Overcoming Imposter Syndrome in a Tough Job Market, with Shannon Grosswiler
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Imposter syndrome can derail even the most seasoned professionals, especially in a tough job market. On this week’s episode of Find Your Dream Job, career coach Shannon Grosswiler explains why self-doubt shows up during a job search and how it affects the way people read job descriptions, talk about their accomplishments, and decide whether to apply for roles they’re fully capable of doing. Shannon shares the common patterns she sees — particularly among women — and why so many talented candidates underestimate their experience or hesitate to market themselves with confidence.
Shannon also offers practical steps to rebuild your confidence and keep moving forward, from gathering LinkedIn recommendations to revisiting the moments you’re proud of and leaning on friends who see your strengths clearly. You’ll walk away knowing how to tell your story with more ease, approach applications with a calmer mindset, and keep going even when the market feels tough. If imposter feelings have been creeping in, this episode will help you reconnect with your value and take the next steps in your search.
About Our Guest:
- Shannon Grosswiler coaches executives, entrepreneurs, and nonprofit professionals through career transitions.
Resources in This Episode:
- Connect with Shannon on LinkedIn.
Transcript
Find Your Dream Job, Episode 529:
Overcoming Imposter Syndrome in a Tough Job Market, with Shannon Grosswiler
Airdate: November 26, 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.
Confidence is vital to a successful job search, especially in this economy.
But many of us, no matter how much we accomplish, may suffer from self-doubt.
Shannon Grosswiler is here to talk about overcoming imposter syndrome in a tough job market.
She coaches executives, entrepreneurs, and nonprofit professionals through career transitions.
Shannon joins us from Portland, Oregon.
Well, let’s start with a basic Shannon. What is imposter syndrome exactly?
Shannon Grosswiler:
Well, impostor syndrome, I think most of us are very familiar with it. And in the workplace, there isn’t a lot of constant –– that relationship where people are telling you, you’re doing a great job, you are, there isn’t a lot of ego stroking.
And honestly, sometimes that turns into there isn’t recognition for the work being done. And that can build up. And also, people are hurting themselves. We’re sort of prone to being negative. We always look at what was the last mistake we made?
So that kind of permeates in the human consciousness. So what we’re doing is we’re sabotaging ourselves. And then when it comes to looking for a job, I get a lot of folks who are like, “I know that I’m acting what I’m doing, but it turns out I have no idea what I’m doing and I feel like an imposter.” And this is a common thread through all of my folks that I’ve worked with over the years.
Mac Prichard:
How does imposter syndrome happen, Shannon, especially to accomplished people?
Shannon Grosswiler:
A lot of the folks that I work with have amazing credentials, and they’ve done incredible things, but they forget, especially when it comes to being in search of a job. They’re like, I don’t know how to sell myself because I haven’t done A, B, or C.
Like, yes, you have. You weren’t part of the team that led this. You led it, or you were part of the team that made this happen for this organization.
We all feel this, and we need to remember our value, and that can be especially difficult when searching for a job.
Mac Prichard:
So I want to talk more about that, but let’s go back to patterns. We talked about how people who have a lot of accomplishments experience imposter syndrome. Do you see any other patterns in terms of gender or background?
Shannon Grosswiler:
I do actually. I think that women especially negate their worth because that is something that are, we’re again, that’s just kind of a place where we end up in our career. Basically, we have maybe a little more self-awareness than, and a little different relationship with our… I’ll just go ahead and say it with our egos.
We do. We tend to be harder on ourselves. And we’ve been taught not to brag, not to take credit when even it is our due. We’ve been taught to be a little quieter about what we’ve done and ownership. We’re not prone to ownership.
And when you’re looking for a job and when you’re marketing yourself, because that’s really what this is about, there has to be that line where you acknowledge your worth and where women can declare in a way that’s comfortable what they’ve accomplished. And that is a pattern that I’ve seen over the years.
Mac Prichard:
You started to talk about how imposter syndrome affects a job search. Say more about that, Shannon. What do you see in the clients you work with?
Shannon Grosswiler:
I see that people either are not remembering, maybe what they’ve, because I tend to work with more senior professionals, they’re not remembering what they’ve put in their resume in the past. And so when we go back and look at it, they’ll read it and they’ll be like, “Well, I didn’t actually do that. Like that was 10 people, and we did this.” And I said, “Well, you did do that. Because of where you are in your career, you led the team to doing that.”
So own that. It’s important to own that when you’re telling your story. Is there a way to say, “I was very proud of the team that I led to do A, B, and C, and was grateful that we were able to do this together,” and you own that, you led that team, or you were part of that team that made a big difference to the organization?
Mac Prichard:
Are there other common blind spots you see imposter syndrome cause when people are doing a job search?
Shannon Grosswiler:
Absolutely. The one that is universal is looking at a job description. And this does happen with my female clients a bit more. Looking at the job description and the first thing that they’re not qualified for or they don’t feel they’re qualified for, they’re like, “Oh, I’m not qualified.”
And I just have to remind them every time. It’s like, first of all, this doesn’t say this is a requirement. If it absolutely said, say for an academic job, you must have a PhD, okay, we can’t do anything about that. But often the quote unquote requirements, especially in the last few years, have been sort of the would be nice if. So that is something I have to point out that I haven’t necessarily seen with male clients, for example.
And that is a trend we’ve known for, again, like male clients are willing to go for something that maybe they’re only 70% qualified for. And yet when women see that, they just, “Nope, I can’t, that’s not me.” And I have to remind them of that. And some of them don’t know that. They read it as being gospel. I’m an imposter, so I’m certainly not gonna go for a job that I already am not qualified for.
And of course that’s ridiculous, as you and I know. You learn on the job, and it’s who you are in that role.
Mac Prichard:
Yeah, and then because of the Mac’s List job board, and I know you know this, I talked to recruiters, and they are looking for candidates who have 60 to 70% of the qualifications, not 100. So thank you for raising that with your clients.
Well, let’s talk about what difference imposter syndrome makes in a tough job market, because we’re recording this during a challenging time, and what difference do you see it make, especially when there’s more competition for jobs?
Shannon Grosswiler:
Yeah, so it’s pretty significant. What the difference is in the most basic sense is that people are not going for certain jobs that they really need to be. And they’re not reaching out to the people they need to reach out to with an assertive, “I’m here, this is what I do, this is what I can do for you.”
What’s happening is that people won’t even apply. When they see, they’re on LinkedIn, and they see that 500 other people have applied. Some have a thousand people, and they’ve stopped sort of doing that; they don’t wanna scare people from applying.
However, when we go through, if you do this, this, this, and this, you’ll easily be in the top 10%. Now, your resume will tell them that you will make sure that you have crafted who you are to fill their role and reach them at a personal level as well, so that they have distinguished themselves.
But that is what I’m finding is that people will not, especially with reaching out to people, I know it’s discouraging to reach out to cold reach outs because there isn’t a lot, sometimes there just isn’t a response. But you can’t stop when one person doesn’t reply.
You can’t stop when 10 people don’t reply. In this market, you can’t take it personally, and you have to keep going. And when you’re feeling like an imposter, it’s, quite frankly, even when you’re not, it’s incredibly, it feels demoralizing, and it’s not personal, and you have to keep at it. And one of the things, you have to get scrappy, and a lot of people don’t know what that means.
And that’s the frustrating part. There are a lot of things you can do to get scrappy. And also, you have to be willing to possibly feel like a pest.
Mac Prichard:
Okay, let’s pause there. I want to talk about how to overcome imposter syndrome, how to get scrappy, and how not to be a pest. We’re going to take a break. Stay with us.
When we return, Shannon Grosswiler will continue to share her advice on how to overcome imposter syndrome in a tough job market.
We’re back in the Mac’s List studio. I’m talking with Shannon Grosswiler.
She coaches executives, entrepreneurs, and nonprofit professionals through career transitions.
Shannon joins us from Portland, Oregon.
Now, Shannon, in the first segment, we talked about imposter syndrome, what it is, how it happens, and how it affects your job search. And let’s talk now about how to overcome it. And you shared some ideas in our first segment, but I want to dig into other suggestions I know you share regularly with your clients.
One of the first ones is you encourage people to ask for 10 LinkedIn recommendations. Now, how does that help you overcome imposter syndrome, especially in a tough job?
Shannon Grosswiler:
Well, it turns out actually the LinkedIn algorithm loves when you do that because it’s more activity in your profile. And again, that’s a new little tidbit. But what that does is you’re reaching out to people that you respect, your former bosses, your former colleagues, and your former clients, and you’re reaching out to them and officially asking them for a recommendation.
And it couldn’t be easier on LinkedIn. You go down and there’s a plus sign, and you press that plus sign, you find the person on LinkedIn, and you write a personal note, you offer to do the same for them.
You let them know that is also a chance to let them know that you’re looking and that you would love to grab coffee or you would love to have a Zoom chat. And it serves so many purposes because you’re offering them a boost, and then they’re gonna write you a great recommendation, and you’re gonna be reminded that you’re, you know, folks are gonna be reminded how great they are.
Because also if they go back and look at prior recommendations. These can be recommendations even from high school for college admissions, can be cards from friends, they can be memories of when you felt great about yourself, and when folks do get that affirmation that their value is of know, great value, whether it was a project in high school or you just earned the company with a campaign, you earned them $50 million.
I mean, these are things that you want to revisit. And those LinkedIn recommendations are gold. They’re gold for your ego, and they’re gold for what people see in the algorithm.
Mac Prichard:
What difference have you seen getting those LinkedIn recommendations, rather, making the confidence of a job seeker, especially someone dealing with imposter syndrome?
Shannon Grosswiler:
Well, is probably my favorite part of the job is probably when we go back and I do an inventory at the beginning of the session when we start talking. It’s an inventory of, I call it, “Why you rock.” And what happens is people don’t often fill it out. I’m like, no, no, no. This is the most important thing. This is going to be the base of which we move forward. So let’s start with your recommendations.
I want you to read them out loud to me. I want you to relive some of these experiences. I see some things on your resume. Tell me what that was about. Tell me what it was like. And the look in their eye when they realize, my gosh, I’ve done a lot. I’ve done a lot that made a real difference to my colleagues, to my organization, and I am still that person. No matter where they are in their career journey. I’m still that person.
Mac Prichard:
What do you do if you send out a request and you don’t hear back? What kind of follow-up do you recommend, Shannon, if you’re looking for LinkedIn recommendations?
Shannon Grosswiler:
I will say that with those, you want to give them more time, but you also, after about a week and a half, you can just send a little ping, especially, and I would recommend this, when you ask for a recommendation and it’s someone you know well, especially if you have their phone number, which a lot of times you will, just send them a text saying, I’m building up my recommendations for LinkedIn, if you wouldn’t mind, and I’d be happy to do the same in return.
I would definitely follow up right after you sent the request. And then if you haven’t heard or they said I’ll get to it, and it’s been a week and a half, then you just say, I’m just checking back in. I know people are busy. This would be great. And again, I’m happy to write one for you.
Mac Prichard:
I found a lot of people don’t check LinkedIn regularly, so I’m so glad you suggested sending a text because you’re likely to get a faster response. Well, another step you recommend for overcoming imposter syndrome is talking with friends and family. Why is this important, Shannon? And what should you talk about exactly?
Shannon Grosswiler:
I always tell my clients, you know what, if your best friend came to you and asked you what you’ve accomplished, what they’ve accomplished, how you feel about them, would you say, “Well, you know, you’ve done some things and you’re fine and you know, whatever?”
No, they would say to you, you would say to your friends, you’d be like, no, “Look at what you’ve done. Look at how much you’ve changed over the years, you’ve matured over the years. This leadership opportunity, how you’ve used your smarts and your gumption, for lack of a better word, to get farther, and how great the successes that you’ve had.”
You’ve been tossed around, we all have. And that’s something to remember, is that in this process, it’s not unusual, especially now, for people to be laid off. And that can really make you feel lousy. So, asking friends and family, saying, “I’m feeling pretty low and pretty like I’ve never done anything worth, I don’t know how to talk about myself, I feel very lost.”
And you can ask them for not only emotional support, but to talk through, like, can I talk through my resume and like have you witness that and give me some strokes for what I’ve done and tell me what you value, not only in our friendship, but also in how I move through the world. I could just use a confidence boost.
And people that love you are gonna do that. They’d be happy to do that. So you just have to always find the people you trust the most. A best friend is a great option. Former colleagues that you became friends with, that’s a great option.
Mac Prichard:
What’s the best way to approach people, especially some people might feel discouraged or embarrassed to ask for that kind of conversation. What have you seen work well for people reaching out to friends and family to talk about these topics?
Shannon Grosswiler:
Absolute transparency and vulnerability. It’s a great practice, and it is something that you want to start with a person that you absolutely trust, that you can be your most vulnerable with. And then it does get easier from there. But I think that we’re all in such a strange place and asking for help is such a powerful choice to make.
And the deepening of your relationship when you’re vulnerable and you say, I need this help. You start with people you trust.
Mac Prichard:
Another step you recommend for overcoming imposter syndrome, especially in a tough job market, is to look at your resume as if it belonged to somebody else. How does this shift in perspective help you with imposter syndrome?
Shannon Grosswiler:
Well, we’ve all been marketed to our whole lives. We’ve all been marketed to. And when you take yourself out of the equation, you start to see, okay, well, if I’m looking at this person and this resume, wow, they’ve done some pretty good things.
They’ve worked at this company. They’ve, they’ve turned this project around. Look at all the things that they’ve done. If it’s yourself, if you’re looking at it and it’s your own resume, the first thing you do is, well, that’s an overstatement. I didn’t do that. I didn’t, well, but that really didn’t go well. No.
If you’re looking at that resume, then if you take your ego out of it, you actually see that this person has accomplished quite a bit. And we go over it line by line. And I remind them, like, okay, so you did this. No, no, I didn’t. Yes, you did. Yes, you did.
Mac Prichard:
So you do that review, you see those accomplishments from a fresh perspective. What difference have you seen those insights make in overcoming imposter syndrome during a job search?
Shannon Grosswiler:
Yeah, it’s been fantastic because what we’re able to do is tell stories based in confidence. So we’ve got, you know, this is what you did, and I want you to be able to tell that story in answer to an interview question. And I want you to be able to own what you did there.
And we’re gonna practice that story, and we’re gonna practice, you know, five or six stories where you are telling the story from a place of authenticity and ownership. And that’s how you move through that so that you embody that confidence so that you can then tell that story and feel it and own that so that it is your story. It becomes your story and becomes the mindset.
Mac Prichard:
It’s been a great conversation, Shannon. Tell us what’s next for you.
Shannon Grosswiler:
I’m having a busy time. Marketing communications is normally, it’s what my field was. And so I moved into coaching other marketing communications professionals around the country.
And people are looking for how to get out of what is a bit of a sticky situation with our economy right now. It’s just very uncertain. And so we coach and get very scrappy. So A to Z, we do the resume all the way to how are you gonna get that hiring manager to pay attention in a way that doesn’t drive them crazy.
And that’s a subtle but important, and then we do, we get scrappy. And I really, I wanna be a cheerleader, but I also wanna direct people to get that job. So there’s a lot of creativity in that.
Mac Prichard:
Terrific. Well, I know that our audience can connect with you on LinkedIn. And when you do reach out, I hope you’ll mention that you saw her on Find Your Dream Job. Shannon, given all the great advice you’ve shared today, what’s the one thing you want our audience to remember about how to overcome imposter syndrome in a tough job market?
Shannon Grosswiler:
I want your audience to remember that they have done great things. They will do great things again. They just need to be reminded and stick with the script of, “I rock,” which is, it can be hard, but it’s important. And that’s the most important thing. Just remember how great you are and figure out how to convey that. And you’ll get there.
Mac Prichard:
Next week, our guest will be Ariane Hunter.
She’s a speaker, an author, and the founder and owner of Ariane Hunter Consulting.
Ariane’s company helps Black women in business to thrive.
You’re ready to change careers.
But you can’t seem to break into your new field.
Join us next Wednesday when Ariane Hunter and I talk about the art of the career pivot.
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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