How Executive Dysfunction Affects Your Job Search (And What to Do About It), with Ben Tobin

You know you need to apply. You’ve blocked out the afternoon. And somehow the garage gets cleaned instead. That may be executive dysfunction, a disruption in your brain’s ability to plan, organize, and follow through. In a job search, it looks like collecting postings you never apply to, over-preparing, or spending months getting ready to start.

This week, ICF-certified career coach Ben Tobin joins Mac with three ways forward. Lower the stakes: make your first goal to bomb an interview, not land one. Sit with the discomfort: that pit-of-your-stomach dread runs its course if you let yourself feel it. And build structure: schedule time, name your very first step, and write a fresh to-do list each day. As Ben says, the meta work is work — give it a place on your calendar.

About Our Guest:

• Ben Tobin is an ICF-certified career coach who works with tech professionals and adults with ADHD. 

Resources in This Episode:

• Connect with Ben on LinkedIn.

Transcript

Find Your Dream Job, Episode 566:

How Executive Dysfunction Affects Your Job Search (And What to Do About It), with Ben Tobin

Airdate: August 26, 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.

Focus, organization, and time management are just three of the executive skills you need as you look for work. And if you struggle with one of these skills or others, you’re not alone.

Ben Tobin is here to talk about how executive dysfunction can affect your job search and what to do about it. He’s an ICF-certified career coach who works with tech professionals and adults with ADHD.

Ben helps you get unstuck, grow into leadership, and build a satisfying, sustainable career. He joins us from Portland, Oregon.

Well, let’s get started, Ben. What do you mean when you say executive dysfunction?

Ben Tobin:

Well, executive dysfunction is a disruption in our brain’s ability to plan, organize, and execute tasks. Often that shows up as trouble getting started, but it can show up in a lot of different ways.

Mac Prichard:

Say more about that. What does executive dysfunction look like when you’re doing a job search, Ben?

Ben Tobin:

I’ve seen it happen where folks will be ready to do the job search knowing that they need to do it. And sometimes they’re searching for jobs, but not applying for any. That can be a form of perfectionism, maybe talking themselves out of all of them or saying, or kind of collecting them.

Other times it can be total avoidance of it, knowing that they need to do the work, and it really is work of job hunting, and all of a sudden the garage needs cleaning. They managed to find anything else to do rather than the work that they need to do.

It can be, yeah, just really getting nervous or over-preparing. All of these things, really just finding anything else to do and then finding that time keeps slipping away and slipping away.

Mac Prichard:

How can you tell that it’s executive dysfunction that’s holding you back, whether it’s applying for a job or perhaps affecting you when you do get interviews, and you don’t feel the interview went well?

Ben Tobin:

Well, it’s, you really look for that sustained chronic pattern where it just keeps happening. You know you need to do it. Maybe you even want to do it on a certain level, and either you sit down to do it, and the distractions overcome you, or you feel so overwhelmed that you can’t proceed or…

You find that day after day goes by and even though you know and planned to do this work, you’re mowing the lawn, you’re scrubbing the grout, things that you would normally avoid doing.

And it can be due to, you know, an actual pathology, know, a neurodevelopmental problem, or it can be from something a little more temporary like depression or anxiety that can absolutely come with, say, losing a job or something like

Mac Prichard:

Well, say more about the causes of executive dysfunction. What might cause it when you’re doing a job search?

Ben Tobin:

Yeah, know, ADHD is a classic cause. Depression and anxiety are also strong ones, and it’s not unusual to have all three. There are some others, though. Autism spectrum disorder can also come with some executive dysfunction.

And there are some, you know, less common things like brain injury, and there are some more common things like just stress and burnout, sleep deprivation, grief, and even physical illness. If you have a cold, your executive function is not going to be what it was.

Mac Prichard:

And in your experience as a career coach, how common is executive dysfunction in all of its different forms among job seekers?

Ben Tobin:

Well, it sure seems common from where I stand, although there’s some bias there because I do focus on ADHD. So a lot of the folks that come to me either have ADHD or suspect they do, or have some similar challenges. But I see it a lot. Folks who say, you know, I’ve been job hunting for a year, two years, sometimes less, sometimes more.

But then I learned that, well, it hasn’t been constant, or it’s been maybe even aspirational, or I’ve been planning to job hunt and trying to upskill and get ready, and I’m never ready. And so I see that a lot. It sometimes even happens to folks listening to podcasts or books or things on how to job hunt without actually doing it.

Mac Prichard:

And how does executive dysfunction affect how employers see you as a candidate? What does a hiring manager see when either interviewing or receiving an application from someone who’s experiencing the kind of executive dysfunction you’ve described?

Ben Tobin:

Boy, that can vary a lot. It’s not always visible, but it can show up in ways that can impact how you perform in interviews. It can lead to being underprepared or overprepared in ways that are maybe a little too narrow. It can…

It can also be that it might show up as a distraction or ADHD specifically; people often have a tendency to ramble and lose track of their train of thought. And that can really rob them of time in their interview to showcase what they want and need to showcase.

And then at the end of the interview, if the interviewer didn’t get what they were looking for, they have to pass. Even if it, even if they weren’t sure that you don’t have it, if they just didn’t see it, you know, they’ll probably pick another candidate.

Mac Prichard:

Well, you’ve got three tips for how to manage executive dysfunction when you’re doing a job search. I’d like to walk through them one by one. Your first tip is to lower the stakes temporarily, is the phrase you use. What do you mean by that?

Ben Tobin:

Yeah, lowering the stakes can help us get started because it can feel like every job application, every interview is so important that we have to be perfect, that we have to nail it. But the reality is that most of us, when beginning a job hunt, bomb at least one interview. It’s kind of part of the process.

So often, when I’m working with clients who are having a lot of that anxiety and worry about that interview, or they get really, really nervous in their interview. I help them adjust their goal to start with.

And their first goal isn’t to get an interview, and that leads to a job. It’s to bomb an interview. Not that you should take it unseriously, but that… You shouldn’t put all your eggs in that basket.

Treat that first one as the learning process that it is, because interviewing is a great way to learn about how you stand in the job market and how ready you are. And there’s almost no better way. You’ll never know you’re really ready until you get out there and do it.

So, starting from that, treat it as a learning process, applying to jobs that you’re not so sure about. You don’t have to accept any offer that you get. It’s kind of changing your mindset about those things so that you can do them without as much attachment.

Mac Prichard:

Let’s pause here, Ben. We’re going to take a break. When we come back, Ben Tobin will continue to share his advice on how executive dysfunction affects your job search and what to do about it.

We’re back in the Mac’s List Studio.

I’m talking with Ben Tobin. He’s an ICF-certified career coach who works with tech professionals and adults with ADHD.

Ben helps you get unstuck, grow into leadership, and build a satisfying, sustainable career.

He joins us from Portland, Oregon.

Now, Ben, before the break, we were talking about executive dysfunction, how it affects your job search, and what to do about it.

And talked about what it looks like, some of the causes, and we started walking through the first of your three tips for how to manage executive dysfunction when you’re looking for work.

And your first tip was to lower the stakes temporarily. You laid out the importance of seeing the job search as a process and taking steps as you move forward.

Say more about what small steps you can take to lower those stakes when you start applying and interviewing for jobs.

Ben Tobin:

Yeah, it can help to set some little goals for yourself, intermediate goals, making sure that they’re more kind of short-term and immediate rather than lofty ones.

Executive dysfunction really makes it hard for us to be motivated by longer-term goals. So something shorter-term, lower-stakes, lower stakes and inherently doable can help a lot.

Focusing on the action rather than the desired outcome initially can help give you some momentum. Maybe it’s setting a goal: today I’m going to apply for three jobs no matter what. And initially you don’t have to set the target all that high.

Maybe you’ll start out with a few easy applies on LinkedIn or something, or some things that aren’t perfect fits. You could even apply for some jobs that you don’t particularly want, which sounds a little odd. I wouldn’t say to apply for things that you’re absolutely sure that you would never take. You don’t want to waste anyone’s time.

Maybe apply for some things that you’re less sure about, that you’re less motivated for, that you’re less… that you’d feel less bad about not getting. And just start to build up your momentum that way. Then slowly raise your goals more in the direction of what you want and need.

Mac Prichard:

All right, so take small, manageable steps, but take them regularly and on a consistent basis. The second of your three tips for managing executive dysfunction when you look for work is to spend time with your discomfort. What kind of discomfort are we talking about? And what do you do exactly,

Ben Tobin:

Yeah, that’s a tough one. We often, and by we, I mean everyone, but especially those with executive dysfunction, we create these associations; we learn them when we have repeated discomfort, emotional pain, a history of failure, or at least perceived failure. And I sometimes call that a wall of awful.

Where this thing that we need to do, we have this emotional response to it that is often not totally connected to how difficult the task actually is. And it can really stop us in our tracks. It’s that feeling of ick, of I hate this, I would rather do anything else but this.

If you’re sitting down to work on your resume or start job hunting, or excuse me, if you’re sitting down to a job hunt or work on your resume and you just feel that pit of your stomach, yuck. That’s, that’s one of the ways that that wall of awful can manifest.

And that is part of what can really fuel the tendency to distraction and procrastination because

it’s totally rational for us to avoid pain.

Mac Prichard:

So, Ben, you hit the wall of awful. You’re feeling that sense of dread in the pit of your stomach. What do you do instead of avoiding the task? How can you actually get the job done, whatever the assignment might be?

Ben Tobin:

One of the big ways, one of the important ways, is to not avoid it. And by that, I don’t mean not avoid the work, that too, but first, not avoid that feeling to let yourself feel it and to not lie to yourself about how that feels.

Often one of the ways that I talk about getting through that for myself is to just feel the heck out of it and then use a little self-talk. Something I do with myself is say, really hate this. I don’t want to do this. I’d rather do anything else, but I’m going to do it anyway.

Sitting with that before you start, not trying to force yourself to start immediately, you know, that feeling is going to run its course. No feeling lasts forever. And it’ll reach a point where you can move past it. You can start anyway, if you let yourself feel it.

Mac Prichard:

Your third and final tip for managing executive dysfunction when you’re looking for work is to build structure for yourself. What does this structure look like and how is it going to help you move ahead in your job search?

Ben Tobin:

Yeah, it’s really connected to the other things that we’ve talked about. It involves a little bit of planning ahead, and often that means setting aside the time to plan ahead. It’s easy to try to skip over that and try to do the work itself, but the meta work, as I sometimes call it, is really important.

So, now, setting up planning, what time are you going to do your job hunting every day or several times a week or however you want to do that? Set some goals for yourself and track them, write them down. And all of this is so much easier said than done.

Often people say to me, this shouldn’t be this hard, but it is. All of this stuff is hard. It’s hard work, and it’s… not particularly friendly work to those of us with executive dysfunction.

So it’s going to take extra planning and support for yourself and really experiment, see what works, pay attention to it and adjust and try to build that into your life for the time being until you reach that next stage of employment. And then you can take some of those lessons forward to the job as well.

Mac Prichard:

And when you’re building that structure, what does that look like exactly, Ben? Are you scheduling your time during the day? Are you making a to-do list? How have you seen the people you work with do that effectively and get the results they want?

Ben Tobin:

I’ve seen both of those scheduling blocks of time, but also getting really specific about when and where and how you’re going to start, and be really specific and clear about the very first steps you’ll take so that you don’t sit down and have something vague and you don’t know where to start. And to-do lists can help, but they need to be small and manageable.

I recommend that people actually write a fresh to-do list every single day. Even if they end up writing the same thing over and over day to day because it keeps slipping, that’s an opportunity for you to ask yourself, am I really gonna do this? Or what’s it gonna take for me to do this?

Mac Prichard:

Well, it’s been a great conversation, Ben. Now, tell us what’s next for you.

Ben Tobin:

Well, I’m going to continue working with clients as a coach, both tech professionals and adults with ADHD. Many of the people I talk to have both, and helping them succeed, however they define success for themselves.

Mac Prichard:

Terrific. Well, I know that our listeners and viewers can learn more about you and your work by visiting your website. That’s bentobin.com. We’ll be sure to include that in the show notes and the website article as well.

Ben, given all the great advice you’ve shared today, what’s the one thing you want our audience to remember about how executive dysfunction affects your job search and what to do about it?

Ben Tobin:

Yeah, I’d say remember that the meta work is work and that you need to set time aside to plan and to prepare yourself to do the work so that you can do it well.

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.

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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.

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