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How to Get Unstuck in a Tough Job Market: Advice From Portland Hiring Leaders

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More than 100 job seekers, career changers, and community members gathered at the University of Oregon Portland on Thursday, Sept. 24, for a conversation about a feeling most of us know: being stuck.

Hosted by Mac’s List and presenting sponsor the Oregon Executive MBA program, Getting Unstuck: The Tools You Need to Accelerate Your Career featured a panel of HR leaders and executives:

The evening opened with a welcome from ​Paul M. Allen, Director, Oregon Executive MBA, Lundquist College of Business at the University of Oregon, followed by a panel discussion moderated by Mac Prichard, founder and CEO of Mac’s List.

The Job Market in One Word

Mac kicked off the panel by asking each panelist to describe today’s job market in one word. James said, “tough.” Jasmine said, “rough.” Marcus offered a different take: “innovative.”

He pointed to friends and colleagues who have made big pivots. One person he worked with in tech led marketing. Years before, that person taught kindergarten.

What they had in common, Marcus said, is that they saw themselves as “a three-dimensional human being,” not a job title. “What actually helps bring me joy?”

Look Past the Job Title

Jasmine said people get stuck when they fixate on a title. Budgets are tight, and workforces are shrinking. The next title may not be there right now.

Her advice: dig deeper into the role you have.

  • Refine the skills you bring to the table.
  • Lean into the parts of the job that interest you.
  • Have strategic conversations with leadership about where your role could go.

“That can help to be sometimes a long-term fix, sometimes a Band-Aid fix,” she said. “But it can be something to reinvigorate in that moment.”

James added that this pays off down the road. Your next employer cares less about your past title and more about the responsibilities you took on.

“When you’re interviewing for the next position, you can speak to the things that you’ve now added,” he said.

See the Possibilities in Plain Sight

Marcus spent about 10 years in recruitment and assumed he’d stay a recruiter. Then he learned how different parts of the business worked and saw he could do more.

He took stock of what he was good at. He listened to friends, family, and coworkers who helped him see himself in new ways. And he learned to trust what they told him.

“I had to trust that I was more than just working at a desk,” he said. “I wanted to do something else. Many of us experienced that in 2020.”

Connect the Dots: Your Why, Your Skills, Your Values

The panelists have done a lot of hiring. So what persuades them when a candidate wants to change careers?

For Jasmine, it’s the why. Strong career changers use the cover letter to connect the dots. They name their transferable skills and explain why they want to work closer to their values.

She gave an example from her field. A candidate may never have worked as a domestic violence or sexual assault advocate. But they can point to strong listening, relationship-building, and advocacy skills from other roles, along with a desire to learn.

Jasmine noted that her organization does not use AI to screen applications. People read each one.

James said his values led him to the nonprofit sector early in his career. “We do our best work when we feel fulfilled,” he said. That doesn’t have to mean a nonprofit. It means work you find rewarding.

He added that many people struggle to show impact on a resume. His tip: think through what you did and the difference it made, whether or not you can measure it. That includes soft skills, such as how you collaborated across your organization.

Jasmine suggested listing specific projects on your resume, each with a one-sentence summary that translates the work for your target industry.

Close the Distance

Marcus urged attendees to think about their proximity to the organizations they want to join. Do you know people who work there? Have you talked with them at an event or on LinkedIn?

“Don’t let that one touch point just be ‘I applied there,'” he said.

Why do referrals matter when employers have hundreds of applications? James said they save recruiters time and help candidates get past applicant tracking systems, which he called “a black hole for most people.” Jasmine said her staff, working with tight budgets, see referrals as a way to get the hire right the first time.

But make sure the connection is real. Jasmine shared a recent example of a candidate who cited a contact in their cover letter. When she followed up, the contact remembered a two-minute conversation.

“It can also work against you,” she said.

So how do you build a meaningful connection from the outside?

  • Start with LinkedIn. James suggested looking at shared connections at your target company. Find someone who knows your work and ask if they’d be willing to make an introduction.
  • Don’t aim too high. Marcus said senior leaders are stretched thin. Someone one or two years into the organization may have more time and a different view of how things work. Jasmine agreed: entry- and mid-level staff tend to have the bandwidth and the commitment to help you succeed.
  • Keep the ask small. James said you don’t need to ask for coffee. Ask them to look at your application.

Tailor Your Story and Track Your Wins

Marcus reminded attendees that each stage of hiring calls for a different message. A recruiter wants to know you’ve done the work. A hiring manager wants specifics.

Practice talking about your accomplishments with mentors or people in the industry, he said. Friends and family will tell you it sounds good, but that won’t get you to the next round.

James shared a habit he’s kept for years: a running document of every accomplishment, big or small.

“I don’t have the best memory,” he said. “I certainly won’t recall it in an interview.”

When you apply for a job, you can scan the list and remember projects you’d forgotten.

Marcus added that community work counts. Skills you build outside your job may apply to the role you want.

Mentors Come in Many Forms

Jasmine pointed to peer mentors: people making similar moves at the same time as you, including the people in the room that night.

Share interview questions with each other, she said. They reveal what an organization needs.

“Hey, we’re both trying to get this job for two different companies,” she said. “What are we learning as we’re going through that journey?”

Marcus said the tech industry on the whole served as a mentor for him. Ideas like four-day work weeks showed him his views on the workplace weren’t far-fetched. That gave him the confidence to raise them with other employers.

Your Questions, Answered

Attendees brought great questions. Here’s some of the advice panelists shared:

  • Getting past AI screening: James recommended a frequency analysis. Review the job postings you want, note the skills and requirements that come up most, and weave those keywords into your resume and LinkedIn profile. “It’s not just one thing,” he said. “It’s a collective.”
  • Listing community experience: Jasmine lists relevant volunteer and community roles under professional experience, with her title and the organization. James said this keeps the experience from getting buried on LinkedIn. Label it as volunteer work.
  • Returning to a 9-to-5 after self-employment: Jasmine recently hired a former business owner. What stood out: she figures things out fast and works on her own. Highlight those strengths.
  • Making a hard pivot: Jasmine said it’s OK to step in a level or two below where you’ve been. You know how to do the work, but you’re new to the industry.
  • Explaining a work gap: Marcus said to address it up front. Jasmine said to give the real reason. James suggested talking about what you’ve done in that time, such as consulting or building new skills.

The Panel’s Top Advice for Getting Unstuck

To close the formal conversation, Mac asked each panelist for their number one tip:

Marcus: Know yourself. Think of yourself as a whole person and notice where you’re making compromises. For him, clarity came from admitting, “I’m tired,” and realizing the organization had no career ladder. 

Jasmine: Lean on your support system. If you don’t have one, you are your support system. Notice which parts of your day feel good and which don’t. And remember that a job can be a means to an end. “Find who you are and what you value,” she said, “and then figure out how the role that you’re going towards or that you’re already in can help you align with what you want to do.”

James: Create a professional development plan. For more than 20 years, he’s written a five-year plan with career and personal goals and reviewed it each quarter with a mentor. The process “takes you to step back and think through your skills.”

Stay Connected With Mac’s List

A big thank you to our presenting sponsor, the Oregon Executive MBA program, and to Paul M. Allen, Kit Alderdice, and Wendy Sierra for hosting us at the University of Oregon Portland. 

Thank you to our Silver Sponsor, The Vellian Group; to our tabling organizations, Portland Women in Technology, Oregon Entrepreneurs Network, Hispanic Metropolitan Chamber, and the Oregon Executive MBA program; and to our wonderful volunteers, Elliana Pastrano, Logan Rosell, Michael Chen, and Megan M. Milligan.

Here is an album of event photos, thanks to our photographer, Andie Petkus. 

Mac’s List will host one more event in 2026 for employers, Build Your Best Team Through Better Hiring Today, on Thursday, Nov. 5. A podcast episode of the Sept. 24 event will be released on Monday, Nov. 2.

In the meantime, you can: