Becoming Known To Uncover New Career Avenues: Meghan Sinnott’s Job Search Success Story

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Becoming Known To Uncover New Career Avenues: Meghan Sinnott’s Job Search Success Story

Airdate: November 9, 2020

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 Meghan Sinnott. She’s the executive director of Portland Made. It’s a collective that organizes networking and educational events to grow local businesses.

Meghan Sinnott doesn’t recommend sending out lots of applications as many job seekers do.

In a story you can find on the Mac’s List website, Meghan suggests instead, that you focus on networking, volunteering, and contract work.

This helped her make connections, improve her skills, and learn about new opportunities.

Meghan, why do you love your job?

Meghan Sinnott:

Oh, I love my job because I get to do a little bit of everything that I would like to do and I get to be the connector that I naturally am. I get to meet new people every day and even virtually, and learn a little bit about the city that I love.

Mac Prichard:

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

Meghan Sinnott:

100%, hands down, intense self-doubt. Yeah, just always second-guessing and not believing that I was qualified for the job that I was applying for.

Mac Prichard:

It’s a common challenge for so many job seekers. When you were dealing with that, Meghan, what worked best for you?

Meghan Sinnott:

Well, you know, it was an interesting thing. When I was technically unemployed, I really didn’t look for work. Instead, I took contract gigs as they kind of fell in my lap and I volunteered and I just kind of hit the streets doing the things that I could to meet people but not as an act of…not to meet the end of a job but more as a nervous habit. It was my way to just keep on going and trudge forward was to not sit. And so, I really did not apply to that many jobs in the time between when I left my job as marketing director and I became director of Portland Made. Instead, it was just figuring out how I could just keep on connecting and doing the things that I like to do.

Mac Prichard:

How did being in the community, volunteering, doing contract work…how did that help you deal with that self-doubt that you mentioned a moment ago?

Meghan Sinnott:

What I found was, as people who I had regularly been volunteering with discovered that I was unemployed, they were ecstatic at the opportunity to be able to plug me into wherever they could find, and that was wildly supportive and it opened my eyes up to what other people were seeing as my skill sets. And so, it was having the opportunity for people who had seen me in action to be able to say, “You’re really great at these many things and would you be interested in doing more here?” Or, “I have a friend looking for somebody to do the things that you already do, may I connect you?”

It was really having those champions in the community surrounding my volunteer world but also just my acquaintances, friends who had seen my work, and been fans of the things that I’d done as a volunteer.

Mac Prichard:

That had to be so affirming. Were there other things that you did during your job search, Meghan, that provided that same kind of affirmation, besides volunteering?

Meghan Sinnott:

Oh man, applying for jobs is…can be really hard for some people, and so for me, I’m dyslexic, among some other learning differences and that really impacts my ability to keep track of edits I’ve made to my resume, to feel like my cover letters are hitting all the points that I want them to hit. And so, aside from those few champions, and honestly, a supportive partner, there wasn’t much other than the successful events that I was hosting. So, as a volunteer and as a contract worker, I was having these really, kick-butt events that had a beginning, middle, and end, and for me, that’s kind of the gold of volunteering. You get to pick and choose projects that you can walk away from and feel like you’ve succeeded.

Having those sort of opportunities can certainly be a boost.

Mac Prichard:

You mentioned the champions that helped you during your job search, who were these people, Meghan, and what difference did they make?

Meghan Sinnott:

It was usually people who I had had the opportunity in the past to support. I say the term, “volunteer,” kind of broadly. I feel like a lot of the work that I’ve done in my life has been volunteer work, but really that’s just the term that I use for getting out, being active, connecting, making friends, making a city that I want to see. So, it’s varied and the people who were able to appreciate the work I’ve done over the years were people, largely, who were a part of nonprofit boards. People who were, themselves, community organizers, people who were big supporters and believers in this beautiful city that we’re in and who were proponents of it in some way,  shape, or form.

It was people who could identify the projects that I’d been a part of and who I’d gifted the time that I had to be the connector that I am and I think there’s…you know, I guess I took for granted all of the times that I had taken an afternoon off to go support someone in a project that they were doing, or had done a friend a favor and taken a visiting journalist around to visit local makers, or whatever the case may be, at the time it seemed fun, like, “Oh, I get to meet someone from out of town and maybe my lunch will get paid for. I’m a sucker for being on camera, maybe I’ll get filmed.”

Whatever the case may be, although it was technically volunteer work, there was a lot of reward for that, both for me and my connections. Often people who were in charge of projects that just simply didn’t have the funding to pay individuals, and I fully recognize now, there’s a huge, good movement to kind of question the world of volunteerism, and question who has the ability to take time and donate time and donate their services, and to be honest, Mac, when I was interviewed for your piece that you have on your website, it got a little pushback and flack.

Specifically, from mothers, women who aren’t afforded the same freedom that, at the time, when I was at this job as director I was just recently in a larger, more serious relationship. I’m now married, but I got some pushback from mothers saying that it’s a privileged place to be to have the opportunity to volunteer. And I hear that and I agree, and I would also say that we all make decisions on how we spend our time, and for me, attending a party or going to a networking event, those kinds of social activities are not good places for me. I get anxious, people see me as an extrovert, and I’m sure there’s a proper term for my introvert/extrovert qualities, but I love being out and about but I really need a reason to be out there.

Volunteering, if that’s what we’re going to call it, basically, being at an event with a purpose is my way to be comfortable in a social setting. Some people volunteer at their kid’s school, some people volunteer at church, and for me, it was largely community events surrounding around the biking world and the maker world. That’s where I ended up getting my job in the end.

Mac Prichard:

I’m curious about those champions, Meghan. Did they step forward and offer their help, or did you reach out to them, or was it a combination of the two?

Meghan Sinnott:

I was never very good at reaching out for help. Instead, it was the champions coming to me and saying, “Hey, I hear that you just left your job and you would like to reset for a moment. That’s great, but how about starting a new gig in two weeks? Are you available for this project that you would never think that you’re qualified for?” I’m like, “I guess, if you think I am.” And so yeah, it was people who saw something in me that I didn’t see in myself.

Mac Prichard:

You mentioned in your article for us that you sent only one formal application for a job. Why was that, Meghan? What was the strategy there?

Meghan Sinnott:

Strategy…geez, Mac. Do we all have to have strategies?

Mac Prichard:

Not at all, Meghan. Tell us your story.

Meghan Sinnott:

I mean, for me it was…applying for jobs is paralyzing, for me, and some people might enjoy it and that’s wonderful but it was hard to land on the job search sites, find a job, understand what the job really is, and then understand how you could convince somebody that you were the fit that you saw that you were, and you know, it’s a bunch of back and forth, self-doubt. “Do you understand what the role is? Do you understand what the company is? Do you think that the company is actually asking for what they need? Do you think you have what it is that they need? Will they understand that when they see you?”

It’s like, you could do anything and at the same time, if you don’t know somebody at the company, what chance do you really have to convince them, and I understand you have the resume, you have your online presence, you have your lovely well-crafted letter, but in a sea of applications, it just goes adrift. I spent my time building my foundation, figuring out who I was, what I wanted to do, where I was making the most impact. And strategies? Plans? I’m not sure, but it was more figuring out, honestly, this is terrible, but it was the path of least resistance.

It was saving up enough money before I left my former job so that I could not rush into anything. And so, I only approached any possible job if I felt like it was a surefire fit, and there was only one that was kind of a cold call, where, oh man, it felt good, I was stoked, and even if it wasn’t the right job, I knew it was an interesting step in a direction I knew I was curious about and, let’s be honest, it was a good-paying job. I was like, “Things are really falling into line here. This would make sense.” And so I applied to that job, didn’t even get a response. No, “Thanks for your letter,” or, “We’ve got you on the list.” Nothing. And that can be really disheartening as well.

Kind of like feeling like, for me, I can’t just sit down and push out a cover letter; it takes time. I really debate about it, I write it, I rewrite it, I write three versions of it. I scrap one, I take pieces, I put it together, I throw them all away, I start over. It’s draining on me, on my partner, on my family, and it really is a full-time job, so what’s more fun than writing a cover letter, again and again, is living life and figuring out who wants you. Who’s saying that they’re interested in your time?

Even if they can’t pay you the thousands of dollars that you want. If it’s a contract gig, they can only pay you a little bit of time. At least that’s experience, at least you get to work with individuals who can appreciate the work that you do, and then through that, you’re making new connections. I guess that was my strategy, although I don’t know that I knew that I had a plan.

Mac Prichard:

It seems very clear, Meghan. What didn’t work in your job search?

Meghan Sinnott:

Any of those…well, I would say, the most frustrating thing was, I had put high hopes in having a recruiter do some of the work for me, and I’m sure that there are recruiting agencies out there who can deal with the Meghan Sinnotts of the world, but I think I really stumped the agencies that I approached. I just…we would have a few meetings and then it would be crickets, not even a single job that they’d push my way. Yeah, so I would say, hoping that somebody else that didn’t really know me could be a champion for me and my future was not a successful move for me.

Mac Prichard:

Finally, what’s your number one job hunting tip.

Meghan Sinnott:

To not take for granted the things that you love, the things that you do well, and the world that you’ve created for yourself. I don’t mean to say that you should post on Facebook that you’re looking for a job. You can certainly do that but it’s more…when possible, being generous with your skills, your time, your knowledge, your support, and being a good community member and friend, and people will recognize your skillset and the value that you bring to the community around you and the community at large.

Simply to not neglect the world that you’ve created and that you want to see, to feed into that, because if you nurture the world around you, it will give back.

Mac Prichard:

Well, thank you for sharing your story, Meghan. To learn more about Meghan Sinnott’s job search, visit

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

In the meantime, thank you for listening to today’s bonus episode of Find Your Dream Job.

As a job seeker, your first inclination is probably to start sending out resumes as quickly as possible. But what if you adopted a different strategy? What if, instead of submitting dozens of applications, you volunteered in your community or took on contract work doing the things you love and are good at? On this bonus episode of Find Your Dream Job, Meghan Sinnott tells us how she used volunteering to build up her self-confidence and skill set, and how strong connections brought her next job to her instead of her having to look for it. Learn more about Meghan’s career history below in this installment of our Success Stories series.

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

As Director of Portland Made, I support local makers by providing networking opportunities and events to support their efforts.  Our Maker Meetups happen once a month. These events are typically in a maker space (a functioning shop). Topics covered range from social media smarts and financial literacy, to perfecting your elevator pitch and intellectual property discussions.

How long did it take you to find this job?

I resigned from my role as Global Marketing Director and Brand Manager at Nutcase Helmets in October, 2017.  Between then and February 2019, I did contract work only, accepting positions that aligned with my interests.  It was a great opportunity to work on dream projects with some of my favorite people, and through the work I gained confidence in what I could offer.

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

I didn’t use any of the “official channels.”  After leaving my 9-5 job, I only reached out to two companies, and officially applied to only one position.  The only opportunities that panned-out were through word-of-mouth or came to me though the groundwork I’d laid with previous networking.  I tried to work with a recruiting agency, but they never sent anything my way…

My biggest recommendation is for people to volunteer and to accept a few jobs here-and-there in the name of building community, making connections, and honing skills.  During my year-plus not tethered to a desk, I took the time to focus my energy, joining boards for organizations I believe in, and sharing my marketing and community organizing expertise with local co-ops and nonprofits.

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

Simply knowing what I ought to apply for was probably the most difficult part of the hunt.  I had a severe case of “I could apply for anything, but I won’t get anything” doubts. As in — I believed I was capable of succeeding at the majority of jobs I came across, but I froze-up when it came time to selling myself.  I couldn’t put into words why I knew I would crush a certain job. In the end, it always came down to someone inside a company being my champion. I would not have gotten as far as I did without the support of people who had seen me in action and advocated for me.

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

Don’t be afraid to dabble.  What may feel like distractions or dead-end opportunities are actually often the best way to get yourself known.  Reframe your understanding of the value of contract work and volunteering so you can see the role they play in providing real-life networking opportunities that far surpass attending “meetups” with your pockets stuffed with fresh business cards…

Why do you love your job?

I get to have my finger to the pulse of the city I love.  Every day I meet new makers and learn about new products and facets of Portland, Oregon.  Makers are at the core of what makes Portland special, and I’m lucky to get to support them.

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