We recently connected with Kelsey Jean and have shared our conversation below.
Hi Kelsey, thank you for being such a positive, uplifting person. We’ve noticed that so many of the successful folks we’ve had the good fortune of connecting with have high levels of optimism and so we’d love to hear about your optimism and where you think it comes from.
It’s hard to pinpoint a time in my life when I wasn’t optimistic. I was raised by a very “woo-woo” mom, which gave me a unique lens through which I’ve always been able to see opportunities where others might only see obstacles. As a woman in this world, it’s easy to be buried by pain and disappointment if you don’t hold onto hope. Not that those struggles don’t still exist, but I’ve learned to stay hopeful that there’s always a rainbow on the other side—and a lot of that comes from within me. It’s about what I put into my life: the decisions I make, the way I engage in conversations, and the actions I take that ripple out into the world. I feel incredibly privileged to have a deep sense of self-awareness. At my core, I know my strengths and weaknesses, and even in times of stress, I have to maintain faith in myself to keep that optimism alive. After all, no one is carving my path for me. My optimism is rooted in the belief that I can shape the future I want—no matter how winding that road may be.
On top of the weight of being a woman, I’m also a queer woman. Every obstacle I’ve faced has helped me cultivate resilience and adaptability, fueling my optimism even when things feel uncertain. I’ve found that optimism often comes from pushing boundaries, fighting for both personal and collective freedom, and challenging the status quo. This sense of agency becomes a powerful motivator, especially when life gets tough.
Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?
Hi, I’m Kelsey Jean.
Born and raised in the Pacific Northwest.
Living and learning in Portland, OR.
I’m a wearer of many hats and usually have my hands in a couple of pots, leaving my fingerprints in the digital marketing realm or on the World Wide Web. From digitally producing quarterly strategic initiatives, program managing custom website builds, project managing multiple schedules or tasks, art directing a music video or marketing campaign, shooting an event or new menu to snapping film behind the scenes, I’m inspired by the versatility and drive. I’m your go-to person when you need an extra hand or someone to call on.
I’m a community-first type of gal. At every turn, I’m looking for the opportunity to find a meaningful way to make a positive impact while fostering strong relationships with like-minded humans. I want my work to embody collaboration with others who share similar values and goals, creating a sense of unity and purpose. It’s important we uplift one another and make sure everyone has a seat at the table. When we work in supportive and empowering environments, we can naturally fuel our passions for making a difference. Together.
If you had to pick three qualities that are most important to develop, which three would you say matter most?
SELF-AWARENESS
Developing a deep understanding of myself—my strengths, weaknesses, and triggers—has been the foundation of my journey. Self-awareness allows me to make choices that align with my values and goals, even when the path feels uncertain. It’s also given me the ability to stay grounded during stressful times, helping me maintain a clear focus on what’s important and how to move forward. Start by doing the inner work. Take time to reflect on who you are, what you want, and where your strengths and weaknesses lie. Journaling, therapy, or mindfulness practices can be powerful tools to help you get clear on your values and goals. The more you understand yourself, the more intentional you can be about the choices you make in your career and personal life.
RESILIENCE & ADAPTABILITY
The ability to bounce back from setbacks and adapt to change has been crucial. As a queer woman navigating a freelance career, there have been plenty of obstacles, but each challenge has taught me something new about perseverance. I’ve learned to embrace discomfort and uncertainty as part of the growth process, trusting that I can handle whatever comes my way. Understand that setbacks and challenges are part of the process, not the end of the road. When things don’t go as planned, take a step back and reframe the situation. Instead of seeing failure, look for the lesson or opportunity in it. And remember, resilience doesn’t mean “toughing it out” alone—seek out support from others when needed. Surround yourself with people who inspire and challenge you, and learn from them.
OPTIMISM & HOPE
I’m naturally optimistic, but that optimism isn’t naive. It’s a mindset rooted in the belief that my actions and decisions have the power to create change. Staying hopeful—even when the world feels heavy—has been critical in keeping me moving forward. It helps me see possibilities where others might see limitations and motivates me to push boundaries and fight for a future that aligns with my values. Cultivate optimism by taking small actions that align with your larger goals. It’s easier to stay hopeful when you see progress, even if it’s incremental. Keep your focus on what you can control—your mindset, your effort, your response to challenges. Practice gratitude regularly; acknowledging the good in your life helps shift your perspective when things get tough. Trust that even if the path is winding, your optimism will guide you through it.
Any advice for folks feeling overwhelmed?
When I feel overwhelmed, I first remind myself to breathe and give myself permission to pause. It’s easy to get caught up in the whirlwind of tasks, deadlines, and external expectations, especially when you’re navigating your own career. But I’ve learned over time that stepping back and reconnecting with myself—whether it’s through a moment of stillness, a walk, or just taking a breath—helps me regain perspective.
One strategy that really helps when I feel overwhelmed is breaking everything down into manageable action items. When I can see the larger picture laid out in bite-sized pieces, it feels less daunting. It’s also incredibly important to prioritize what needs to be done first and let go of the perfectionism that sometimes holds me back (a Virgo’s constant struggle!). Not everything needs to be perfect; it just needs to be done. That is STILL an active practice for me every dang day.
Another piece of advice I always turn to is to reach out for support. You do not have to be in this alone. This could mean asking for help from a friend, seeking advice from a mentor, or simply talking things out with someone in or outside of your life. I’ve learned that resilience doesn’t mean doing it all alone—it’s okay to lean on others when things get tough. Community is such a powerful source of strength, and it’s important to remind ourselves that we don’t have to carry the weight of the world by ourselves.
Finally, I focus on what I can control, take one step at a time, and trust that the pieces will fall into place. Staying hopeful has been a key tool in navigating overwhelming moments because it keeps me grounded in the bigger picture and reminds me that even the toughest times are temporary.
Contact Info:
- Website: https://www.kelseyjean.com
- Instagram: https://www.instagram.com/kelsey_helpme/
- Linkedin: https://www.linkedin.com/in/kelsey-jean-woodward/
- Other: All my links & where you can find me: https://msha.ke/klsyjean
Image Credits
1st image (holding fabric) taken by Melissa Achten https://www.instagram.com/harpistemology/
2nd photo (behind white sheer wall) taken by Boone Rodriguez https://www.instagram.com/boonerodriguez/
3rd photo (me on set) Taken by J Yunn at Nice Touch Co. https://www.instagram.com/c_a_s_h_o_n_l_y/
4th photo (talking to person) source unknown
5th photo (polaroid) taken by Aubrey Janelle https://www.instagram.com/aubrey.janelle/
6th photo (me in soaking pool) taken by Aubrey Janelle https://www.instagram.com/aubrey.janelle/
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