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Stop Waiting to Be Picked: The 3 Questions That Can Transform Your Job Search, with Jamila Brown

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On this bonus episode of Find Your Dream Job, Mac joins Jamila Brown on the 5 Minute Career Hack Podcast to share the three questions every job seeker needs to answer: What do you want? Where do you want to go? What do you offer? Mac talks about why job searching is a skill you build through study and practice, and why doing your homework through networking and informational interviews before you apply gives you an edge over the competition.

He and Jamila also dig into how to turn your objections into questions for people who’ve done what you want to do, and why saying your goal out loud, specifically and often, makes it so much easier for people to help you. Listen in for Mac’s closing advice: don’t wait to be picked.

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Transcript

Find Your Dream Job, Bonus Episode 95: 

5 Minute Career Hack, with Jamila Brown

Airdate: September 8, 2026

Mac Prichard:

This is Mac Prichard, founder of Mac’s List.

As a listener to Find Your Dream Job, I know you’re interested in learning how to find work and improve your career.

I’m often asked by other podcasts to share insights from my work with the job seekers and employers who use Mac’s List.

So every other week we’re publishing one of these conversations.

Here’s one of my guest interviews that I think you’ll enjoy.

Employers hire problem solvers. They want people who are gonna help them solve the problems that are keeping them up at night. And the more you know about those challenges before you apply for a position, before you walk into the interview room, the more successful you’re gonna be compared with your competitors.

Maybe I’m living in the wrong place; I don’t have the right college degrees. Turn those objections into questions and find people who have done what you want to do.

We have a goal that we may think it’s unachievable. I could never do that because I’m too old, or I’m not living in the right place, or I don’t have the right credentials. But you don’t know that. And so often I’ve found that people, whatever the reason, are reluctant to share that goal.

And if you say it out loud and you’re specific, a couple things happen. One is you get clear about what you want. But you’re also, by saying it out loud, being clear about your goal and telling others, you’re making it so much easier for people to help you.

Jamila Brown:

Welcome back to the 5 Minute Career Hack Podcast. I’m your host, Jamila Brown, and I’ve got an incredible guest, someone I also like to call a mentor who has been instrumental in helping us grow here at the 5 Minute Career Hack Podcast, Mac Prichard.

I’m not gonna go into an in-depth introduction of Mac, but just know he’s got the Find Your Dream Job podcast, an incredible website where he helps individuals actually do that as well. And he’s recently been on CNBC Make It as well.

So welcome to the podcast, Mac. How are you doing today?

Mac Prichard:

I’m doing well. Thank you for having me on the show. And I wanna say I learned from you too before you hit record. We were talking about my show’s transition to video. Footsteps, thank you for the excellent tips.

Jamila Brown:

Thank you too, Mac. It’s been a joy and a pleasure to not only be on your podcast, consume your podcast, but also learn from you behind the scenes. And with that being said, let’s get into it. I like to consider you one of the gurus in the space, and you’ve had a multitude of career coaches on your podcast.

And I’d love to hear from you: what are some fundamental building blocks of a successful career transition, especially when someone feels stuck in their career?

Mac Prichard:

Well, it’s been a gift to interview more than 500 career experts. Our show celebrates its tenth anniversary. And it took me a while to learn this lesson, but one of the most important things I do is I don’t try to figure out what the topic for the interviews might be.

I ask the guests themselves. And when people talk about something they’re excited about, you not only have a great conversation, you’re likely to learn about unexpected things.

But I will say when I reflect back on those conversations, the one thing that stands out is that the fundamentals really matter when you’re making a career transition or doing a job search. And when I talk about fundamentals, what I hear from the guests on our show is you gotta know the job you want. You have to know the employers that interest you. You need a target list, maybe 10, 15, 25.

But you really need to focus. And the third thing you need to know is what you offer. What are the skills and experiences that you provide that are invaluable to employers?

If you pay attention to those three fundamentals –– what you want, where you want to go, what you offer –– you’re not only going to have an easier and shorter job search in the long run, you’re much more likely to have an enjoyable and satisfying career.

Jamila Brown:

Yeah, I think sometimes we overcomplicate things as human beings trying to reinvent the wheel. And you know, there’s nothing new under the sun, Mac, and I think you nailed it with those three tips.

And in sports we say, you know, you gotta do the blocking and tackling in football, and in basketball, you gotta rebound, and you gotta put the ball through the hoop. It’s pretty simple in order to win.

Mac Prichard:

It is. And I have struggled with answering those questions earlier and even mid-career. So I know it’s hard work. The answers don’t come easy sometimes.

But if you find yourself sitting down at the start of a job search at the computer and that’s all you’re doing is looking at positions that you could do or you might do or that sound interesting, you’re you’re making your job much harder than it has to be.

And you really need to step away from that computer. And before you send out your first application, have the answers to those three fundamental questions.

Jamila Brown:

Yeah, and one of my keys to life and one principle that I live by is doing my best to collapse time frames.

And that’s what you just described by s basically stopping the actual job search process, stepping back, answering those questions, and getting that targeted list and understanding how to present the value that you provide through your resume, career story, and being ready for the interview, you’re actually taking time that is going to collapse the time frame in the job search.

And I think that’s so key.

Mac Prichard:

It’s such an important point you’re making. And the reason why it matters is that when you do apply for a position, if it’s something you’re not c certain about, if you don’t know a lot about the employer or anything at all, you are competing against somebody who does.

They have decided that’s the position they want and that’s the place they want to be. And you may get an interview because perhaps your credentials are exceptional and/or maybe there’s not a lot of competition for the position, but when you walk into that interview room, you’ll be one of, say, five, perhaps seven people.

Two or three of those people know they want to be there and they know what they offer and what and why that job is a perfect fit. If you’re uncertain, that uncertainty is going to shine through. So the other thing that’s happening is employers manage for risk when they hire. We’ve all had hires that have gone bad.

But we’ve had colleagues who’ve come in; they didn’t work out. It’s not good for the candidate who got the position, it’s not good for their peers at that place, and it’s not good for the organization.

And so to avoid those kinds of problems, employers look for people who are clear about what they want and what they offer, and they’re going to try to reduce the risk as much as possible when making hiring decisions.

Jamila Brown:

Right. So in essence, on the other side of the table, they’re gonna do their homework inside that interview process as well as that background research to understand how they avoid that risk in the future.

So they’re gonna take a little time on the front end that you should take on the front end as well to then ultimately get a perfect match or as close to a perfect match as possible. And I think you bring up an excellent point.

And that’s probably a mistake that a lot of people are making out there, thinking that the time needs to be spent during that interview process and there’s some preparation that needs to happen before that.

Mac Prichard:

Yes, don’t use the interview process as a research project to find out if that’s the job you want or that’s the place you want to be.

Sure, you might have some detailed questions, but instead, before you apply, if you’re interested in two or three positions or you have a list of employers that interest you, through networking meetings and informational interviews, you can have those conversations and find out if that’s the job you want and if those are the employers you want to be at.

And when you do that informally before you apply, you’re not only gonna be a better candidate because you’ve done your homework, you’re also gonna have insights into what matters to that employer and what kinds of challenges they have. And that’s gonna give you a leg up on your competitors because in the end, employers hire problem solvers.

They want people who are going to help them solve the problems that are keeping them up at night. And the more you know about those challenges before you apply for a position, before you walk into the interview room, the more successful you’re gonna be compared with your competitors.

Jamila Brown:

So I think that’s incredible. You answered my second question for you, which is what are the biggest mistakes high performers can make during this process, trying to interview and find that dream job that they’re looking for?

So what’s maybe one tactic on the front side or even during the interview process that they can help them avoid that mistake, that same mistake?

Mac Prichard:

Well, I think if not paying attention to the fundamentals is a mistake, another one that I see high-performing individuals make is not investing in job search skills. And learning how to look for work is a skill, and like any skill, you can learn how to do it well through study and practice.

Too many people, I think, because job search can be an infrequent event, think that, well, what you need to do is send out applications online or maybe just put the word out there. And candidly, sometimes I think everybody who’s listening to this interview can reflect on the time when that worked.

And the reason it worked is that referrals matter so much when we look for work. And sometimes, just through chance, we can generate referrals by telling someone we’re looking for work and let me know if you hear of anything.

But you can’t rely on chance. You’ve got to learn how to look for work in a thoughtful, systematic way. And so the people I see who spend the time to learn those skills are again having easier searches and more rewarding careers.

Jamila Brown:

Right. So, in fact, what you’re saying is that actually looking for a role, preparation and looking for a role is a skill set because it’s not something that you do every day, every week. Right. So sometimes you gotta dust off, like dust off the rust, if you will, if you haven’t done it in years.

Mac Prichard:

You do, and you also have to learn the skills in the first place. And so it’s easy; it doesn’t take a lot of skill, and I said this respectfully, to send out an online job application.

It does take some skill and practice to figure out what the job is you want, who the employers where you want to work, and then it takes skill and practice to learn how to network well, how to do informational interviews, how to ask people for help when you’re looking for work, how to to follow up, how to send thank you notes, how to how to negotiate a job offer, how to prepare for interviews and and practice questions.

These are all things that anyone who’s successful in the workplace has learned, and this is another set that you need to get good at, and you can do it with study and practice, but you do have to put in the time.

Jamila Brown:

Right. So what do you think is the best approach? Obviously, I’m a career coach. I help people with career strategy, and I know you’ve worked with so many people, right? And you’ve interviewed a lot of career coaches.

What do you think’s the best approach for someone who’s been out of the job market, you know, for ten years, let’s say, and now they’re having to look for something? They’re having to look for a job, or they’re looking to transition.

Do you recommend that they get a career coach to collapse time frames, or do you think it’s something they can invest in personally and do successfully in the time that they want?

Mac Prichard:

Yeah, I think you wanna start with the things that you’re not sure how to do or that make you uncomfortable, and think about those areas and think about how in the past you’ve learned how to learn new skills. And maybe you’re a person who likes to l read books or listen to podcasts or work with a coach.

Whatever works best for you, the most important thing, and you’re a coach, is to get started. And I think it’s okay to acknowledge that you don’t know everything, that you need help, and to recognize how you like to learn and play to that and tap into that preference.

So I think, you know, start with what you’re struggling with. Maybe you don’t know how to

run an informational interview. Maybe you don’t know how to tell people that you’re looking for work. Maybe you’re uncertain about how to interview.

You can find books and online resources that will help you. You can also talk to a coach. If you’ve gone to a community college or a university and have a degree, there’s always a career services center, and often you can get free services as a grad.

Every state has an employment department, which has offices with job search counselors who can help you and provide advice. But you gotta be specific about what your needs are.

Jamila Brown:

Yeah, that’s good. And I think especially the tip about those who have degrees or gone to college and are tapping into those resources. I think sometimes we get our diploma and forget that as an alum we have access to resources continually as a part of our time there. So I’m happy you mentioned that point.

And for the college students listening, be sure to tap into those resources. I do think there’s a way to do it. And my suggestion is once you start it.

Right, because that’s important. Get started. Find out where you’re uncomfortable, like you said. And then if you find pain points or ones that you don’t want to hurdle on your own, or it’s taking too long, reach out to a coach, right? Reach out to a coach at that point. So I think that’s incredible advice.

So I’d love to talk a little bit so the audience can understand a little bit about everything that you’re doing at the Find Your Dream Job podcast. How’s your experience been building such a successful podcast over the last decade?

And what are some things that you can share with the audience through that experience, as well as helping individuals in their career?

Mac Prichard:

I think you touched on a key point there, which is we’ve been doing it for almost ten years. So it’s taken me perhaps longer than most people to learn how to run the show well. But I think one of the most important lessons is one you touched on a moment ago, which is get started.

I thought about starting a show for about a year before I actually did it. And what got us on the air was I finally picked a launch date, rec set up interview dates, and it was going to happen on a Monday. I had a list of equipment that someone had given me that I needed to buy, and it’s embarrassing to admit this, but I think my interviews were gonna be at 10 a.m. on Monday.

And I drove out to Guitar City on Sunday night at 6 to buy this stuff. I just kept putting it off.

But once you get going and just do it as with any project. It was a lot of fun. I learned a lot. And I think one of the principles that I’ve learned is applicable to anyone. You don’t have to have a podcast to do this. If you’re interested in a topic, find people who are knowledgeable about it, and you will learn so much by being curious.

Jamila Brown:

Yeah, and that’s the one thing that I’ve gotten from Mac every time I’ve interacted with him, at least five or six times at this point. And then of course we stay connected virtually as well. But every time, as much as I try to ask Mac as many questions as possible from behind the scenes, Mac is coming back with twice as many. He’s extremely curious.

And to your point, that’s helped your growth and development, your podcast, your successful business in the Pacific Northwest.

And all the work that you’ve done across the nation and the world and the people that you’ve helped started with a question, right? I know Simon Sinek always says start with why. And you’ve mastered it, right? You’ve mastered it. So kudos to you and your team that do a phenomenal job.

Susan as well. Your entire team does a phenomenal job around you. So with that being said, one other question I’d like to ask you is for someone in the audience that might feel overwhelmed.

Right, and we’ve really nailed home the point that you have to start. You have to start, like you said, with your podcast. If you’re curious about a topic, curious about an industry, curious about a job, you have to start.

But what if someone’s feeling overwhelmed? What’s one action step that you believe they could take today that could accelerate their job search?

Mac Prichard:

Tell people what you want. Many of us struggle with this because we have a goal, and we may think it’s unachievable. I could never do that because I’m too old or I’m not living in the right place or I don’t have the right credentials. But you don’t know that. And so often I’ve found that people are, whatever the reason is, reluctant to share that goal.

And if you say it out loud and you’re specific, a couple of things happen. One is it helps you get clear about what you want, but you’re also, by saying it out loud, being clear about your goal and telling others, you’re making it so much easier for people to help you. So if you tell someone, I’m doing a job search, and let me know if you hear of anything, well, there’s nothing wrong with that, but that’s very general.

But if you say, I’m looking for a marketing position with an agency that works in sportswear. Let me know if you do. Do you happen to know of anybody who works at an agency like that? Or have you had any experience? You may hear no, but that’s a very specific question. And it’s clear what you want and where you want to go. And people you tell that to will remember that, even if they don’t have a suggestion for you.

And if you say that, if you if you’re saying out loud what you want and where you want to go often enough, eventually you will start to make connections and you will also gain in confidence because you, you know, you you’re good at what you do and and by sharing your goal and hearing people nod and say, Yeah, that sounds great, or have you thought about this or that? That’s affirming, and that reinforces what you want to do and where you wanna go.

So say it out loud; that would be my main suggestion.

Jamila Brown:

I love that, especially the confidence piece around it. So consistently saying it, right? Because this could have been swirling around in your subconscious mind forever. And now speaking it out loud, number one, you’re telling the other person, but it’s also going back into your subconscious mind.

And once you say it out loud, it’s going to drive you towards it, and it’s gonna open up doors. And to your point, even if that person, the first person, second, third, fourth, fifth, doesn’t know anyone or doesn’t know of a situation that matches what you asked for.

They’re gonna remember it. And so as they’re going through their life and hearing conversations, someone else may say something that brings you back to their mind, and they connect you today, tomorrow, a year, two years from now.

I’ve had that happen for so many of my clients. One in particular, it wasn’t the right fit because they were looking for something specific and a specific compensation. But they were clear about what they wanted. Six months later, they got a call back.

And got more than what they wanted and a job in a situation more than what they could have ever imagined. But they were very specific about what they wanted. So I think that’s incredible advice. It’s an incredible one tip that you can take away, audience, for sure.

Mac Prichard:

Well, here’s a quick bonus tip. So when you think about that goal, and you say it out loud, and you reflect, and look back on the objections you might have about achieving that goal. Again, maybe I’m too old, maybe I’m living in the wrong place, I don’t have the right college degrees. Turn those objections into questions and find people who have done what you want to do. And don’t reach out to them and say, ” I don’t think I’ll ever be able to do this.

You know, you wouldn’t do that, but instead turn your objections into questions and say, what advice would you have for somebody who wants to do this, who doesn’t have a degree in that field?

How have you seen people make that transition? What concerns might an employer have had about say, the absence of that credential? How have you seen people address it? You’ll get great insights into what works and doesn’t work.

And as you talk to more and more people who are doing what you want to do or working at the employers where you want to be, you will make a good impression. People will think of you, and they will remember your thoughtful questions. And again, you’ll get good insights that you and information that you can use when you do interview for jobs.

Jamila Brown:

Yeah, that’s so good, Mac, because so many times we stop with the thoughts, the negative thoughts, the self, you know, sabotaging thoughts. But once you ask that question and you get an answer, you’re effectively overcoming your someone else is helping you to overcome your own objections for the role. I love that. That’s an incredible tip.

So I’d love for the audience to know a little bit of what you have going on at Find Your Dream Job Podcast as well as with your business. If you could share some of the things that are happening and ways they can connect and work with you.

Mac Prichard:

Well, you can find the Find Your Dream Job podcast wherever you get your shows. Every week I talk to a different career expert about the nuts and bolts of job search. The reason we do the show is that I run a regional job board in Portland, Oregon. We serve employers and job seekers in Oregon and Washington State, and we help people find jobs that matter and employers find people who are great candidates.

But we also know, as you and I have talked about, that candidates who have good job search skills make not only better applicants for the employers who advertise on our site, but they also have better careers. So the podcast is part of our educational efforts to help people learn those skills. We also have several books, hundreds of online articles, and some free online courses.

And while our jobs are only in those two states, the advice that you’ll find on our site works anywhere. We also have lots of advice about how to hire smarter because often the employers who post on our site, the person was hired to do something else. You know, many organizations don’t have an HR professional until they have 25 or more employees.

So often our advertisers weren’t trained in how to write a job posting. So we provide lots of content about how to do that too. You can find us at macslist.org, and we would love to have you come and check out the site.

Jamila Brown:

Yeah, incredible resources there and, obviously, honestly, the podcast, ten years’ worth of absolute gems that have evolved with the current job market. That’s, to me, the beauty of your podcast is that with every iteration of whatever’s happening in the economy or the job market, you’ve been a staple in the job market for everyone to access and get these resources and get it in real time as things are changing.

So I think that’s incredible. I think there are great resources on your website. I’ve checked them out. I’m a consumer as well. So I appreciate you being on the podcast. And I’d love for you to leave the audience with your final five words, Mac.

Mac Prichard:

Don’t wait to be picked. Don’t wait to be picked. And the reason I say that is I was this way myself, and I meet many people this way too. We see a position that we want, and we apply online, or we wait for it to appear on a website. If we know what we want, then we need to go out and, as you and I talked about.

Tell people what we want and ask for advice. And again, if we’re specific, my experience has been people will help you. If we don’t hear back, often I think it’s because people are uncertain about how to help. And if we have a specific ask and we have a specific goal, the help will follow. And the reason you don’t want to wait to be picked is when your dream job does appear on the careers page, you’re going to be competing against a hundred, two hundred, maybe three hundred more people.

I mean, we’ve all seen those counters with those depressingly high figures. And so how do you get around that? You practice the fundamentals that you and I discussed at the start of the conversation. You know what you want, you know where you want to go, you know what you offer. And you step away from the computer.

Look at job boards like mine, but if you’re spending more than, depending on where you are in your career, 30 to 50 percent of your time on job boards, you’re making your search harder and longer than it has to be. So don’t wait to be picked. Get out and tell people what you want. Talk to people who are offering those positions. Connect with people in the companies where you want to go, and you will be amazed at the results that follow.

Jamila Brown:

That’s incredible advice. I had a conversation that you reminded me of earlier this week. Yeah. And it was actually about basketball. I was recapping my weekend with a good friend of mine. And we were just talking about how it was when we were younger, kids playing outside, right?

And the worst scenario that could ever happen when you’re a kid growing up, and you’re playing outside. I know kids don’t play outside as much anymore, but the worst thing was if you didn’t get picked.

Yeah. Right? The worst feeling, the worst sensation, and you wanted to make sure you did everything from a preparation standpoint, you know, networking, building relationships, all those things, working on your skills so that when the moment came, they called your name. Right. And once they called your name, and you proved yourself on the job, at that point you’re always gonna get picked in the neighborhood. And I don’t think what you’re talking about is any different than what we’re talking about as kids.

Being picked on the playground or at recess or outside your home playing with your friends. It’s no different. The stakes are probably equally as high, right? They’re equally as high, in my opinion, compared to a young kid in that scenario. So I appreciate that wonderful advice. Make sure you get picked out there, right? And I appreciate you, Mac, for everything that you’ve done for the 5 Minute Career Hack podcast.

I appreciate you on behalf of myself, Candace, and Alicia. You’ve sewn into our lives, into our podcast, into our business in an incredible way. And I just wanna appreciate you while you’re here in front of the audience and thank you for all your time, your effort, not just for us, but for the rest of the world.

Mac Prichard:

Yeah, well, that’s so gracious of you, and I appreciate the work you and your colleagues do. I know you’re in this for all the right reasons, and you wanna help people make their dreams come true. So kudos to you.

Jamila Brown:

Thanks so much, Mac, and have an incredible rest of your day. And I can’t wait till the video version of your podcast comes out this summer. I’ll be sitting down with my popcorn, tuning in.

Mac Prichard:

I’ll be asking you for tips between now and July.

Jamila Brown:

So I bet. I bet. Have a wonderful rest of your week. Talk to you soon, Mac. Thank you.

Mac Prichard:

Thank you for listening to Find Your Dream Job.

You can support our show and help others find it by leaving a review and rating on Apple, Spotify, or wherever you get your podcasts.

Have a question or a suggestion? Email me at mac@macslist.org, or connect with me on LinkedIn.

To make sure you never miss an episode, sign up for our free weekly newsletter at macslist.org/podcasts.

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 Megan Hattie Stahl. Our music is by Freddy Trujillo.

This is Mac Prichard. See you next week.

XXX