We were lucky to catch up with Katie Pobjecky Orr recently and have shared our conversation below.
Katie Pobjecky, we’re thrilled to have you sharing your thoughts and lessons with our community. So, for folks who are at a stage in their life or career where they are trying to be more resilient, can you share where you get your resilience from?
Resilience has been something I’ve had to cultivate over time, shaped by challenges and setbacks, but also by moments of unexpected support and discovery. Growing up in an educated family, with my dad being a tax attorney and my mom an English teacher, I was expected to succeed academically. But school was a struggle for me, though I didn’t know why at the time. It wasn’t until later that I learned I had ADHD, something that wasn’t widely understood in the 90s. Being held back in second grade deepened my insecurities, but I found solace in art. I loved drawing and creating things, though I was too shy to share that side of myself until high school, when I discovered ceramics. My teacher encouraged me to think outside the box, and that’s where I found my confidence.
After being diagnosed with ADHD, I was prescribed medication, and for the first time, I started making good grades outside of art. I began to love English and writing, and by the time I was in community college, I felt like I was finally on the right track. I was excited to study art therapy at a university, but that excitement was short-lived. I was abruptly taken off my medication, and without the support I needed, I spiraled. I dropped out and worked retail to make ends meet. However, fate had a different plan when I met someone in marketing for an air museum, which led to a job as a marketing assistant. I threw myself into my work and learned the ropes, eventually moving up to a sales role, selling field trips to local schools.
Despite my career progress, the arrival of two new colleagues made me realize I needed to go back to school and finish my degree. So, in my mid-20s, planning my wedding, I re-enrolled. It was terrifying to do so without the support of medication, but I kept going, and my efforts paid off when I was accepted into a Fine Arts program. I was determined to succeed this time. However, life threw more challenges my way. After years of trying, I learned I was pregnant and my pregnancy was high-risk, and once again, I had to put my education on hold to work full-time. Still, I found joy in creating art on the side, even having my work accepted at a prestigious local art show.
During the next few years, I divorced and started a fine art business that I named after my daughter, Lilly-Bug Art. Making sure she understood to never give up on her dreams. later, after a divorce and a period of personal upheaval, When I couldn’t afford to buy gifts for my family one Christmas, I started painting small, affordable art pieces—decorated sketchbooks. They sold quickly, and my small business grew. I even became a competitive mountain biker, though I eventually had to give that up to focus on my family and my work.
Despite the setbacks, I kept learning. After moving to a new state, getting remarried to the man of my dreams. It was my husband, Steve, who encouraged me to finish my degree. This time, I was ready. I sought help for my ADHD, and at 43, I enrolled in a Graphic Design program. It was a grueling three years—tears, frustration, and self-doubt, especially as I navigated the challenges of being an older student, even older than the majority of my professors. Regardless, I pushed through, determined not to give up. Even after losing my father and my best friend in the same semester, I kept going, finishing my degree with all As except for one B.
Now, at 49, I’m a graphic designer for a large nonprofit, the only designer on staff. Every day presents new challenges, but I remind myself: “How badly do you want it?” Resilience is a combination of hard work, a little bit of luck, and the support of the people who love you. I’m thankful for all of it—every challenge, every failure, and every triumph along the way.
Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?
I work for a large non-profit in Tampa, Florida, that meets the most urgent needs of the Tampa Area’s Families in need. I am also currently working on publishing a children’s book I wrote and illustrated. After losing so much time, I was focused on finishing my degree. My main focus is my beautiful Lilly who is now 16 and my husband Steve and my two French bulldogs, Pippi and Tootsie.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
The three qualities that have been most impactful in my journey are perseverance, self-awareness, and resilience.
Perseverance – I’ve learned that success is rarely immediate. There were many times when things didn’t go as planned or when I faced setbacks. What kept me going was a deep belief that, through hard work, I would eventually get there. It might take longer than expected, but I trusted that if I kept moving forward, I would reach my goals. For anyone just starting out, my advice is this: don’t expect the path to be linear. Understand that the journey may take time, and there will be bumps along the way, but keep your eyes on the prize. Your perseverance will pay off in ways you can’t predict at the start.
Self-awareness – I’ve had to learn about myself—the ways I work best, the areas where I need help, and how to manage my challenges. Recognizing my ADHD, for example, was a turning point in understanding how I function and how to seek the right support. For those early in their journey, take the time to reflect on your strengths and areas of improvement. Self-awareness is key to building a plan that plays to your strengths while addressing your weaknesses.
Resilience – Life is full of obstacles, and it’s not always easy to stay positive when things get tough. What has helped me the most is viewing obstacles as something I can overcome. I learned to embrace challenges as opportunities for growth, and I celebrated each small victory along the way. My advice to others is: don’t be afraid to fail. Failure isn’t the end—it’s part of the process. The more resilient you are, the more equipped you’ll be to handle whatever comes your way.
Ultimately, the key is to stay true to your story and your desired outcome. Embrace both the struggles and the successes, and know that each experience, good or bad, is shaping you into the person who will ultimately succeed.
Looking back over the past 12 months or so, what do you think has been your biggest area of improvement or growth?
Over the past year, my biggest area of growth has been letting go of past insecurities. For much of my life, I carried around a lot of doubts about myself—stemming from my struggles in school, my challenges with ADHD, and the fear of not measuring up. These insecurities held me back from fully embracing opportunities and stepping into my own potential.
But in the last 12 months, I’ve worked hard to release those old fears and self-imposed limitations. I’ve learned to trust in my abilities more and to understand that my worth isn’t defined by past mistakes or the opinions of others. It’s been freeing to stop letting my inner critic dictate my choices. As a result, I feel more confident, more authentic, and more willing to take risks in both my personal and professional life.
Letting go of these insecurities hasn’t been easy, but it’s been transformative. It’s allowed me to embrace new challenges with a fresh perspective, and to show up as my true self without fear of judgment. I’m proud of this growth, and I’m excited to continue moving forward with that newfound confidence.
Contact Info:
- Website: https://www.katieorr.net/
- Instagram: https://www.instagram.com/lillybugart/?hl=en
- Facebook: https://www.facebook.com/LillyBugArt/
- Linkedin: https://linkedin.com/in/katie-orr-bb4b7515
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