybe you do, unless you really owe the money, right. Or maybe all money or you feel like some other sense of stewardship to stay.

Maybe you work in a small company and

Hannah: Which is fine. 

Ryan: Yeah. This, you know, the owner or the manager really helped you out in a tough spot in life and okay. That, you know, then we're not talking to you. Right. Sure. If that's what you want to say, the perfect stay there. You know, if you're happy there. Awesome. But if you want to see what the market has in store for you or what is out there.

Yeah. Don't feel guilty about it, right? Like it's just a business transaction. You are providing a service and they are paying you for it. 

Be as objective as the company would be if they had to downsize. But be proactive. So be as objective as a company, if they had to downsize and that if they had to cut you, they would, and you should be as objective as a company in that if you had to leave, you could. Right.

Hannah: I feel like that's a good mentality to have, like, it doesn't mean that you don't like the company doesn't mean you're disloyal. It means that you know what your options are and you are, you, you know, what you could do at any given time. 

Ryan: Yeah. Definitely 

I think the last thing that we would want to talk about is going to be like, should we do this kind of stealth or not stealthy?

So what I mean by that is like, should you post your resume on job boards? Like discuss this with your coworkers, like 

Hannah: Post on LinkedIn, that you're looking for a new job. 

Ryan: Exactly. Those, 

Hannah: Open to work 

Ryan: I think the most important thing that's gonna be the factor here is going to be the company culture.

Right? Like some companies are going to be okay with it. Right? Some companies want you to go out there and they want to have, you know, what you're worth out on the market. Right. If you're worth more out there and they can't match it, go work over there. If they did, you're going to be happier there. Go for it.

Right. That's fine

Okay. Most companies are not like that. That's got to be 

a negative ghost rider. 

Yeah. If you are in one of those companies, that's awesome. That's great. I hope that you can have all the conversations with your coworkers and your boss about how you have 10 resumes out there and you know, and you're looking for a job.

That's great. 

Most companies don't like them. 

Hannah: No. And I think the one that really gets people here is that people talk to their coworkers about things that they shouldn't talk to their coworkers about. I think if you were going to tell someone Maybe your boss would be the only one. I would definitely not tell a coworker.

That to me seems to really unwise. Just because if you're talking and the coworkers talking and you guys are just talking, eventually they're going to talk to someone else and someone else is not going to have that information. And you don't know who's going to get that information. And now it just becomes the same where a lot of people know your business and you lose any strategic advantage you may want to have, or you just now don't have your own business being your own business and what's everyone's business.

So I just feel like, keep your, keep your cards close until you need to play. 

Ryan: Yeah. So

Hannah: That's the lesson I learned the hard way. Cause I'm a talker. I like to talk to my coworkers. 

Ryan: So I would say that as a default, we're going to want to keep this as discreet as possible. Right. And so, yeah, maybe, you know, during this time you're definitely going to be updating your LinkedIn, right.

You're going to make sure that you're going to make sure that it's has the keywords that you needed to have, and it has the current jobs and responsibilities that you're currently doing. All that. And that's all regular things to be doing. Right. And maybe you don't want to just click that on looking actively looking for work, right?

Okay. Maybe, you do it's up to you, but yeah. Talking to the coworker. I don't know about how I feel about that either. Right. Or like one of the things too is like asking, you're asking for your current boss or your current coworkers to be references, right. Like, I think generally speaking, if you haven't told them.

Definitely don't put them on as references. No, 

Hannah: Just be considerate of them too. Cause they're going to get very, they're going to be very surprised by 


Ryan: Yeah, exactly. 

Hannah: Yeah, it's like saying an uninvited guest over to knock on someone's door. 

Ryan: Right. 

So, you know, you can put the references for your last job on there.

Right? That you know, you left already. 

Hannah: All right. So I have, I have a theoretical question. So let's say you are on a call. Let's say you work remotely, you're on a call with your boss and they say, I have a friend who works as a recruiter at X company, and they have your application and they just received your application.

And that's all they say, 

What do you do? 

Ryan: Well, that's super specific. Like, I have a friend at Acme Corp, 

Hannah: or they saw on your LinkedIn that you apply that you apply for something, something like that. 

Ryan: Right. Well, but I'm just saying, like, if it happened to that question, like if they said I have a friend that's a recruiter at Acme corporation that has got your resume. And you did just put your resume through to Acme corporation. And then like, you really don't have a alternative, right? Like it just come clean, the jigs job, you know, it was like, all right. If it's something softer, if it's like, you know, oh, I heard you're throwing your resumes out.

I don't know. I feel like, I feel like the jig is still up, right. I mean, What is the goal of this conversation that this manager or this coworker is trying to get out of you? Right? I mean, what's, what's the point of this. And I, at that point, if they obviously care whether or not this is fact or fiction at that point, I would just, I'd be like, yeah, I'm, I'm doing it out there.

I'm not sure if I'm leaving. I just wanted to see what else out there. 

Okay. I 

Hannah: think, I think along those lines, that's, that's what I would say. I would say I, I apply regularly for other jobs to know what my value is on the market 

Ryan: Yeah. Exactly. 

Hannah: And make it a standard matter of practice. And if you want it to go a step further, you could say, yeah, I send out three to four resumes.

So that I know what my value is on the market. Do you do that, 

Ryan: Yeah right . Exactly. 

Hannah: But do you want help?

Ryan: Right. Exactly.

Hannah: You know, and, and not in any kind of way, but just, not only go. Yeah, of course I did.

You know, 

I like what you said there 

Ryan: about like, this is standardizing it because then it's just like a thing. Eventually it will just become a thing that you do, assuming that they don't fire you.

Hannah: Right. They are not going to buy. I seriously doubt that if you had somebody that fired you for doing that, you should probably be leaving anytime. 

People are crazy.

Ryan: Yeah. 

You can inform the current company that you're working for about the job hunt, when you've secured an offer that you're going to take, right? Or that you are like, then you secured an offer and they might match it.

Right? Like they might match it. It'd be like, oh,

Hannah: I'd be really careful doing that. Intentionally. If you're trying to play chess with a company, I would be very careful going out to get an offer that you have no intention of following through with, or that you don't actually want to. And then taking it back to your company in an effort to make more money.

Because I think that you may, you may get your way the first time. But I think you lose a lot of leverage in other ways. That's my opinion. 

Ryan: So yeah, that's pretty much the episode. As far as how often you should be applying, just pick a number 10 is a nice round number. Every six to 12 months, try to send out 10 resumes, send out 10 applications, just see what you get back.

Right. The job market is crazy right now and it's ever changing. It's good to see what you're worth. 

Hannah: Definitely, definitely would recommend doing that. Just so you always know where you 

Ryan: stand. Yeah, definitely. And yeah. Thanks so much for listening guys. If you guys liked this episode, please subscribe. If you guys want to help out the podcast, the best way that you can do that is by leaving us an honest review anywhere you get your podcasts.

Hannah: Oh, and before you leave, if you want to get more information about Degreefree. And by that, I mean, degree free job ideas, companies that are down credentialing, their listings, tips, resources, courses that Ryan and I have found helpful. Then you're going to want to run over to, and you will get our free newsletter delivered to your inbox once a week.

Ryan: Yeah. And that's pretty much it guys until next time.

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