Smart Money Podcast: Is It Time to Leave Your Job? Tips for Smart Moves and Strategic Growth

Welcome to NerdWallet’s Smart Money podcast, where we answer your real-world money questions. In this episode:

Learn how to decide if it’s time to change jobs or careers and understand how to strategize before you make a big career move.

How do you know if it’s time to leave your job? What steps should you take before making a big career move? Host Sean Pyles talks to author and SiriusXM host Dawn Graham about how to evaluate your current job satisfaction and recognize the signs that it might be time for a change. They begin with a discussion of identifying personal values, assessing career alignment, and tips for navigating conversations with managers. They also delve into strategies for approaching major career shifts, from exploring new fields to building the skills and network necessary to succeed. They discuss actionable strategies for testing a new career path, overcoming the challenges of starting over, and networking effectively to stand out.

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Episode transcript

This transcript was generated from podcast audio by an AI tool.

Sean Pyles:

How is the job going? Nobody has 100% great days at work, but are you generally satisfied with your career and the daily grind, or are you thinking it might be time for a change? It is, after all, a new year and change is in the air. How do you know if it's time to go?

Dawn Graham:

Whether you're in a job search now, whether you're going to be in a job search soon, you bring a lot of value to the market, and don't forget that because confidence breeds confidence. You have a lot to offer, so when you show up, remember that.

Sean Pyles:

Welcome to NerdWallet's Smart Money podcast. I'm Sean Pyles. For better or worse, we tend to think of a new year as a good time to make changes. Maybe we want to get in better shape or eat healthier foods. Maybe we want to move to a new home, city or state. Maybe we want to stop procrastinating or keep our homes better cleaned or both, or maybe we're thinking about a change in our careers. A new survey out from The Gallup Organization finds that employees across the U.S. are looking for new opportunities at the highest rate since 2015. That's even beyond what we saw after the pandemic with the Great Resignation. Gallup calls it the Great Detachment.

With this episode, we continue our January series, Your Money in 2025, by taking a look at how you know when it's time to move on from your current job situation, whether it's looking for a change within the company that you currently work for or looking outside to something entirely different. There's a lot to consider, from what you're getting paid to who you're working with to basically what you want to do with the eight-plus hours a day that you're putting in.

Today, we're going to talk with a careers expert about some of the questions you should be asking yourself if you're looking for a change in your work life, and we'll get to some advice for how to start that process in a way that doesn't jeopardize your current work situation.

Meantime, we want to hear what you think. What are you working on in your financial life as we start the new year? Are you thinking it might be time to take a second look at your job and your career? How are you handling that? Leave us a voicemail or text the Nerd hotline at (901) 730-6373. That's (901) 730-N-E-R-D, or email a voice memo to [email protected].

Our guest today is Dawn Graham. She's a corporate psychologist, career switch coach, LinkedIn learning instructor, and former host of the popular call-in show Dr. Dawn on Careers on Sirius XM Radio. Her book is Switchers: How Smart Professionals Change Careers and Seize Success. Dawn Graham, welcome to Smart Money.

Dawn Graham:

Thanks, Sean. Happy to be here.

Sean Pyles:

Let's start with a very basic question, which is how do you know when it's time to start looking for a new job? What are some signs to pay attention to?

Dawn Graham:

Sounds basic, but when you start to do it, there are so many factors to consider. One of the biggest ones is taking a look at what you've learned over the last year and how you're building your skill set. If you're starting to find that you’re feel stagnant and you're not growing, that could be one of the biggest signs because what we know is the world is changing at warp speed, and we're all going to need to make career changes.

One of the things that's going to make that easier is that we're constantly growing and building our skill set. There are a lot of tactical factors. If you're in a situation at work that is untenable or your role recently went from being remote to in-person, and that's not working for your family, there are certainly a lot of those types of reasons I see people making changes as well.

I think you have to make sure that where your career is going is aligned with your values, and if being home for dinner is one of the things that's important to you, you can certainly sustain that for a while, but you're going to get burned out pretty quickly if you start to notice that your career has shifted in a way that is misaligned.

And then, of course, there's the "I'm bored, and I want to do something new." This is a great time to look at what you have in your day-to-day job, and see if you can maybe shift things around and create the environment that has more of what you want. I always recommend starting there first because you're in the company, you've built relationships, you've probably proven yourself. But if that organization or environment doesn't offer you what you want, my recommendation is to start having conversations with people who seem to be doing what you want to do and go from there.

Sean Pyles:

What would you say is the difference between looking for a new job and looking for a new career?

Dawn Graham:

Both are hard. Looking for a new career can feel a little bit more intimidating because you have to step outside of your comfort zone, where you probably feel pretty accomplished and experienced in your current function or industry. When you start changing careers, you start to feel a little bit intimidated because a lot of the people around you seem to have more experience or more skills in that area.

I would say that if you're looking to make a career switch, that's a great thing. Don't shy away because it's a little bit more difficult, but really start introspecting, figure out what you want to do and why you want to do it, and then start to think about what's realistic. A career change will come with certain things that may or may not appeal to you. You might need to change geographies, you might need to return to get a certification or a degree, you might need to take a temporary salary cut. Some of those things might be doable; others may not. It doesn't mean that a career switch isn't in your future — it just might mean now is not the time, and you can start preparing for it a little bit earlier so that when you are ready to do those things, you are set to go.

Sean Pyles:

Let's focus on this idea of a new job. Basically, you are staying in the same line of work, maybe even at the same company, but you want a different job or different responsibilities. How do you start to think about what it is that you want to do?

Dawn Graham:

The introspection really starts with: Where's your professional energy? I like to call it professional energy because I think the word "passion" is a little bit too intimidating for many of us — it just implies a lot of big life things, when in fact, our professional energy is a little bit more targeted and focused. Where do you lose time during the day? What types of activities really make you feel energized afterward?

For example, when I coach clients, sometimes it's that camaraderie and collaboration around a project where everybody's doing their own piece. For others, they love working up against a deadline, and they like that pressure of working with clients who have that 11th-hour change, and they have to scramble to get it done. Other people are really focused on data analytics and finding stories in the numbers. So it's really about: Where is that professional energy for you, and how can you expand it? How can you build on it? How can you add more of it to your day-to-day job?

Sometimes you can do that in a very similar job; other times, it might be that you have to make a pretty big pivot to get more of that into your job. But I say start there, and then always make sure that things align with your values. I had a client once who wanted to switch into finance and found that a lot of his evenings were spent having dinner with clients or traveling, and that took him away from his family. So, as much as he loved doing the day-to-day work, it really didn't align with where he was in his life. That said, it doesn't mean it won't in 10 years, but he really had to struggle to resolve that. So don't forget to look at the lifestyle, the environment and the other factors that are really going to be part of your day-to-day.

Sean Pyles:

It also seems like part of the task of finding a new job in the same career field that you're currently in may just be understanding all the facets of similar jobs to yours and then pursuing one that might align better with your current desires professionally.

Dawn Graham:

That's a great point, Sean. A lot of us see the surface — we see someone's title, we see them in maybe 10% of their job, and we imagine that this is what it's like. But I think one of the biggest things we can do is constantly have conversations with people who seem to be doing interesting work. Whether that's inside your company or people you find on social media or LinkedIn, reach out, ask for 20 minutes, and say, "Hey, what you do seems really interesting. I'd love to learn more about it. Can I have 15-20 minutes of your time just to hear what your day-to-day is like?"

A lot of times you'll find out, "Wow, this is just as interesting as it looks on the surface," and sometimes you'll learn, "Wow, that's not at all what I expected it to be, and thank goodness I don't have to do that job."

I think that's one thing I see a lot of people shying away from. Reach out to people. It doesn't matter if they're in a different field, it doesn’t matter if they’re at a different level. Some people won't get back to you, but a lot of people will, especially if you approach them in a thoughtful manner and you're not looking to take up too much time. People love to talk about the work they do, and you can learn a lot from somebody who's actually in the field, on the ground, doing that work — much more than you're going to learn on the internet.

Sean Pyles:

Let's talk about changing jobs within your current company. What do you see as some of the immediate challenges to switching things up within your current workplace?

Dawn Graham:

It really depends on your culture. Some companies are great at encouraging and supporting people in moving around, learning different parts of the business, and growing in that way. They even have rotational programs or side gigs where you can work with different departments and learn about what they do. Other companies are a little bit more structured and prefer that you stay on the path that you're on.

A lot of that comes back to your relationship with your manager, who can play a big role in your success and your future. But I don't think we necessarily need permission from anyone to have conversations. If this is something you're thinking about, I think it's absolutely fine to reach out to somebody if you want to do something in marketing, or in finance, or in the legal department, or HR, and just have a conversation. Get a coffee, learn more about what they do, and if it seems like something you want to pursue seriously, that's when you may need to have that conversation with your manager and talk to them about what those next steps are.

But I think to initially get started, we can all be having these conversations. And then when you are ready, if you are in a culture where that's supported, I'm sure there’s ways that they will support you throughout that. But if you're not, you may find that you have to go somewhere else in order to do that or in order to be taken seriously in a different role. So a big part of it depends on the environment you're in.

Sean Pyles:

Yeah, and if you find that you are at a company that isn't encouraging you to look for different roles or opportunities within the same employer, that might be a signal that you want to hop to a different employer.

Let’s talk a little more about the conversation that you need to have with your supervisors once you do decide that you need a change. Maybe you’ve had those coffees with colleagues in other departments. What’s the best way to approach that without totally playing your hand and telling your supervisor that you’re unhappy? Or should you tell your supervisor that you’re unhappy?

Dawn Graham:

First, you want to make sure you’re not catching your manager off guard because you’re going to get a poor reaction if you do that. Set aside time. Maybe you have annual reviews or semiannual reviews, and get prepared to have the conversation during that time because everybody’s coming to that meeting with the expectation that you’re going to be talking about growth and where you want to go.

The other thing I would say is don’t make it an ultimatum and don’t make it a “This has to happen in the next two weeks, or I’m leaving,” because again, most of those types of switches internally can’t happen within that short period of time. If you come to your manager with a well-thought-out plan and say, “Hey, I’d like to make this transition over the next six months. Here’s what I’m thinking we can do to make that smooth,” maybe there’s somebody on your team who’s ready for the next level that you can start to train. Maybe there’s an opportunity to bring an intern in to start doing some of your work so you can transition.

Putting yourself in the manager’s position and getting into their mind and saying “What’s going to be their concern?” Their concern is they’re losing a great resource. Their concern is, how am I going to backfill your role. If you can start to really think about how you can partner with them to solve those concerns, you’re probably going to get a lot more support.

Sean Pyles:

Let’s move on to some advice for if you’re wanting to look outside of the organization that you’re already in, but you don’t necessarily want to switch careers. I think we’re all aware that networking is key and that really knowing what you want to go after instead of just “spray and pray” with your resume. What are some other really key steps that you need to take to get ready for the job hunt?

Dawn Graham:

You have to know what you want, why you want it, and build ambassadors. And what ambassadors are — and how it goes beyond networking is — is people who know you and want to help you. They are your cheerleaders. Do they know what you want to do? Are they aware that you are looking for something new? And are they aware specifically? And I would challenge people to say that the people closest in your life — if you ask them, “Hey, in a sentence or two, tell me what I do in my job.” And I’m not talking about, “Oh, you work in technology,” or, “You do something at Disney.” I’m talking about, what do I specifically do? Most people who know you well, are your cheerleaders and want to help you, have no idea what your job is.

So I think that's the best place to start. If you can give them a very layman's terms of the type of work you do and give them an assignment saying, "If you see this, if you hear of anything like this, bring it back to me." That's one of the biggest things we can all do is make sure the people closest to us are out there being our ambassadors.

Sean Pyles:

Dawn, what if you just feel uninspired or maybe bored, not enough to leave your current job, but also you’re just kind of going through the motions? If you’re not looking for a major change, how can you get back to being passionate about the job that you do have?

Dawn Graham:

It’s a great question. It’s coming up a lot these days, and I think one of the things you need to do is pinpoint the source. What is it that is causing that? Sometimes it’s the job, and sometimes it’s something outside the job. You have to be really honest with yourself around what is it that’s really causing this.

The other thing is that no job is perfect and no job is all bad, although there might be a few that people might contest on that point, but what is it that initially drew you to the job? Is some of that still here? Is it just that you've gotten bored in it?

The other thing I would say is focus on the things that are going great and allow you to do the things you want to do. Hey, my job's remote, which allows me to go to pilates. It allows me to have dinner with my family. It allows me to not have to spend two hours commuting. Tap into those things. But if you really find that you struggle, it may be time to find something new.

Sean Pyles:

All right. In a moment, we’ll be back with tips and advice for if you want to make a really big change and try for a whole new career track. Stay with us.

Dawn Graham, we’ve been talking mostly about how to think about a job change, something that’s already in your wheelhouse, possibly already in your workplace. Now let’s move on to what happens if you start having a desire to completely switch career tracks. Maybe you’re working for the Office of Management and Budget at the White House, and then suddenly you want to own a specialty food store in the Hamptons, like my hero Ina Garten did. What are some questions to ask yourself if it’s the new year and you’re feeling like you just don’t want to do that thing that you’ve been doing for 10 or 15 or 20 more years?

Dawn Graham:

The biggest thing to ask yourself is what am I willing to sacrifice to do this? And that’s often not the first question people ask themselves. But when you do, you start to get real. It could be temporary, but it could be forever. So I think that’s the first question. What am I willing to give up? What are my non-negotiables? Because those are going to be some of the things that either get in your way or will prevent you from succeeding.

Sean Pyles:

What are common things that people do have to sacrifice when they’re switching careers? I’m thinking about possibly salary or time just spent getting up to speed on what you need to do for a new career.

Dawn Graham:

Those are two of the big ones that often people don’t want to give up. It might be that if you’re switching careers, you’re now reporting to somebody who has a lot less experience than you. It might be that you’ve built a career where you have great autonomy because you’re the boss, or you have built great relationships and now you don’t, now you have to adhere to a schedule.

Maybe that you’ve built a remote career, now you have to go in the office. It may be that you have to travel more, that you have to pay for certifications, that you have to start at the bottom. Money is most people can relate to, but a lot of these other things come down to ego. It’s a real thing, right? Can you tolerate this when you’ve become successful in a career, when you’ve become the boss, when you’ve become somebody who is respected and has built a reputation, can you tolerate making mistakes and kind of feeling insecure and feeling like you’re not the most experienced in the room? And most people say, "Yes, yes, yes" until they get to that point and then they think, "Okay, this isn’t as pleasant as I thought."

Sean Pyles:

So clearly, getting a new career is a bit more difficult than just getting a new job. You’re going to need to highlight or gain new skills, you may not have a natural group of people to go to for advice, and you might not really have that network going into a new career. What are some ways to start gaining those things in a new field? And obviously in some instances you are going to need to go back to school.

Dawn Graham:

What I would say about school is that should never be your first step. Unless you’re going to a highly regulated field like becoming a nurse where those things are going to be a make-or-break it, you’re still going to have a hard job search at the end of your degree. If you think that’s the easy first step because it feels structured, and I know people hate ambiguity, so it does feel like an easy first step, that’s a lot of time, money and resources to invest in something when you still have that difficult job search on the tail end.

The human brain is wired for the lowest-hanging fruit, and unfortunately, in a switch, often that’s not what’s required. What’s required is shadowing people who are doing the work, reaching out to strangers who you don’t know, and building relationships with them, uncovering what’s beneath the surface and all of the things that you probably don’t even have a clue about regarding this career, and then trying them on to see if they fit.

So it’s a hugely ambiguous self-experiment, I would call it, if you’re looking to switch careers — of course, unless you know somebody who’s doing that job currently who you’re very close to. But even then I would say branch out and talk to more people because chances are that there’s a lot more than that one person’s experience, so you really need to be comfortable with ambiguity, and you really need to be comfortable with self-direction. Every day you’ll uncover something new that you now need to explore, so if you enjoy that or at least you can tolerate that, then I think you would be a good candidate for a switch.

Sean Pyles:

All of this assumes that you know what you want to go into. What if you don’t know? You know you want to change jobs, maybe you’re very tired of what you’ve been doing. You want something new career-wise, but you’re just not sure what that thing is.

Dawn Graham:

I think some of the same rules apply. You have some general ideas, and you start to explore them, you start to have conversations, and through those conversations you start to pivot. Herminia Ibarra, who’s done a lot of work in this area, talks about this multistep process where you create experiments, you build connections and then you evaluate. So you continuously go through that iteration, almost like design thinking, if you will. You come to the career that you ultimately want to pursue as you keep going through these iterations. It’s not necessarily quick. A lot of people don’t like that either — they want to know, and they want to just dive in — but it can be a lot of trying things on for size, maybe testing it out in terms of doing some volunteer work, maybe testing it out in terms of doing some projects, because, again, what you read on paper is often very different than what’s applied in the actual environment.

Sean Pyles:

What would you say are some ways to get yourself in front of decision-makers in the career that you’re hoping to move to? Maybe someone who could say yes to you having a job at their company?

Dawn Graham:

I would say be bold. Not something that a lot of people love to do because our human mind loves to rationalize reasons why we shouldn’t be bold. I’m an introvert by nature. This is where you have to practice that 15 seconds of courage because you really, really do need to have those conversations and be willing to do the hard work. A lot of people want to do the first thing, which is apply online. But if you think about how jobs are sourced, if you had to hire somebody, what’s the first thing you would do, Sean?

Sean Pyles:

Talk to people I know in my network and ask if they are interested, or if they know anyone, right?

Dawn Graham:

Exactly. That’s what hiring managers do. They look in their network, they look within the company, they look at maybe people who’ve worked for the company in the past. By the time it gets to the posting — the public posting — think about all the people who could have taken that job who haven’t. Why haven’t they? That’s a great question.

The reality is that if you apply online, absolutely use LinkedIn, use social media, find the hiring manager, find someone in that department. It’s not as hard as it sounds, and reach out to them on LinkedIn 100% every time, because that is the only way you’re going to get noticed. You’ve already mentioned networking, but be strategic about it. Start to build relationships with people in that company. It doesn’t matter if it’s the person in the mailroom or the person in the boardroom, start to build as many relationships, become a known entity, and this comes back to really focusing on where you want to be. You obviously can’t use this strategy in 300 companies, so having a clear Plan A, as I call it, is going to make this even more effective.

Sean Pyles:

I want to go back to something that you mentioned earlier around almost the emotional side of changing careers. I imagine if you are starting a completely new career, you have to start pretty far down the ladder, and that could be a mental and emotional challenge. It’s that hit to the ego you mentioned earlier. How do you think people can process that and feel good about this uncomfortable mental place they may be in?

Dawn Graham:

First and foremost, you have to know what’s coming because when you expect it, the blow tends to be not as hard-hitting. Expect that this is going to be tough, that it’s going to feel uncomfortable, and that uncomfortable is part of the process. Another thing to do is to avoid comparing yourself at all costs. Comparison is the devil in this process, because inevitably what you see online, what you’re probably looking at, and reaching out to people who are successful — you’re not yet. So be careful about starting to compare your start to somebody else’s triumphs out there. That’s another thing you can do.

And next, talk to people who’ve done it. You may be surprised, but I will tell you, everyone out there who has a LinkedIn profile or a bio that looks like it is all neat and tidy and planned out — they’re not. We put it online that way because we want it to look that way, so you’re seeing somebody’s career in its ideal form. So be careful about making assumptions like that because it’ll only make you feel worse.

Sean Pyles:

What about the question of whether you should stay in your current job while looking for this new career or if you should leave the job, maybe take some time off if you can swing it, and then use that time to explore what you’re hoping to get into?

Dawn Graham:

This is the ultimate question, and I think the general career advice out there is keep the job you have until you have the one you want. I do think that is good advice in this market, because it has increasingly been harder over the past year for people who are not switching careers to find internal roles, never mind people who are making big career switches. So unless you have a stellar network or your uncle is the CEO of the company that you want to work for, it’s probably a good idea to do your exploration. And I would even venture to say, start a side gig, start your own consulting business around this, start to do projects, even if you do them for free.

I know people are thinking, "I don’t have time. Who has time for that?" But you really want to lay the groundwork as much as you can for the next role you’re doing and get the requisite skills, requisite resume-builder-type certifications before you actually need it. Because there’s a difference when you’re interviewing, when you’re networking, when you need a job versus when you want a job, and it is very, very perceptible to people. Unfortunately, you’re going to find a lot of your network contacts, if they know you are needing a job, are going to back off. And that’s sad because it shouldn’t be that way. If you can swing it — if you’re not in a toxic situation, if you’re not in a situation where you’ve been laid off, and you can look while you’re in a current organization — that is always going to be helpful.

Sean Pyles:

Dawn, do you have any final words of advice for anyone who’s thinking about a big career move as we head into 2025?

Dawn Graham:

I would say this. Security comes within ourselves. A lot of us feel like we need to be inside a company, and there’s a security that comes with that, but we know looking at the last year — I’ve been laid off twice in my career, and a lot of people I know have been laid off — and that’s a scary, scary thing. But when you know that your career lies within you — the skills you build, you take with you; the experience you build, the relationships you build — those are all part of who you are, whether you’re attached to a job, attached to a company, or not. So what I would say is: Maintain that confidence. Whether you’re in a job search now, whether you’re going to be in a job search soon, you bring a lot of value to the market, and don’t forget that because confidence breeds confidence. You have a lot to offer. So when you show up, remember that.

Sean Pyles:

Dawn Graham, thank you so much for your help today.

Dawn Graham:

Thank you. I’ve enjoyed being here, Sean.

Sean Pyles:

That wraps up our series on Your Money in 2025. Over the past month, we’ve covered budgeting, housing, investing, and financial goals. If you missed any of these episodes, take some time to listen to them and see how they can help you get what you want from your money in 2025.

Do you have a money question of your own? Turn to the Nerds and call or text us your questions at (901) 730-6373. That’s (901) 730-N-E-R-D, or email us at [email protected]. And remember, you can follow the show on your favorite podcast app, including Spotify, Apple Podcasts, and iHeartRadio, to automatically download new episodes.

This episode was produced by Tess Vigeland. I helped with editing. Amanda Derengowski helped with fact-checking. Megan Maurer mixed our audio, and a big thank you to NerdWallet’s editors for all their help.