Starting Fresh in a New City: Clarke Hylton’s Job Search Success Story

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Find Your Dream Job, Bonus Episode 52:

Starting Fresh in a New City: Clarke Hylton’s Job Search Success Story

Airdate: May 2, 2022

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.

One of the best ways to get good at job hunting is to talk to people who do it well. 

That’s why once a month, I interview a Mac’s List reader who found a job they love. 

Our guest today is Clarke Hylton. He’s the multimedia content manager at Capital Community Media in Salem, Oregon.

Clarke Hylton believes in the power of serendipity. 

In a story you can find on the Mac’s List website, Clarke says networking with others helped him find an opportunity he never saw coming. 

Why do you love your job, Clarke? 

Clarke Hylton:

Well, Salem is, what I’d say, in the media shadow of Portland and, to a lesser extent Eugene, but especially Portland, and what we get to do as a multi-platform media center is that we get to offer media content for Salem and Marion County, which is otherwise under-represented a lot unless, as I like to say, something tragic happens here, or unless the legislature’s in town. Salem’s kind of forgotten about. 

But also, being a nonprofit, we are freed from a lot of the commercial pressures that, otherwise, these stations up in Portland might have, and we can delve into subjects in our local community that might not have a voice elsewhere, and in a lot of ways, they don’t, and I get to work with some smart, passionate people who believe in the mission. And that’s exciting. 

Mac Prichard:

Well, let’s talk about your job search. What was the biggest challenge you faced? 

Clarke Hylton:

I would say, at times, it was inertia; also despair at times, too. I mean, that’s what happens. So, the first thing I had to do was really figure out what it is that I wanted to do, and that took a long time. When I eventually got to the point where, hey, you know what, I think it’s content creation. I like doing that. 

I started networking with people, trying to reach out to folks who could talk to me at various agencies. I tried networking. Now, this was right when COVID was starting. So I was trying to do some networking in Salem via Zoom; turns out I was meeting a lot of people in Portland via Zoom, which still was useful information, but it wasn’t really getting me where I had wanted to be in the city. 

But through these various network conversations, I started questioning, is this really what I want to do? Do I want to sell widgets for someone? And through content creation, and by chance, I was taking some classes through Capital Community Media – they were offering online classes during the pandemic – and during the orientation, I happened to meet their brand new radio station manager, and she and I got to talking, and we would talk about once a month. My wife put together a podcast that I was the audio designer for, and I was able to get that on the radio station, and so that gave us a natural way, the radio station manager and I, to connect, and from there, a job opportunity popped up. 

It wasn’t with the radio. It was as this multi-media content manager. It was a brand new position. I would be managing the content staff, which is largely the video staff for the tv stations, the cable channels that we manage. But it also, in some ways, is going to involve radio. It would involve web because a lot of content would be going there. And so I thought, you know what? I’m gonna give this a shot. It wasn’t exactly what I’m looking for, but it allows me to stay in media in a way that I’d be happy with. Because I’d made the decision that the commercial end, it’s not what I want to do anymore. If I’m going to stay in the media, I’ve got to have a bigger purpose than, you know, surveying shareholders and things like that. 

So, I went through the process, turned out to be great. I got along well with everybody that I interviewed with, and it also seemed like a really good fit for both of us, and so here I am. It’s been almost half a year. 

Mac Prichard:

You mentioned that when you were starting your search, inertia and getting clarity about what you wanted to do next were your two biggest challenges, and then, that you spent time networking, talking to people in Salem, the state capitol here in Oregon, as well as in Portland, which is about an hour north of the capitol. How did that networking and those conversations help you overcome inertia and get clear about what your goal was going to be? 

Clarke Hylton:

Yeah, so as I talked with a lot of people who I met from agencies, that’s where it started to become clear to me that, oh, you know, content creation in helping sell things maybe isn’t exactly what I’d like to do. I felt like I was still right as far as what I generally wanted, content creation. But maybe, I needed to take a different focus, and as I had these conversations with the radio station manager and got to know a little bit more about what Capital Community Media inc. does, in general, in the community, I thought, well, this would be the place for me. 

Now, I just have to see if they’re ever going to have an opening because they don’t have a lot of those. It’s a small group, and people enjoy working there, and this just happened to be a brand new position that was created as the media center starts moving into some different directions, takes a different focus, and my radio background and media background, in general, were both helpful.

So, it took some time to get to that point, and, you know, I guess you could say networking also can help you figure out what it is that you don’t want to do, and in some ways, that’s how this had worked. And it led me into a media job that I hadn’t seen coming, that looked really great, but that I hadn’t really been putting my initial focus on. 

Mac Prichard:

Many people are uncomfortable with networking, Clarke. How did you learn your networking skills and improve them over time? 

Clarke Hylton:

Oh, let me tell you, Mac, I don’t like networking either. It’s very uncomfortable. But I found the book – actually, it was recommended to me – The Twenty Minute Networking Meeting; it’s by Nathan Perez and Marcia Ballinger. It’s a very digestible book about how to basically get out there and make these informational interviews worthwhile, to both the person who’s conducting the interview and for the people who you want to meet, and I learned some things from that that I hadn’t really thought of before, like, you know, that I need to drive the agenda. I need to make sure that I keep it to the twenty minutes because that’s all you really need to do before you start eating into people’s time. 

And one tip that I found remarkable that people didn’t always know what to do with was, try to make it worth – since it’s networking; it’s not just an informational interview, it’s networking – asking them at the end, what can I do for you? And a lot of times, that just stunned people. They would say, oh, well, I haven’t thought of that. Or, you know what, why don’t you pay it forward when you have an opportunity like this with someone else? 

And so, I thought that that was a good way to also become memorable because a lot of people take from these informational interviews or networking events. Because they’re trying to get something, they’re trying to get a job. They’re trying to meet people. But they don’t always give back, and I think that that is a helpful thing to do, to make sure that everybody is benefiting from networking.

And it still was a matter of having to put yourself out there. It was a little bit easier during COVID because most of the stuff would happen via Zoom. No one was meeting in person. So for me, that took a little bit of the edge off. But also having a clear plan, as to here’s how I’m gonna conduct this meeting, here’s what I’m gonna ask, and here’s how I hope to see it go. That made all the difference in the world. Otherwise, things can kind of seem aimless. In the past, when I’ve done informational interviews and then they’d seem to go on too long, and there was no real clear-cut way to end them. 

But that book was very helpful in just making it compact, making it bearable for everyone and also useful. 

Mac Prichard:

You also mentioned in your story for us on the Mac’s List website that you turned to a local career coach in Oregon, Jenny Foss, who offers online courses, and you took two of her classes; the first one, I think, was on resume writing. How did those online courses help with your search? 

Clarke Hylton:

Oh, well, for starters, I was able to just finally rip up my resume and start over, and I figured out how to really tailor resumes to specific jobs that you are applying for. Now, that takes a lot of work. But if you get the foundation built, it becomes a lot easier, and really, the end product was, I thought, a lot more useful as a marketing document, as opposed to just, you know, your resume being like a rap sheet. Right? So, here’s what I did, here’s what I think I can contribute, things like that.

The cover letter course was also helpful in that, that is to me, has always been the most difficult part of the process to work on in a job application. It feels redundant. You’re never really sure if people are even reading these things. But the way she had lined things out was how to really tailor it to things that you hadn’t been able to mention in your resume that made sense. It gives you a little bit more chance to be creative in your approach. It’s not a marketing document like the resume is, but it can have some personality to it, and I thought that it was very helpful. 

Finally, I have a cover letter from that particular job that I’m still proud of today. It worked out really well, and it wasn’t a long one. It was just, it made the points it needed to make and hopefully inspired them then to read the resume. 

Mac Prichard:

The internet is a vast place, Clarke. There are lots of online resources for job seekers. What advice do you have for somebody who’s trying to find good books or good online courses that can help them in their search, as the resources you consulted helped you? 

Clarke Hylton:

Yeah, so I’d say there’s a couple of things that I would suggest to job seekers. The networking because, you know, as we’ve talked about a little bit today, as you network, you may discover that what you thought you wanted to do for work maybe isn’t as interesting as something that pops up along the way and that’s okay. It can lead to new opportunities that you never saw coming. 

The other thing and this is a big deal, I think. It’s really worth mentioning because this affected me with this particular job, and I know it affects other people. Don’t be afraid to apply for a job that you’re interested in, even if you don’t check every box on the job description. These, as I’ve had some bosses tell me, those are often wish lists. Now, there are some core competencies that they’re obviously looking for. But a lot of times, those jobs are going to change once you’re in them, and they figure out what you’re capable of or maybe some gaps that aren’t as important, but that they’ll bring other people in to fill. 

Jobs should make you stretch a little bit, and so, you don’t have to have the perfect experience and, oh, I can do a, b, c, d, e, f, g. Sometimes if you can do a, b, c, d; e, f, and g they can probably teach you, or you will figure out as you go. I mean, you want to have some challenge in the job. Otherwise, you’re just kind of moving around, but being willing to stretch. Don’t apply for jobs that you’re not qualified for, but if you’re interested in it and you believe that you’ve got the capabilities, even if you don’t check every box, I recommend you still apply for it. 

Mac Prichard:

What didn’t work in your job search? 

Clarke Hylton:

Well, for starters, not really knowing what it is that I wanted to do. That took, I mean, I had to really think about that. Otherwise, you’re just, if you’re just looking for another job. Because I was ready to move on well before I did., I just struggled with, well, you know, what am I gonna do? And if you can’t figure that out, then you just kind of wander in the desert for a while, and no one can really help you if you have people that you talk to on your job search. 

And I encourage people to talk to others as they’re looking just because it’s good for people to know, hey, I’m looking. Maybe there’s things that people can do to help, but if they don’t know how to help you, it’s not helpful to you. Right? 

So, knowing what you want to do, and the sooner you can get that figured out, the better off you’re gonna be in actually moving forward. Otherwise, you just get stuck, and, you know, you end up applying for jobs that maybe you don’t really want, but it’s just something different because you want something different. 

So, that would be the one thing that I would recommend that you just know what you want to do and be willing to, as I’ve mentioned before, sometimes that path will lead you down other areas, but until you start nailing things down, there are way too many options. 

Mac Prichard:

Finally, Clarke, what’s your number one job hunting tip? 

Clarke Hylton:

So, the networking, I think that is gonna be the most important thing that anybody does, and I can hear people just sighing like, really? And I’d say yes. You’re gonna learn some things about yourself along the way. You are going to learn some things about the industry that you’re maybe wanting to join. You may find that that industry isn’t what you want to do, but something else may interest you. But you really do need to meet people because without that, you’re just kind of wandering around. 

Mac Prichard:

Well, Clarke, thank you for sharing your story. To learn more about Clarke Hylton’s job search, visit macslist.org/stories.  

And check out the Mac’s List website for dozens of other success stories. 

On the second Friday of every month, we add a new interview with a Mac’s List reader who has found a dream job. Go to macslist.org/stories.

In the meantime, thank you for listening to today’s bonus episode of 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 is Matt Fiorillo. Ryan Morrison at Podfly Productions edits the show. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week. 

Searching for your next job can lead to discouragement and even despair. Where do you find the motivation to keep moving forward when you feel like it’s too hard? On this bonus episode of Find Your Dream Job, Clarke Hylton and I discuss the steps he took to overcome inertia and discouragement during his own job search. Clarke says the first step is figuring out what it is you really want to do. And from there, networking is the fastest way to the job you want. Learn more about Clarke’s career history in this installment of our Success Stories series.


What do you do for a career? Who do you work for?

I have spent most of my career in broadcast media in various roles, some time in audiobook and podcast production, and a brief interlude in home entertainment packaging. I now work for Capital Community Media (CC:Media) in Salem. We’re a nonprofit media center that offers community-produced content on TV and radio, multimedia education and training, and in-house produced content. My new job is also a new role for the organization as Multimedia Content Manager. I oversee staff and content produced by CC:Media.

How long did it take you to find this job?

I was employed during my search, which took place during the pandemic, so it took a while – over a year. But I was also exploring ideas of what that next job would be, deciding what was most important, and trying to network from home (Hello, Zoom!) in a city I had recently moved to.

How did you find your job? What resources did you use? What tool or tactic helped the most?

I was aware of CC:Media and took some online classes they offered during the pandemic. In a virtual orientation meeting, I met the new radio station manager by chance. I got her contact information, and the two of us had many conversations over the months. We were actually in touch weekly, as a podcast I produced got on the air at the new station. Several months later I discovered a rare opening at CC:Media. The radio station manager alerted me to it as well, thinking it would be a good role for me.

Networking was really important in the search. I met quite a few people and learned some things about myself along the way, including what I might not want to do for work. I had been a subscriber to Mac’s List for several years, and as a result, heard of “Job Jenny” Foss. Job Jenny was great! It was so helpful to tear up my old resume and cover letter ideas and rebuild everything. When I got serious about looking for a new job, I was in good shape.

Another resource Mac suggested to me during a conversation was “The 20 Minute Networking Meeting” by Nathan Perez and Marcia Ballinger. It was invaluable in helping me, someone who is really uncomfortable with the whole networking idea, make these interviews focused and fruitful – even if they didn’t lead to a job within an organization.

What was the most difficult part of your job search? How did you overcome this challenge?

Inertia and sometimes despair. It happens. What was helpful was to remember why I wanted to move on to a different job. I wanted a new challenge, to be closer to home (the daily commute from Salem to Portland was wearing on me and my poor car), to see my family more, and to do something I felt mattered in the bigger scheme of things. Sometimes I just needed a break and counsel/encouragement from trusted friends that the change would occur; I just happened to be looking for a job during a remarkable time in history that presented new challenges to job seekers.

What is the single best piece of advice you would offer other job-seekers?

Two things, really. Don’t be afraid to apply for a job you’re interested in, even if you don’t check every box on the job description. And networking. As you network, you may discover that what you thought you wanted to do for work isn’t as interesting as something new you discover along the way. That’s okay, and it might lead to an opportunity you never saw coming. (In the job I have now, both of these points were the case.)

Why do you love your job?

Salem is in the media shadow of Portland and to a lesser extent, Eugene. At CC:Media we get to be a multimedia platform for Salem and Marion County, which are otherwise underrepresented. Being a nonprofit, we are freed from commercial pressures and can delve into subjects in our local community that might not have a voice elsewhere. I get to work with smart, passionate people who believe in our mission.