Should You Really Change Careers? with Cynthia Pong

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Are you unhappy in your current job and considering a career change? How can you know whether you should change careers or just switch jobs within the same field? Find Your Dream Job guest Cynthia Pong says you need to know why you want to make a change before starting over. You begin by asking questions about why you’re unhappy and what your career goals are. Cynthia recommends making small pivots unless you’re paralyzed and feeling miserable in your job. If that’s the case, Cynthia says to go ahead and make any change and course-correct later. 

About Our Guest:

Cynthia Pong is a feminist career strategist, speaker, and author. Cynthia is on a mission to help women of color to get the money, power, and respect they deserve.

Resources in This Episode:


Find Your Dream Job, Episode 267:

Should You Really Change Careers? with Cynthia Pong

Airdate: October 28, 2020

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life.

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps you find a fulfilling career.

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Are you ready to not only change jobs but switch careers?

Our guest today says that before you get started, you need to get clear about why you want to pivot. You also need to make sure your decisions align with other professional and personal goals.

Cynthia Pong joins us today to talk about if you should really change careers.

She’s a feminist career strategist, speaker, and author. Cynthia is on a mission to help women of color get the money, power, and respect they deserve.

She joins us today from New York City.

Well, Cynthia, here’s where I want to start, why is it important to be clear about your why if you’re considering changing careers?

Cynthia Pong:

It’s important because it could really affect what you choose to do next in your career. Because there are obviously reasons why you’re unhappy where you currently are or why you’re even considering to change to something new. But depending on what the underlying reasons are and the root causes of that dissatisfaction, you may be better served by a smaller pivot within the same career, rather than a full-on career change. That’s why I always encourage people to think about, what are the reasons precipitating this thought process for you?

Are you finding that you ended up in a career because other people chose it for you? Did your family pressure you to go one way whereas you, in your heart, wanted to go one way? Or is it because you got tied to that field because that’s what you majored in in school? Are you unhappy for other reasons? Where is that misalignment between you and your career goals, and what you’re doing with your day to day work life?

It could also be that you’re seeing other people who appear to be way more happy and “fulfilled” by their work, and so you think, “Oh, maybe I should be doing this other stuff because I see my friends doing that.” Or it’s a new area that’s taking off, in which case, I’d have a set of questions for you on whether or not you should make that leap.

Mac Prichard:

Well, let’s talk about reasons why you see people consider making career pivots that maybe aren’t the right reasons? What are some common reasons, besides the grass being greener on the other side? Are there other reasons that come to mind, why you shouldn’t change careers?

Cynthia Pong:

Yeah, I mean, sometimes people are in the right career but simply in the wrong job or the wrong organization, or maybe in the wrong role, even. That’s why, if someone has tried a few smaller pivots within their career and they’re still coming to me and saying, “No, I want to change careers.” Then I’m like, “Yeah, you probably do.” Because you have tried these smaller, more low stakes, low-risk pivots, and it’s not changing how you feel about your work-life. But if somebody is thinking that…maybe they’re in a toxic work environment and they’re not getting along with their boss- you know, so many people leave jobs because of their direct supervisor or manager- I would encourage them to pause for a second, and reconsider what’s actually going on, and then what would be the right solution for them.

Mac Prichard:

Let’s talk about that example. If you’re in a situation where you’re unhappy and you think the answer is to change careers entirely, what should you do instead, before trying to find a new job in another sector?

Cynthia Pong:

I think taking stock of what’s working and what’s not working in your current situation will help give you some clarity on that. So, literally sitting down and writing down, “What’s going well in my current job and what is not?”

And then also, giving consideration, Mac, to what are your actual goals for this stage of your career? I’m not even saying your overall career goals, over the trajectory of your 20, 30, 40-year career. I’m talking about right now, with the reality that you’re facing, what do you want to prioritize? And then looking at those priorities, how well do they line up with the work that you’re doing? If they line up well, then maybe there’s some other way that we can resolve your source of unhappiness.

Maybe it’s the particular way that you’re looking at your work or the way that you feel about it, and we can change both of those things. You can change your thoughts, you can change your emotions, without necessarily having to take a big leap, right now. Especially in a time where the economy is not doing well overall and some industries are really taking a hit. You want to be careful about what you do.

Mac Prichard:

Let’s keep talking about that situation where someone is unhappy. Maybe it’s a toxic work environment, as you said, or they’re not getting along with a supervisor. You sit down, you make those lists of short term goals and lists of things that are working well and maybe not so well. How do you act on that information, Cynthia?

Cynthia Pong:

Yeah, so I like to encourage people, especially because I work mostly, almost predominately with women of color who are at different stages of their career and there’s…a lot of us have been socialized over time, in a way that actually disconnects us with our gut feelings, our sense of intuition about what we should and shouldn’t do. There’s a lot of second-guessing and self-doubt that develops from being a woman or a woman of color who lives in our society.

I would tell someone to go through this introspective exercise and do some deep thinking. And then looking at how well or poorly those things line up, think about what your gut instinct is on how to proceed based on this. Should you really take the leap and change to something else? Do you have something else in mind that is really pulling you? Like another career, or are you simply in a place where you’re incredibly unhappy doing what you do.

Then think about whether your instinct tells you if you should stay or leave, what the general timeline might be on that, and I would really encourage someone to try to put aside any feelings of second-guessing themself, and think, “What is the first thought that comes to my mind when I look at this landscape of my current career?”

Aside from that, I do think that there is a lot of benefit in working with someone as an external support, who can give you some advice from a little bit of distance, who can see things perhaps a little more objectively, and help you find your way because that’s what they do for a living. Getting help, whether it’s from a coach, or sometimes even therapy can help with this kind of thing, or a mentor, or a friend. But I would be a little wary of talking to too many people to get outside input. Again, because it can start to be like a “too many cooks in the kitchen” situation.

Mac Prichard:

Do you find, when the people you work with go through that process, that they may conclude that the answer isn’t to switch careers but simply to change jobs?

Cynthia Pong:

Yes, that happens, not infrequently. I think part of what happens, Mac, and I experienced this myself when I went through a period of burn out in my first career, sometimes we need something else to think about. It’s almost like this escapist, survival strategy, or like a way to cope with how miserable we are with our day to day. To dream about these other careers that we think we would rather do, but ultimately they turn out to be either a non-starter or not the real destination for us. I definitely work with people who come to me and they think they want to leave their job and start their own business or something like that, and then, in the end, they end up going for a promotion at their job or finding a different job in the same industry and finding happiness there.

Mac Prichard:

Let’s talk about the people who go through that process and decide the issue isn’t the job or the employer or the boss, it is the career. What do they do next, Cynthia, once they reach that conclusion?

Cynthia Pong:

Yeah, I think the first thing is to do your research. So, do a lot of informational interviews if you can. Reach out to people who work in that industry, who you either know directly or can reach through your contacts, or people who you find who are cold contacts, through LinkedIn or other places like that. The best way to find out what it’s really like to work in a particular industry, aside from actually working in the industry, is to talk to people who do, so once you talk to a bunch of people and ask a lot of open-ended questions, do a lot of deep listening, then that will give you an idea, not only of what that’s like so that you can be more confident in your decision but also you can get their advice about how you can more successfully pivot into that industry.

There are different ways to pivot, and so, you want to be strategic about how you do it. Sometimes for people, the easier path is, if you want to change into tech or something and you currently are an accountant at an accounting firm, it might be easier for you to lateral over to a tech company in an accounting role in order to then switch into software development or something, which is what you actually want to do because you’re in that organization at that point, and you can make those connections and put your name in the hat for the work that you really want to do.

A more difficult pivot would be if you were going to go straight from being an accountant to doing that software developing, without any prior track record in doing that work, and for someone like that, I would recommend really putting in the time first to demonstrate why and how you can do that work. Whether it’s on your own time for unpaid or volunteer jobs, or taking courses or something, to have a portfolio to show that you can do that job. Otherwise, think about it, why would anybody hire you for that kind of role if you have no experience in it?

Mac Prichard:

Well, let’s take a break, Cynthia, and when we come back I want to talk more about these small pivots and big pivots, too, actually, moving from one sector to another.

When we come back after the break, we’ll continue our conversation with Cynthia Pong about whether you should really change careers, or not.

You can’t change careers without knowing your why.

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Now, let’s get back to the show.

We’re back in the Mac’s List studio. I’m talking with Cynthia Pong.

She’s a feminist career strategist, speaker, and author, and she joins us today from New York City.

Cynthia, before the break, we were talking about if you should really change careers or not, and we talked about going through a process and getting clear about that and some people decide that, no, what they really need to do is change jobs or seek a promotion or switch companies, and then there are the people who start making a career change, and you were talking about small pivots. You shared the example of an accountant moving, who wants to break into tech, moving to an accounting position in a tech company.

Are there other examples of small pivots that you’ve seen your clients make or others?

Cynthia Pong:

Well, when I was saying small pivots, I was actually thinking more of changes that are less drastic than a full-on career change. Thinking about, if your industry is education and you’ve been a teacher for 10, 15, 20 years, but you really get that sense that you’re destined for something else at this stage of your career; maybe you think that you want to get into television or something like that…well, first I would ask you, what are your reasons for being on focused on that other industry, and if I thought that this was more of a situation where you were using that as a coping mechanism to get through your day to day, then I would ask, actually, what you thought going into an education-adjacent field would be like.

For example, becoming a consultant for some type of area of specialty, within education, that you have experience in, or going into administration, or changing the type of students that you teach. Maybe going from secondary education to higher ed or vice versa. Changing geography, changing the type of school, public to private to charter to what have you.

I would ask about these smaller less drastic changes and see what the person thought of them and how they reacted because sometimes we also say things but our nonverbal cues or whatnot give away how we really feel. So I’d watch for those things too, to get a sense of whether something, like a smaller pivot, would be more appropriate for them.

Mac Prichard:

What do those reactions tell you, as you watch the client and draw them out in that conversation?

Cynthia Pong:

Yeah, I can see, I can tell when people are more excited, or when they’re saying something that they just think that I want to hear. I love to look for those signs of somebody lighting up, like if they start to talk and their speech pattern becomes more excited, I can tell they’re more engaged with a particular idea. Or those moments when we’re really not censoring ourselves as much and that first reaction, I get a glimpse of that first reaction, whether it’s dread or something negative or it’s something positive, and I just kind of follow that and go. I like to follow where someone is clearly interested because making any kind of change in your career, whether it’s big or small, you need to be committed to it.

Otherwise, you’re going to give off, in those nonverbals, to other people, that you’re not really sure. This is something I learned from marketing but you know, “The confused mind says no.” I don’t if you’ve heard of that, but I fully believe that that applies in the job world in interviewing and hiring, networking conversations. People pick up on your hesitation and they’ll interpret it however they want to interpret it. The more important thing is that they’ll sense that something’s off and it will make them not want to choose you or not think that you’re serious.

Mac Prichard:

As you have those conversations with clients, and you’re seeing that excitement and people light up, I imagine your clients are feeling positive energy, too. How do they talk about that with you and how should they pay attention to that?

Cynthia Pong:

Oh, well, I’ll just straight up tell them. I mean, I’ll just tell them that I noticed that they seemed more engaged and more excited about one idea versus another, and my clients tend to be receptive to that. I mean, obviously, they hired me, so they trust me, at least to a certain degree. So, when I tell them things, I find that they hold it with a good deal of weight and I take that responsibility pretty seriously but it helps them feel more self-assured as they move forward, too. I think hearing that reflected back by me helps them also see it in themselves as they go. That in itself is a learning process. Which I think is pretty cool.

Mac Prichard:

As we talk about this, I would guess that people would feel that excitement but do you think sometimes they’re just not aware of it? Or as you say, that state of confusion somehow prevents them from feeling it or experiencing it fully?

Cynthia Pong:

Yes, I think we get very tied to certain ideas and pre-existing expectations for ourselves, especially in high stake areas like work and career. So, I think it often can be, like if something comes as a surprise to them and that wasn’t what their preconceived notion as of their next step, then it can really take people aback and I think that they may not even realize that they were excited about something. Also, I think sometimes people are so burned out and in such a negative mind-space, not because of their own fault but because of their situation, that they can lose sight a little bit of what actually makes them excited or not. Or it could be that the sign of them being excited is so subtle that they can’t pick up on it. But I try to be hyper-attuned to what’s happening and I’m looking for certain things, so it may be easier for me to spot.

Mac Prichard:

What I like about what you’re describing is that it’s- as you take your clients through this process of considering these, what you call, small pivots- it’s a path forward that allows people to make a change but it’s not a dramatic change. Sometimes, people dream about starting a bed and breakfast in Vermont or opening a bookstore or moving into an entirely new sector, and you can do that but it’s pretty challenging and most people never get started doing that, do they?

Cynthia Pong:

Yes, and I have to say, that really resonated with me because when I was very burnt out, some of my pipe dreams were to start a food truck, or to start a community center that was very based on health and wellness. And those two things would have been such huge endeavors that would have required so much investment, not only of finances and money and time but sweat equity. It would have been, if not a non-starter, then it would have been a painful and short-lived experiment but costly in multiple ways. Helping people understand that maybe that’s not exactly the way to go, it’s an important thing to try to do but I also want to say that it’s not like we each have…I don’t believe that we each have some predetermined path that is meant for us in our careers that we have to seek out and find, like a needle in a haystack.

I don’t really believe that. I think that each step that we take in our career is going to lead us to the next step, and the more important thing is that you take a step. So, what I think is more of a shame is if someone is so paralyzed, that they don’t even move, so, then they’re just stuck in this paralysis at their miserable job being miserable about it and they don’t make a small pivot, they don’t make a big change, they’re still there. I think that’s really the situation that we all want to avoid. So, if someone is feeling like they’re overthinking to this point that they can’t even move forward, then I would say just do anything.

Make any change. You will course-correct after that. You know, you tried to start a food truck, you realize that it’s going to cost x amount of money and you don’t want to invest in it or whatever. That will then propel you to the next thing. So, I know we’re really dissecting this first set of decisions but I don’t want people to lose sight of the fact that the path is made by walking, so take that next step.

Mac Prichard:

Well, let’s talk about the other steps along the way of that path. Once you get through that self-diagnosis, Cynthia, what else do you recommend someone do as they consider whether to change careers or not?

Cynthia Pong:

Yeah, I think, you know, we talked about the importance of talking to people who actually have the knowledge that you’re seeking. I think once you get a sense of what their advice is for you and how to successfully make this change, then it’s about applying it.

First, there’s a discernment process. So, you know, the people who you talked to, do you feel like they were trustworthy? Is there a lot of overlap in what people are telling you? For example, did you speak to 5 people and 4 of them all said the same thing? That makes me think, “Okay, then you should probably do what those four people said.”

That will tell you what to do. Like, do you have to get some more skills? Are you ready to make a change right now? Should you start applying to jobs, and if so, in what way do you do that? How can you leverage your network? How do you package your prior career experience in order to maximize your chances of getting your foot in the door?

Those are kind of the real nitty-gritty, granular things that would start happening once you’ve decided which way to go.

Mac Prichard:

How long do you recommend, Cynthia, people spend doing this type of research, talking to others, and self-reflection?

Cynthia Pong:

Yeah, well, it can vary depending on how burnt out the person is, and how much time they have to invest week to week. But I would say, generally, between a month to three months. Let’s say you only have an hour every week to devote to this type of stuff, then it’s probably going to take closer to three months but I wouldn’t want you to wait too much longer than that because you want to gain some momentum early on to propel you through this. Because the change is not necessarily going to be easy, it’s not necessarily going to be hard, but you will need to put time and energy into it.

Mac Prichard:

We talked a lot about switching careers and career goals, but what about your personal and professional goals? What part should they play in this decision making?

Cynthia Pong:

I don’t think that you can really, fully separate the two. And I also am someone who thinks that we should really make sure not to conflate our worth as human beings with what we do for work to support ourselves and our loved ones. I think, even when we’re between jobs, we have definite worth and value as human beings. That’s number one.

Personal considerations, clearly, I think, factor in and that comes up a lot in my conversations with my clients. If they have children they need to support, that’s clearly going to be a factor that will influence what they want to change into, and also my advice to them. Certain sectors are much less friendly, to be totally honest, to women and women with families than others. Looking at that, looking at whether a particular industry or set of organizations has good policies for work-life balance. Whether they support their employees in certain ways.

I think that’s where the intersection of personal and professional goals kind of comes together. And one thing that I like to actually walk my clients through is this exercise of identifying what your life mission is and what your mission in work is. You can even do a more specific one that’s your mission in a particular job, but the life and the work ones, a lot of people don’t take the time to think about that, but I think it’s so important. How are you going to know if you’re going in the “right direction” if you don’t know what your “North Star” is?

Thinking about that and making sure that both of those missions align, I think will make everyone’s lives a lot happier and more fulfilled.

Mac Prichard:

Well, Cynthia, it’s been a terrific conversation, now tell us, what’s next for you?

Cynthia Pong:

Yeah, so I am going to continue to get the word out about my new book which is, “Don’t Stay in Your Lane: The Career Guide for Women of Color.” And it’s a step by step instruction manual that walks you through your career change. From that first lightbulb moment of realizing that something is wrong to actually transforming your career and ending up in that new place. It’s a combination of my unfiltered career change story, the good, the bad, and the ugly, and a lot of practical, how-to advice and strategies, so that the reader can really coach themselves. Including about finances, which a lot of other books gloss over. I really get into all of the nitty-gritty stuff like that.

Mac Prichard:

I know listeners can learn more about that book as well as many free resources you offer on your website by going to

Cynthia, given all the great advice you’ve shared today, what’s the one thing you want a listener to remember who’s considering changing careers?

Cynthia Pong:

Nothing is irreversible in career. You can always course-correct, so just take that first step, don’t be too afraid or bogged down by the details if you feel like you’re getting stuck. The more important thing is to continue moving forward.

Mac Prichard:

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Again, that’s

Next week, our guest will be Mandy Allen. She’s the talent and culture manager at AHA Strategy and Creative Agency.

You see a job you know you could do. It’s not what you want, but you apply anyway.

And in your application and your interview, you say what you think the employer wants to hear.

You’re making a big mistake, says Mandy, and it will make your job search longer and harder.

Mandy and I will talk about why you need to stop trying to be all things to all employers and instead, focus on what you really want in your next job.

I hope you’ll join us. Until next time, thanks for letting us help you find your dream job.