We’re excited to introduce you to the always interesting and insightful Kelsey Woodward. We hope you’ll enjoy our conversation with Kelsey below.

Kelsey, thanks for joining us, excited to have you contributing your stories and insights. One of the things we most admire about small businesses is their ability to diverge from the corporate/industry standard. Is there something that you or your brand do that differs from the industry standard? We’d love to hear about it as well as any stories you might have that illustrate how or why this difference matters.

In a world brimming with pretense, I decided it was time to cut the bullshit. After a sudden layoff from my full-time gig in December 2023, I made 2024 my personal renaissance—a year dedicated to rediscovering my passions and, most importantly, putting myself first.

Let’s rewind a bit. Just a year ago, I was riding high, achieving the pinnacle of my career as a Senior Digital Producer & Community Leader at a small agency. I poured my heart and soul into that role, sidelining my freelance endeavors and creative projects to give the company everything I had. But when the dust settled post-layoff, I realized I had lost more than just a job—I had lost my sense of purpose.

I spent so much time advocating for the growth of others that I neglected my own journey. Sure, I was passionate about helping my colleagues and clients evolve into better versions of themselves, but in the end, I was doing it for a company that would ultimately prioritize its own survival over my contributions.

So, what did I do? I decided it was time to reclaim my narrative. In 2024, I embraced honesty and authenticity like never before. I began applying for jobs where I knew I would not only thrive but be truly valued—where I was seen as a whole person, not just a cog in the corporate machine.

Gone were the days of sugarcoating my experiences in interviews. I started telling it like it is, unapologetically. It might not have been everyone’s cup of tea, but it was mine, and that made all the difference.

This newfound clarity has been liberating. I’ve learned to cut through the noise, zeroing in on what truly matters—my passions, my needs, and my future.

Kelsey, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Oh, hi! I’m Kelsey Jean, and if there’s one thing you should know about me, it’s that I believe in transparency. I’ve never been one to claim expertise in areas where I have little experience, but what I do have is a decade of experience in digital marketing and content creation, where I’ve learned that the heart of communication—be it through traditional media or digital platforms—remains the same: connecting and engaging with people.

Photography has always been a big passion of mine. I honed my skills in the darkroom during high school, transitioning to digital photography as technology evolved. Although I initially considered pursuing a formal education in photography, I chose to dive headfirst into freelancing and the service industry instead. That hands-on experience ignited my love for digital production, leading me to embrace roles in sales, studio management, and event production. My journey has been all about effective communication, service orientation, and motivational leadership. I thrive on collaboration and encourage my teams to ask questions; after all, every employer has their own unique rhythm.

Collaboration is my superpower. I excel at aligning diverse skills and personalities to achieve a collective vision while managing expectations with finesse. I understand that every challenge requires a tailored approach, and I pride myself on adaptability and fearlessness within any team dynamic.

Over the years, I’ve donned many hats—from Digital Producer to Senior Program Manager—while continuing to freelance in digital and film photography. Whether I’m planning a campaign, orchestrating a lifestyle shoot, or capturing product shots, I love getting my hands dirty in the creative process. My journey in event production has been nothing short of exhilarating. I began as a Creative Assistant at Escape Collective and quickly discovered my passion for thriving in chaos.

Planning is my secret weapon. Every successful project I’ve tackled has started with clear objectives, a detailed plan, and a realistic budget. I believe in thorough monitoring and tracking to keep everything on course—ensuring projects are organized, resources are utilized efficiently, and timelines are met.

Beyond work, I’m deeply rooted in my Portland community. As a former small business owner and a freelance creative, I’ve dedicated the last six years to community leadership. I believe that true beauty lies in inclusion, and I’m passionate about diversity, equity, and inclusion (DEI) work. Fostering a sense of belonging in our community is essential, and I’m proud to help keep the heartbeat of organizations alive.

Can you talk to us about how your side-hustle turned into something more.

In 2024, I made a bold commitment: it was time to put myself first. This year has been all about exploring my side hustles and diving back into freelancing with gusto. Two of those hustles blossomed into more of a full-time focus: reselling vintage and thrifted treasures, and dog walking and watching.

Let’s start with my love for vintage and thrifted items. It’s a passion that goes way back! Growing up, I learned the art of finding quality pieces at bargain prices—my parents navigated low-income homes, and I quickly developed a knack for treasure hunting. For the first part of my childhood, I was fortunate enough to have a dad who brought home the big bucks. But everything shifted between 2002 and 2004 when he left his corporate job to spend more time with us. While I’m incredibly grateful for his choice to prioritize family, we faced some tough times financially.

I still remember my first job at 15, motivated by my mom’s comment that I had to cover the cost of my back-to-school clothes. Suddenly, I was that kid at a wealthy high school sporting secondhand outfits. Rather than feeling ashamed, I embraced it, and it’s amusing to think back on how “in” I actually was. Fast forward to today in Portland, OR, where vintage and thrifted fashion reign supreme. I focus on online sales and local markets, and my favorite gig? A monthly summer day party at White Owl Social in Southeast PDX called Sunday Best hosted by some good pals from Believe You Me and Hold Music.

Now, let’s wag our tails over to my other side hustle: dog walking and watching. Who doesn’t adore dogs? I’ve always been the go-to friend for pet-sitting, so in 2024, I decided to devote more time to this furry endeavor. What sets me apart from the pack? It’s all about the personal touch. I thrive on good old-fashioned word of mouth; no fancy apps are needed here. Just genuine connections and trusty referrals keep those tails wagging with joy.

For me, dog walking isn’t just a gig—it’s a chance to create something truly paw-some. I love ensuring my four-legged friends feel at home and happy. Plus, the added bonus? I get to be outdoors, soaking up some exercise while hanging out with the best companions around. Who could ask for anything more?

Do you have any insights you can share related to maintaining high team morale?

When it comes to managing a team, here’s my golden rule: DON’T TAKE IT PERSONAL.

The dynamic of a team is ever-evolving, and the challenges that arise often have nothing to do with you as a leader. It’s easy to feel like you’re under fire when issues pop up, but taking things personally can cloud your judgment and hinder your ability to lead effectively.

Instead, focus on fostering an environment of open communication and trust. Encourage your team to share their thoughts and concerns without fear of judgment. When you approach situations with a calm mindset and a genuine willingness to listen, you create a culture where everyone feels valued and heard.

Remember, your team members are individuals with their own perspectives and pressures. By acknowledging that their challenges might not be a reflection of your leadership, you can better support them through tough times. This mindset not only helps in resolving conflicts but also boosts morale and strengthens team cohesion.

So, keep your cool, stay empathetic, and remember: it’s all part of the journey. By prioritizing understanding over personal feelings, you’ll create a thriving team atmosphere where everyone can shine.

Contact Info:

• Website: https://www.kelseyjean.com
• Instagram: https://www.instagram.com/kelsey_helpme/
• Linkedin: https://www.linkedin.com/in/kelsey-jean-woodward/

Image Credits

Cover photo captured by Melissa Achten
Photo by campfire by Adam Kingman
Photo on set at Nice Touch Co. by J Yun
Polaroid photo by Sam Gehrke