Why You Should Never Stop Planning Your Career, with Anne Lapour

Most people plan their careers only a few times in life: when graduating college, during a career change, or due to a move. But according to Find Your Dream Job guest Anne Lapour, you should continue to plan your career on a regular basis. Anne says our personal life changes affect our careers, so as we evolve in life, we evolve in our work, as well. Self-reflection can give you clarity on what matters to you, and research will allow you to develop new skills that you can use to plan your next step. Networking is also a crucial piece and can lead to opportunities you might not have known about otherwise. 

About Our Guest:

Anne Lapour is the executive director of career initiatives for Willamette University, where she oversees career programming, education, and advising.

Resources in This Episode:

• Connect with Anne on LinkedIn.
• Use promo code DREAMJOB at the link below to get an exclusive 60% off an annual plan at incogni.com/dreamjob.

Transcript

Find Your Dream Job, Episode 507:

Why You Should Never Stop Planning Your Career, with Anne Lapour

Airdate: June 25, 2025

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.

You may change jobs five to seven times in your career.

And when you look for your next position, you need to have clear goals and know what you offer employers.

Anne Lapour is here to talk about why you should never stop planning your career.

She’s the executive director of career initiatives for Willamette University, where she oversees career programming, education, and advising.

Anne joins us from Salem, Oregon.

Well, let’s get going, Anne. Why is career planning something you should do throughout your working life rather than just when you’re looking for a job?

Anne Lapour:

Yeah, I think a lot of it comes down to the fact that our personal lives and our professional lives are very much intertwined. And so, in the same way that you as a person evolve, your career should evolve, too, so that you don’t stop learning. You don’t stop changing.

But if you reach a point in your career where it’s not evolving along with you, then it can feel, it can feel tough to stay motivated or to feel like you’re, you’re growing and changing in your career, along with your own self.

Mac Prichard:

And how does making career planning an ongoing habit help you in the long run? What difference does it make?

Anne Lapour:

Well, I think there’s a few things. I think that it is, it obviously contributes to your overall sense of happiness, your overall sense of purpose.

We all like to feel that the work that we’re doing is, is meaningful, both to ourselves and maybe to the people that we work with. Job satisfaction, job growth, advancement, these are all things that most people want anytime they make a career transition or maybe re-enter the job market after having taken some time away from it.

And allowing yourself to kind of re-examine your priorities, re-examine who you are as a person, is gonna help you feel more settled and more productive and just enjoy getting up and going to work a little bit more.

Mac Prichard:

Some people hear “career planning” and they think, well, that’s something that students or perhaps recent graduates do.

Why is it important to do not only mid-career but later in your career as well?

Anne Lapour:

Yeah, so one of the things that I really enjoy doing in my work is not only talking with college students, which I do a lot, but also talking to alumni, who are re-entering a job search.

And a lot of things for them have potentially changed. Some of that’s logistics, just, you know, maybe they’re moving. Maybe they’ve started a family. Or maybe they’re moving somewhere with a partner.

So sometimes it’s logistical changes that they just need to account for. But sometimes there’s just, somebody’s just ready for a change. And I think when you ignore that, it can become easy to feel a little stagnant or a little just demotivated in the work you’re doing every day.

So we all change throughout our lives. I find career to be a cyclical process where you learn about yourself, you learn about what’s other there, and then you make a decision about what you want to pursue. And there’s no time frame for that.

So it’s not just this thing that you do when you’re 18 or 22. It’s a constant, you know, replicating process that happens over and over again. And it keeps life exciting and challenging, and meaningful.

Mac Prichard:

What are some other misconceptions about career planning, besides that it’s something only students or recent graduates might do?

Anne Lapour:

I think one thing that people do a lot is focus on only one part of themselves when they’re doing career planning. They might focus only on what are they interested in or what are they good at. And while those are both really important things to think about, cause we want to feel competent in our work and we want to feel interested in our work, there’s other things that are important.

There’s your value system. And that can apply to both sort of the values of your own life but also the values that you hold in your work life. So, what do you want your organization to value? What type of work feels most meaningful to you? So it’s important to look at those things.

It’s also important to look at your personality and where do you thrive best. So I often encourage folks at all stages of career development to pay attention to not just, oh, I’m interested in this one thing, but to know and to understand that it’s okay to be A- interested in multiple things, to find multiple ways of fulfilling your interests. But also to factor in those other pieces of yourself that are gonna help you feel most at ease and congruent in the work that you’re doing.

Mac Prichard:

And I want to talk more about how to do career planning in a moment, Anne.

But before we get there, what stops people from doing this?

Anne Lapour:

Oh, I think that, you know, it’s, it’s nerve-wracking, right? Anytime you have to make a change. Change can be a scary thing. There’s sort of the thing that you know.

So if you’ve been in a job for a while, even if it doesn’t necessarily feel like the perfect fit anymore, and maybe it was when you started. Maybe it was a great fit early on, and so you feel like it should always be that way. And it can feel a little scary to try something new or unknown.

So I think that’s a factor. And I think also sometimes it feels scary to walk away from a job that’s providing you a living. That can be unsettling to walk away from.

At the same time, though, there are a lot of ways to ensure that, or to at least increase the probability of finding something that’s as fulfilling or more fulfilling than what you’re currently doing.

Mac Prichard:

You talk to so many candidates who are chasing jobs out there.

What difference do you see, Anne, in the people who’ve invested the time and effort in career planning versus those applicants who haven’t done this work?

Anne Lapour:

Yeah, it’s, it is really that self-knowledge piece comes across so clearly from the second I look at a cover letter, quite frankly, to the in-person interview. I think somebody who has really taken the time to understand not just the role that they’re applying for, cause you can really understand what’s involved in a job, but if you don’t necessarily understand yourself, or what you’re looking for, or what your priorities are, then it’s difficult to articulate to the hiring manager or the employer how you are a fit.

And that’s really what people want to know. They want to know what is it that you’re going to bring to this role, why is it a fit for you, and why are you are the person that’s going to really take this role and run with it? And in order to be able to say those things and to articulate those things in a compelling way, that self-knowledge piece is really critical.

Mac Prichard:

Well, let’s talk more about that, because coincidentally, that’s the first step you recommend people take, is to know yourself when doing career planning.

And you talked about why this is important. How do you do this exactly, this kind of self-reflection?

Anne Lapour:

Yeah, it’s, I think it differs a little bit for the person. And again, this is related to your own personality, the way that you make decisions.

But I think there’s a couple of things that I encourage people to do, and this is something I encourage, again, not just for college students but people at all stages of their career. Which is to, this is gonna sound kind of simple and maybe even a little silly, but to pay attention.

When you’ve had a great day at work, why? Write it down. Keep a document. Keep a Google doc, keep an old-school journal, whatever works for you. But what was it that energized you that day at work? Was it the people you were around? Was it a specific project, a specific task?

We all have great days at work, and we all have tough days at work. Sometimes those are things that are outside of our control. But sometimes we can look to replicate those. So that’s one thing that I recommend doing.

The other thing I recommend doing is any type of, sort of, hypothesis testing. Or just being able to dip your toes into something new can be really important.

Let’s say you’ve never really done presentations or speaking, but you have a hunch that that’s something you might enjoy. You know, asking your supervisor for an opportunity to do those things. To engage in a project that you suspect might be a little bit more engaging or exciting to you.

But just finding little ways to do that. Even volunteering outside of your work can be a great way to sort of hypothesis test and get to know yourself and see if there’s something else out there that’s a better fit.

Mac Prichard:

I want to talk more about this, but we’re gonna take a break.

Stay with us. When we return, Anne Lapour will continue to share her advice on why you should never stop planning your career.

We’re back in the Mac’s List studio. I’m talking with Anne Lapour.

She’s the executive director of career initiatives for Willamette University, where she oversees career programming, education, and advising.

Anne joins us from Salem, Oregon.

Now, Anne, before the break, we were talking about why you should never stop planning your career.

And in the first segment, we talked about the benefits of career planning, who should be doing it, and how to get started.

And the first step you recommended was self-knowledge, and you talked about why that’s important and the benefits of that, particularly to job seekers. And how you might get started.

And you encouraged listeners to reflect back on things that you enjoy doing, as well as trying on new things.

What about things that might make you uncomfortable? How important is it to try things like that as you think about your career planning?

Anne Lapour:

Yeah, that’s a great question. I mean, I do think that not everything is gonna feel easy at first. So giving yourself the space to not be perfect at things the first time around is really important.

I think looking at new projects, new tasks, and deciding whether this is something that you want to get better at, or does it just feel like a mismatch from the get-go. And looking for patterns amongst the new things that you try. What are the things that, usually, there’s some glimmer, some little hint, that this is something that was exciting?

Even if it was hard, and also if there’s a particular industry, or role that most of it is something that you’re really interested in or you really wanna do, but there’s this one little skill that you really need to get better at, you can always tackle that skill. Maybe if it’s only 20% of that job, or 10% of that job, maybe it’s worth it to build some new skills in a different area. Which is just gonna make you more marketable.

Mac Prichard:

And how do you recommend applying this self-knowledge? When you make these lists, you have these experiences, you try new or different things.

How do you apply that both to your career planning and if you’re doing a job search?

Anne Lapour:

Yeah, I think it’s really, you know, if you have a list of things that are really important to you in a job, so whether it’s the working conditions, whether it’s the projects that you’re involved in, or the tasks and skills that you’re being asked to use.

And those are things that you can do a lot of online research about. It’s also helpful to talk to other people, which I know we’ll get to here in a bit.

But to start examining job descriptions. Even before you’re ready to start actually applying. You know, really take a highlighter to that job description, and how much of that job is something that you’re excited about, what is looking, what makes your, you know, yourself light up? What makes your stomach sink?

What is it when you read that job description and start imagining yourself in that role, what do you feel and what do you, and what makes you eager or not eager to approach that role?

Mac Prichard:

Some of us can research a subject to death. How long do you recommend you do this self-reflection and these new experiences to get the self-knowledge you need that you can apply both to your career and your job search?

Anne Lapour:

Well, it’s sort of like not too long and also forever.

So, essentially, you want to dive in at some point. I always say that sometimes applying for a job is the best way to know whether or not you actually want that job. Hopefully, you have a little bit more of that self-knowledge and that self-insight, but sometimes even sitting down and crafting a cover letter helps you understand whether or not you really want it.

But also, you want to continue to do this throughout your life. So even as you’re applying for things, even as you’re interviewing, it’s helpful to pay attention. You are interviewing that organization, that place, that job, as much as they’re interviewing you, too.

Mac Prichard:

Well, let’s talk about your other two steps.

The second one is: connect with others so you can learn about the career that interests you, and that you may want. And you talked about this a moment ago.

Why is it important to do this, and how do you do it well, Anne?

Anne Lapour:

Yeah, so I think that probably talking to people about their work is one of the best ways to really start examining the reality of a job.

So again, you know, you can research jobs and you can read job descriptions online all day long. But there’s something about talking to somebody who’s doing that job and letting them share with you how they got there, what they like about it, maybe what’s challenging for them about that. That can be really helpful and help create insight for you into whether or not you’d wanna do that.

Maybe they tell you all about a day at work that’s great for them, and internally you’re thinking, ooh, I don’t know about that, and vice versa. And that, that’s a pretty low-stakes way of both learning the ins and outs of an organization or a job or a career, and also, in the meantime, you’re essentially networking.

You’re creating a relationship, you’re building potential mentorship relationships, and you’re building your network at the same time that you’re engaging in this meaningful career research.

Mac Prichard:

How do you find these people, and what’s the best way to approach them?

Anne Lapour:

Yeah, I mean, we always encourage folks that are alums of our university to look at their alumni network. That’s helpful for a lot of people. At the very least, hopping on LinkedIn, reaching out to people in a courteous and succinct way.

I think people underestimate the extent to which, if somebody likes their job, they enjoy talking about their job. And so, as long as you are, you know, being curious, not asking somebody for an opportunity. Not asking somebody for a job. Simply asking them for their expertise and their guidance, most people are really happy to do that.

So an email, a LinkedIn connection, an alumni referral, or even a referral from your own personal life is a great way to start.

Mac Prichard:

How do you apply what you learn both to your career planning and your job search, if you’re in the middle of looking for work?

Anne Lapour:

Yeah, so I mean, I think taking notes. I think following up. I think asking for the next person to talk to. Always, you know, when you’re connecting with somebody, always ask, is there somebody else that you would suggest that I talk to? It becomes sort of a snowball, and you can continue to learn and continue to connect with people.

And then oftentimes having your resume ready to go, your application materials ready to go, so if something does start to crystallize and an opportunity falls in your lap, not be afraid to go ahead and follow it. Sometimes those chance encounters, those chance events, those chance meetings, or the more intentional ones, can lead you somewhere that is a surprise. And it’s helpful to follow up on it and see where it takes you.

Mac Prichard:

So step one is: self-knowledge.

Step two is: connect with others.

And your third step in career planning is to take that self-knowledge and pair it with what you’ve learned from your conversations, and move into your desired industry.

What’s the best way to take that third step, Anne?

Anne Lapour:

Yeah, I mean, I think beginning the process of making some change to your work situation. So that could be applying for a new job. That could be moving to a different organization. Maybe what you uncover is that your job is great, but maybe you’re interested in a slightly different organization, for whatever reason.

Sometimes it’s fully moving industries, sometimes it’s just looking for opportunities for promotion or advancement, or new projects at where you work currently.

So you don’t necessarily have to leave your current place or your current job in order to find something that’s going to be a bit more fulfilling to you if you feel like you’re a bit stuck. So there’s a lot of different solutions, and honestly, listening to other people share how they’ve navigated those changes in their professional lives can be great fodder for ideas and next steps.

Mac Prichard:

Give us some ideas about what those next steps might be.

Anne Lapour:

Yeah, so it might be simply talking with a supervisor, asking for a new challenge, asking for an opportunity to try a different task. Maybe lead a team, supervise another person, take on a project that would allow you to build some new skills that you suspect might be rewarding to you. So it could just be all of that.

It could be starting to research the job market and analyzing those job descriptions, using the relationships you’ve built as you’ve done all of that networking to ask about, you know, do they know of somebody you might wanna talk to, that could be hiring or looking for somebody.

Could also be volunteering your time somewhere. I think that that’s a really great way to sort of reality test whether or not something that’s new is a good fit for you.

Mac Prichard:

Some people who are unhappy with their careers or the current job they have, their first step is to sit down and look at job boards like Mac’s List or LinkedIn, or Indeed.

You’ve outlined a very different process here. Tell us more about what you see happen to the people who follow the steps that you’ve outlined versus someone who looks at job boards every day.

Anne Lapour:

I think it’s more intentional, and it is more likely to result in something that is a fit. Job boards, even ones that are slightly more niche or more focused, maybe geographically, there’s still a lot out there. And they only tell one side of the story.

And so, I think that if you’re going into those without having some idea of what you’re looking for, they can just feel overwhelming. But if you approach those job boards with a little bit more intentionality, then they’re going to, things will jump out at you.

And instead of being in a sea of job postings, they will be opportunities to follow up on and to explore, and that will match up on some level with some of the things that you’ve set out for yourself as being priorities. There may not be a perfect fit, that’s okay.

But our career lives and our personal lives have areas of overlap and they also have areas of distinction, and you’re looking for some places where you feel like you can be your authentic self when you show up to your job.

Mac Prichard:

Well, it’s been a terrific conversation, Anne. Now tell us, what’s next for you?

Anne Lapour:

Yeah, I’m gonna keep doing what I’m doing here at Willamette University. I love what I do. I love leading our different teams. I think one thing that’s been really exciting to see shift and change at Willamette is the different disciplines and the different schools that we have a part of our community.

So I get to work with students and alums who are part of our undergraduate Willamette College, who are part of our graduate programs, and Data Science and Computer Science and Business Administration, and Management. And also Fine Arts, and some of the work that they’re doing up at the Pacific Northwest College of Arts.

So I get to explore lots of different areas, which, for somebody like me who loves to learn all the time and basically never wants to stop learning, it’s been a really fascinating interdisciplinary time to be a part of this University.

Mac Prichard:

Terrific. And I also know, Anne, that you invite listeners to connect with you on LinkedIn. When you do reach out to Anne on LinkedIn, I hope you’ll mention you heard her on Find Your Dream Job.

Now, Anne, given all the great advice you’ve shared today, what’s the ONE thing you want a listener to remember about why you should never stop planning your career?

Anne Lapour:

I think I would just say that you are an evolving person, and you should let your career evolve along with you. Let those two things happen in tandem.

Mac Prichard:

Next week, our guest will be Shannon Aniciete.

She’s the director of business career services for the School of Business at Portland State University. Her team helps students achieve meaningful career outcomes.

Ask Google for a list of the most stressful events in life, and job loss always pops up near the top.

Even if you didn’t lose your job, doing a job search can take a toll on your health.

Join us next Wednesday when Shannon Aniciete and I talk about five wellness tips for your job search.

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.

Our sound engineer and editor is Matt Fiorillo. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week.