Shannon Kobylarczyk grew up in Green Bay, Wisconsin, in a busy home filled with five children, three of whom were adopted. Life there was loud, warm, and full of movement. She learned early how to listen, share space, and understand people—skills that would end up shaping her entire career. Sports, dance team practices, and hours spent reading helped her build discipline and curiosity, two themes that still guide her today.
After graduating college in just three years, Shannon spent 12 years working in accounting. But even with a stable career, she couldn’t shake the dream she’d carried since she was young: becoming an attorney. So she took a leap. She enrolled in law school part-time, worked full-time, and raised two young sons at the same time. Her oldest son was diagnosed with a brain tumor on her first day of classes, a moment that tested her strength more than anything before. But with support from her husband and her son’s care team, she kept going.
Shannon went on to build a respected legal career in securities, corporate governance, ethics, and compliance, eventually rising into senior leadership. Yet her story isn’t only about professional success. It’s also about learning to prioritize mental health, accept imperfection, and rebuild after difficult moments.
Today, Shannon focuses on family, wellness, reading, travel, and baking her signature cupcakes. Her voice is calm, thoughtful, and grounded—shaped by a life that hasn’t been linear but has always been meaningful.
What is your typical day, and how do you make it productive?
My days follow a rhythm that keeps me grounded. I start early with coffee and a quiet moment before the world wakes up. That first half hour sets the tone for everything else. After that, I focus on whatever requires the most mental clarity—usually writing, legal research, or reviewing documents. I keep my afternoons lighter: exercise, errands, reading, and family time. Productivity isn’t about speed for me anymore. It’s about pacing myself so I still have energy for the people I love.
How do you bring ideas to life?
I talk them out. Growing up in a family of five kids taught me early that thinking alone doesn’t get you far—you need conversation. When I have an idea, I start with a rough outline, then let it evolve through discussions with people I trust. That process helps me see blind spots and sharpen what matters.
What’s one trend that excites you?
I’m inspired by the growing openness around mental health. Ten years ago, most people hid their struggles. Now you see honest conversations everywhere—workplaces, schools, friendships. It makes healing feel less lonely.
What is one habit that helps you be productive?
Time-blocking. I give myself a specific window for each task and stick to it. Knowing there’s a defined limit actually helps me finish more.
What advice would you give your younger self?
Slow down. You don’t need to prove your worth by doing everything at once. Rest isn’t a weakness.
Tell us something you believe almost nobody agrees with you on?
I think cupcakes are underrated therapy. Baking them—measuring, mixing, decorating—forces you to slow down. It’s a type of meditation no one talks about.
What is the one thing you repeatedly do and recommend everyone else do?
Take a 10-minute walk with no phone. No playlist. No distractions. You’d be surprised how much clearer your mind feels.
When you feel overwhelmed or unfocused, what do you do?
I step away completely. I’ve learned that powering through stress never actually works. Sometimes folding laundry or taking a drive gives my mind the space to reset.
What is one strategy that has helped you grow your business or advance in your career?
Asking questions—even the uncomfortable ones. Early in my legal career, I didn’t always feel like the most confident voice in the room. But the moment I started asking questions instead of pretending I already knew everything, my growth accelerated. Curiosity builds competence.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
A mental health crisis led to a moment that cost me my job. At first, I felt ashamed. But over time I realized I had ignored every warning sign. I overcame it by being honest—with myself, my family, and eventually others. The lesson was simple: you can’t carry everything alone. And admitting you need help can be the bravest thing you do.
What is one business idea you’re willing to give away to our readers?
A “Cupcake Conversations” workshop—an informal gathering where people bake together while discussing stress, work, or personal goals. It’s easier to open up when your hands are busy and the environment feels warm.
What is one piece of software that helps you be productive? How do you use it?
Notion. I use it to track projects, books I want to read, travel ideas, and even cupcake flavor experiments. It keeps my brain organized.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
I love Educated by Tara Westover. It’s a reminder that learning can look very different for everyone and that resilience can take you far beyond your circumstances.
What’s a movie or series you recently enjoyed and why?
I recently enjoyed The Bear. I appreciate stories about messy, complicated people trying to rebuild their lives while juggling expectations. It feels real.
Key learnings
- Personal growth often requires slowing down rather than speeding up.
- Open discussion and curiosity are powerful tools for career advancement.
- Mental health needs attention long before it reaches a breaking point.
- Simple daily habits—quiet walks, structured time, honesty with yourself—create long-term resilience.