Alright – so today we’ve got the honor of introducing you to Katie Winchenbach. We think you’ll enjoy our conversation, we’ve shared it below.
Alright, Katie thanks for taking the time to share your stories and insights with us today. We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.
My first job out of law school while stable and respectable, felt ill-fitting. As days turned into months, the feeling grew stronger, and I knew I had to make a change. I hadn’t even been at the position for a year, so I wasn’t even sure what other job I could get with my limited experience, but I put myself out there.
I found a position online as an in-house attorney at a local startup. The moment I read the job description, something clicked. It seemed like a dream job and much to my surprise I interviewed and was offered the position!
As I shared my plans with colleagues, friends, and family, I was met with raised eyebrows and concerned looks. Their words of caution emphasized the risk in leaving an established law firm for a startup. One individual even told me it could be a career ending move.
Despite my enthusiasm for the new job, doubt began to creep in, and I wondered if I should even take the chance. I had student loans, rent, a car payment, I couldn’t be unemployed! As I grappled with the decision, I realized something crucial. The person who had to live with this decision wasn’t my everyone else – it was me. The voice that mattered most was my own. And my internal voice was screaming at me to take the leap.
The startup job was a whirlwind of challenges and opportunities. It wasn’t exactly the dream job I had pictured, but it did allow me to grow in ways I never anticipated and to develop skills that would prove invaluable in my future endeavors.
Looking back, I can trace a clear line from that pivotal decision to where I stand today. The skills I gained during my time at the startup became the stepping stones for further career moves and more importantly I learned a profound lesson about trusting myself.
It takes courage to follow your gut, especially when it goes against the grain of conventional wisdom. But there’s a gut feeling we all have, a compass of sorts that often points true north even when our mind is clouded by doubts and external opinions. Through my career I’ve learned to honor and trust that inner voice and to own the fact that I am the author of my own story. While it’s valuable to consider advice and feedback, the final decision – and the responsibility for that decision – rests with me.
This experience has instilled in me a confidence that goes beyond career choices. Some of the best opportunities might not look perfect on paper but feel right in our hearts. It’s a lesson I constantly remind myself that and I try to apply to any significant decision, whether professional or personal.
To anyone standing at a similar crossroads, I offer this: Listen to the advice of others, but don’t let it drown out your own inner wisdom. You know yourself better than anyone else. Trust that knowledge, trust your gut, and have the courage to follow where it leads. The journey might be challenging, but it will be yours.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I’m a self-proclaimed “contracts nerd” and I thrive on providing legal advice to enable businesses to grow and succeed. I currently work a Regional Lead Counsel for Motorola Solutions, Inc. where I lead the Enterprise and T6 legal team to create, negotiate, and finalize complex product, service, and software agreements.
Being a first-generation law student challenged me, but it also inspired me to help pave the way for women like myself who are chasing big dreams. That desire to uplift, empower, and inspire rising women leaders is at the heart of everything I do. I host my own podcast, Lead Fearlessly, which empowers women to unleash their inner strength and embrace leadership with confidence. Additionally, I serve as the Vice-President of Women Standing Together, a Maine-based organization that elevates women leaders and entrepreneurs through leadership training, networking, and professional development opportunities.
On top of all this I am a pageant competitor, currently serving as the reigning National United States Maine Mrs. 2025. Pageantry allows me to use my platform to advocate for women leaders.
I earned my J.D. from Quinnipiac University School of Law, summa cum laude with a concentration in Intellectual Property Law, and received an MBA from the University of Maine. Prior to attending law school, I earned my B.A. in Journalism and Sociology from Hofstra University.
We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
Growing up I thought I would have a linear path to success. I spent my summers in middle school and high school honing my writing and attending writing programs. I started college confident in my choice of Journalism as a major and with the end goal to work of working at a magazine. Fast forward to my senior year. I was interning at a top fashion magazine and I hated it.
The realization that this was not what I wanted to do with my life was terrifying. I had been so confident, so sure, of the path that I wanted to take and how I would get there. My 10-year plan was now useless and I had no clue what to do next.
To make a long story a bit shorter, I ended up taking a law class, loved the content, and decided (a bit on a whim) to go to law school which catapulted me to the career I have now.
I threw out my 10-year plan and I didn’t make another one. Instead of trying to make my journey linear and to plan out everything I wanted to accomplish, I decided to set shorter term goals and stay open to the possibilities.
I’m proud to say I accomplished many of the goals I set, including passing the bar exam and working for an international corporation. I’m also proud to say I accomplished many things I never set out to accomplish. I won a pageant and started competing nationally. I took acting and speaking lessons and started getting speaking engagements on an international scale. I’ll do my first TED talk in 2025!
These opportunities only came about because I stayed open to the possibilities and tried new things that excited me instead of trying to make my path fit in a box.
How’d you build such a strong reputation within your market?
When I first started out as a lawyer, I tried to be super professional, dress conservatively, and mirror the attorneys I’d seen during my internships an on the top TV shows. The problem was that I hated wearing suits. They felt uncomfortable and stuffy. What I learned pretty quickly was that when I felt uncomfortable and stuffy, my clients did too! They weren’t necessarily looking for the type of attorney you see on TV. What they really wanted was someone they felt comfortable with, and someone who made them feel heard.
I leaned into what that looked like. At the firm, I still dressed more formally, but I tried to infuse color or fun accessories. When I started working at tech companies, I let my true style shine through and retired my dress pants for good. I became known as someone who not only was a good attorney, but who had a bold, energetic style and a personality to match.
What I hope this story conveys is that it’s important to be authentic. Whether it’s your fashion sense or the way you show up as a leader, your unique set of skills and personality traits are what will help you build your reputation. Never hide those away or try to blend in.
Contact Info:
- Website: https://kdwinchenbach.com
- Instagram: https://www.instagram.com/heyitskdw
- Linkedin: https://www.linkedin.com/in/katiedw/
Image Credits
Ashley Ball Photography
Yolanda Christine Photography