Give Yourself Permission to Change Careers, with Carissa Kerrissey
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Changing careers can feel daunting, especially when fear, guilt, or long-held beliefs about who you should be start to surface. On this week’s episode of Find Your Dream Job, guest expert Carissa Kerrissey explains why career pivots are far more common than people realize and how our brain’s natural negativity bias can make change feel harder than it is. Carissa breaks down myths like “I’m too old to start over” and shows how identity, purpose, and shifting values often signal that it’s time to explore a new direction.
She also shares practical steps for navigating the inner critic, recognizing the transferable skills you already have, and using your core values to guide your next move. If you’re burned out, feeling stuck, or simply ready for a fresh start, Carissa’s advice offers a clear, encouraging path toward work that fits who you are today.
About Our Guest:
- Carissa Kerrissey is the founder of Future Forward Careers. Carissa’s company helps burned-out teachers and mission-driven professionals reclaim energy, rediscover purpose, and transition into fulfilling work.
Resources in This Episode:
- Connect with Carissa on LinkedIn.
Transcript
Find Your Dream Job, Episode 533:
Give Yourself Permission to Change Careers, with Carissa Kerrissey
Airdate: January 7, 2026
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.
Every Wednesday, I talk to a different expert about the tools you need to get the work you want.
Making a career pivot can be challenging.
And to do it successfully, you need to commit to the change.
Carissa Kerrissey is here to talk about giving yourself permission to change careers.
She’s the founder of Future Forward Careers.
Carissa’s company helps burned-out teachers and mission-driven professionals reclaim energy, rediscover purpose, and transition into fulfilling work.
She joins us from outside of Portland, Oregon.
Well, Carissa, let’s jump right into it. Here’s where I want to start. Why might people be reluctant to change careers? What’s going on there?
Carissa Kerrissey:
Yeah, there are numerous reasons why someone would be hesitant to change careers, but I want to back up for a minute, and I just want to acknowledge that changing careers is actually a completely normal process in our lifetime.
The average amount of times that an American will change jobs is around 12, and careers, it’s anywhere between three and seven. So I just want to first acknowledge that it’s normal. It’s a normal process for us to go through.
As we move through different phases of our lives, things shift, our values shift, our priorities and our goals shift. So I just wanna first start by acknowledging how common and normal this process really is. When we are thinking about making a big change in our life, we are going to have a lot of fears that pop up because what we’re really doing is we’re stepping into the unknown, and that’s scary.
This actually goes back to neuroscience, studying the brain and why we are so prone to fear change, is that we’re all born with a negativity bias, which means that we are focused, laser-focused on the things that could go wrong. And that can look like in a career change, these thoughts that pop up around, I’m too old to start over. I don’t have the right skills or experience. This isn’t going to work for someone like me.
Mac Prichard:
So those are common objections, and fear is a natural reaction. You see that, and I’m glad you brought up the fact that many of us will change careers in our time in the workplace. In your experience, I know you come out of the world of education. That’s a profession where people do see themselves, many of them, not all, staying in the same profession for the rest of their career.
Are there other professions like that outside of education where you find that people think, I’m going to be doing this for 30, 40 years?
Carissa Kerrissey:
I think there are a lot of different professions. You know, the medical field, nursing is definitely one of them. There are a lot of similarities between folks who decide that they want to change careers with that. But really, what it comes down to is when we move into a career that we feel like is a part of our identity, and we feel really connected to the purpose of that career, like we’re doing really meaningful work.
It is extremely challenging to pause and say, “I am choosing to do something different” because we’re talking about an enormous loss in our lives. And there’s guilt that can pop up through that. There’s shame of, you know, who am I to leave? And when you feel like you’re doing really meaningful work, let’s take a teacher, for example, right? Many teachers go into the profession because they want to make a difference. They want to support students.
And so there’s a lot of guilt and shame that can come up and arise when we feel like this isn’t working for me anymore, or my values or my priorities have shifted, and it’s time for me to pursue something else. We’re really talking about an identity shift, which can be so challenging to work through.
Mac Prichard:
But let’s talk about the benefits when you do change careers. What kind of benefits do you see people enjoy both personally and professionally when they switch careers?
Carissa Kerrissey:
When you give yourself permission to switch careers and to change course, you’re actually realigning with what truly matters to you in that phase of life. And that is going to lead to greater fulfillment in your life, overall happiness. For educators, you know, improved wellbeing is usually because burnout is one of the number one reasons that educators are leaving the profession. And I believe that the pandemic cracked something open for a lot of us.
We started as… you know, folks in our careers, established in our careers, to reevaluate how we really wanted to live our lives and how we wanted our careers to align with that. And so well-being became a priority, purpose, doing meaningful work became a priority, flexibility and autonomy and freedom became a priority.
And so when we have awareness that we’re not feeling fulfilled, or we know that something needs to change within our careers, it’s really important to listen to that, or it can lead to feeling disengaged in work. It can lead to more burnout. It can lead to health problems. So, giving yourself the permission to actually change course and listen to that voice that says it’s time to do something different. It’s time for a change, which will lead to more fulfillment in life.
Mac Prichard:
At the start of our conversation, you mentioned some of the objections people might raise internally. I’m too old to do this. What are some other common objections, and are these myths, Carissa?
Carissa Kerrissey:
Yeah, yes, these are all so common and yes, they are myths. So it’s too late to start over. A lot of folks, especially educators, feel like they’re starting over and they’re starting from scratch, which means losing everything that they’ve built in their career. And that is just not true because really, at the heart of that, is we’re looking at identifying transferable skills that can be applied to most professions.
So it’s not, “I’m starting over. I’m actually starting from experience with some really valuable skills that will help me in this new career.” When we think about changing careers, and like I mentioned before, we have what is called these limiting beliefs or these, I like to call it the inner critic. Some people call it imposter syndrome. But really, these are these thoughts that pop up in order to try to keep us safe from stepping into the unknown.
These fears tell us, “Hey, this is too scary to do, you’re too old, you don’t have the skill set, this isn’t going to work for you, or maybe even it’s selfish, how could you be so selfish to think about this? What about everything you’ve built? What about your family?”
And this is an opportunity for us to actually meet this thought and make a decision on whether we’re going to believe it or not. And there are some tools that we can practice that actually help us move through that.
Mac Prichard:
Okay. And I want to get to those tools in a moment. Before we get there, Carissa, we’ve talked about what stops people from giving themselves permission to change careers. You mentioned fear, and also people who are committed want to keep doing purpose-driven work if that’s something that they’ve chosen.
And then there are these myths that, or limiting beliefs that can prevent people from moving forward. If people do decide to make the leap, what mistakes do you see them make that prevent them from switching careers?
Carissa Kerrissey:
Yeah, that’s a great question, Mac. The number one mistake that I see career changers make is not doing the internal work of finding career clarity. And what I mean by that is just applying to anything and everything, doomscrolling, which is the quickest way to burn out and can really leave you feeling hopeless in your job search, especially in this market, where it’s really tough right now for job seekers.
And so getting really clear on what are your values, what do you want, what are your skill sets, what are the unique strengths that you have, and what kind of impact do you want to continue to make in the world –– that is key to finding career clarity, and that really is a part of a successful transition.
Mac Prichard:
Okay, let’s pause there. I want to take a break and when we come back, I want to talk about how to move forward after you’ve given yourself permission to change careers. Stay with us. We’ll return in just a moment.
We’re back in the Mac’s List studio. I’m talking with Carissa Kerrissey.
She’s the founder of Future Forward Careers.
Carissa’s company helps burned-out teachers and mission-driven professionals reclaim energy, rediscover purpose, and transition into fulfilling work.
She joins us from Portland, Oregon.
Now, Carissa, before the break, we were talking about giving yourself permission to change careers, and you shared common reasons why people don’t want to change careers. You mentioned fear. You mentioned limiting beliefs. Some common myths, like I’m too old to do this or it’s too late to make a change.
Let’s talk about how you see people move forward and give themselves permission. And one of the tips I know that you share is to pay attention to what you call the inner critic or limiting beliefs.
Tell us more about that. Why is it important, and how can it lead to giving yourself permission to change careers?
Carissa Kerrissey:
It is so critical for us to bring awareness to these thoughts as they pop up when we’re going through any type of big change or making a transition, and not let them become our reality, meaning not to believe them.
And so we actually have a choice if we are bringing awareness to a thought that pops up. And it’s really important because our thoughts determine our behaviors and our beliefs, which then determine our outcomes or our results that we get. So it’s critical to have awareness on these thoughts.
And there are some hacks or techniques that we can practice in order to do that. One of them is called naming our inner critic. And really, what we’re doing with this practice is we’re creating some separation between the self, us, and this thought. So I have clients who’ve named their actual, give a name to this voice that pops up and says, you know what? I’m just gonna throw out a name, Karen.
“Not today, Karen. I hear you trying to keep me safe, and I’m choosing not to believe this thought right now because it’s not helpful.” And it seems really silly, but neuroscience tells us that it actually works because we’re creating separation between us and that thought. So when these thoughts pop up, what I like to work with my clients on is ask three questions. Ask yourself, “Is this true? And how do I know it’s true?”
Then ask yourself, “Is this thought helpful or is it actually holding me back from what I want?” And if it’s holding me back from what I want, giving ourselves permission to release that thought. And then ask, take it one step further, “What would I tell a really good friend who is going through the same thing?” And that can help shift us into what’s called our inner mentor.
And this is work that comes from Tara Mohr, where she actually has practices of name the inner critic and then move into inner mentor or inner friend. And it can be really helpful when we’re going through scary change.
Mac Prichard:
Is there a common situation that you find your clients are always applying those three questions to when they’re considering giving themselves permission to make a career change?
Carissa Kerrissey:
Yes, there are several, but I think the number one in terms of educators would be around that “I don’t have the skill set or the experience to change into a new industry.” And I really just want to tell any listeners out there that this is not true. We have all acquired a tremendous amount of experience in our careers.
We have unique skill sets, we have strengths, and we have transferable skills that can be applied to almost any career path that we choose. And so it’s so important for us to recognize this thought as it pops up and choose not to believe it because it’s not going to help us in the end.
Mac Prichard:
What examples do you share when you’re working with a client who has perhaps been a public school teacher for decades and is thinking, “I could never make this change?” What do you point to to help them understand that that thought isn’t true?
Carissa Kerrissey:
Well, one of the first things we do is we do a career skills inventory. And so we actually look at what are the skills that you have been using in your day-to-day that are transferable? And for educators, I mean, they’re a powerhouse of skills, problem solving, conflict resolution, emotional intelligence, leadership, project management. I mean, you name it, an educator does all of these skills on a day-to-day basis.
So we really ground ourselves in what’s the actual truth here? And they begin to see, especially as we’re putting it on paper, wow, I do have a lot of transferable skills that I can apply to a new career.
Mac Prichard:
Okay, so it starts with asking that question, doing the analysis. Sounds like it’s helpful to actually write it down. The second of your three questions is, “Does this idea or this thought help me grow or hold me back?” How do you walk people through that?
Again, go back to that example of a school teacher who’s been doing great work and is just ready for a change, but is thinking, even after completing that skills assessment, how do you help them understand whether that thought is helping them grow or holding them back?
Carissa Kerrissey:
Well, the first thing I would do is ask them, “What is the end result of believing this thought? Right? Where is this going to get you?” And as we reflect on that and we talk through that, it’s going to cause us to probably not take the leap or to give up in the process when it does become challenging.
And, you know, that’s where I work with clients to say, okay, let’s shift into, if I chose not to believe this, what could happen? So this is where we really want to live, and anything is possible realm. We don’t want to live in it, it’s not going to work for me. I can’t do this, right? Because then that’s going to become our reality, and that’s going to determine our results.
And so we really want to live in, it is possible, and here are all the ways it has been possible before. Something that can also be really helpful is to think about all the times that you have gone through hard times and big leaps or big transitions and made it out, and what the end result of that was.
And we all have examples of that in our lifetime, right? And this is a part of building our resiliency is reminding ourselves that we know how to do hard things. We’ve done it before in our lives, and we’ll do it again.
Mac Prichard:
When you encourage people to do that, think about past hard challenges that they’ve overcome. Are there common examples that come to mind in your work with clients that you share with them to perhaps prompt that thinking?
Carissa Kerrissey:
Thank you. Yeah. You know, this is very different depending on the human that we’re talking to, but especially if we’re talking to educators, it is hard to be a teacher. It is hard, hard work. And so we can think about times in our career where we’ve had to pivot. COVID is an example where, suddenly, teachers had to be online and learn a whole new system for educating kids. That is a very common one that we’ll talk through.
But it could be anything challenging in life we’ve gone through, a divorce, a separation, loss of a loved one, putting ourselves through school, moving across the country, losing a job, and having to quote unquote start over again, right? Like these are all examples of hardships that we go through in life as humans, and we make it through.
And so it’s really important to remind ourselves that we have the strength and the courage to do this.
Mac Prichard:
Yeah, we’ve been in hard situations before, and we’ve been successful. The three questions, “Is the thought true? Is this helping me grow or hold me back?” The third one is, “What would I say to a good friend who’s having this thought, this limiting belief?” Why does that help, Carissa, to take that perspective? What happens when you ask people to do that?
Carissa Kerrissey:
Again, this question is helping us separate ourselves from this thought. And really, that’s what this entire practice is, is creating separation between the thought and us so that it doesn’t become a belief set. And this allows us to move into a space of supporting ourselves and showing up with care, compassion, and empathy, just like we would a good friend.
And we would never tell a good friend, “No, you can’t do that. That’s not possible for you.” Right. But we’re so quick to do that to ourselves. And this allows us to move from this negativity bias that we have to possibility.
Mac Prichard:
Okay. Finally, I know that values are important in addition to mindset, in how you approach giving yourself permission to make a career change. Why is it important to pay attention to your values when you’re contemplating making a pivot?
Carissa Kerrissey:
Yeah, this is the number one thing to pay attention to upfront, first and foremost, is do the values work. Know what your compass is, know your North Star, know what direction you want to move in, because that will determine the path that you take. And, you know, when we’re talking about doing purpose-driven work and meaningful work or work that matters to us, we have to know what our values are and what our strengths are.
And one way I like to recommend doing that is to ask, do some reflecting, do some journal writing, some reflecting on looking back in times in my life, whether that’s my career or my personal life, and think about the times where I just felt so alive. I felt like I was on fire. Some people call it flow, where maybe you even just lose track of time, and you’re your best self. What was going on? What was being honored in that moment?
Take note of that. And then ask, when are some times in my career or my life where I just felt really frustrated, and things weren’t working, or I was really unhappy with what was going on? And see if you can pinpoint what was actually happening in that moment and do some deep reflection there.
Another thing that can be really helpful is to come already with a set of core values, 50 core values. And as you’re asking yourself these questions, you can reference these values, and then you start to group them.
So at first, you’re gonna have a whole lot of core values, and then you start to notice where are there similarities and where are there patterns or themes, and then you start to narrow them down. I say no more than five, because then it just becomes overwhelming.
And these are the five core values that matter most to you in this phase of life. And I do think it’s really important to acknowledge that values shift. This is why giving ourselves permission to change careers is so important, because a value I had when I was 21 is not the same as when I’m 50.
Right? Maybe. So doing this on a regular basis is really important so that we’re staying in alignment with what we truly want and what matters to us. And then this becomes our path forward.
Mac Prichard:
Terrific. It’s been a great conversation, Carissa. Now tell us what’s next for you.
Carissa Kerrissey:
I offer full transition support to any educator that is looking to change careers or any purpose-driven professional. And one of the unique things about me is that I love to offer complimentary career clarity calls so that you can just hop on a call with me, talk through any questions you might have, what support might look like for you, barriers that you’re facing, where you’re getting stuck, because we are not meant to take these huge leaps and transitions alone.
Mac Prichard:
Well, I know that our audience can learn more about you and your services by visiting your website that URL is futureforwardcareers.com.
We’ll be sure to include that in the newsletter. And you also invite our audience to connect with you on LinkedIn.
When you do reach out to Carissa, please mention you saw and heard her on Find Your Dream Job.
Now, Carissa, given all the great advice you’ve shared today, what’s the one thing you want our audience to remember about giving yourself permission to change careers?
Carissa Kerrissey:
I would like the listeners to remember that it is possible that we are going to have these limiting beliefs and these fears that pop up that tell us we can’t do it or it’s not going to work for us. And I really want us to challenge that belief and to lead with our values, to incorporate our own wellbeing in the process, build our resiliency, and know that it is possible for you.
One of the best ways to do that is gratitude. Be thankful for everything that you’re learning on this journey and keep your North Star in mind.
Mac Prichard:
Next week, our guest will be Cory Steward.
He owns and runs the top career coaching firm, Get Career Confidence.
Cory is a certified career coach and specializes in interviews and salary negotiation.
It’s never been easier to send your resume to employers.
And your competitors are doing the same thing. Many jobs now attract hundreds of applications.
Join us next Wednesday when Cory Steward and I talk about how to stand out and get hired.
Until next time, thanks for letting us help you find your dream job.
Until next time, thanks for letting us help you find your dream job.
This show is produced by Mac’s List.
Susan Thornton-Hough schedules our guests and writes our newsletter. Lisa Kislingbury Anderson manages our social media and creates our transcripts.
Our sound engineer and editor is Anna McClain. And our music is by Freddy Trujillo.
This is Mac Prichard. See you next week.
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